We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes and Apartments Shelter Island, NY and nearby

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
Max
Bedrooms
Any
Amenities
Select
More filters
All 59 Rentals in the Shelter Island Area
loading...
From
$1,538
Per Night
View Details
1 / 16
Shelter Island
House Rental - 
5 Bedrooms, 3 Bathrooms, Sleeps 9
Details Reviews (3) Make Enquiry
From
$192
Per Night
View Details
1 / 11
Shelter Island
House Rental - 
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (3) Make Enquiry
From
$383
Per Night
View Details
1 / 7
Payment Protection
Shelter Island
House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
Details Make Enquiry
From
$1,794
Per Night
View Details
1 / 7
Payment Protection
Shelter Island
B and B - 
6 Bedrooms, 7 Bathrooms, Sleeps 17
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
About Seven Newly renovated in 2014, SEVEN offers a selection guest rooms for various combinations of guests, with king, queen, double queen and double twin rooms. Each guestroom includes air conditioning, a flat screen television, light seasonal goose down comforters, 100% cotton linens, and a... View all property information
Make Enquiry
From
$769
Per Night
View Details
1 / 35
Shelter Island
House Rental - 
3 Bedrooms, 3 Bathrooms, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Contemporary, light filled 3 bedroom, 3 bath home located near South Ferry with easy access to the Hamptons. The lovely open floor plan features an array of contemporary art and sculptures, a living room with vaulted ceiling and fireplace, state-of-the art kitchen and dining room, all having access... View all property information
Make Enquiry
From
$511
Per Night
View Details
1 / 16
Payment Protection
Shelter Island
House Rental - 
4 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Beautiful 1875 Historic Shelter Island Heights Gingerbread Victorian Home: 4 bedrooms (we have two master bedrooms with their own porches), 2 baths, plus outdoor shower, large kitchen with double farmhouse sink and new GE washer/dryer, full dining room, large living room with large brick fireplace,... View all property information
Make Enquiry
From
$416
Per Night
View Details
1 / 20
Shelter Island
Cottage - 
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
With it's Caribbean flair, 3 waterfalls, 2 pools and 75' Koi pond, our Vacation home is possibly the most Romantic Hamptons Hideaway Vacation Cottage Home Rental ever. Located in the Estate Section of Shelter Island. Available weekly, monthly or for the entire season contact us early for your... View all property information
Make Enquiry
From
$513
Per Night
View Details
1 / 30
Shelter Island
House Rental - 
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
New for 2011-2012 season. We have just installed Martha Stewart wall to wall carpeting on the entire upper level. The third week of August 2011 we replaced the just 8 year old kitchen with a beautiful new kitchen, including professional level stainless steel side by side refrigerator, a 5 burner... View all property information
Make Enquiry
From
$449
Per Night
View Details
1 / 16
Shelter Island
House Rental - 
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This eclectic 'Round' house is a one of a kind on Shelter Island. Sited on 1.5 acres in Hay Beach with slices of bay views, this upside down house offers 4 Bedrooms and 2 Baths on the ground floor with an open layout upstairs which includes the living and dining room, kitchen, ½ bath, and covered... View all property information
Make Enquiry

The following rentals are within 10 kilometres of Shelter Island, Long Island, New York.

From
$627
Per Night
View Details
1 / 4
Greenport, NY
Apartment - 
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (20) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
As featured by New York Magazine, the Cliffside Resort entertains the perfect vacation! This 68 unit complex, located directly on the Long Island Sound with incredible sunset views, offers brand new 2 bedroom 2 bathroom luxurious accommodations. Cliffside Resort Waterfront Condominiums at... View all property information
Make Enquiry
5 of 5 stars Reviewed 7 August 2014
Enjoyed four night stay .condo unit &entire complex was clean and well maintained.Location was perfect for touring vineyards ,Shelter Island and Greenport attractions.Pool with...
5 of 5 stars Reviewed 26 April 2014
Great Visit to the Wine Country again....It like going home...Very Clean ...always updated....Great Water Views riight on the Ocean...Great Food & Shopping..
