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Jan 29 - Jan 30
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Feb 6 - Feb 8

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Our top choices for Shelter Island hotels

Exterior

Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
2.5 star property
Clinton
6.4 out of 10, (228 reviews)
"Would stay again. "
United States
pamela
The price is ₩92,915
₩106,852 total
includes taxes & fees
Feb 1 - Feb 2
Lamplighter Motel - Clinton, Connecticut
Property grounds

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (301 reviews)
"The room was comfortable and clean. A good value for the money."
United States
Michael
The price is ₩111,498
₩128,223 total
includes taxes & fees
Feb 1 - Feb 2
Clinton Motel
Individually decorated, individually furnished, desk, laptop workspace

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, (466 reviews)
"All good it met our expectations as a budget hotel. Large clean room bed was comfortable although the pillows were past it. "
United States
Hilary
The price is ₩95,817
₩110,189 total
includes taxes & fees
Feb 4 - Feb 5
Econo Lodge Inn & Suites Old Saybrook Westbrook
Fireplace

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (178 reviews)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is ₩294,254
₩326,622 total
includes taxes & fees
Feb 1 - Feb 2
Westbrook Inn B&B
IPod dock, MP3 dock

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (260 reviews)
"The Inn and staff were warm and welcoming, the facility exceptionally clean. Breakfast exceeded my expectations for a continental breakfast! Would absolutely stay again! "
United States
Lisa
The Captain Stannard
Desk, laptop workspace, iron/ironing board, free cribs/infant beds

Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook
2.0 star property
Old Saybrook
7.0 out of 10, Good, (912 reviews)
"Excellent "
United States
David
The price is ₩96,489
₩114,300 total
includes taxes & fees
Feb 2 - Feb 3
Super 8 by Wyndham Old Saybrook
Deluxe Double Room, 1 King Bed, City View | In-room safe, individually decorated, individually furnished, desk

Hampton Bays Hotel on Main

Hampton Bays Hotel on Main
2.0 star property
Hampton Bays
7.2 out of 10, Good, (70 reviews)
"Loved the 2 bar options on the property."
United States
Jennifer
The price is ₩202,069
₩230,862 total
includes taxes & fees
Jan 31 - Feb 1
Hampton Bays Hotel on Main
Private kitchen

Canoe Place Waterfront Residences

Canoe Place Waterfront Residences
4.0 star property
Hampton Bays
10.0 out of 10, Exceptional, (1 review)
The price is ₩1,859,013
₩2,251,358 total
includes taxes & fees
Jan 31 - Feb 1
Canoe Place Waterfront Residences
Beach nearby

The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (105 reviews)
"Inn has been newly renovated. Room was spotless. Staff were wonderful. Had an excellent stay. Highly recommend! "
United States
Valerie
The price is ₩511,832
₩599,058 total
includes taxes & fees
Feb 12 - Feb 13
The Huntting Inn
Indoor pool, open 9:00 AM to 9:00 PM, sun loungers

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,001 reviews)
"Hotel was very clean, staff was wonderful and the pool was so relaxing. It was a quick visit but definitely would stay again if I was in that area. "
United States
Kathleen
The price is ₩138,515
₩159,293 total
includes taxes & fees
Feb 15 - Feb 16
Quality Inn Old Saybrook - Westbrook
Front of property - evening/night

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (78 reviews)
"the rooms are outdated and the front desk staff was overbearing the location is great but it’s noisy the breakfast was awesome as was the chef "
United States
Sharon
The price is ₩357,365
₩449,122 total
includes taxes & fees
Feb 8 - Feb 9
Mill House Inn
Exterior

Sea Haven Resort Motel

Sea Haven Resort Motel
2.0 star property
Southampton
7.8 out of 10, Good, (31 reviews)
"Great staff"
United States
Douglas
The price is ₩160,942
₩205,941 total
includes taxes & fees
Feb 28 - Mar 1
Sea Haven Resort Motel
Desk, free WiFi, bed sheets

