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Compare 1518 Vacation Homes in Shelter Island with updated reviews, rates, and availability.

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
20x40' pool has two shallow ends and stadium steps on both sides

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready

9.8 out of 10, Exceptional, (97)
"Nothing negative to say. The owner came to greet us on our arrival, and showed us around the property. The house and grounds are family friendly with safety features for toddlers. Plenty of room for a large group. Parking for one car at the beach, and a short walk if all cannot fit in the car. The two outdoor showers are great when returning from the beach."
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Gorgeous private Hamptons house with pool and volleyball court
Exterior

Gorgeous private Hamptons house with pool and volleyball court

8.4 out of 10, Very Good, (17)
"Enjoyed this house in a great location. It was perfect for attending a family wedding!"
Gorgeous private Hamptons house with pool and volleyball court
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Pool

Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!

10.0 out of 10, Exceptional, (33)
"The house was perfect, a home away from home located in a nice quiet area, with stores and restaurants close by. House was clean, spacious and stocked with the essentials. The kids loved the pool and the ping pong table. Thank you Val for the perfect weekend, hope to see you next Summer!!"
Cozy Hamptons get away, pool, minutes from beaches, shops, restaurants and more!
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
Beach Path 150 yards

Unobstructed Ocean Views ! A Beautiful Montauk Getaway

10.0 out of 10, Exceptional, (47)
"We thoroughly enjoyed staying here, short walk to town, beautiful scenery, quiet and clean. "
Unobstructed Ocean Views ! A Beautiful Montauk Getaway
Charming beach home, complete with pool & cozy guest house!
Exterior

Charming beach home, complete with pool & cozy guest house!

9.6 out of 10, Exceptional, (23)
"Wonderful property. Plenty of room for 7 adults. Would definitely stay there again. "
Charming beach home, complete with pool & cozy guest house!
Exquisite New Hampton Home in a Perfect Location
Exterior

Exquisite New Hampton Home in a Perfect Location

Exquisite New Hampton Home in a Perfect Location
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach
Outdoor dining

COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach

10.0 out of 10, Exceptional, (13)
"Steps to probably the most beautiful beach in the Hamptons. Thoroughly enjoyed our stay, as did the dogs. We will definitely be back."
COZY COTTAGE WITH PRIVATE BEACH ACCESS IN THE DUNES - Half a block to the beach
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (86)
"Very cute ranch in a lovely neighborhood. Good location for access to area sites like Hammonasset Beach, Chamard Vineyard, and the Water's Edge. Not truly a "water's view", but the house had all the amenities needed for a fun stay! "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Fall in thešŸŒ…beautiful sunsets
1860 farm house

Fall in thešŸŒ…beautiful sunsets

10.0 out of 10, Exceptional, (24)
"Margaret is just wonderful. We felt like we were staying at a dear family memberā€™s home. Stayed in her very private upstairs suite and it was perfect for me, my wife and our pup. He had a blast running around the yard, meeting the chickens going to the bay beach etc. We had the best time! Thank you Margaret!!"
Fall in thešŸŒ…beautiful sunsets
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
Sprawling pool with outdoor kitchen

Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping

10.0 out of 10, Exceptional, (17)
"Had the best girls weekend with old college roommates! The house is stunning and incredibly clean. Was well stocked with everything we needed for our stay. Great location as well for checking out downtown, the beach, wineries, etc. "
Delightful Southampton Retreat with Heated Pool & Jacuzzi, Near Beach & Shopping
A Quiet Place in the Hamptons
Come on in.

A Quiet Place in the Hamptons

9.8 out of 10, Exceptional, (34)
"We had a very nice time. The house was exactly what we needed and was close to everything. "
A Quiet Place in the Hamptons
Center of Town - Ideal for Beach, Golf & Tennis
Dining

Center of Town - Ideal for Beach, Golf & Tennis

10.0 out of 10, Exceptional, (58)
"Had a Wonderful Time !! Ryan is great , was available to help at any time .. House is beautiful Very comfortable. Great location .. just as nice as the photos .. Very Clean , Modern and super convenient to town. Ditch Plains and of course Montauk Downs Loved It !!!"
Center of Town - Ideal for Beach, Golf & Tennis
Cozy Seaside Cottage
Exterior