See all reviews
Get the List
From
$641
Per Night
View Details
1 / 22
Payment Protection
Sag Harbor
House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This lovely 3 bedroom, 2 bath home in the Village of Sag Harbor is located conveniently 1 mile from Sag Harbor's Main Street and a 1/2 mile to Haven's Beach,1 mile to public golf course and 10 min to Sag Main Ocean. No car necessary, you can hop a bus anywhere on the East End and North Forks! This... View all property information
Make Enquiry
From
$224
Per Night
View Details
1 / 21
Payment Protection
Southold, NY
Apartment - 
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees. On the sought after 'Bayside' of the North Fork In the heart of the North Fork... View all property information
Make Enquiry
5 of 5 stars Reviewed 15 October 2014
Mark & Mona's historic apartment was a delight. It was small but cozy and clean. Our only surprise was that we didn't realize the bathroom was located inside one of the bedrooms...
See all reviews
From
$524
Per Night
View Details
1 / 4
Greenport, NY
Apartment - 
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (24) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Beautiful 2 Bedroom 2 Bathroom Poolside Unit. All that Cliffside Resort and the Sound have to offer are just steps away. Additional amenities include: close to town, in-room entertainment system, kitchenette, private walkway to the sound, refrigerated wine cooler, on sound, washer & dryer... View all property information
Make Enquiry
5 of 5 stars Reviewed 3 September 2014
6 Girlfriends with children wanted a quick easy trip with no traffic to end the summer. We got exactly that! The Cliffside Resort was perfect. I honestly can't say what I liked...
5 of 5 stars Reviewed 11 June 2014
My son got married this past weekend at a Vineyard near Cliffside and my family, the bride's family and some guests spent the weekend there. In total, we rented about 23 units...
See all reviews
From
$378
Per Night
View Details
1 / 21
Payment Protection
Sag Harbor
Apartment - 
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
From its commanding position on Main Street in the heart of Sag Harbor village, this spectacular vintage Victorian is an authentic testament to the history of Sag Harbor. With distinctive architecture and classic styling, the impressive house features the Upstairs Apartment with five rooms,... View all property information
Make Enquiry
From
$319
Per Night
View Details
1 / 14
Payment Protection
East Marion, NY
House Rental - 
4 Bedrooms, 3 Bathrooms, Sleeps 9
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Contemporary 4 bedroom 3 bath house with private Long Island Sound beach access and community tennis and bocce courts in East Marion. Secluded lot with swing set. 2 adult bikes and 2 kids bikes, beach chairs and toys included. Cook's kitchen, large deck. 10 rooms total, including master bedroom... View all property information
Make Enquiry
5 of 5 stars Reviewed 22 October 2014
I stayed here with my wife, young daughter (15 months) and parents for three nights. The house was amazing. It really is a home - as Jane (the owner) had told me, and a big home...
5 of 5 stars Reviewed 11 September 2014
The house is warm, cheerful, spacious and bright. It was wonderful to have breakfast, moon-lit dinners on the deck. Indeed the bunnies and deers visited us in the garden as Jane...
See all reviews
From
$319
Per Night
View Details
1 / 14
Payment Protection
Greenport, NY
Apartment - 
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Private Fishing...
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Overview: Waterfront Water's Edge luxury suite, Suite C-204, accommodates up to 6 guests (see below) with two bedrooms and two bathrooms located on the North Fork of Long Island at The Cliffside Resort Condominiums in Greenport, New York. Quoted rental rates include all taxes. Details: Offered by... View all property information
Make Enquiry
5 of 5 stars Reviewed 18 September 2014
My friends and I really enjoyed our stay here. VERY clean, comfortable and the location was perfect for our visits to the local wineries. The private beach was very clean and we...
5 of 5 stars Reviewed 9 August 2014
Terrific Two bedroom condo on the water. Was there for July 4th, tons to do. Minutes from shelter island and views to die for.
See all reviews
From
$378
Per Night
View Details
1 / 17
Payment Protection
Southold, NY
House Rental - 
3 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (11) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Private Fishing...
  • Safe
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Bright private sunny renovated three bedroom waterfront house on private street adjoining Arshamamague Pond. The sun is out and all we need is you to complete the picture. Join us at our three bedroom one bath renovated house. Private waterfront. Central AC. Beautiful hardwood floors and... View all property information
Make Enquiry
5 of 5 stars Reviewed 29 August 2014
We had such a wonderful time in Maureen and Alan's cottage. First and foremost, it's on Arshamomaque Pond, which looks like a lake but is actually an inlet of Peconic Bay. It's...
