Photo by Brian V. Rowe

Find hotels in Shelter Island, NY from Rp1.790.283

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Filter by

Guest rating
Guest rating
Star rating

Our top choices for Shelter Island hotels

Kenny's Tipperary Inn

Kenny's Tipperary Inn
2.0 star property
Culloden Shores
8.4 out of 10, Very good, (879)
"Really clean and nice location"
United States
Tiara
Kenny's Tipperary Inn

Montauk Manor

Montauk Manor
3.5 star property
Montauk
9.2 out of 10, Wonderful, (1272)
"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 Rp2.320.303
Rp2.978.559 total
includes taxes & fees
12 Jan - 13 Jan 2026
Montauk Manor

Hyatt Place Long Island East End

Hyatt Place Long Island East End
3.0 star property
Riverhead
9.2 out of 10, Wonderful, (1001)
"Our room had a great view of the river and marina. we also loved the seating area in the room. Very comfortable"
United States
Helen
The price is Rp1.841.510
Rp2.103.926 total
includes taxes & fees
19 Jan - 20 Jan 2026
Hyatt Place Long Island East End

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, (1001)
"Staff was courteous, and bed was comfortable. The room hasn't had decor updated for decades. Fine for an overnight if you are just traveling through area for the price. "
United States
sue
Pier Blue Inn Old Saybrook - Essex

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1001)
"The very friendly staff made this stay enjoyable from The beginning. The hotel was very clean and comfy. "
United States
Virginia
The price is Rp1.693.352
Rp1.947.354 total
includes taxes & fees
18 Jan - 19 Jan 2026
Quality Inn Old Saybrook - Westbrook

Shorewood Inn

Shorewood Inn
2.5 star property
Riverhead
8.4 out of 10, Very good, (711)
"Couldn't have been easier! The woman at the front desk was warm and welcoming, the room was super clean and cute with the heat turned on full blast in anticipation of my arrival. Adorable backyard with seating, too. Super hot water in the shower. Perfect for an impromptu winter getaway. "
United States
Mahlon
Shorewood Inn

Offshore Montauk

Offshore Montauk
2.0 star property
Montauk
9.4 out of 10, Exceptional, (85)
"Hotel was beautiful !!"
United States
Erica
The price is Rp1.943.630
Rp3.176.928 total
includes taxes & fees
22 Jan - 23 Jan 2026
Offshore Montauk

Hamlet Inn

Hamlet Inn
2.0 star property
Southampton
8.6 out of 10, Excellent, (444)
"Great weekend stay! staff was super kind and property was beautiful! "
United States
Chyanne
The price is Rp1.491.623
Rp1.927.894 total
includes taxes & fees
28 Dec - 29 Dec
Hamlet Inn

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, (463)
"We came in for a family wedding in the area and this hotel was a great location. The mexican restaurant that was down the street is fantastic, great margaritas ! Would definitely use this location again if we were out this way. Thank you for a wonderful stay !"
United States
Robert
The price is Rp1.122.149
Rp1.290.471 total
includes taxes & fees
19 Jan - 20 Jan 2026
Econo Lodge Inn & Suites Old Saybrook Westbrook

The Bentley Hotel Southampton

The Bentley Hotel Southampton
2.0 star property
Southampton
9.6 out of 10, Exceptional, (405)
"Room was beautiful and spacious. Staff was courteous and on point. "
United States
Ron
The price is Rp2.094.727
Rp2.409.966 total
includes taxes & fees
9 Jan - 10 Jan 2026
The Bentley Hotel Southampton

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.6 out of 10, Excellent, (600)
"Staff was amazing , room clean view phenomenal "
United States
Denise
The price is Rp2.665.167
Rp3.500.141 total
includes taxes & fees
1 Jan - 2 Jan 2026
Sound View Greenport

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (549)
"Awesome stay!!! Great Location "
United States
Bryan
The price is Rp2.265.790
Rp3.044.506 total
includes taxes & fees
25 Jan - 26 Jan 2026
The Harbor Front Inn