Cozy Seaside Cottage

10.0 out of 10, Exceptional, (34)
"Really enjoyed our short weekend at this cottage. Owners were very helpful in providing recommendations for wineries in the area. Home was clean and tidy. Be aware if you're tall as the second floor ceilings are rather short, and the light fixture in the primary bedroom is easy to bang your head on in the bed."
Cozy Seaside Cottage
East Hampton Luxury: Heated Pool, Hot Tub & Expansive Yard with 6 Bedrooms
Heated custom gunite Pool & Hot Tub w/ marble dust finish overlooks massive lawn

East Hampton Luxury: Heated Pool, Hot Tub & Expansive Yard with 6 Bedrooms

10.0 out of 10, Exceptional, (39)
"We had the best time at the property. It was perfect for 7 of us! Great pool and very helpful. "
East Hampton Luxury: Heated Pool, Hot Tub & Expansive Yard with 6 Bedrooms
Beautiful Private 4 BR, Heated Pool. Close to Everything.
New Teak Lounge Chairs, Decking and Pool Liner

Beautiful Private 4 BR, Heated Pool. Close to Everything.

9.6 out of 10, Exceptional, (42)
"We were in the Hamptons to celebrate my sisters upcoming wedding and had a fantastic time in our rental the only complaint we had was that wish we were there longer!"
Beautiful Private 4 BR, Heated Pool. Close to Everything.
Aqua Vista
Living area

Aqua Vista

10.0 out of 10, Exceptional, (11)
"My sister and I stayed at Aqua Vista the last weekend in October. The weather was amazing. The house is located just a block form the ferry to Shelter Island and a couple of blocks to all the shops in Greenport.The apartment was clean well equipped and well maintained. Located in a lovely area close to all the shops. We would definitely stay there again . The"
Aqua Vista
The beach is waiting.
Exterior

The beach is waiting.

10.0 out of 10, Exceptional, (24)
"Susan's place was perfect for my family to visit the neighborhood where I grew up! It was clean, comfortable and had everything we needed. It's also a few steps from the beach and the amenities GNB has to offer."
The beach is waiting.
North Fork seaside retreat for design lovers
Living room with unobstructed water views on three sides

North Fork seaside retreat for design lovers

10.0 out of 10, Exceptional, (2)
"Awesome property with everything you need for a great getaway. European chic touches throughout and a location that is just fantastic!! Spectacular Sunrises on the deck with breakfast overlooking Orient Harbor, Bug Light, and Shelter Island are mesmerizing. The view and the setting just never gets old-a real gem!! Nicole was terrific to deal with - weā€™ll be back!!"
North Fork seaside retreat for design lovers
Exclusive location with spacious interior offering many amenities.
Pool

Exclusive location with spacious interior offering many amenities.

7.8 out of 10, Good, (7)
"Everything was exactly as advertised! We appreciated the space as it made our weekend extra special, location was especially convenient. Overall a great experience! Thank you."
Exclusive location with spacious interior offering many amenities.
Secluded Southampton Home That Has It All
Living area

Secluded Southampton Home That Has It All

10.0 out of 10, Exceptional, (1)
"This was a perfect getaway for a multigenerational family reunion! It's a beautifully maintained property. The bathroom to bedroom ratio was great for many families/couples. Great amenities included a heated pool and jacuzzi, and it's ideally located with easy access to Southampton and Sag Harbor downtown areas. Bob was a wonderful host and easy to reach. I recommend this place for anyone planning a family getaway. "
Secluded Southampton Home That Has It All
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Shelter Island

Montauk Manor
Exterior

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1087)
"We have stayed at the Montauk Manor for the holidays many times and find it friendly, peaceful and comfortable."
The price is AEDĀ 481
AEDĀ 621 total
includes taxes & fees
7 Jan - 8 January 2025
Montauk Manor
Montauk Oceanside Suites
Front of property

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very Good, (347)
"Needs to have someone man the phonesā€¦"
The price is AEDĀ 500
AEDĀ 607 total
includes taxes & fees
1 Jan - 2 January 2025
Montauk Oceanside Suites
Windward Shores Ocean Resort
Property grounds

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (264)
"Stayed for the second time at Windward and have no complaints. will book again next time I'm in Montauk!"
The price is AEDĀ 464
AEDĀ 609 total
includes taxes & fees
5 Jan - 6 January 2025
Windward Shores Ocean Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.