Find hotels in Shelter Island, NY from ฿2,320

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27 Dec - 28 Dec
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28 Dec - 29 Dec
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2 Jan - 4 Jan
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Our top choices for Shelter Island hotels

Front of property
The Preston House & Hotel

The Preston House & Hotel

The Preston House & Hotel
3.5 star property
Riverhead
9.8 out of 10, Exceptional, (373)
Sophisticated accommodation just minutes from Suffolk Theatre and All Star Bowling. Enjoy free breakfast, WiFi, and parking while staying active at the 24-hour fitness centre. After exploring, unwind with refreshing drinks at the beach bar.
"Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!"
United States
Nakia
The price is ฿4,885
฿5,581 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Preston House & Hotel
Beach nearby, white sand, sun-loungers, beach umbrellas
The Roundtree, Amagansett

The Roundtree, Amagansett

The Roundtree, Amagansett
4.5 star property
Amagansett North
10.0 out of 10, Exceptional, (91)
Luxurious retreat minutes from Hamptons beaches with complimentary continental breakfast and bike rentals. Just a 10-minute walk from Amagansett Station, this hotel offers easy access to Amagansett Square while providing free WiFi and parking in a serene garden setting.
"Located right in the center of town, the grounds on this property are wonderful with clean and comfortable suites. The staff are engaging and sweet. And the late night cookies are a sweet touch."
United States
adam
The price is ฿18,446
฿22,129 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Roundtree, Amagansett
Beach bar
Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (142)
Soak in bay vistas at this Greenport beach hotel with 2 bars and 3 dining options. After a massage at the full-service spa, grab a complimentary bike to explore nearby Railway Museum and East End Seaport Maritime Museum.
"Great get away "
United States
Charles
Silver Sands Motel & Beach Bungalows
Garden
The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn

The 1770 House Restaurant & Inn
4.0 star property
East Hampton
9.8 out of 10, Exceptional, (161)
This coastal retreat offers 2 restaurants serving American cuisine, one being the signature 1770 House Restaurant. Enjoy the serene garden and convenient bar/lounge, all while being close to Guild Hall and Mulford Farm with complimentary WiFi and parking.
"The staff was incredibly genuine and the property felt intimate and comfortable."
United States
Aniya
The price is ฿9,155
฿12,516 total
includes taxes & fees
29 Dec - 30 Dec
The 1770 House Restaurant & Inn
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas
Canoe Place Inn and Cottages

Canoe Place Inn and Cottages

Canoe Place Inn and Cottages
4.0 star property
Hampton Bays
9.8 out of 10, Exceptional, (60)
Immerse yourself in coastal luxury at this spa hotel offering 2 bars, a seasonal outdoor pool, and a 24-hour fitness centre. Located near Meschutt Beach with easy access from Hampton Bays Station, enjoy relaxing treatments at the on-site spa after exploring nearby attractions.
"Amazing property. Really enjoyed our stay."
United States
Dave
Canoe Place Inn and Cottages
Terrace/patio
Westbrook Inn B&B

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (177)
Enjoy seaside charm at this welcoming Westbrook Inn B&B, offering complimentary full breakfast and bicycle rentals. Near Westbrook Town Beach and Tanger Outlets, with hiking trails, a snack bar, and terrace for relaxation. Includes free WiFi and parking.
"Our stay was amazing! All the staff were so accommodating and kind. The inn has a rustic charm and was so festive for the holidays! Rooms are a good size, clean, and have everything you need. The breakfast was delicious and they even had free tea/coffee/cookies for all guests to enjoy :) "
United States
Chewon
The price is ฿7,028
฿7,801 total
includes taxes & fees
29 Dec - 30 Dec
Westbrook Inn B&B
IPod dock, MP3 dock
The Captain Stannard

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (259)
Enjoy the historic atmosphere of this Westbrook B&B with complimentary breakfast, WiFi, and parking. Explore local hiking trails or borrow bikes to visit Westbrook Town Beach and Tanger Outlets. The garden terrace offers a peaceful retreat after adventurous days.
"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
Property entrance
The Menhaden

The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (172)
"Wonderful stay in a quaint hotel..The small town was amazing and had such cozy welcoming atmosphere! "
United States
Cory
The price is ฿8,348
฿10,780 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Menhaden
Exterior
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1001)
Immerse yourself in coastal tranquility at this Old Saybrook retreat, where 3 pools, marina access, and spa services create a peaceful haven. The waterfront Fresh Salt restaurant complements stunning views just minutes from the train station.
"Wonderful stay in a beautiful setting."
United States
Deborah
The price is ฿9,590
฿11,804 total
includes taxes & fees
29 Dec - 30 Dec
Saybrook Point Resort & Marina
Beach/ocean view
Stirling House Bed & Breakfast