Southampton Long Island Hotel

Southampton Long Island Hotel
2.5 star property
Southampton
8.6 out of 10, Excellent, (206 reviews)
"Staff was amazing. The room was very clean. I've stayed here numerous times, even on the night before my wedding as I was married in the Hamptons and I highly recommend! "
United States
Martine
The price is ₩150,093
₩178,982 total
includes taxes & fees
Jan 31 - Feb 1
Southampton Long Island Hotel
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
4.0 star property
Hampton Bays
9.8 out of 10, Exceptional, (61 reviews)
"Wonderful stay! "
United States
Lindsay
Canoe Place Inn and Cottages
Interior

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful stay"
United States
Judy
Vine & Sand
Bar (on property)

The Hampton Maid

The Hampton Maid
2.5 star property
Hampton Bays
9.0 out of 10, Wonderful, (688 reviews)
"Great place to stay"
United States
Mitchell
The Hampton Maid
Interior detail

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very Good, (148 reviews)
"Great spot!"
United States
Keith
Harpoon House
Property grounds

Liberty Inn

Liberty Inn
2.0 star property
Old Saybrook
7.6 out of 10, Good, (641 reviews)
"Great little place to stay with friendly staff and clean room"
United States
Carolan
The price is ₩127,222
₩146,305 total
includes taxes & fees
Jan 31 - Feb 1
Liberty Inn
Property entrance

The Maidstone

The Maidstone
4.0 star property
East Hampton
8.0 out of 10, Very Good, (150 reviews)
"We had a wonderful stay "
United States
Sabrina
The price is ₩253,943
₩290,129 total
includes taxes & fees
Feb 3 - Feb 4
The Maidstone
View from property

Journey East Hampton

Journey East Hampton
4.0 star property
East Hampton North
9.2 out of 10, Wonderful, (162 reviews)
"Amazing stay"
United States
Liana
The price is ₩263,729
₩331,443 total
includes taxes & fees
Feb 4 - Feb 5
Journey East Hampton
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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Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most.
Center console boat on Long Island, NY. Photographed by drone.

Silver Beach

Silver Beach offers a tranquil coastal retreat on Shelter Island with direct access to the sound. This charming neighborhood features weathered cottages and natural shorelines perfect for peaceful waterfront strolls. Shell Beach provides a serene spot for swimming and sunbathing. The neighborhood's calm waters make it ideal for kayaking and small boat activities. Enjoy the scent of salt air mixed with pine and beach roses. Most visitors bring supplies or travel to nearby island markets since Silver Beach maintains its residential character.

Welcome To The Beach. Driftwood beach hut with handwritten welcome sign. Port Crescent State Park. Port Austin, Michigan.

Menantic Creek

Menantic Creek on Shelter Island offers a peaceful waterfront escape where natural beauty takes center stage. This residential haven features classic Hamptons-style homes with private docks nestled among mature trees. The winding creek waters create a tranquil backdrop for a truly authentic island experience. The neighborhood provides excellent opportunities for kayaking, paddleboarding, and birdwatching along pristine shorelines. Visitors can easily explore nearby attractions like Wades Beach and Shelter Island Historical Society. Those seeking quiet relaxation will appreciate the gentle creek sounds and salt-tinged air that define this serene coastal retreat.

A sweeping view of the natural beauty at Mashomack Preserve on Shelter Island which is situated between the North and South Forks of Long Island, New York.

Coecles Harbor

Coecles Harbor offers a peaceful retreat where pristine waterfront paths wind along Peconic Bay. Luxury yachts and sailboats dot the protected marina, creating a classic New England coastal scene. Wooden docks extend into calm waters, providing perfect sunset viewing spots. This upscale Shelter Island neighborhood balances authentic maritime character with vacation amenities. Visitors can enjoy swimming at Menhadden Lane Beach or explore by kayak and paddleboard. The quiet atmosphere, with only the sounds of lapping waves and seabirds, makes it ideal for those seeking a serene coastal escape.

view of wetland from the Marine Park Salt Marsh Nature Trail in brooklyn, new york (with gil hodges bridge to the rockaways int he background) cloud reflections in bay, water (shell bank creek)

Hay Beach

Hay Beach offers a tranquil peninsula retreat on Shelter Island, away from the bustling Hamptons scene. This residential haven is surrounded by water on three sides with several beach access points for scenic coastal views. Private waterfront homes and cottages create a peaceful atmosphere where natural beauty takes center stage. Visitors can explore Menhadden Lane Beach or take short trips to nearby Gardiner's Bay Country Club. The neighborhood's charm lies in its uncrowded shoreline paths and pristine waters. Perfect for kayaking, swimming, and sunset watching, Hay Beach delivers a genuine low-key coastal experience.