House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (79)
" 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 Rp1.743.240
Rp1.991.844 total
includes taxes & fees
26 Jan - 27 Jan 2026
House on Chase Creek

Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (298)
"Great staff and clean rooms"
United States
Tyler
The price is Rp1.305.798
Rp1.501.668 total
includes taxes & fees
9 Jan - 10 Jan 2026
Clinton Motel

The Atlantic Hotel

The Atlantic Hotel
2.5 star property
Southampton
7.2 out of 10, Good, (975)
"Great hotel for a quick stay - very friendly staff"
United States
Dianne
The Atlantic Hotel

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (231)
"Great stay, will definitely go again"
United States
ANTONIO J
The price is Rp3.105.288
Rp3.547.790 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Shoals Suites and Slips

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (215)
"Clean & amenities, staff friendly Thank you "
United States
Archil
The price is Rp2.696.975
Rp3.750.724 total
includes taxes & fees
25 Jan - 26 Jan 2026
The Sagaponack

Daunt's Albatross Motel

Daunt's Albatross Motel
2.0 star property
Downtown Montauk
9.0 out of 10, Wonderful, (290)
"Daunts is our home away from home when we visit Montauk. From the convenience to the superb hospitality and comfortable rooms. If you’re visiting MTK you have to stay at Daunts, and their pet friendly "
United States
Yohayna
Daunt's Albatross Motel

Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.4 out of 10, Exceptional, (1001)
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
The price is Rp2.661.819
Rp3.061.092 total
includes taxes & fees
6 Jan - 7 Jan 2026
Inn at Harbor Hill Marina

The Preston House & Hotel

The Preston House & Hotel
3.5 star property
Riverhead
9.8 out of 10, Exceptional, (373)
"Staff was amazing, include the restaurants’ staff! 2nd time staying there, will be back for many more!"
United States
Nakia
The price is Rp2.635.201
Rp3.010.869 total
includes taxes & fees
18 Jan - 19 Jan 2026
The Preston House & Hotel
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

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 Shelter Island Historical Society 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.

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

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.

Central Park summer

Top Shelter Island Hotel Reviews

More cheap stays in Shelter Island

Find out more about Shelter Island

Top reasons to visit Shelter Island

  • Stunning Beaches: Shelter Island boasts picturesque beaches, perfect for relaxation and romantic getaways.
  • Outdoor Adventures: Enjoy a variety of activities, from hiking to skiing at nearby resorts.
  • Natural Beauty: Explore the island's scenic landscapes and tranquil parks, ideal for unwinding.
  • Charming Accommodations: Choose from delightful bed and breakfasts and family-friendly lodgings.
  • Cultural Experiences: Discover historic buildings and immerse yourself in the local charm.

Find great hotels near Shelter Island

Whether you're seeking a charming bed and breakfast or an agritourism property, Shelter Island offers a delightful array of accommodation options to suit every traveller. With a focus on pet-friendly facilities and family-friendly experiences, you'll find hotels equipped with essential amenities such as accessible rooms, air conditioning, and restrooms. Enjoy a memorable stay amidst the island's natural beauty and adventure-filled activities.

  • The Harbor Front Inn: This charming 3.5-star hotel offers a delightful blend of business convenience and a pet-friendly environment, making it a perfect choice for both leisure and work travellers. Situated 4.8km from Shelter Island, The Harbor Front Inn features modern amenities to cater to your needs, including spacious rooms that allow dogs and a welcoming atmosphere for pets. With its proximity to local attractions, guests can enjoy both the tranquillity of the area and the comfort of their furry companions.
  • SEVEN - Shelter Island Guest House: A haven for adventure seekers and golf enthusiasts, SEVEN - Shelter Island Guest House is a delightful 3.5-star bed and breakfast located just 1.6km from Shelter Island. This accommodation is tailored for those seeking excitement, with easy access to various outdoor activities such as kayaking, surfing, and snowshoeing. The guest house embraces a pet-friendly policy, ensuring that your four-legged friends are welcome. Guests can enjoy a unique golfing experience right at the property, providing a perfect blend of relaxation and adventure.
  • Fordham House: Offering a warm and inviting atmosphere, Fordham House is a quaint 3-star bed and breakfast located 4.8km from Shelter Island. Guests can indulge in complimentary full breakfasts during their stay, giving them a delightful start to each day. The property’s charming features and attentive service create a homely feel, making it an excellent choice for those looking to unwind and enjoy a peaceful getaway. With its emphasis on comfort and hospitality, Fordham House is a lovely retreat after a day of exploration.