5 of 5 stars Reviewed 14 July 2014
My family was very pleased with these accommodations. We were all very comfortable. The place was very clean and well equipped for our 5 day stay. The location is absolutely...
See all reviews
From
$320
Per Night
View Details
1 / 11
Southold, NY
Cottage - 
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
John Andrew's Cottage is a 'turnkey' experience accommodating two adults and children including: -a cozy bedroom with its full size bed, which beckons you after a sun-filled day at the private beach (within walking distance) which overlooks Shelter Island -a complete kitchen and full bath -a... View all property information
Make Enquiry
4 of 5 stars Reviewed 22 August 2014
my daughter (5 1/2 year old) and i had a great visit here. the cottage was cute and comfortable. having the backyard was great too. the hosts were very friendly and...
5 of 5 stars Reviewed 27 August 2013
We stayed at John Andrew’s cottage for my best friend’s bachelorette getaway and loved it. Karen was extremely helpful, had great recommendations all around (The Blue Canoe!) and...
See all reviews
From
$224
Per Night
View Details
1 / 21
Payment Protection
Southold, NY
Cottage - 
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Come listen to the bands while tasting the local wines (See local vineyards and events). Walk to Southold Village or Beautiful Bay Beaches or just relax on your own patio while overlooking green lawns and mature trees. On the sought after 'Bayside' of the North Fork In the heart of the North... View all property information
Make Enquiry
5 of 5 stars Reviewed 4 June 2014
I rented both units in this cottage a few years back and was pleased to see that the property was lovely as ever. I rented both cottages again this time for a girl’s getaway...
See all reviews
From
$378
Per Night
View Details
1 / 12
Payment Protection
Sag Harbor
Apartment - 
Studio, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
PHEASANT ESCAPE GUEST SUITE An Accommodation for Particular People. Escape to Nature Without Roughing It. INFANTS and CHILDREN ALWAYS WELCOME. Special Promotion Option A: Stay 2 weekdays and get 25% off the 2nd weeknight. Special Promotion Option B: Stay 3 weekdays and get 50% off the 3rd... View all property information
Make Enquiry
From
$2,883
Per Night
View Details
1 / 27
Payment Protection
Sag Harbor
House Rental - 
5 Bedrooms, 8 Bathrooms, Sleeps 10
Bookings
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
This property is only for the very discerning renter. It is a designer's own home. Please read rental rates before inquiring. Minimum rental is one month during High Season unless you see an availability between rentals. During the off season 2 week rentals may be possible. This elegant 6000... View all property information
Make Enquiry
From
$641
Per Night
View Details
1 / 19
Southold, NY
House Rental - 
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Easy to reach, hard to leave! Relax in this charming setting overlooking one of the most beautiful vineyards on The North Fork, complete with a stunning and private sugar sand beach on Southold Bay, one of the best beaches anywhere on the North Fork or The Hamptons, yours to enjoy throughout your... View all property information
Make Enquiry
4 of 5 stars Reviewed 17 June 2014
We found the farmhouse to be charming and spacious for our seven family members. The location was beautiful with the vineyards and private beach, and it was also very handy for...
See all reviews
From
$1,666
Per Week
View Details
1 / 19
Southold, NY
House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (8) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This charming farmhouse is just what you’ve been looking for: A beautiful, newly renovated 1890's house with all the modern conveniences, perfectly located a few short blocks to Founders Landing Beach Park, Town Beach and Southold Village. About the House The house is a very bright and airy, and... View all property information
Make Enquiry
5 of 5 stars Reviewed 19 August 2013
This is a beautiful, well maintained house· Decorated and furnished to a very high standard. Fantastically situated for the beach in the lovely town of Southold. We used for our...
