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Our top choices for Shelter Island holiday rentals

10.0 out of 10, Exceptional, (9 reviews)
"It was PERFECT way to spend USCGA Parent’s Weekend!!"
United States
Kerri G.
The price is £296
includes taxes & fees
25 Feb - 26 Feb
Beach Cottage, private beach and pass
9.6 out of 10, Exceptional, (37 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is £136
includes taxes & fees
25 Feb - 26 Feb
1-bedroom cottage with Grove Beach 🏖️ access.
8.0 out of 10, Very good, (2 reviews)
"So close to a peaceful lovely beach. Walking distance to food and even a synagogue!The bed was very comfortable and big. I enjoyed having coffee in my room before heading out to the beach. "
United States
October P.
The price is £158
includes taxes & fees
25 Feb - 26 Feb
The Anchor at Soundview · Beach+Ocean+Sunrise
10.0 out of 10, Exceptional, (21 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is £194
includes taxes & fees
2 Mar - 3 Mar
The gardners Cottage 1 mile from long Island Sound - pet friendly
10.0 out of 10, Exceptional, (11 reviews)
"We had a nice stay. Kitchen well stocked and house was clean and comfortable."
United States
Elaine A.
The price is £282
includes taxes & fees
25 Feb - 26 Feb
Luxurious-Modern feel w/ custom features - AC, short walk to the Beach and parks
10.0 out of 10, Exceptional, (16 reviews)
"Convenient location. The property had everything we needed for a one-night stay. "
United States
Jane E.
The price is £227
includes taxes & fees
25 Feb - 26 Feb
Cozy Renovated Cottage with Game Room, WiFi, AC - Mins to Beach & Boardwalk
10.0 out of 10, Exceptional, (5 reviews)
"My family and I came for an 8 day event from a different state and wanted a clean and comfortable place to stay with our at the time 9 month old daughter. And this place did exactly that. Comfortable and CLEAN. The owner did a great job with details. Even when we had unexpected check out delays the owner showed human empathy. Great place!"
United States
Hemie J.
The price is £342
includes taxes & fees
25 Feb - 26 Feb
Rogers Lake House (87) · CT College+Beach+USCGA
10.0 out of 10, Exceptional, (76 reviews)
"Wonderful stay at such a special spot. "
United States
Meg B.
The price is £258
includes taxes & fees
28 Feb - 1 Mar
Cottage on Beach front Estate with Dockage .Walk to Village
9.6 out of 10, Exceptional, (15 reviews)
"Nice house. Photos and descriptions represent it very accurately. "
United States
Will K.
The price is £917
includes taxes & fees
25 Feb - 26 Feb
Black Swan: Beachfront Home w/ Year-Round Jacuzzi

Aparthotel in Napeague

Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (306 reviews)
"Quiet place, went off season, cooked all meals in the room, good home base to explore the area."
United States
Jerry
The price is £132
includes taxes & fees
26 Feb - 27 Feb
Windward Shores Ocean Resort

Aparthotel in Montauk

Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1,297 reviews)
"Nice pool, great restaurant "
United States
April
The price is £112
includes taxes & fees
25 Feb - 26 Feb
Montauk Manor
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful home in a quiet neighborhood. We greatly enjoyed staying at Glass House. "
United States
Elya D.
The price is £367
includes taxes & fees
4 Mar - 5 Mar
LONG-TERM Skiing, Tubing 30 mins away and the Ocean 5 mins!
The price is £323
includes taxes & fees
4 Mar - 5 Mar
Cozy&Chic Beach Cottage - wineries, beach and perfect for all seasons
The price is £273
includes taxes & fees
25 Mar - 26 Mar
Floating Nest on Private River. Serene Views & Ultimate Relaxation
9.6 out of 10, Exceptional, (43 reviews)
"Great property, would stay here again."
United States
charles b.
The price is £358
includes taxes & fees
25 Feb - 26 Feb
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
10.0 out of 10, Exceptional, (1 review)
"Very Clean and New. Location very convenient to Shopping , Coffee and Winery. Place very very small but Shower was huge and token gifts such as wine and toiletries a big plus . As well as guest for TV for Netflix. Added bonus outdoor space makes up for lack of living room. I would recommend this place and stay again for sure. Also, conveniently located to major highway and safe. "
United States
Kelly Z.
The price is £249
includes taxes & fees
25 Feb - 26 Feb
Stylish Modern Stay Steps from the Ocean
10.0 out of 10, Exceptional, (3 reviews)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
United States
Lylian
The price is £162
includes taxes & fees
26 Feb - 27 Feb
The Stern at Soundview · Beach+Ocean+Sunrise
9.0 out of 10, Wonderful, (4 reviews)
"We thoroughly enjoyed our stay!"
United States
Parent From The Heart, Inc. E.
The price is £150
includes taxes & fees
25 Feb - 26 Feb
American Beech in Greenport - Petite King Room 7
The price is £286
includes taxes & fees
25 Feb - 26 Feb
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
9.6 out of 10, Exceptional, (23 reviews)
"Overall really great stay! Would definitely stay here again was so peaceful. Had a great weekend!"
United States
Annie B.
The price is £982
includes taxes & fees
25 Feb - 26 Feb
Villa Luz: Cozy Family Home with Jacuzzi Year-round & Heated Pool in Summer
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

Find out more about Shelter Island

Everything you need to know about Shelter Island holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Shelter Island holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Shelter Island holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Shelter Island holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Shelter Island. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Shelter Island holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Shelter Island holiday rentals we have selected for you start as low as £112 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Shelter Island rentals

At Expedia, we put the best Shelter Island holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Shelter Island rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Shelter Island holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Shelter Island. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Beautiful Waterfront, Sun, Sky, Hot Tub Open Year Round & Gameroom!: This holiday home rental outside of Shelter Island is located on the beach, and has a fireplace, a patio and a BBQ to put you at ease 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 garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals are there in Shelter Island?

Choose from 88 Expedia holiday rentals in Shelter Island for a memorable holiday.

What can I see and do in Shelter Island?

Sunset Beach and Wades 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 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.