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Shelter Island Holiday Rentals

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Holiday Rentals in Shelter Island

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1216)
"Not very walkable but the shuttle makes up for it. Pool is very nice too, a break from the crowded beaches"
The price is AU$842
includes taxes & fees
23 July - 24 July
Montauk Manor

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (262)
"Quiet, relaxing place to stay, great access to the beach and town!"
The price is AU$672
includes taxes & fees
23 July - 24 July
The Surf Club

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (289)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is AU$783
includes taxes & fees
27 July - 28 July
Windward Shores Ocean Resort

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (393)
"great place to stay"
The price is AU$603
includes taxes & fees
23 July - 24 July
Montauk Oceanside Suites

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (228)
"Very nice, clean and cosy place! Highly recommend!"
The price is AU$656
includes taxes & fees
27 July - 28 July
Cliffside Resort Condominiums

Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

8.6 out of 10, Excellent, (25)
"This adorable, cozy cottage was perfect for our family getaway to Montauk. We have tried various rentals and hotels each summer and Robert’s cottage was by far our favorite. It fit our family of 5 perfectly, with enough room that we didn’t feel on top of each other. The decor was light and airy and just what we were hoping to find. From the awesome location, just a walk to the ocean, to the indoor pool and back up to a comfortable stay, our entire family agree that we can’t wait to return!...
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill

Driftwood Resort

3.5 star property
9.0 out of 10, Wonderful, (225)
"Phenomenal property and our room had a private sand patio. Service was extremely attentive and friendly. The beach was very spacious and pretty clean."
The price is AU$898
includes taxes & fees
28 July - 29 July
Driftwood Resort

Canoe Place Waterfront Residences

4.0 star property
Canoe Place Waterfront Residences

Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

2.5 star property
9.6 out of 10, Exceptional, (9)
"Great place! Great communication with property owner!"
The price is AU$971
includes taxes & fees
28 July - 29 July
Cozy Bungalow Available Nearby Bridgehampton and Sag Harbor

Hamptons Retreat

Hamptons Retreat

NORTHFORK COTTAGE with POOL & HOT TUB

4.0 star property
9.8 out of 10, Exceptional, (130)
"Loved our stay and will be back"
NORTHFORK COTTAGE with POOL & HOT TUB

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (69)
"We had a wonderful vacation at the Fairy Tale Guest Cottage. The location was awesome and we loved the accommodations, especially the fancy bathroom. Mark and Eunyoung are impeccable hosts. Would absolutely stay again!"
Fairy Tale Guest Cottage in Magic Garden by Pool

Sag Harbor Suite by the Beach

8.8 out of 10, Excellent, (10)
"Trvis and Alice are great host and the property was a great place to stay close to the beach and downtown Sag Harbor."
Sag Harbor Suite by the Beach

Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

10.0 out of 10, Exceptional, (90)
"Beautiful house with lots of light and comfort. Excellent quiet location by the ocean with outstanding communication with the host who answered all pertinent questions and addressed all outstanding issues. "
Mid-Century Modern Beach House: Private Beach Access, Pool, and Chef’s Kitchen

Walk to town, Bike to beach, Private pool oasis !

10.0 out of 10, Exceptional, (18)
"Nice house with very great outdoor. Well located, with the bikes, we can access the beaches, the city center and some restaurants very easily."
Walk to town, Bike to beach, Private pool oasis !

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (2)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is AU$386
includes taxes & fees
19 Aug - 20 Aug
The Stern at Soundview · Beach+Ocean+Sunrise

Shoreline Oasis

9.0 out of 10, Wonderful, (4)
"A very comfortable, clean, convenient apartment close to the shore and all the natural attractions near Madison and Clinton. We particularly appreciated that the owners quickly replaced the bedroom air conditioner when it broke. Great hosts!"
The price is AU$408
includes taxes & fees
24 July - 25 July
Shoreline Oasis

Southampton cozy cottage by the beach

The price is AU$1,110
includes taxes & fees
23 July - 24 July
Southampton cozy cottage by the beach

The Anchor at Soundview · Beach+Ocean+Sunrise

2.0 star property
8.0 out of 10, Very good, (1)
"Great stay. Clean, all amenities provided, located short walk from beach. I wouldn’t call it an apartment or studio, though. It’s the size of a bedroom and includes only a bed, dresser, fridge and microwave. Not even a chair. Description made me expect a bit more but if you know the size going in, it’s a marvelous place to stay. "
The price is AU$305
includes taxes & fees
30 July - 31 July
The Anchor at Soundview · Beach+Ocean+Sunrise

Perfect Mid-Century Private Waterfront East Hampton Retreat!

10.0 out of 10, Exceptional, (79)
"Very nice and relaxing stay in Springs! "
Perfect Mid-Century Private Waterfront East Hampton Retreat!
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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Top Shelter Island Hotel Reviews

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.

What are some of the best holiday rentals that Shelter Island has to offer?

Hamptons Retreat: This holiday home rental outside of Shelter Island offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Shelter Island?

Choose from 87 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. Shelter Island Historical Society and Wades Beach 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.