Aerial Views of Mamaroneck, New Rochelle, and Larchmont

Shorewood

Shorewood offers a peaceful retreat on Shelter Island with pristine shorelines and scenic waterfront paths. Classic Hamptons-style cottages with cedar shingles and white trim line the quiet, tree-lined streets. The neighborhood's charm lies in its natural beauty and exclusive residential character. Wades Beach beckons with sandy shores and calm bay waters perfect for swimming and kayaking. Visitors appreciate the minimal tourist crowds and opportunities for stargazing at night. The salt air mingles with pine scents while gentle waves create a soothing natural soundtrack.

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 harbor 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

Montauk Manor

Montauk Manor

10/10 Excellent
"Everyone was perfect for our stay at the Montauk Manor!!! The lobby is beautiful and clean. The staff was friendly and very welcoming. We enjoyed massages with Amy, which I highly recommend. Breakfast was delicious at Monte’s (restaurant in the lobby). We loved our room it was immaculate and had everything we needed for a perfect weekend getaway!! We are looking forward to returning again in the spring. "
Phyllis 2-night trip
Posted 4 days ago
Montauk Manor

More cheap stays 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 ₩133,797 per night from Jan 31 to Feb 1
₩133,797
₩152,866 total
Jan 31 - Feb 1
includes taxes & fees
6.6/10 (793 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 traveler data. Other good choices for your trip to the area are Pier Blue Inn Old Saybrook - Essex and Montauk Blue Hotel. 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, the majority of hotel room reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your scheduled arrival. If you booked a non-refundable reservation, you might be able to still cancel and get a refund within a 24-hour period of your booking. Filter your search by fully refundable to find flexible hotel deals in Shelter Island.
Where can I learn more about changing or cancelling my trip to Shelter Island?
For additional details about picking new dates or cancelling your trip to Shelter Island, click here.
What's the best pet-friendly accommodation in Shelter Island?
Sunset Beach Hotel is a top hotel for people traveling with their pets, and offers a restaurant and free WiFi for its human guests. See more pet-friendly hotel accommodations in Shelter Island.
Where is the best hotel to stay with easy access to Mashomack Preserve?
The Harborfront Inn is one of the top choices for your stay based on our traveler data, and this 3.5-star hotel offers free breakfast and a 24-hour fitness center. It's located 3.7 mi (6 km) from Mashomack Preserve.
What about the best place to stay near Havens House?
One of the top choices for your stay is The Harborfront Inn, located 3.1 mi (4.9 km) from Havens House, and this 3.5-star hotel offers free breakfast and a 24-hour fitness center.
What's the best place 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 accommodations with pools in Shelter Island?
Gurney's Montauk Resort & Seawater Spa: Resort, 13-minute walk from The Hamptons Beaches. Features a seasonal outdoor pool, an indoor pool, and a private beach. Montauk Blue Hotel and Sound View Greenport are a couple of other choices that feature an onsite pool. View all hotels with pools in Shelter Island.
What is the best accommodation for staying close to John F. Kennedy International Airport (JFK)?
Holiday Inn Express Kennedy Airport is a popular hotel, featuring free breakfast and free WiFi. It's located a short 1.5 mi (2.5 km) from John F. Kennedy Intl. Airport. Other options near the airport are Fairfield Inn by Marriott JFK Airport and Radisson Hotel JFK Airport.
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 97 hotels and other accommodations 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 Mashomack Preserve. A couple of additional sights to add to your agenda are Shelter Island Whale's Tail and Shell Beach. Check out what more to see and do in Expedia's Shelter Island guide.
What's the weather like in Shelter Island?
The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Shelter Island is 57 inches.