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Check prices for these dates

Tonight
20 Feb - 21 Feb
Tomorrow
21 Feb - 22 Feb
This weekend
21 Feb - 23 Feb
Next weekend
28 Feb - 2 Mar

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Top hotels and accommodation in Shelter Island

Montauk Oceanside Suites
Apartment | Private kitchen

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (362)
"I didn’t realize the property was mobile check-in and that all communication would be automated in the winter season. if you guys had that more clear on the Expedia it would be awesome. Otherwise the stay was great, clean room, no hassle to get in, right by the beach. "
The price is AU$218
includes taxes & fees
27 Feb - 28 Feb
Montauk Oceanside Suites
Daunt's Albatross Motel
Exterior

Daunt's Albatross Motel

2.0 star property
8.8 out of 10, Excellent, (247)
"SOO BEAUTIFUL !! Love the property & how clean it was "
The price is AU$427
includes taxes & fees
28 Feb - 1 Mar
Daunt's Albatross Motel
Hero Beach Club
View from room

Hero Beach Club

4.0 star property
9.0 out of 10, Wonderful, (162)
"Beautiful place to stay! Right next to the beach, it was quiet and had so many nice things to do all around the property. The bed was comfy and the rooms were very nice. "
The price is AU$618
includes taxes & fees
17 Mar - 18 Mar
Hero Beach Club
Kenny's Tipperary Inn
Seasonal outdoor pool, pool umbrellas, pool loungers

Kenny's Tipperary Inn

2.0 star property
8.4 out of 10, Very good, (777)
"Very quiet and comfy stay."
The price is AU$231
includes taxes & fees
23 Feb - 24 Feb
Kenny's Tipperary Inn
Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1115)
"Nice, pleasant, staff was warm and friendly "
The price is AU$266
includes taxes & fees
24 Feb - 25 Feb
Montauk Manor
Gurney's Montauk Resort & Seawater Spa
Outdoor wedding area

Gurney's Montauk Resort & Seawater Spa

4.0 star property
8.2 out of 10, Very good, (610)
"Beautiful views. Great staff and amenities."
The price is AU$817
includes taxes & fees
17 Mar - 18 Mar
Gurney's Montauk Resort & Seawater Spa
Sea Crest Resort
Studio Unit Upper Oceanfront 'San Remo' | Terrace/patio

Sea Crest Resort

2.5 star property
9.2 out of 10, Wonderful, (445)
"The only problem I had is with a shade on a door , bad design not hotel’s problem. And that I wanted to rebook for another time and no matter what dates I put in they weren’t available "
The price is AU$433
includes taxes & fees
23 Feb - 24 Feb
Sea Crest Resort
The Hermitage
Seasonal outdoor pool

The Hermitage

3.5 star property
9.2 out of 10, Wonderful, (153)
"Access to the dunes and the beach "
The price is AU$323
includes taxes & fees
23 Mar - 24 Mar
The Hermitage
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (271)
"Beautiful location, clean property, and nice staff. Just hard to turn in to the parking lot but not much that the hotel can do for that. The private beach is stunning. "
The price is AU$271
includes taxes & fees
20 Mar - 21 Mar
Windward Shores Ocean Resort
The Roundtree, Amagansett
Beach nearby, white sand, sun-loungers, beach umbrellas

The Roundtree, Amagansett

4.5 star property
9.8 out of 10, Exceptional, (85)
"My wife and I stayed a couple nights in October. We felt very pampered. Felix served us up late night snacks with homemade cookies and ice cream! Beautiful and charming hotel with attentive staff."
The price is AU$1,311
includes taxes & fees
23 Feb - 24 Feb
The Roundtree, Amagansett
Journey East Hampton
Exterior

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (123)
"Enjoyed our stay here. Room was spacious. Really friendly staff. "
The price is AU$397
includes taxes & fees
2 Mar - 3 Mar
Journey East Hampton
East Hampton House Resort
Deluxe Studio | Living area

East Hampton House Resort

3.0 star property
9.0 out of 10, Wonderful, (245)
"Perfect location and super clean"
The price is AU$326
includes taxes & fees
18 Mar - 19 Mar
East Hampton House Resort
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (67)
"What a lovely space and wonderful thoughtful staff! Absolutely loved everything about it, and the breakfast was beyond excellence! Hats off to the chef you can tell she cooked with ❤️ love. Highly Recommend you experience it for yourself. "
The price is AU$494
includes taxes & fees
23 Mar - 24 Mar
Mill House Inn
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (61)
"What a beautiful, quiet, peaceful place to stay, even in the dead of winter. The home itself is modern, welcoming, bright, everything you could dream of. The hosts are very active and successful artists who all but gave us a private master class in how their work is imagined and created. I don’t know when we’ve had a more delightful weekend. The walks to the beach were lovely, too. "
The price is AU$759
includes taxes & fees
25 Feb - 26 Feb
East Hampton Art House Bed & Breakfast
The Huntting Inn
Exterior

