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Vacation Rentals in Shelter Island, NY and nearby

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All 23 Rentals in the Shelter Island Area
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From
$375
Per Night
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1 / 15
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Shelter Island
4 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$299
Per Night
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1 / 7
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Shelter Island
3 Bedrooms, 2 Bathrooms, Sleeps 4
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From
$1,100
Per Night
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1 / 28
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Shelter Island
6 Bedrooms, 8 Bathrooms, Sleeps 12
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From
$150
Per Night
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1 / 11
Shelter Island
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Satellite TV
  • Parking
  • Stove
  • Linens Provided
  • Washer
  • Grill
  • Internet Access
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • 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 August 16, 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 August 5, 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
$750
Per Night
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1 / 16
Shelter Island
5 Bedrooms, 3 Bathrooms, Sleeps 9
Details Reviews (3) Make Inquiry
Amenities & Details
  • DVD Player
  • Refrigerator
  • Stereo System
  • Stove
  • Patio
  • Fireplace
  • Dishwasher
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
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
$350
Per Night
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1 / 16
Shelter Island
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Make Inquiry
Amenities & Details
  • Patio
  • Refrigerator
  • Parking
  • Garage
  • Fireplace
  • DVD Player
  • Dishwasher
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • 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
$325
Per Night
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1 / 20
Shelter Island
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Refrigerator
  • Stove
  • Patio
  • Fireplace
  • Grill
  • Parking
  • Dishwasher
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • 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
$570
Per Night
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1 / 35
Shelter Island
3 Bedrooms, 3 Bathrooms, Sleeps 5
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Garage
  • Stove
  • Stereo System
  • Fireplace
  • Washer
  • Grill
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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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From
$400
Per Night
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1 / 30
Shelter Island
4 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Parking
  • Hot Tub
  • Washer
  • Patio
  • DVD Player
  • Fireplace
  • Refrigerator
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • 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
$457
Per Night
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1 / 4
Shelter Island
3 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Stereo System
  • Refrigerator
  • Grill
  • Washer
  • Satellite TV
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
1970’s modern, completely remodeled in 2013 and a 5 minute walk to Wades Beach. Contemporary open floor plan with gourmet Viking kitchen and honed marble countertops stocked with gourmet cooking equipment and utensils. Privately located on a small wooded slope in the idyllic Fresh Pond... View all property information
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The following rentals are within 5 miles of Shelter Island, Long Island, New York.

From
$200
Per Night
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1 / 14
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East Marion, NY
4 Bedrooms, 3 Bathrooms, Sleeps 9
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Refrigerator
  • Stove
  • Parking
  • Microwave
  • Fireplace
  • Patio
  • Garage
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • 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 October 21, 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 September 10, 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
$249
Per Night
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1 / 14
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Greenport, NY
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Inquiry
Amenities & Details
  • Refrigerator
  • Satellite TV
  • Parking
  • Deck
  • Dryer
  • Grill
  • Dishwasher
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • 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
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5 of 5 stars Reviewed September 17, 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 August 8, 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.
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From
$250
Per Night
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1 / 18
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Greenport, NY
3 Bedrooms, 2 Bathrooms, Sleeps 7
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Stove
  • Dryer
  • Deck
  • Grill
  • Parking
  • Microwave
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • 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
$200
Per Night
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1 / 21
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Greenport, NY
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Grill
  • Satellite TV
  • Washer
  • Stove
  • Deck
  • Refrigerator
  • Dishwasher
  • Porch
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
The Space Located on a tree lined street this sun-filled two story house has 3 bedrooms, 2 bathrooms, eat in-kitchen and spacious living area with TV and wifi. The private backyard offers plenty of space to unwind with a covered porch, BBQ facilities and deck chairs. Note - we have a separate... View all property information
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From
$200
Per Night
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1 / 9
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Greenport, NY
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Grill
  • Parking
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Refrigerator
  • Deck
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Built in 1828 for a ship’s captain, this historic property remains as one of the oldest structures in the village. Large, bright & airy rooms. Perfect for a quiet weekend retreat. The second floor of our home is available on select weekends. View all property information
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From
$145
Per Night
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1 / 23
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Greenport, NY
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Satellite TV
  • Ceiling Fans
  • Grill
  • Safe
  • Dishwasher
  • Porch
  • Internet Access
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Can be used as a full house on rent separately downstairs apt 1) enjoys two bedroom w eat in kitchen & dining room, two bedroom sleeps four ) Or our one bedroom dining room, kitchen & foldout queen size couch in living downstairs sleeps four comfortable . Backyard garden. Just forty yard walk to... View all property information
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5 of 5 stars Reviewed August 29, 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
$250
Per Night
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1 / 23
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Greenport, NY
4 Bedrooms, 2 Bathrooms, Sleeps 10
Details Reviews (3) Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Satellite TV
  • Local Guides/Maps
  • DVD Player
  • Towels Provided
  • Fireplace
  • Housekeeping...
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • 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 September 23, 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 October 14, 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
$409
Per Night
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1 / 4
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Greenport, NY
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (20) Make Inquiry
Amenities & Details
  • Microwave
  • Heated Pool
  • Air Conditioning
  • Deck
  • Internet Access
  • Satellite TV
  • Waterfront
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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 Inquiry
5 of 5 stars Reviewed August 6, 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 April 25, 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..
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From
$449
Per Night
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1 / 4
Payment Protection
Greenport, NY
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (24) Make Inquiry
Amenities & Details
  • Dishwasher
  • Refrigerator
  • Waterfront
  • Microwave
  • Deck
  • Internet Access
  • Air Conditioning
  • Heated Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
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
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5 of 5 stars Reviewed September 2, 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 June 10, 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...
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From
$143
Per Night
View Details
1 / 7
Greenport, NY
3 Bedrooms, 2 Bathrooms, Sleeps 5
Details Make Inquiry
Amenities & Details
  • Stove
  • Microwave
  • Washer
  • Dishwasher
  • Refrigerator
  • DVD Player
  • Garage
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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
$2,143
Per Night
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1 / 17
East Marion, NY
6 Bedrooms, 5 Bathrooms, Sleeps 12
Details Make Inquiry
Amenities & Details
  • TV
  • Grill
  • Parking
  • Fireplace
  • DVD Player
  • Dishwasher
  • Garage
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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
$171
Per Night
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1 / 12
East Marion, NY
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Dryer
  • VCR
  • Stereo System
  • Refrigerator
  • Parking
  • Washer
  • DVD Player
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Lovely 2 bedroom cottage with new kitchen and bath on oversized property. Large screened-in porch overlooking tree-lined backyard. Walk to water and very close to town beaches and quaint town of Greenport. Also close to all ferries to Shelter Island and Connecticut ferries to Foxwoods, Mohegan... View all property information
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1 / 3
Payment Protection
Greenport, NY
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Number Of Bedrooms
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
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 Inquiry
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