Shelter Island Vacation Rentals

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Check prices for these dates

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

Our top choices for Shelter Island holiday rentals

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 RM736
RM841 total
includes taxes & fees
5 Apr - 6 Apr
North Fork Cottages & RV 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 RM609
RM775 total
includes taxes & fees
15 Apr - 16 Apr
Montauk Manor
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 RM580
RM837 total
includes taxes & fees
29 Apr - 30 Apr
Cliffside Resort Condominiums
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 RM597
RM791 total
includes taxes & fees
6 Apr - 7 Apr
Windward Shores Ocean Resort
Iron/ironing board, free WiFi

Montauk Oceanside Suites

Montauk Oceanside Suites
3.0 star property
Downtown Montauk
8.6 out of 10, Excellent, (420 reviews)
"Great spot- walkable and nice accommodations! "
United States
Lesley
The price is RM548
RM670 total
includes taxes & fees
16 Apr - 17 Apr
Montauk Oceanside Suites
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

Aqua by American Beech - Adults Only

Aqua by American Beech - Adults Only

6/10 Okay
"We were unhappy with two aspects. The shower is extremely small -- about 2 feet by 3 feet. Very tight. I personally would rip out the closet next to it in a heartbeat and enlarge the shower. The TV was also difficult to figure out and the staff on duty at the desk was unable to assist. Breakfast was fine, just monotonous -- it was always bagels, which isn't great with no toaster to toast them in."
Murray 4-night trip
Posted 3 hours ago
Aqua by American Beech - Adults Only

Find out more about Shelter Island

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

  • View our selection of featured holiday rentals in Shelter Island
  • Use the map to find apartments and other holiday homes in the Shelter Island neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Shelter Island while they last

Look no further and take a look at our great range of rental properties in Shelter Island!

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 90 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.