Stirling House Bed & Breakfast

Stirling House Bed & Breakfast
3.0 star property
Greenport
9.8 out of 10, Exceptional, (24)
Wake up to a full breakfast at this waterfront retreat in Greenport. Enjoy the terrace views, then walk 11 minutes to the train station or explore nearby attractions like Greenport Harbour Brewing Company and Farmers' Market.
"Our stay was only 2 nights but felt like 5. Well rested 3 days. Would return in a Heart Beat. Clay was awesome and the breakfasts were over the top !"
United States
Adam
The price is ฿10,393
฿11,874 total
includes taxes & fees
23 Jan - 24 Jan 2026
Stirling House Bed & Breakfast
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, (1001)
Overlooking the harbour in Niantic, this charming B&B offers free breakfast, WiFi and parking. Explore the area using complimentary bike rentals or try nearby hiking trails and kayaking. The terrace provides a peaceful spot to enjoy marina views after a day of adventures.
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
The price is ฿4,935
฿5,675 total
includes taxes & fees
29 Dec - 30 Dec
Inn at Harbor Hill Marina
Garden Suite King | Premium bedding, down duvets, individually decorated
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, (231)
Discover coastal charm at this waterfront Southold retreat offering free bicycles for exploring nearby wineries. Unwind with drinks at the bar after a day visiting The Old Field Vineyards or relaxing at Crescent Beach, all while enjoying attentive service from the friendly staff.
"Great stay, will definitely go again"
United States
ANTONIO J
The price is ฿5,757
฿6,577 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Shoals Suites and Slips
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)
Escape to this guesthouse on Chase Creek, where a serene golf course setting meets waterfront tranquility. Enjoy convenient self parking and WiFi, plus a welcoming terrace. Shelter Island Country Club and Sylvester Manor await nearby.
" This was my husband and my first time visiting Shelter Island and I feel lucky that my stay was at the House of ChaseCreek. Bill was excellent in helping us navigate our stay on the Island which made for an enjoyable experience. The house was charming , very clean , and had easy access to the town restaurant s, and Ferry. Highly recommend ! "
United States
Maureen
The price is ฿3,232
฿3,693 total
includes taxes & fees
6 Jan - 7 Jan 2026
House on Chase Creek
Terrace/patio
The Bentley Hotel Southampton

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (407)
This welcoming hotel offers free WiFi and parking just 15 minutes from The Hamptons Beaches. Enjoy the seasonal outdoor pool after exploring nearby attractions like Sebonack and Shinnecock Hills golf courses, with water activities moments away.
"Room was beautiful and spacious. Staff was courteous and on point. "
United States
Ron
The price is ฿3,883
฿4,468 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Bentley Hotel Southampton
Exterior
Madison Beach Hotel

Madison Beach Hotel

Madison Beach Hotel
4.0 star property
Madison Center
9.4 out of 10, Exceptional, (341)
Embrace seaside tranquility at this beach hotel featuring American cuisine at The Wharf restaurant and rejuvenating spa services. Adjacent to a golf course with private beach access, fitness centre, and bar. Near Deacon John Grave House and Madison Station.
"The Spa was wonderful and the staff was attentive and helpful. "
United States
Emma
The price is ฿8,560
฿9,844 total
includes taxes & fees
1 Jan - 2 Jan 2026
Madison Beach Hotel
Outdoor pool
Sag Harbor Inn

Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (580)
Relax at this waterside Sag Harbour hotel with an inviting outdoor pool and complimentary continental breakfast. Just minutes from The Hamptons Beaches and the Whaling Museum, enjoy free WiFi and parking while exploring the charming coastal village.
"Very clean, helpful staff and convenient location."
United States
Gordon
The price is ฿6,681
฿7,633 total
includes taxes & fees
29 Dec - 30 Dec
Sag Harbor Inn
Outdoor wedding area
Bridgehampton Inn

Bridgehampton Inn

Bridgehampton Inn
3.5 star property
Bridgehampton
9.4 out of 10, Exceptional, (218)
Unwind at this charming inn with easy train access and proximity to Hampton Classic Horse Show Grounds. Enjoy room service, stroll through the lush garden, or relax with a drink at the welcoming bar while friendly staff cater to your needs.
"Great place!!!"
United States
Leslie
The price is ฿9,279
฿10,602 total
includes taxes & fees
29 Dec - 30 Dec
Bridgehampton Inn
Interior entrance
Vine & Sand

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (13)
Relax at this cosy retreat near Croteaux Vineyards and Corey Creek Winery. Enjoy complimentary breakfast, WiFi, and parking. Borrow free bicycles to explore local attractions, then unwind in the seasonal pool, garden, or terrace.
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
United States
Sandra
Vine & Sand
Ocean View 2 Queens | Premium bedding, pillow-top beds, blackout curtains, free WiFi
Offshore Montauk

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (87)
"Hotel was beautiful !!"
United States
Erica
The price is ฿3,603
฿5,889 total
includes taxes & fees
11 Jan - 12 Jan 2026
Offshore Montauk
Front of property – evening/night
Montauk Manor

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1273)
Unwind at this Italian-inspired aparthotel offering both indoor and outdoor swimming. Enjoy Monte's dining, 24-hour fitness centre, and in-room kitchenettes. Located minutes from Montauk Station with Shadmoor State Park and Fort Pond nearby.
"The room was very clean, comfortable and quiet. The hotel was decorated beautifully for the holidays. The pool area with hot tub was clean and enjoyable "
United States
Kathleen
The price is ฿4,301
฿5,522 total
includes taxes & fees
5 Jan - 6 Jan 2026
Montauk Manor
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 for the activities you enjoy most.

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 Sunset Beach and Crescent 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 Shelter Island Whale's Tail.

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

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 Shelter Island Historical Society.

Stay near popular Shelter Island attractions

Colorful pebbles and shells on a beach

Shell Beach

Why not spend a care-free afternoon at Shell Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
See properties
Man watching sailboat on Long Island Sound

Wades Beach

Why not spend a care-free afternoon at Wades Beach during your travels in Shelter Island? Amble around the area's parks or experience its museums.
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

Offshore Montauk

Offshore Montauk

10/10 Excellent
"Hotel was beautiful !!"
Erica 1-night trip
Posted 5 days ago
Offshore Montauk

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 ฿2,905 per night from 28 Dec to 29 Dec
฿2,905
฿3,319 total
28 Dec - 29 Dec
includes taxes & fees
6.6/10 (785 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 Sound View Greenport. 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?
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 97 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.