1 / 14
Shelter Island Villas and Homes
-
Review
Review a place you’ve visited
- JOIN
- LOG IN
-
$
-
-
Shelter Island
- Shelter Island Tourism
- Shelter Island Accommodation
- Shelter Island Bed and Breakfast
- Shelter Island Holiday Rentals
- Shelter Island Holiday Packages
- Shelter Island Flights
- Shelter Island Restaurants
- Shelter Island Attractions
- Shelter Island Travel Forum
- Shelter Island Photos
- Shelter Island Map
- Shelter Island Guide
- Hotels
- Flights
-
Holiday Rentals
- Restaurants
- Things to Do
- Forum
- Best of 2016
-
More
Holiday Rentals in Shelter Island, NY
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
Max per night
$100
100
100
700
$200
200
200
1400
$300
300
300
2100
$400
400
400
2800
$500
500
500
3500
$600
600
600
4200
$700
700
700
4900
$800
800
800
5600
$900
900
900
6300
$1,000+
+1000
+1000
+7000
Studio + 0,30
1 Bedroom + 1,30
2 Bedrooms + 2,30
3 Bedrooms + 3,30
4 Bedrooms + 4,30
5 Bedrooms + 5,30
6 Bedrooms + 6,30
7 Bedrooms + 7,30
8 Bedrooms + 8,30
Filters
clear all Bedrooms
Price
Neighbourhoods
Amenities
Filters
clear all There are no pins in your viewport. Try moving the map or changing your filters.
- {providername} {price}
{sold_out_text}
We can't find prices for this accommodation
From {rate_price} {rate_periodicity}
List your property
Owner log in
Payment Protection
Use a credit card to book with our Payment Protection.Learn more
Studio + 0,30
1 Bedroom +
1,30
2 Bedrooms +
2,30
3 Bedrooms +
3,30
4 Bedrooms +
4,30
5 Bedrooms +
5,30
6 Bedrooms +
6,30
Bedrooms
Any
Amenities
Any
Sleeps
Any
Any
0,10
1 +
1,10
2 +
2,10
3 +
3,10
4 +
4,10
5 +
5,10
6 +
6,10
7 +
7,10
8 +
8,10
9 +
9,10
10 +
10,10
Any
0,4
1 +
1,4
2 +
2,4
3 +
3,4
4 +
4,4
loading...
Sort:
10 Holiday Rentals in Shelter Island
Travellers to Shelter Island are booking May dates now. Secure your holiday rental today, and have the perfect trip.
4 Bedrooms, 3 Bathrooms, Sleeps 8 |
Quick View
other travellers have booked this property
Amenities & Details
- Wi-Fi
- Parking
- Satellite TV
- Air Conditioning
Suitability
- Pet-friendly
- Child-friendly
- ?
- ?
- Smoking allowed
- ?
About this property
About Seven
Newly renovated in 2014, SEVEN bed and breakfast 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%...
View all property information
Location Information
Shelter Island, Hamptons
3 Bedrooms, 2 Bathrooms, Sleeps 4 |
Quick View
other travellers have booked this property
Amenities & Details
- Patio
- Air Conditioning
Suitability
- Pet-friendly
- Child-friendly
- x
- ✓
- Smoking allowed
- x
About this property
Large Shelter Island Farmhouse<BR>Beautiful Shelter Island is the most enjoyable, preserved, natural beauty on the North Fork and is yours to explore. Relaxing is mandatory...<BR>The farmhouse is close to all - steps from the golf course and beach<BR>46 West Neck Road - overlooks Town Golf Course+...
View all property information
Location Information
Shelter Island, Hamptons
4 Bedrooms, 3 Bathrooms, Sleeps 6 |
Quick View
other travellers have booked this property
Amenities & Details
- Balcony
- Air Conditioning
- Washer
- Porch
- Terrace
- Private Garden
- Internet Access
Suitability
- Pet-friendly
- Child-friendly
- ?
- ✓
- Smoking allowed
- x
About this property
Beautiful 1875 Historic Shelter Island Heights Gingerbread Victorian Home:
Rental includes: Two kayaks, Tennis Court, Shelter Island Heights Private Beach Club Use (private beach, picnic area, playground, showers, cabanas) for you and your family
Details:
4 bedrooms (we have two master bedrooms...
View all property information
Location Information
Shelter Island, Hamptons
Amenities & Details
- Parking
- Wi-Fi
- Satellite TV
- Private Outdoor...
- Air Conditioning
- Private Garden
Suitability
- Pet-friendly
- Child-friendly
- x
- ✓
- Smoking allowed
- x
About this property
Located on Shelter Island, NY down a quiet lane within walking distance of Wades Beach and the Nature Conservancy's Mashomack preserve. This impeccably maintained hilltop traditional, reminiscent of a European country home, is situated on 2 acres. Entering the front foyer, your eye will be drawn...
View all property information
Location Information
Shelter Island, Hamptons
Amenities & Details
- Hot Tub
- Satellite TV
- Washer
- Internet Access
- Air Conditioning
- Waterfront
- Private Outdoor...
- DVD Player
Suitability
- Pet-friendly
- Child-friendly
- ✓
- ?
- Smoking allowed
- x
About this property
DURING THE PEAK MONTHS, THIS HOUSE IS ONLY AVAILABLE BY THE WEEK OR LONGER!
We just completed remodeling 2 of the baths and some additional painting.
We just had custom plush white leather seating in the eat in kitchen nook as well as the window seat in one of the bedrooms. We are in the...
View all property information
Location Information
Shelter Island, Hamptons
My wife and I are very hard to please when it comes to travel and accommodation. However, Shelter Island Hideaway left us wanting more. The pergola, the décor, the pool, the semi...
Amenities & Details
- DVD Player
- Internet Access
- Air Conditioning
- Grill
- Satellite TV
- Private Outdoor...
- Washer
- Patio
Suitability
- Pet-friendly
- Child-friendly
- ✓
- ?
- Smoking allowed
- 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
Location Information
Shelter Island, Hamptons
Amenities & Details
- Private Outdoor...
- Grill
- Satellite TV
- Washer
- Patio
- Air Conditioning
- Internet Access
- Porch
Suitability
- Pet-friendly
- Child-friendly
- ✓
- ?
- Smoking allowed
- 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
Location Information
Shelter Island, Hamptons
List your property for free!
List your holiday rental where TripAdvisor travellers can find it.
Add a Listing
1-10 of 10
Payment Protection
Use a credit card to book with our Payment Protection.
Explore Shelter Island
- Holiday Rentals near GLORY
- Holiday Rentals near Osprey's Dominion Vineyards
- Holiday Rentals near Greenport Harbor Brewing Co.
- Holiday Rentals near Bay Street Theatre
- Holiday Rentals near Antique Carousel
- Holiday Rentals near Orient Beach State Park
- Holiday Rentals near Horton Point Lighthouse and Nautical Museum
- Holiday Rentals near The Old Field Vineyards
- Holiday Rentals near Sag Harbor Whaling and Historical Museum
- Holiday Rentals near Corey Creek Vineyards
© 2016 TripAdvisor LLC All rights reserved. TripAdvisor Terms of Use and Privacy Policy.
* TripAdvisor LLC is not a booking agent and does not charge any service fees to users of our site... (more)
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.
We support the following browsers: Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
TripAdvisor LLC is not responsible for content on external web sites. Taxes, fees not included for deals content.