See all reviews
From
$641
Per Night
View Details
1 / 10
Payment Protection
Sag Harbor
Cottage - 
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Beech Tree Cottage is a charming two-bedroom, one-bath guest cottage conveniently located in the historic district of Sag Harbor, NY - a 5-minute walk along the waterfront to Main Street and the center of the village. The beach is a short drive or bike ride away. The owners are full-time residents... View all property information
Make Enquiry
From
$513
Per Night
View Details
1 / 27
Payment Protection
Sag Harbor
House Rental - 
4 Bedrooms, 2 Bathrooms, Sleeps 10
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Enjoy the historic and beautiful town of Sag Harbor while staying in a modern, comfortable and family friendly home with amazing hilltop views. Bring the whole family, the house comfortably sleeps 8-10.The home is set within two miles from Sag Harbor Village and less than a mile walk to the bay... View all property information
Make Enquiry
From
$3,076
Per Week
View Details
1 / 12
Payment Protection
Southold, NY
House Rental - 
2 Bedrooms, Sleeps 6
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
**New for 2013 Summer: Central Air, Paver Stone Patio Charming, bright, airy, two-bedroom home sits on cozy lot at the heart of the beautiful North Fork, just a minute walk to Southold's most sought after private community beach (Founders Beach). Our beautiful beach features a playground,... View all property information
Make Enquiry
From
$186
Per Night
View Details
1 / 11
Payment Protection
Greenport, NY
House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Our one bedroom,kitchenette/ dining room & foldout queen size couch in living downstairs sleeps four comfortable . Backyard garden. Just forty yard walk to our block pier. 150 yard walk into town. The heart of Greenport Village on the best block in our Village no need for your once you arrive... View all property information
Make Enquiry
4 of 5 stars Reviewed 4 December 2014
The place is in a great location - a short walk to downtown Greenport but far enough to have some peace and quiet. The apartment itself is nicely furnished and is charming. Keep...
5 of 5 stars Reviewed 30 August 2014
I hate to let anyone know about this place since my family (husband and two teenagers) had such a wonderful time and want to return next year and worry that if people discover...
See all reviews
From
$276
Per Night
View Details
1 / 23
Greenport, NY
House Rental - 
4 Bedrooms, 2 Bathrooms, Sleeps 11
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Our house is an historic Dutch colonial, both cozy and spacious, with warm wood trim and wood floors throughout. The 20 x 20ft. Great Room, a perfect gathering space for family and friends is complete with a baby grand piano, cable TV, children's toys and books, classic novels and wood burning... View all property information
Make Enquiry
5 of 5 stars Reviewed 24 September 2014
The pictures of this house do not do it justice. It is spacious although an older home, with wide floorboards, a great room with fireplace, toys for kids, deck for eating or just...
4 of 5 stars Reviewed 15 October 2013
We just returned from renting for Columbus weekend. Very happy with the house. We needed a ground floor room & shower for my 88yr old Mother & this worked out perfect. A few steep...
See all reviews
From
$1,281
Per Night
View Details
1 / 7
Sag Harbor
House Rental - 
5 Bedrooms, 3 Bathrooms, Sleeps 16
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
GREAT HOUSE FOR A GATHERING OF FRIENDS OR FAMILY LARGE YARD, 50 FOOT POOL, HOT TUB KITCHEN WITH GRANITE COUNTER TOPS GREAT LIVING ROOM WITH LARGE SCREEN HDTV, GOLD CABLE, WIFI 5+ 2 MORE BEDROOMS SHORT DRIVE/BIKE TO SAG HARBOR VILLAGE OR OCEAN BEACHES. Beds: 4 King Beds, 2 Double... View all property information
Make Enquiry
5 of 5 stars Reviewed 4 October 2014
Hawk Haven is a wonderful escape, ideal for relaxing away from it all . Wild turkeys and deer gather on the vast lawn in the early evening and it is hard to believe you are right...
See all reviews
From
$288
Per Night
View Details
1 / 12
Payment Protection
Southold, NY
House Rental - 
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Enquiry
Amenities & Details
  • Grill
  • Internet Access
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This cottage is beautifully located on Great Pond on one-half acre in the heart of Long Island's North Fork. The lakefront is secluded from neighboring properties and is superb for swimming, boating and fishing. Swimming in Long Island Sound is just six blocks away at Kenney's Beach. Dine on the... View all property information
Make Enquiry
From
$320
Per Night
View Details
1 / 19
Sag Harbor
Cottage - 
1 Bedroom, 1 Bathroom, Sleeps 3
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Forever Cottage is a charming, one-bedroom guest cottage plus newly added separate, modern 'boutique' Studio which rents separately, just steps from Main Street in the scenic village of Sag Harbor, NY, available to rent for weeks, weekends or longer stays- year-round. Sag Harbor is a beautiful,... View all property information
Make Enquiry
5 of 5 stars Reviewed 19 September 2014
After spending our first night out in the Hamptons at what was described as a luxury hotel which turned out to be a 1960's rehabbed motel we were THRILLED when we got to our...
