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Holiday Homes and Apartments Greenport, NY and nearby

All 24 Rentals in the Greenport Area
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From
$526
/ Night
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1 / 4
5 of 5 stars (20) Excellent
Greenport
2 Bedrooms / 2 Bathrooms / Sleeps 6
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From
$449
/ Night
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1 / 4
4.5 of 5 stars (24) Very good
Greenport
2 Bedrooms / 2 Bathrooms / Sleeps 6
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From
$320
/ Night
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1 / 14
5 of 5 stars (2) Excellent
Greenport
2 Bedrooms / 2 Bathrooms / Sleeps 6
travellers have booked this property
Overview Reviews (2) Make Enquiry
From
$322
/ Night
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1 / 23
4.5 of 5 stars (3) Very good
Greenport
4 Bedrooms / 2 Bathrooms / Sleeps 10
Overview Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
The house is a comfortable Dutch colonial with a very cozy yet spacious feel to it. The 20 x 20ft. great room with a baby grand piano and wood burning fireplace opens to a large deck. There are toys and children's books as well as nature field guides and classic novels. The tall privet hedge and... View all property information
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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...
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From
$187
/ Night
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1 / 11
4.5 of 5 stars (2) Very good
Greenport
3 Bedrooms / 2 Bathrooms / Sleeps 4
travellers have booked this property
Overview 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
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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...
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From
$322
/ Night
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1 / 16
Greenport
3 Bedrooms / 2 Bathrooms / Sleeps 7
traveller have booked this property
Overview 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
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From
$322
/ Night
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1 / 29
Greenport
3 Bedrooms / 2 Bathrooms / Sleeps 9
traveller have booked this property
Overview 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
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From
$184
/ Night
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1 / 7
Greenport
3 Bedrooms / 2 Bathrooms / Sleeps 5
Overview 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 newly renovated, immaculate ranch on georgous 1/2 acre complete with gardens and decks is designed to make your summer visit to the North Fork of Long Island memorable. 3 bedrooms, 1 1/2 baths with outdoor shower(hot and cold water). House is complete with fully equipped kitchen, seperate... View all property information
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From
$360
/ Night
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1 / 19
Greenport
4 Bedrooms / 9 Bathrooms / Sleeps 8
Overview 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
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The following rentals are within 10 kilometres of Greenport, North Fork, Long Island, New York.

From
$320
/ Night
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1 / 14
5 of 5 stars (2) Excellent
East Marion
4 Bedrooms / 3 Bathrooms / Sleeps 9
travellers have booked this property
Overview 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
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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...
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From
$193
/ Night
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1 / 11
4.5 of 5 stars (3) Very good
Shelter Island
2 Bedrooms / 1 Bathroom / Sleeps 6
Overview Reviews (3) Make Enquiry
Amenities & Details
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Our Quaint two bedroom house offers easy access to everything on Shelter Island. Large backyard offers room to kick back or to run around. Bedrooms are comfortable. one with a queen size bed, another with two twins - for those kids of yours, or push them together for a king size bed for extra... View all property information
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4 of 5 stars Reviewed 17 August 2014
This is a reasonably priced and clean place to stay. The furniture and furnishings are dated from the 60's/70's and it has a slightly musty feel. Other than that, it's a good deal...
5 of 5 stars Reviewed 5 August 2013
Everything about this rental was outstanding. The space is clean, airy, as shown in the photos. The yard is large and very beautiful, and the place is peaceful. The location is...
