Shelter Island Holiday Rentals

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Holiday Rentals in Shelter Island

Outdoor pool, a heated pool
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
10.0 out of 10, Exceptional, (11)
"We really enjoyed our stay in this house. Very safe and clean place to stay. Plenty of parking spaces, logs for fireplace, kitchen accessories. All china is very good quality."
Sagaponack Grand Estate, With Tennis Court, Newly-Furnished and 8 Bedrooms
Outdoor pool, a heated pool
Beautiful Family Home Nestled In The Heart Of Sagaponack
10.0 out of 10, Exceptional, (24)
"Had a wonderful time with friends in this lovely home. We had everything we needed. Excellent communication with our host. Perfect location. Thank you, Michelle 💕"
Beautiful Family Home Nestled In The Heart Of Sagaponack
Outdoor dining
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
10.0 out of 10, Exceptional, (27)
"Just had a great stay at this home. Pictures are extremely accurate and this home is so comfortable, clean and well equipped. Location is excellent. Close to town, hiking, beaches, vineyards. It really has it all! Host was wonderful and responsive. Would love book another stay."
Modern Farmhouse/Out Door Theater Fire Pit/ and Bocce court- WATCH VIDEO!!!
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Smart TV, fireplace, stereo
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (71)
"We loved this property. It’s open floor plan made it a great gathering place. Great location, clean and comfortable. Highly recommend"
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Lobby
MONTAUK MANOR-DELUXE STUDIO APARTMENT
10.0 out of 10, Exceptional, (54)
"Studio was perfect and grounds of property were breaking. Would definitely stay there again. Got to enjoy Montauk and have a beautiful place to stay."
MONTAUK MANOR-DELUXE STUDIO APARTMENT
On the beach, sun-loungers, beach towels
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
9.8 out of 10, Exceptional, (89)
"We unfortunately had bad weather during our stay but we were cozy in this home which is spacious and conveniently located. For those with kids, there are safety gates and toys available. There’s a lot of outdoor seating and in the summer we look forward to returning to take advantage of the pool. Carter is very responsive - a terrific host!"
Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready
Lobby
Montauk Mansion With Outdoor Pool
9.8 out of 10, Exceptional, (78)
"We had a wonderful week and enjoyed being in this beautiful manor immensely. We strolled the grounds and caught gorgeous sunsets. The shuttle into downtown Montauk (5 mins away) allowed us to untether from our car and parking worries, and to spend time at the ocean and wandering the quaint downtown. It was the perfect spot and we would go back again."
Montauk Mansion With Outdoor Pool
On the beach
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
9.8 out of 10, Exceptional, (73)
"We enjoyed our stay. No complaints. Great location."
Newly Renovated Montauk Oceanfront Condo- steps to Beach, Fishing, Golf, & Town!
Beach nearby, sun-loungers, beach towels
Beach House
9.8 out of 10, Exceptional, (42)
"Great place to stay! Nice neighborhood. Joseph was very nice and great to deal with."
Beach House
Outdoor pool, a heated pool
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
9.6 out of 10, Exceptional, (48)
"We had a lovely stay at this home. It was very clean, comfortable and spacious so we could all spread out. We were glad to have a nice warm house to stay in because the weather was terrible! I also went swimming in the warm pool even though it was 60 and raining! Would highly recommend."
Discounted rates Sag Harbor house with bay beach access and Heated Lap Pool
Beach nearby, sun-loungers, beach towels
Newly Renovated Montauk Condo with Ocean Views!
9.6 out of 10, Exceptional, (60)
"Perfect spot in Montauk, close to the beach and town. We walked to town with a 3 year old and infant in the stroller and very doable nice walk. The condo is clean and equipped with basic necessities so bring anything you might need cooking wise. Kept the baby in the bedroom and our 3 year old in the living room but we made it work. Kelly is extremely responsive and a pleasure to rent from."
Newly Renovated Montauk Condo with Ocean Views!
Interior
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
9.4 out of 10, Exceptional, (27)
"Rainy but good weekend"
Montauk Manor -1 BR 925 sq. ft. loft in resort overlooking Block Island Sound
4 bedrooms, desk, iron/ironing board, free WiFi
North Fork Escape Near Wineries, Beaches And Hamptons
9.4 out of 10, Exceptional, (18)
"Lovely quaint home. Very clean and spacious. Perfect for a family getaway . Highly recommend."
North Fork Escape Near Wineries, Beaches And Hamptons
Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1016)
"The hotel was beautiful. Town is very close by and they offer a shuttle service to take you around. It's nice overall."
The price is AU$290
per night
15 May - 16 May
Montauk Manor
Smart TV
Location and views! Located directly on Shinnecock Bay!
9.2 out of 10, Wonderful, (11)
"Since I stay for 2 days only it was fine. Check the shades , toilet paper and more towels. "
Location and views! Located directly on Shinnecock Bay!
Beach nearby
Cliffside Resort Condominiums
3.0 star property
9.0 out of 10, Wonderful, (180)
"Always a very nice time staying at this property. The sunset on the beach was amazing. Convenient to all area restaurants, wineries, breweries and Matchbook Distilling. "
The price is AU$424
per night
12 May - 13 May
Cliffside Resort Condominiums
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (233)
"Everything was just as described!"
The price is AU$265
per night
14 May - 15 May
Windward Shores Ocean Resort
Apartment, 1 Bedroom | Private kitchen
Driftwood Resort
3.5 star property
8.8 out of 10, Excellent, (182)
"Every room in the hotel has a little garden in the backyard which is linked with the park, it’s super natural and quiet and definitely worth to stay"
The price is AU$280
per night
2 June - 3 June
Driftwood Resort
On the beach, white sand
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (219)
"Very nice location and nice condo"
The price is AU$364
per night
12 May - 13 May
The Surf Club
Apartment | Private kitchen
Montauk Oceanside Suites
3.0 star property
8.4 out of 10, Very good, (295)
"Only wish it was more affordable in the summer to take my family. Besides that, clean, confortable, very pleasant."
The price is AU$269
per night
22 May - 23 May
Montauk Oceanside Suites
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See all available properties in Shelter Island
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.