The Huntting Inn

3.5 star property
8.6 out of 10, Excellent, (87)
"One of the very few options in East Hampton that offered a one night stay, most have a 2-night minimum. An old, charming inn that was very welcoming and clean. Our king bed room was spacious enough and decorated nicely. The bathroom was very clean and modernized. We did have to walk up a flight of stairs with our luggage which wasn’t difficult for us but may be for some."
The price is AU$773
includes taxes & fees
23 Feb - 24 Feb
The Huntting Inn
The 1770 House Restaurant & Inn
Reception

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (147)
"Property was adorable and the staff very pleasant and helpful!! "
The price is AU$595
includes taxes & fees
2 Mar - 3 Mar
The 1770 House Restaurant & Inn
The Maidstone
Front of property - evening/night

The Maidstone

4.0 star property
7.8 out of 10, Good, (120)
"private and elegant"
The price is AU$559
includes taxes & fees
6 Mar - 7 Mar
The Maidstone
The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (136)
"We had an unexpected trip to sag harbor and had to reserve quickly. The property was clean very pretty and quaint. The room was comfortable and quaint as well. "
The price is AU$306
includes taxes & fees
23 Feb - 24 Feb
The Sagaponack
Inn at Harbor Hill Marina
Property grounds

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1004)
"We really enjoyed our stay! This was our second time staying on the property - in the same room. We love the fireplace and the bathroom was great too! Beautiful view of the marina and the water beyond. Breakfast was absolutely delicious every morning as well! "
The price is AU$221
includes taxes & fees
23 Feb - 24 Feb
Inn at Harbor Hill Marina
Topping Rose House
Outdoor pool

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (125)
"Topping Rose House is beautiful, and the staff is excellent. I am looking forward to returning on my next visit"
The price is AU$807
includes taxes & fees
23 Feb - 24 Feb
Topping Rose House
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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Learn more about Shelter Island

Escape to Shelter Island! Enjoy its island views, natural setting and beaches.

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Photo by tom owens
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Frequently asked questions

Where is the best place to stay in Shelter Island?

Located 20.3 mi (32.7 km) from the heart of Shelter Island, Montauk Manor is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Water's Edge Resort & Spa and Pier Blue Inn Old Saybrook - Essex. See all available top hotels, or vacation rentals in Shelter Island.

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

Hither Hills Beach Retreat; Walk to Ocean Beach & Town; Pool; Jacuzzi; Kid Ready: This holiday home rental outside of Shelter Island is located on the beach, and has an outdoor pool, a fireplace 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 balcony, a garden and a selection of games so that you can immerse yourself in your holiday. See all vacation rentals in Shelter Island.

If I need to cancel my hotel reservation in Shelter Island, will I receive a refund?

Yes! You'll find that most hotel bookings are fully refundable if you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of the scheduled arrival. If your reservation is non-refundable, you might be able to cancel it and receive a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Shelter Island.

What's the best dog-friendly accommodation option in Shelter Island?

Sunset Beach Hotel is a top hotel for people travelling with their pets, and offers a restaurant and free WiFi for its human guests. See more pet-friendly hotel accommodations in Shelter Island.

What's the best hotel to stay near the beach in Shelter Island?

Sunset Beach Hotel is a top beachfront hotel with free WiFi and free parking, and it's located on Sunset Beach . See more stays near the beach in Shelter Island.

What are some accommodation options with pools in Shelter Island?

Montauk Manor: Aparthotel, 14-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool and 3 outdoor tennis courts. Water's Edge Resort & Spa and Hyatt Place Long Island East End are a couple of other choices that offer an on-site pool. View all hotels with pools in Shelter Island.

What is the best spa hotel in Shelter Island?

Waterfront House With Dock And Private Beach

What's it like to stay in Shelter Island?

Visitors can enjoy all that Shelter Island has to offer, including the parks, beaches and museums. This city also attracts tourists with its scenic landscape. In Shelter Island, there are 89 hotels and other accommodation options to choose from. Find out more about Shelter Island.

What should I see while I'm in Shelter Island?

Natural beauty is on display at Sunset Beach, Crescent Beach and Shell Beach. A couple of additional sights to add to your itinerary are Shelter Island Historical Society and Havens House. Take a look at what more there is to see and do in Expedia's Shelter Island guide.

What's the seasonal weather in Shelter Island?

The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Shelter Island is 1452 mm.