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From
$965
/ Night
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1 / 16
4.5 of 5 stars (3) Very good
Shelter Island
5 Bedrooms / 3 Bathrooms / Sleeps 9
Overview Reviews (3) 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
A time and place you will remember fondly forever. Owned and run by the proprietors of the Trip Advisor #1 rated accomodation on Shelter Island - The House on Chase Creek- this home is not a cottage at all, really, but when built by the Burns Family in 1900 that was what all the vacation homes were... View all property information
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From
$515
/ Night
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1 / 11
3 of 5 stars (1) Average
Orient
3 Bedrooms / 2 Bathrooms / Sleeps 5
travellers have booked this property
Overview Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Fireplace
  • Grill
  • Internet Access
  • Safe
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Pernchief Cottage Located In The Village Of Orient Is The Perfect Place To Summer With Family And Friends. Front Porch Offers Lovely Views Of The Bay. Wide Pine Floorboards, Great Architectural Detils Abound. Property Is Beautifully Set On 1/2 Acre With Lovely Gardens And A Tranquil Pond. Charming... View all property information
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3 of 5 stars Reviewed 30 May 2014
Great area but home is in poor condition. Decorated very cute and clean but all uneven floors, very cold inside house, no tv (although it was promised), not worth the price...
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From
$1,094
/ Night
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1 / 28
Shelter Island
6 Bedrooms / 11 Bathrooms / Sleeps 14
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Fireplace
  • Grill
  • Housekeeping...
  • Internet Access
  • Ocean Views
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Private luxury Island Compound. Ultra clean and bright! Tastefully modern decor! Very quiet, private, peaceful location!! - Main House AND Guest House included!!, Wood Burning Fireplace, Wrap-around covered Porches, decks, BBQ, 2 kitchens, Screened outdoor dining room, 2 large screen media centers!... View all property information
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From
$515
/ Night
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1 / 30
Shelter Island
4 Bedrooms / 4 Bathrooms / Sleeps 10
Overview 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
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From
$385
/ Night
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1 / 7
Shelter Island
3 Bedrooms / 2 Bathrooms / Sleeps 4
traveller have booked this property
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Large Shelter Island Farmhouse Close to all - steps from the golf course and beach 46 West Neck Road - overlooks Town Golf Course+ 1 Block to Sunset Beach + Town Boat Launch 3 bedrooms with AC (one queen, 2 twins, bring sheets + towels), 2 baths + outdoor shower, Dining Room, Living Room, Large... View all property information
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From
$1,802
/ Night
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1 / 7
Shelter Island
6 Bedrooms / 7 Bathrooms / Sleeps 17
Overview 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
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From
$552
/ Night
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1 / 23
Orient
4 Bedrooms / 4 Bathrooms / Sleeps 8
Overview 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
  • x
  • ?
About this property
Enjoy gorgeous water views of Gardiner 's Bay from this immaculate Victorian home situated on 1 acre. This spacious and beautifully decorated home comfortably accommodates 8 adults. Beds: 1 King Bed, 2 Queen Beds, 1 Double Bed View all property information
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From
$450
/ Night
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1 / 16
Shelter Island
4 Bedrooms / 4 Bathrooms / Sleeps 10
Overview 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
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From
$513
/ Night
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1 / 15
Shelter Island
4 Bedrooms / 2 Bathrooms / Sleeps 6
travellers have booked this property
Overview 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
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From
$404
/ Night
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1 / 10
Orient
2 Bedrooms / 2 Bathrooms / Sleeps 8
Overview Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
All newly renovated and exquisitely appointed home sits on a half acre in the private community of Green Acres steps away from the beaches in unspoiled Orient Point. Designer Rena Wilhelm decorated the home in a crisp ‘beachy’ décor. House amenities include central air conditioning, cable TV with... View all property information
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From
$2,758
/ Night
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1 / 17
East Marion
6 Bedrooms / 5 Bathrooms / Sleeps 12
Overview 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
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Escape to a private pastoral compound comprised of a historical home and a guest carriage house sitting on eight lush acres. The main country manor house offers three spacious bedrooms, including an en suite master with an attached private office, 2.5 baths, living, dining, entertaining spaces and... View all property information
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From
$418
/ Night
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1 / 20
Shelter Island
2 Bedrooms / 2 Bathrooms / Sleeps 6
Overview 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
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From
$734
/ Night
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1 / 35
Shelter Island
3 Bedrooms / 3 Bathrooms / Sleeps 5
Overview 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
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