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Shelter Island Holiday Rentals

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Check prices for these dates

Tonight
5 Jul - 6 Jul
Tomorrow
6 Jul - 7 Jul
Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul

Holiday Rentals in Shelter Island

Work and Play Special! Extended Stay Discount
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount

10.0 out of 10, Exceptional, (43)
"We had a lovely time at Cottage Green. Ingrid was a lovely owner and was very easy to communicate with!"
Work and Play Special! Extended Stay Discount
Montauk Manor
Front of property – evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1205)
"The property was gorgeous, and the staff were very friendly and eager to assist. Also, the restaurant was very good!"
The price is HK$3,637
HK$4,309 total
includes taxes & fees
6 Jul - 7 Jul
Montauk Manor
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (286)
"Easy checking in and out Easy access few steps to beach from first floor unit "
The price is HK$2,672
HK$3,223 total
includes taxes & fees
9 Jul - 10 Jul
Windward Shores Ocean Resort
The Surf Club
On the beach, white sand

The Surf Club

3.5 star property
8.6 out of 10, Excellent, (260)
"Quiet, relaxing place to stay, great access to the beach and town!"
The price is HK$2,640
HK$3,443 total
includes taxes & fees
7 Jul - 8 Jul
The Surf Club
Montauk Oceanside Suites
Private kitchen

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (388)
"great place to stay"
The price is HK$2,003
HK$2,374 total
includes taxes & fees
6 Jul - 7 Jul
Montauk Oceanside Suites
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (224)
"After some lengthy travel to get to LI this was an excellent choice to start our vacation. Great accommodations, comfortable and great location. "
The price is HK$1,757
HK$2,348 total
includes taxes & fees
6 Jul - 7 Jul
Cliffside Resort Condominiums
Driftwood Resort
Private kitchen

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 HK$3,117
HK$3,817 total
includes taxes & fees
7 Jul - 8 Jul
Driftwood Resort
Canoe Place Waterfront Residences
Front of property

Canoe Place Waterfront Residences

4.0 star property
Canoe Place Waterfront Residences
Escape to Sag Harbor
Interior

Escape to Sag Harbor

10.0 out of 10, Exceptional, (47)
"Amazing house and location!! Would stay again "
Escape to Sag Harbor
Fairy Tale Guest Cottage in Magic Garden by Pool
Outdoor pool

Fairy Tale Guest Cottage in Magic Garden by Pool

10.0 out of 10, Exceptional, (67)
"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
Oceanfront, Private Beach, Outdoor Shower, Indoor Heated Pool, Wifi, Grill
TV, fireplace, video games, DVD player

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
Shoreline Oasis
Exterior

Shoreline Oasis

6.0 out of 10, (1)
"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "
The price is HK$1,405
HK$2,045 total
includes taxes & fees
8 Jul - 9 Jul
Shoreline Oasis
Private Beach Community in East Hampton! Pool, HotTub, Trampoline & Pirate Ship!
A heated pool

Private Beach Community in East Hampton! Pool, HotTub, Trampoline & Pirate Ship!

10.0 out of 10, Exceptional, (85)
"Great time"
Private Beach Community in East Hampton! Pool, HotTub, Trampoline & Pirate Ship!
East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard
Outdoor pool, a heated pool

East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard

10.0 out of 10, Exceptional, (75)
"Stayed here over Thanksgiving. Beautiful house, well appointed, great location. The Hamptons at Thanksgiving are very vibrant. Highly recommend a stay here. "
East Hampton- Beautiful 4 Bedroom Home, Large Heated Pool, Private Backyard
Charming East Hampton Home, private yard with fenced in pool, perfect for...
Microwave, oven, stovetop, coffee/tea maker

Charming East Hampton Home, private yard with fenced in pool, perfect for...

Charming East Hampton Home, private yard with fenced in pool, perfect for...
Walk to town, Bike to beach, Private pool oasis !
Outdoor pool

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 !
Lovely North Fork Beach Cottage (2 BR/2 bath)!
Terrace/patio

Lovely North Fork Beach Cottage (2 BR/2 bath)!

10.0 out of 10, Exceptional, (114)
"We were pleased with our stay. The house was very clean. My contact with the property manager were great. Would stay again."
Lovely North Fork Beach Cottage (2 BR/2 bath)!
Southampton cozy cottage by the beach
Beach

Southampton cozy cottage by the beach

The price is HK$3,760
HK$7,470 total
includes taxes & fees
27 Jul - 28 Jul
Southampton cozy cottage by the beach
Retro Modern 3-Bedroom House with Heated Pool, Large Deck, WiFi in East Hampton
Terrace/patio

Retro Modern 3-Bedroom House with Heated Pool, Large Deck, WiFi in East Hampton

Retro Modern 3-Bedroom House with Heated Pool, Large Deck, WiFi in East Hampton
Freeboard at Soundview · Beach+Ocean+Sunrise
On the beach

Freeboard at Soundview · Beach+Ocean+Sunrise

2.0 star property
"I love everything about this property. Excellent response from host. Excellent cleanliness of place. OVERALL TOP EXPERIENCE. 1000 PERCENT will be back."
The price is HK$566
HK$1,491 total
includes taxes & fees
7 Jul - 8 Jul
Freeboard at Soundview · Beach+Ocean+Sunrise
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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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?

Escape to Sag Harbor: 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 3 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 patio, a garden and a pool table 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. Gardiner's Bay Country Club and Mashomack Preserve 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.