Shelter Island Vacation Rentals

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Check prices for these dates

In two weeks
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Shelter Island vacation rentals

Cottage, 2 Bedrooms, Patio | Free WiFi, bed sheets

North Fork Cottages & RV Resort

North Fork Cottages & RV Resort
3.0 star property
Greenport
8.6 out of 10, Excellent, (11 reviews)
"great place to stay, clean and quiet....loved it"
United States
Darlin
The price is ₩276,087
₩315,430 total
includes taxes & fees
Apr 1 - Apr 2
North Fork Cottages & RV Resort
Individually decorated, individually furnished, iron/ironing board

Windward Shores Ocean Resort

Windward Shores Ocean Resort
3.0 star property
Napeague
8.8 out of 10, Excellent, (310 reviews)
"Amazing stay! Place was perfect and staff was so friendly."
United States
Heather
The price is ₩223,998
₩297,017 total
includes taxes & fees
Mar 31 - Apr 1
Windward Shores Ocean Resort
Lobby

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1,309 reviews)
"Great property "
United States
brian
The price is ₩228,486
₩290,654 total
includes taxes & fees
Apr 15 - Apr 16
Montauk Manor
Condo | Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (249 reviews)
"Great stay - beautiful place"
United States
Rebecca
The price is ₩217,606
₩314,274 total
includes taxes & fees
Apr 29 - Apr 30
Cliffside Resort Condominiums
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

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

6/10 Okay
"Room could have been cleaner. The floor was dirty. The room also looked worn and in need of updating. The tub faucet dripped constantly, but the shower was nice. Staff was friendly. I was surprised they don’t offer daily housekeeping. Bed was comfortable. It was great that the room had a microwave and a fridge. It was not warm and inviting at all. Definitely wouldn’t stay more than one night."
Lisa 1-night trip
Posted 7 hours ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Shelter Island

Search for Vacation rentals in Shelter Island on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Shelter Island using one of the methods below:

  • View our selection of featured Vacation rentals in Shelter Island
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Look no further and take a look at our great range of rental properties in Shelter Island!

Frequently asked questions

Can I find vacation rentals in Shelter Island?

Yes, we have vacation rentals in Shelter Island close to Shelter Island Whale's Tail, or you can select a more secluded option if you'd like a relaxing place to 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 vacation rentals are there in Shelter Island?

Choose from 90 Expedia vacation rentals in Shelter Island for a memorable vacation.

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 vacation rentals like in Shelter Island?

Vacation rentals are private properties you can reserve for a couple days or more in Shelter Island. Vacation rentals offer extras such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for family trips.