Where to stay near Shelter Island

Embark on a delightful journey in Shelter Island, where outdoor adventures and romantic beach getaways await. Explore the stunning American Beech, immerse yourself in charming experiences, and enjoy the scenic beauty of adjacent islands. With a family-friendly atmosphere and opportunities for excursions, Shelter Island offers a perfect blend of relaxation and exploration, even in the colder weather. Discover the magic of this enchanting destination during your stay.

  • Greenport: Located a mere 4.8km from Shelter Island, Greenport is a charming coastal village known for its vibrant maritime culture and scenic waterfront. The travel experience here is marked by a blend of outdoor adventures and romantic escapes, particularly during the peak summer months of June to August. Visitors can enjoy activities such as golfing, attending live music concerts, and exploring recreational areas. Notable local attractions include family-friendly beaches and parks that provide a perfect backdrop for relaxation and enjoyment.
  • Hamptons: Approximately 14.5km from Shelter Island, the Hamptons are synonymous with sophistication and leisure, attracting a diverse array of tourists. The area experiences a similar seasonal pattern, with the highest visitor numbers from June to August. Renowned for its stunning beaches and outdoor activities, the Hamptons offer an idyllic setting for a romantic getaway. Guests can partake in golfing, visit picturesque recreational spots, or attend various music events. The nearby beaches and tranquil lakes are perfect for sunbathing and engaging in water sports.
  • Sag Harbor: Situated just 8.0km from Shelter Island, Sag Harbor is a historic whaling village that exudes charm and character. The travel experience here is equally seasonal, with peak visits occurring in the summer months. Known for its outdoor and beach experiences, Sag Harbor entices visitors with opportunities for golfing and even skiing in winter. Key attractions include scenic beaches, a family beach, and the iconic lighthouse, making it a delightful destination for both relaxation and exploration.

Things to do in and around Shelter Island

Shelter Island offers a perfect setting for outdoor and romantic beach vacations. Visitors can indulge in a variety of activities, including skiing at nearby resorts for adventure seekers. Day trips to the island present opportunities to explore its natural beauty and tranquillity, making it an ideal destination for those looking to unwind or seek adventure amidst picturesque surroundings.

Shopping

The Greenport Farmers' Market, located 4.8km away, offers a vibrant public market atmosphere with local produce and artisan goods. The Style Bar, 8.0km from Shelter Island, provides a chic shopping experience. If you're up for a drive, Love Lane, 17.7km away, features family-friendly boutiques and shops.

Recreation

Shelter Island Whale's Tail offers a fun-filled mini golf experience, perfect for families and adventure seekers. For golf enthusiasts, Noyac Golf Club provides a picturesque outdoor setting just 9.7km away. Meanwhile, Cedar Point County Park, located 8.0km away, is ideal for relaxation and wellness amidst nature.

Adventure

Experience the thrill of freefall at Long Island Skydiving Center, located 43.5km from Shelter Island, where adventure and adrenaline await. For family fun, visit Splish Splash Water Park, 37.0km away, offering exhilarating water rides. Explore the stunning scenery along Walking Dunes Trailhead, situated 25.7km away.