5 of 5 stars Reviewed 13 August 2011
This cottage was charming and centrally located. The owner lives near by and was very sweet and helpful. It rained the whole time we were there, but even so, we had the best...
See all reviews
From
$320
Per Night
View Details
1 / 13
Payment Protection
Southold, NY
House Rental - 
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Internet Access
  • Satellite TV
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away... View all property information
Make Enquiry
1 of 5 stars Reviewed 2 September 2012
The photos in the add looked good, particularly the garden and the proximity of the lake. We rented the place for four days. When we arrived, the first thing that struck us was...
See all reviews
From
$320
Per Night
View Details
1 / 7
Payment Protection
Southold, NY
House Rental - 
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Internet Access
  • Private Fishing...
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
This ranch house is beautifully located on a freshwater lake in the heart of Long Island's wine country, just minutes from the beach. Enjoy abundant bird life in a garden setting. The lake is perfect for swimming, fishing, kayaking or canoeing. Swimming in Long Island Sound is just six blocks away... View all property information
Make Enquiry
From
$192
Per Night
View Details
1 / 19
Payment Protection
Southold, NY
Apartment - 
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Step back in time as you enter a Historic Home in the heart of Southold....the charm of the historic home is clear as you enter the front door of your unit into the inviting hallway and stairs to the entire upstairs of the home. Just part of the charm is the refinished original 1830 floors, lower... View all property information
Make Enquiry
From
$577
Per Night
View Details
1 / 5
Payment Protection
East Marion, NY
Cottage - 
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
North Fork- East Marion- Charming unique twin cottages with cedar roof and historical significance. Each cottage is new and elegantly appointed. Wide plank flooring and knotty pine doors. Complete kitchen with granite counters and dishwasher. New bath with Italian tiles. Central air conditioning... View all property information
Make Enquiry
From
$1,602
Per Night
View Details
1 / 32
Payment Protection
Sag Harbor
House Rental - 
7 Bedrooms, 5 Bathrooms, Sleeps 14
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Drive through private gates to this secluded property with 7 over sized bedrooms; 5 baths. The house is an architect's resort-inspired vacation home. The property sits on a 2+ acre lot for complete and utter privacy. Beautifully Landscaped with a Koi Pond. 75'L-shaped heated pool, hot tub, outdoor... View all property information
Make Enquiry
From
$384
Per Night
View Details
1 / 40
Payment Protection
Southold, NY
House Rental - 
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Come experience a Northfork summer, golfing, biking, beaching, Estate sale hunting, in the Heart of Wine Country, Long Island. Centrally Located in the Town of Southold, South of the main road, 3 houses from the water in the elite Founders Landing section of North Fork, The cottage is minutes'... View all property information
Make Enquiry
From
$641
Per Night
View Details
1 / 10
Payment Protection
Sag Harbor
House Rental - 
3 Bedrooms, 1 Bathroom, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
85 Milton Ave is a charming, comfortable family home where warm memories are made. Enjoy the house, beach and historic Sag Harbor from the conveniently located residence. The 1 mile walk to town is down pristine lanes past beautifully landscaped homes and water views. Sag Harbor was the first... View all property information
Make Enquiry
From
$2,563
Per Night
View Details
1 / 12
Payment Protection
Sag Harbor
House Rental - 
4 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Beautiful waterfront estate with beach, boat dock, pond, minutes to Sag Harbor, in the heart of the Hamptons. Three acre manicured property. Fantastic view of boats cruising Shelter Island Sound. Walk to village playground, tennis, basketball, and hiking trails. Available for Memorial Day to... View all property information
Make Enquiry
From
$2,563
Per Night
View Details
1 / 18
Payment Protection
Sag Harbor
House Rental - 
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The feeling of Zen surrounds you as you enter upon this European designer's hideaway..Custom appointments of quality and luxury fill this Hampton's home. Located 12 minutes walk to Main Street of the prestigious Sag Harbor Village....0.4 acres of beautifully manicured totally private lawns with... View all property information
Make Enquiry
From
$1,281
Per Night
View Details
1 / 7
Payment Protection
Sag Harbor
House Rental - 
6 Bedrooms, 4 Bathrooms, Sleeps 12
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
OPEN HOUSE!! Sunday May 18 One of the last houses in the area with pool AND tennis! MD-LD $60,000 Please call first. Welcome to my paradise! My home has everything you need for a fantastic summer. 6 bedroom/4 bath contemporary home on 10 secluded acres. Heated in ground 20x40 pool, all weather... View all property information
Make Enquiry
From
$320
Per Night
View Details
1 / 16
Payment Protection
Greenport, NY
House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 7
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
The Space The Old Schoolhouse tells a family story, dating back to the 1880's. This charming farmhouse, built by the Burt family in the 1880's, was first used as a schoolhouse, then transformed into a farmhouse. The Burt family updated the house in 2005 with the most energy efficient systems, so... View all property information
Make Enquiry
From
$359
Per Night
View Details
1 / 19
Payment Protection
Greenport, NY
House Rental - 
4 Bedrooms, 9 Bathrooms, Sleeps 8
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Safe
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
A gem of a getaway! There are four bedrooms, of which three are located upstairs. Two of the upstairs bedrooms share one new en-suite bathroom. One bedroom upstairs has it's own en-suite bathroom. The bedroom on the ground floor has an en-suite water closet and another full bathroom. The cottage... View all property information
Make Enquiry
From
$481
Per Night
View Details
1 / 7
Payment Protection
Sag Harbor
Cottage - 
Studio, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Private Fishing...
