Shelter Island Hotels from S$111

    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
27 Jul - 28 Jul
Tomorrow
28 Jul - 29 Jul
Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug

Filter by

Guest rating
Guest rating
Property class

Top 10 trending Shelter Island hotels

Liberty Inn
Stroll through the serene garden, surrounded by lush greenery and a tranquil water feature.

Liberty Inn

2.0 star property
7.4 out of 10, Good, (610)
"Great property owner…Clean and well located for the Old Saybrook area…"
The price is S$129
includes taxes & fees
28 Jul - 29 Jul
Liberty Inn
Pier Blue Inn Old Saybrook - Essex
Welcome to Pier Blue Guesthouse, surrounded by lush greenery and vibrant flowers.

Pier Blue Inn Old Saybrook - Essex

2.0 star property
7.8 out of 10, Good, (1005)
"Great location. "
The price is S$118
includes taxes & fees
30 Jul - 31 Jul
Pier Blue Inn Old Saybrook - Essex
Clinton Motel
Situated in a landscaped area, this single-story building offers a convenient parking space.

Clinton Motel

2.5 star property
8.6 out of 10, Excellent, (260)
"For the money this reservation was a real win Clean lovely pool area convenient to everything"
The price is S$116
includes taxes & fees
28 Jul - 29 Jul
Clinton Motel
Quality Inn Old Saybrook - Westbrook
Relax by the oval-shaped pool surrounded by lounge chairs and a high ceiling with a grid-like pattern.

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1016)
"Great location and pool, close to a wonderful restaurant "
The price is S$163
includes taxes & fees
3 Aug - 4 Aug
Quality Inn Old Saybrook - Westbrook
Econo Lodge Inn & Suites Old Saybrook Westbrook
Surrounded by lush greenery, a serene pond with a central fountain offers a peaceful escape.

Econo Lodge Inn & Suites Old Saybrook Westbrook

2.0 star property
7.2 out of 10, Good, (439)
"Room was very comfortable. I would definitely use again."
The price is S$119
includes taxes & fees
3 Aug - 4 Aug
Econo Lodge Inn & Suites Old Saybrook Westbrook
Shorewood Inn
Relax in a serene outdoor space surrounded by lush greenery, perfect for dining and socializing.

Shorewood Inn

2.5 star property
8.4 out of 10, Very good, (661)
"Good place to stay"
Shorewood Inn
Super 8 by Wyndham Old Saybrook
Surrounded by lush greenery, this parking area offers a serene escape.

Super 8 by Wyndham Old Saybrook

2.0 star property
7.0 out of 10, Good, (887)
"A simple, affordable, conveniently located, and pleasant stay."
The price is S$128
includes taxes & fees
28 Jul - 29 Jul
Super 8 by Wyndham Old Saybrook
Lamplighter Motel - Clinton, Connecticut
Classic two-story motel with a symmetrical facade and central entrance.

Lamplighter Motel - Clinton, Connecticut

2.5 star property
6.2 out of 10, (206)
"Would stay again. "
The price is S$111
includes taxes & fees
28 Jul - 29 Jul
Lamplighter Motel - Clinton, Connecticut
Greenporter Hotel
Relax by the fire pit surrounded by comfortable seating and a serene pool view.

Greenporter Hotel

2.0 star property
9.2 out of 10, Wonderful, (144)
"Great place "
Greenporter Hotel
Hampton's Vacation Inn
Enjoy cooking in this well-equipped kitchen with a dishwasher, coffee maker, and stainless steel appliances.

Hampton's Vacation Inn

2.5 star property
9.0 out of 10, Wonderful, (292)
"The location was great. The room was beautiful. The grounds were beautiful. Had a great time."
The price is S$297
includes taxes & fees
28 Jul - 29 Jul
Hampton's Vacation Inn
The Niantic Inn
Guests can enjoy a beachside retreat with access to the ocean and scenic views of the surrounding landscape.

The Niantic Inn

2.0 star property
9.2 out of 10, Wonderful, (103)
"Enjoyed my stay"
The price is S$290
includes taxes & fees
30 Jul - 31 Jul
The Niantic Inn
Copper Beech Inn
Enjoy dining in this spacious room with a high ceiling and glass roof, featuring a dining area with wooden tables and chairs.