Other types of properties in Shelter Island you may be interested in

Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1016)
"The hotel was beautiful. Town is very close by and they offer a shuttle service to take you around. It's nice overall."
The price is AU$290
per night
15 May - 16 May
Montauk Manor
Indoor pool, outdoor pool
Hyatt Place Long Island East End
3.0 star property
9.0 out of 10, Wonderful, (1002)
"Its a family trip to celebrate my wife's birthday. We love the hotel and the surroundings. The staff is so friendly, and service is superb! They even give us nice gifts like wine and chocolate.... Thanks so much, we definitely will return."
The price is AU$262
per night
19 May - 20 May
Hyatt Place Long Island East End
Outdoor wedding area
Gurney's Montauk Resort & Seawater Spa
4.0 star property
8.2 out of 10, Very good, (561)
"front desk staff irritating as can be "
The price is AU$768
per night
12 May - 13 May
Gurney's Montauk Resort & Seawater Spa
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.

Frequently asked questions

Can I find holiday rentals in Shelter Island?

Yes, there are holiday rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you're looking for a relaxing stay. Shelter Island is known for its parks and beaches. Make sure you have time to check out the museums while you're in the area.

How many holiday rentals are there in Shelter Island?

Choose from 86 Expedia holiday rentals in Shelter Island for a memorable holiday.

What can I see and do in Shelter Island?

Sunset Beach and Crescent Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Shelter Island Whale's Tail. Gardiner's Bay Country Club and Shelter Island Historical Society are other places to visit while you're in town.

What are holiday rentals like in Shelter Island?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Shelter Island. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from shared hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive choice for a small group gathering.