Photo by tom owens

Shelter Island Hotels

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
22 Apr - 23 Apr
Tomorrow
23 Apr - 24 Apr
This weekend
25 Apr - 27 Apr
Next weekend
2 May - 4 May

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Shelter Island hotels

House on Chase Creek
View from property

House on Chase Creek

2.5 star property
9.4 out of 10, Exceptional, (69)
"Beautiful setting and big rooms close to ferry and town center. "
The price is €122
includes taxes & fees
28 Apr - 29 Apr
House on Chase Creek
The Chequit
Outdoor dining

The Chequit

3.0 star property
8.8 out of 10, Excellent, (29)
"Excellent "
The price is €314
includes taxes & fees
24 Apr - 25 Apr
The Chequit
The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, pool loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (57)
"Fantastic property. Rooms are beautifully appointed, decor is super chic and comfortable. Gorgeous views and amenities. Absolutely enjoyed our second stay at The Pridwin!"
The price is €301
includes taxes & fees
11 May - 12 May
The Pridwin Hotel
The Harbor Front Inn
Harbor View King | View from room

The Harbor Front Inn

3.5 star property
8.8 out of 10, Excellent, (451)
"The experience was very good. everything was what I expected. only thought was the $25 parking was a bit much"
The price is €197
includes taxes & fees
24 Apr - 25 Apr
The Harbor Front Inn
The Menhaden
Property entrance

The Menhaden

3.5 star property
9.6 out of 10, Exceptional, (149)
"it was a great experience "
The price is €379
includes taxes & fees
6 May - 7 May
The Menhaden
Silver Sands Motel & Beach Bungalows
View from room

Silver Sands Motel & Beach Bungalows

4.0 star property
9.8 out of 10, Exceptional, (82)
"Very cool motel renovated to be modern yet old school. "
The price is €193
includes taxes & fees
24 Apr - 25 Apr
Silver Sands Motel & Beach Bungalows
Greenporter Hotel
Property grounds

Greenporter Hotel

2.0 star property
9.2 out of 10, Wonderful, (97)
"Everything was as expected. Staff was helpful and professional. Room was clean and cozy. Thanks !!"
Greenporter Hotel
Stirling House Bed & Breakfast
Property grounds

Stirling House Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (23)
"Very comfortable king size bed. Excellent gourmet breakfast, discreet host. Older house, but all the comforts. Absolutely every need provided for. "
The price is €337
includes taxes & fees
24 Apr - 25 Apr
Stirling House Bed & Breakfast
American Beech Hotel
Exterior

American Beech Hotel

3.5 star property
8.8 out of 10, Excellent, (181)
"Room was small, but clean. Very bright at night. Breakfast could have come earlier! Shower good, bed comfy. "
The price is €295
includes taxes & fees
24 Apr - 25 Apr
American Beech Hotel
The Shoals Suites and Slips
Garden Suite King

The Shoals Suites and Slips

3.5 star property
9.4 out of 10, Exceptional, (157)
"Beautiful property "
The price is €190
includes taxes & fees
6 May - 7 May
The Shoals Suites and Slips
Cliffside Resort Condominiums
Condo

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (210)
"The apartment was beautifully decorated and clean. However, the stove did not work, the iron did not work and the TV in the Livingroom did not work."
The price is €193
includes taxes & fees
7 May - 8 May
Cliffside Resort Condominiums
Hotel Moraine
Seasonal outdoor pool, open 8:00 AM to 7:00 PM, pool umbrellas

Hotel Moraine

2.0 star property
9.8 out of 10, Exceptional, (22)
"Comfortable and stuff is supper noce"
The price is €345
includes taxes & fees
24 Apr - 25 Apr
Hotel Moraine
Sound View Greenport
Seasonal outdoor pool, pool umbrellas, pool loungers

Sound View Greenport

4.0 star property
8.4 out of 10, Very good, (519)
"It was amazing. The staff were friendly and accommodating, the room was very comfortable and the views were spectacular. I upgraded the room to include a sitting area and it was huge. Like a one bedroom. Fifty Area restaurants were very nice and affordable and tasty. Very relaxing getaway and I will definitely come back. "
The price is €264
includes taxes & fees
6 May - 7 May
Sound View Greenport
Sag Harbor Inn
Outdoor pool

Sag Harbor Inn

3.5 star property
9.4 out of 10, Exceptional, (511)
"It was a very relaxing and enjoyable couple of days."
The price is €213
includes taxes & fees
24 Apr - 25 Apr
Sag Harbor Inn
Baron's Cove
Front of property – evening/night

Baron's Cove

4.0 star property
9.0 out of 10, Wonderful, (229)
"Excellent stay while visiting our son!"
The price is €268
includes taxes & fees
28 Apr - 29 Apr
Baron's Cove
EHP Resort & Marina
Cottage

EHP Resort & Marina

3.5 star property
7.8 out of 10, Good, (8)
"Beautiful property and the cottages were clean, gorgeous, and comfortable. It was just hard to get in touch with anyone for service related issues. The restaurant on site, Si Si was amazing and the staff there went above and beyond!"
The price is €376
includes taxes & fees
27 Apr - 28 Apr
EHP Resort & Marina
A Room At The Beach
Outdoor pool

A Room At The Beach

3.0 star property
9.0 out of 10, Wonderful, (83)
"Beautiful property and amazing staff, I will definitely be back soon!"
The price is €436
includes taxes & fees
24 Apr - 25 Apr
A Room At The Beach
Topping Rose House
Outdoor pool

Topping Rose House

4.5 star property
9.2 out of 10, Wonderful, (131)
"Had an excellent stay at Topping Rose House! Can’t wait to be back soon!"
The price is €395
includes taxes & fees
27 Apr - 28 Apr
Topping Rose House
Bridgehampton Inn
Property grounds

Bridgehampton Inn

3.5 star property
9.4 out of 10, Exceptional, (213)
"Lovely inn, with very accommodating staff. "
The price is €296
includes taxes & fees
24 Apr - 25 Apr
Bridgehampton 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 €412
includes taxes & fees
12 May - 13 May
East Hampton Art House Bed & Breakfast
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
Sign in
Sign up, it's free

Learn more about Shelter Island

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

See all hotels in Shelter Island
Photo by tom owens
Open Photo by tom owens

Frequently asked questions

Where is the best place to stay in Shelter Island?

Located 21.1 mi (34 km) from the heart of Shelter Island, Montauk Yacht Club 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 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?

Oceanfront Beach House lay in bed and hear the waves, boats , birds: This holiday home rental outside of Shelter Island is located on the beach, and has a BBQ, a selection of books and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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 Yacht Club: Hotel, 5-minute walk from The Hamptons Beaches. Features 2 outdoor swimming pools, a children's pool and a private beach. Montauk Manor and Water's Edge Resort & Spa 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 90 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 Wades Beach. A couple of additional sights to add to your itinerary are Shelter Island Historical Society and Shelter Island Whale's Tail. 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.