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Redwood Cottage has two bedrooms each with a queen size bed. One bathroom with tub/shower. It overlooks the Upper Cove in the Village of Sag Harbor. It is very nicely decorated inside with a full kitchen, dinning room, lovely living room with a water view! It is within walking distance of the... View all property information
Make Enquiry
From
$256
Per Night
View Details
1 / 6
Payment Protection
Sag Harbor
House Rental - 
1 Bedroom, 2 Bathrooms, Sleeps 3
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Read the article in Newsday about one of my houses, by Alex Mc Cord of the Real Housewives of NY ,She has been renting from me every time she is out here. THIS home was also written up in the NY Post Earlier this year in an article on June 24th 2010 called 'Be My Guest' as new great places to stay!... View all property information
Make Enquiry
From
$639
Per Night
View Details
1 / 8
Southold, NY
House Rental - 
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Stunning views, master suite, deck, sunrooms, private lane and beaches Completely renovated and enlarged to double the footprint this winter with new kitchen, two and a half new bathrooms with tubs and showers and large master bedroom suite overlooking the Ashamomaque inlet in Southold, with... View all property information
Make Enquiry
From
$1,153
Per Night
View Details
1 / 17
Payment Protection
Sag Harbor
House Rental - 
4 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Walk in to the view of the sky and bay through the living room. The master suite is its own floor. the house is modern, there are three other bedrooms. Perfect home for a summer vacation. A short ride to Main Street, Sag Harbor, short walk to bay beach. View all property information
Make Enquiry
From
$384
Per Night
View Details
1 / 15
Payment Protection
Southold, NY
House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
3 bedrooms, 2 full bathrooms, sleeps 6 Pristine, year round, vacation getaway, within short walk to two white, sandy, Sound beaches. Nestled in the North Fork wine country, this home away from home is everything you need to make your stay memorable. A very comfortable, clean, smoke free home.... View all property information
Make Enquiry
From
$384
Per Night
View Details
1 / 29
Payment Protection
Greenport, NY
House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 9
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
The Space Located on a tree lined street this sun-filled two story house sleeps 8 people +. It features 3 bedrooms, 2 bathrooms, an eat in-kitchen and spacious living area with TV and wifi. There are 2 queen size beds, 2 full size beds and a queen size sleeper sofa. The private backyard offers... View all property information
Make Enquiry
From
$641
Per Night
View Details
1 / 16
Southold, NY
House Rental - 
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Idyllic retreat in North Fork beach and wine country. Quiet and peaceful, at the end of a private road, our charming, renovated 1830's farmhouse features lots of sunlight, a stainless steel kitchen, all wooden floors, jacuzzi bathtub, mudroom, washer/dryer, wifi, cable tv, air conditioning and... View all property information
Make Enquiry
Go to map view
Book Online(36)
Use filters to find the best results!

Suitability

  • Wheelchair access (6)
  • Elder access (22)
  • Suitable for children (11)
  • Pet friendly (19)
  • Smoking allowed (3)

Amenities

  • Other outdoor space (53)
  • Air Conditioning (49)
  • Internet (49)
  • Grill (45)
  • Parking (41)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities