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17 Dec - 18 Dec
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18 Dec - 19 Dec
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Our top choices for Shelter Island hotels

Beach nearby
The Niantic Inn

The Niantic Inn

The Niantic Inn
2.5 star property
Niantic
9.2 out of 10, Wonderful, (128)
"Nice and clean room and property"
United States
Eric
Travelling for leisure
The price is AU$153
includes taxes & fees
22 Dec - 23 Dec
The Niantic Inn
Golf
Hamlet Inn

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (443)
"The location was very convenient."
United States
Chanynn
Travelling for leisure and business
The price is AU$174
includes taxes & fees
18 Dec - 19 Dec
Hamlet Inn
Individually decorated, individually furnished, desk, laptop workspace
Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook

Econo Lodge Inn & Suites Old Saybrook Westbrook
2.0 star property
Old Saybrook
7.2 out of 10, Good, (460)
"I was pleasantly surprised by how clean and updated the room was."
United States
Robin
Travelling for leisure
The price is AU$116
includes taxes & fees
4 Jan - 5 Jan 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook
Ocean View 2 Queens
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.2 out of 10, Wonderful, (81)
"The coffee maker was great"
United States
Marc
Travelling for business
The price is AU$286
includes taxes & fees
1 Jan - 2 Jan 2026
Offshore Montauk
Seasonal outdoor pool, pool umbrellas, pool loungers
Kenny's Tipperary Inn

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (878)
"The rooms were very clean"
United States
Tillina M
Travelling for leisure
The price is AU$207
includes taxes & fees
4 Jan - 5 Jan 2026
Kenny's Tipperary Inn
Property grounds
Clinton Motel

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (297)
"the pool area and surrounding were very well kept and quiet"
United States
Betty
Travelling for leisure
The price is AU$135
includes taxes & fees
18 Dec - 19 Dec
Clinton Motel
Property grounds
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
2.0 star property
Saybrook Manor
8.0 out of 10, Very good, (1000)
"The rooms are very clean, and quiet."
United States
David
Travelling for leisure and business
Pier Blue Inn Old Saybrook - Essex
Lobby
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1268)
"Beautiful place to stay, friendly and profesional staff, great room with nice balcony very comfortable suite."
United States
Ratibor
Travelling for leisure
The price is AU$268
includes taxes & fees
18 Dec - 19 Dec
Montauk Manor
View from property
House on Chase Creek

House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (79)
"Beautiful setting and big rooms close to ferry and town center."
United States
Diane
The price is AU$179
includes taxes & fees
6 Jan - 7 Jan 2026
House on Chase Creek
Exterior
Shorewood Inn

Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very good, (710)
"welcoming, the room was super clean and cute with the heat turned on full blast in anticipation of my arrival"
United States
Mahlon
Travelling with pet
Shorewood Inn
Indoor pool, open 9:00 AM to 9:00 PM, pool loungers
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1004)
"The beds were very comfortable"
United States
Charles
Travelling for leisure
The price is AU$175
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Old Saybrook - Westbrook
Deluxe Double Room, 1 King Bed, City View
Hampton Bays Hotel on Main

Hampton Bays Hotel on Main

Hampton Bays Hotel on Main
2.0 star property
Hampton Bays
7.2 out of 10, Good, (69)
"The location is excellent, with easy access to Southampton, Bridgehampton, and East Hampton, plus a nearby train station."
United States
Monique
Travelling with friends
Hampton Bays Hotel on Main
BBQ/picnic Area
Hyatt Place Long Island East End

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1002)
"View from the room was beautiful"
United States
Anthony
Travelling with partner
The price is AU$193
includes taxes & fees
14 Jan - 15 Jan 2026
Hyatt Place Long Island East End
Lobby lounge
The Harbor Front Inn