Nightlife

On Shelter Island, the Greenport Carousel offers a charming outdoor atmosphere, perfect for a nostalgic evening. For a dose of culture and romance, Bay Street Theatre enchants with its performances. Alternatively, Regal UA East Hampton cinema provides a delightful family-friendly experience, showcasing the latest films in a relaxed setting.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Shelter Island

To save money on your visit to Shelter Island, consider travelling during the off-peak months from January to March, when accommodation prices are cheaper. Booking your stay on a Tuesday can also reduce costs, while Fridays tend to be the most expensive. Utilise Expedia's search tool to filter hotels by budget and location, and explore package deals that combine flights, hotels, and activities for added savings. Additionally, take advantage of free attractions and public transport to keep your expenses down while enjoying the island's offerings.

  • The most and least expensive months on average to stay in a hotel: The hotel pricing in Shelter Island is moderately seasonal. The cheapest months to stay in Shelter Island are January to March, where the prices are moderately lower. This is in comparison to June to August, where prices are moderately higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Shelter Island is Tuesday. The most expensive day to stay in Shelter Island is Friday.
  • Find cheap hotels on Expedia: Utilise Expedia's search tool to refine your preferences, such as your budget, desired location, and the type of hotel you favour. To discover the most affordable prices and offers, arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your hotel reservation on Shelter Island with your flights and activities through an Expedia package.

Find the best attractions in and around Shelter Island

Shelter Island offers a charming blend of outdoor adventures and romantic beach getaways, perfect for a delightful vacation. Visitors can explore captivating beaches, serene urban parks, and historic buildings, catering to those seeking cultural experiences and natural beauty. With its picturesque settings, Shelter Island is an ideal destination for travellers looking to unwind and connect with nature.

  • 67 Steps Beach: Experience the serene beauty of 67 Steps Beach, just 6.4km from Shelter Island. This beach offers a perfect escape with its laid-back vibes, allowing you to bask in the sun, enjoy the gentle surf, and take leisurely strolls along the shoreline.
  • Orient Point County Park: A mere 12.9km away, Orient Point County Park is an urban oasis ideal for families. With its spacious areas for picnicking and various outdoor activities, visitors can relish the vibrant atmosphere while exploring the park's natural beauty.
  • Gardiner's Bay Country Club: Located within Shelter Island, Gardiner's Bay Country Club is a golfer's haven. Enjoy a round of golf surrounded by stunning views, and unwind in the club's friendly atmosphere, making it a perfect spot for both novice and seasoned golfers.

Best time to go to Shelter Island

The best time to visit Shelter Island is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January35.6°F (2.0°C)Light RainMostly SunnyAverageModerately Low
February35.8°F (2.1°C)Light RainMostly CloudyAverageModerately Low
March39.7°F (4.3°C)Light RainMostly SunnyAverageModerately Low
April47.5°F (8.6°C)Light RainMostly SunnyAverageAverage
May55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
June64.9°F (18.3°C)Light RainMostly SunnyHighModerately High
July73.0°F (22.8°C)Light RainMostly SunnyHighModerately High
August73.4°F (23.0°C)Light RainMostly SunnyHighModerately High
September68.2°F (20.1°C)Light RainMostly SunnyAverageAverage
October59.7°F (15.4°C)Light RainMostly SunnyLowAverage
November49.6°F (9.8°C)Light RainMostly SunnyLowAverage
December42.1°F (5.6°C)Light RainMostly CloudyLowAverage

The nearest major airports for your trip to Shelter Island

Reaching Shelter Island, New York, is convenient via several major airports. Islip, NY (ISP-MacArthur) is located 70.8km away, with nearby accommodation options such as Jake's 58 Casino Hotel, 6.4km from the airport, and the Holiday Inn Long Island-Islip Arpt East, 8.0km away, both offering shuttle services. New Haven, CT (HVN-Tweed) is 51.5km from Shelter Island, featuring the Omni New Haven Hotel at Yale, just 4.8km from the airport. East Hampton, NY (HTO) is the closest at 14.5km away, with The Maidstone, a 4-star hotel located 4.8km from the airport, providing easy access for travellers.

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.