Photo by tom owens

Shelter Island Hotels

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Shelter Island hotels

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (353)
"Location, location..."
The price is €161
includes taxes & fees
24 Jan - 25 Jan
Montauk Oceanside Suites

Daunt's Albatross Motel

2.0 star property
8.8 out of 10, Excellent, (247)
"SOO BEAUTIFUL !! Love the property & how clean it was "
Daunt's Albatross Motel

Kenny's Tipperary Inn

2.0 star property
8.4 out of 10, Very good, (774)
"Very quiet and comfy stay."
The price is €139
includes taxes & fees
21 Jan - 22 Jan
Kenny's Tipperary Inn

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1093)
"Duplex room equipment for the kitchen "
The price is €164
includes taxes & fees
21 Jan - 22 Jan
Montauk Manor

Gurney's Montauk Resort & Seawater Spa

4.0 star property
8.2 out of 10, Very good, (609)
"All good would like to go back - very accommodating "
The price is €425
includes taxes & fees
3 Feb - 4 Feb
Gurney's Montauk Resort & Seawater Spa

Sea Crest Resort

2.5 star property
9.2 out of 10, Wonderful, (443)
"Our unit was updated and it was quiet and relaxing. "
The price is €243
includes taxes & fees
4 Feb - 5 Feb
Sea Crest Resort

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (267)
"Perfect location for a peaceful winter weekend getaway. We’ve stayed here before and definitely will again. "
The price is €161
includes taxes & fees
21 Jan - 22 Jan
Windward Shores Ocean Resort

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 €694
includes taxes & fees
21 Jan - 22 Jan
The Roundtree, Amagansett

Villa Spectrum

3.5 star property
The price is €3,063
includes taxes & fees
21 Jan - 22 Jan
Villa Spectrum

Journey East Hampton

4.0 star property
9.0 out of 10, Wonderful, (122)
"Enjoyed our stay here. Room was spacious. Really friendly staff. "
The price is €295
includes taxes & fees
27 Jan - 28 Jan
Journey East Hampton

East Hampton House Resort

3.0 star property
9.0 out of 10, Wonderful, (243)
"A fantastic place for a short weekend getaway. Would love to do it again"
The price is €209
includes taxes & fees
14 Feb - 15 Feb
East Hampton House Resort

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (62)
"Greeting was so welcoming n informative "
The price is €306
includes taxes & fees
26 Jan - 27 Jan
Mill House Inn

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (60)
"Beautiful grounds, pool and hot tub! Beautiful breakfast!"
The price is €469
includes taxes & fees
21 Jan - 22 Jan
East Hampton Art House Bed & Breakfast

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 €408
includes taxes & fees
10 Feb - 11 Feb
The Huntting Inn

The 1770 House Restaurant & Inn

4.0 star property
9.8 out of 10, Exceptional, (145)
"Property was adorable and the staff very pleasant and helpful!! "
The price is €353
includes taxes & fees
21 Jan - 22 Jan
The 1770 House Restaurant & Inn

The Maidstone

4.0 star property
7.8 out of 10, Good, (120)
"private and elegant"
The price is €445
includes taxes & fees
2 Feb - 3 Feb
The Maidstone

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (129)
"We had a wonderful stay! We will definitely be back!"
The price is €211
includes taxes & fees
26 Jan - 27 Jan
The Sagaponack

Villa Bridgehampton Village

3.5 star property
The price is €5,846
includes taxes & fees
22 Jan - 23 Jan
Villa Bridgehampton Village

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1004)
"We stay this and all night kept hearing someone walking back and forth. I would go back and stay on the second floor. Place is beautiful. "
The price is €142
includes taxes & fees
21 Jan - 22 Jan
Inn at Harbor Hill Marina

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (121)
"Great location and very comfortable "
The price is €504
includes taxes & fees
22 Jan - 23 Jan
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.
Don't see what you're looking for?
See all available properties in Shelter Island
Save an average of 15% on thousands of hotels when you're signed in

Frequently asked questions

Where is the best place to stay in Shelter Island?

Located 19.5 mi (31.4 km) from the heart of Shelter Island, Hyatt Place Long Island East End is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Montauk Manor and Quality Inn Old Saybrook - Westbrook. 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?

Mid-Century Winter Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!: 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 patio, 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?

Hyatt Place Long Island East End: Features an indoor pool, an outdoor pool and 2 bars. Montauk Manor and Quality Inn Old Saybrook - Westbrook 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?
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 91 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, Wades Beach and Crescent 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.