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (547)
"Lovely area easy check in clean rooms amazing view"
United States
Taylor
Travelling for leisure
The price is AU$305
includes taxes & fees
18 Dec - 19 Dec
The Harbor Front Inn
Reception
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (398)
"It was a suite and very clean and spacious."
United States
Rob
Travelling with family
The price is AU$217
includes taxes & fees
4 Jan - 5 Jan 2026
The Bentley Hotel Southampton
Resort view
Sound View Greenport

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (598)
"Rooms are great with a beautiful view."
United States
Nicole
Travelling for leisure
The price is AU$348
includes taxes & fees
21 Dec - 22 Dec
Sound View Greenport
Property grounds
Liberty Inn

Liberty Inn

Liberty Inn
2.0 star property
Old Saybrook
7.4 out of 10, Good, (640)
"The bed was very comfortable."
United States
Marjorie
The price is AU$139
includes taxes & fees
18 Dec - 19 Dec
Liberty Inn
Terrace/patio
American Beech Hotel

American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
8.8 out of 10, Excellent, (195)
"Beautiful rooms and bar on the property."
United States
Kimberly
Travelling with partner
The price is AU$369
includes taxes & fees
18 Dec - 19 Dec
American Beech Hotel
Exterior
The Shoals Suites and Slips

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (228)
"there is an amazing restaurant within walkable distance"
United States
Chelsea
Travelling for leisure
The price is AU$272
includes taxes & fees
23 Dec - 24 Dec
The Shoals Suites and Slips
Property grounds
Inn at Harbor Hill Marina

Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.4 out of 10, Exceptional, (1000)
"the bathroom was great too!"
United States
Tian
Travelling for leisure
The price is AU$275
includes taxes & fees
6 Jan - 7 Jan 2026
Inn at Harbor Hill Marina
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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Our guide on 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

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

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.

Menantic Creek

While there might not be top attractions in Menantic Creek, you can explore the larger area and discover places like Sunset Beach and Crescent Beach.

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 Mashomack Preserve and Sunset Beach.

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.

Stay near popular Shelter Island attractions

Colorful pebbles and shells on a beach

Shell Beach

This peaceful shoreline offers a tranquil escape with abundant shells and wildflowers framing its natural beauty. Enjoy both calm harbour waters and more dynamic waves, perfect for beachcombing and wildlife spotting.
See properties
Man watching sailboat on Long Island Sound

Wades Beach

Wades Beach offers calm, shallow waters and a broad sandy shoreline perfect for families seeking safe swimming. Lifeguards patrol in summer, and the pavilion provides a comfortable spot to enjoy the tranquil setting.
See properties

Learn more about Shelter Island

Nestled between Long Island's forks, this serene island offers pristine beaches and kayaking through Mashomack Preserve's coastal wetlands. Rent bikes to explore historic mansions and stop at Sunset Beach for seafood with spectacular evening views across Shelter Bay.

See all hotels in Shelter Island
Central Park summer

Top Shelter Island Hotel Reviews

Recent Reviews in Shelter Island

The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"crystal clean, great location and PRICE! large rooms. plenty of space. absolutely amazing "
olivia 1-night trip
Posted 3 days ago
The Bentley Hotel Southampton

More cheap accommodation in Shelter Island

Budget Host East End Hotel in Riverhead

Budget Host East End Hotel in Riverhead

30 Lake Avenue Riverhead NY
The price is AU$161 per night from 18 Dec to 19 Dec
AU$161
18 Dec - 19 Dec
includes taxes & fees
6.6/10 (780 reviews)

Frequently asked questions

Where is the best place to stay in Shelter Island?
Located 18.4 mi (29.7 km) from the heart of Shelter Island, Gurney's Montauk Resort & Seawater Spa 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?
Work and Play Special! Extended Stay Discount: This highly rated holiday home rental in Shelter Island is located near the beach, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a garden. 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?
Gurney's Montauk Resort & Seawater Spa: Features a seasonal outdoor pool, an indoor pool and a private beach. Water's Edge Resort & Spa and Sound View Greenport are a couple of other choices that offer an on-site pool. View all hotels with pools 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 98 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, Mashomack Preserve and Crescent 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.

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