Copper Beech Inn

4.0 star property
8.6 out of 10, Excellent, (501)
"Tired, expensive needs update"
The price is S$411
includes taxes & fees
28 Jul - 29 Jul
Copper Beech Inn
Wainscott Woods Retreat
Exterior

Wainscott Woods Retreat

2.0 star property
10.0 out of 10, Exceptional, (1)
"HIDDEN GEM IN THE HEART OF HAMPTONS! What a special place to stay in the Hamptons! I am so happy we found this wonderful gem! This hotel is clean, quiet and well managed. The pool is beautiful the rooms are modern, sleek and clean! The grounds are beautifully manicured. The location is perfect! This new hotel has the charm of a bed and breakfast. The hotel is a short car ride from either East Hampton or Southampton which is perfect if you chose to explore all the little towns the Hampton's has...
The price is S$1,713
includes taxes & fees
3 Aug - 4 Aug
Wainscott Woods Retreat
Hampton Bays Hotel on Main
Relax in a spacious room with a large bed, desk, and flat-screen TV.

Hampton Bays Hotel on Main

2.0 star property
6.4 out of 10, (41)
"Very happy"
Hampton Bays Hotel on Main
The Shoals Suites and Slips
Relax on a bench amidst lush surroundings, with a covered patio just steps away.

The Shoals Suites and Slips

3.5 star property
9.6 out of 10, Exceptional, (186)
"Third stay here, always a pleasure and so close to my favorite southold vineyards"
The price is S$563
includes taxes & fees
28 Jul - 29 Jul
The Shoals Suites and Slips
The Captain Stannard
Cozy up by the fireplace in this stylish living room, featuring a comfortable sofa, armchair, and decorative artwork.

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (235)
"Everything was fantastic, will stay again!"
The Captain Stannard
The Bentley Hotel Southampton
Relax in this serene outdoor seating area with a round table, potted plant, and two chairs.

The Bentley Hotel Southampton

2.0 star property
9.6 out of 10, Exceptional, (294)
"Place was clean and close to beach and town! "
The price is S$458
includes taxes & fees
19 Aug - 20 Aug
The Bentley Hotel Southampton
Inn at Harbor Hill Marina
Relax in a serene outdoor space surrounded by lush greenery and beautifully manicured lawns.

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1002)
"Really cute bed and breakfast! Great location on the marina. The food was good and the people were very friendly. "
The price is S$396
includes taxes & fees
28 Jul - 29 Jul
Inn at Harbor Hill Marina
Ruschmeyers Hotel
Exterior

Ruschmeyers Hotel

3.0 star property
7.8 out of 10, Good, (56)
"The staff was unbelievable and went out of their way to help . Kind and knowledgeable. "
The price is S$1,508
includes taxes & fees
15 Aug - 16 Aug
Ruschmeyers Hotel
Budget Host East End Hotel in Riverhead
Relax in a cozy seating area with a sofa and armchair, perfect for unwinding.

Budget Host East End Hotel in Riverhead

2.0 star property
6.6 out of 10, (726)
"Nice place"
The price is S$152
includes taxes & fees
10 Aug - 11 Aug
Budget Host East End Hotel in Riverhead
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Where to stay in Shelter Island

Find the best Shelter Island areas for the activities you enjoy most. Learn more about Shelter Island
Learn more about Shelter Island
Menantic Creek map

Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Wades Beach and Shelter Island Historical Society.

Silver Beach map

Silver Beach

While Silver Beach may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Crescent Beach and Sunset Beach.

Coecles Harbor map

Coecles Harbor

While Coecles Harbor isn't home to many top sights, Shelter Island Whale's Tail and Gardiner's Bay Country Club are some notable places to visit nearby.

Hay Beach map

Hay Beach

When in Hay Beach, you can plan a visit to Gardiner's Bay Country Club and Greenport Carousel, some noteworthy sights in the nearby area.

Shorewood map

Shorewood

While Shorewood may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.

Hotels near Shelter Island Attractions

Shelter Island Whale's Tail

Shelter Island Whale's Tail

You can take time to visit Shelter Island Whale's Tail during your travels to Shelter Island. Wander the beaches and waterfront in the area.

See properties in Shelter Island Whale's Tail

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

Top Shelter Island Hotel Reviews

Montauk Manor

Montauk Manor

10/10 Excellent
"We go to Montauk Manor every year as a family. It’s clean quiet and if you need to get anywhere, they provide a shuttle."
Scott 3-night trip
Posted 2 days ago
Montauk Manor

Frequently asked questions

Where is the best place to stay in Shelter Island?

Located 21 mi (33.9 km) from the heart of Shelter Island, Marram is a top choice for your stay, based on our traveller data. Other good choices for your stay in the area are Quality Inn Old Saybrook - Westbrook and Montauk Yacht Club. See all available top hotels, or 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?

Marram: Hotel, 6-minute walk from The Hamptons Beaches. Features free self parking, a seasonal outdoor pool and sunloungers. Quality Inn Old Saybrook - Westbrook and Montauk Yacht Club 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 94 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 Whale's Tail and Gardiner's Bay Country Club. 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.