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Our top choices for Shelter Island hotels

1. The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (98 reviews)
"Stunning hotel! Will def stay again!"
United States
Anna
The price is NT$22,596
NT$28,398 total
includes taxes & fees
Sep 3 - Sep 4
The Pridwin Hotel

2. Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very Good, (63 reviews)
"This boutique hotel is a true gem. Set among lush trees and beautiful landscaping, and with excellent indoor space, it provides a welcoming and relaxing atmosphere."
United States
Dorothy
The price is NT$10,217
NT$11,673 total
includes taxes & fees
Aug 17 - Aug 18
Shelter Island House

3. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (85 reviews)
"We had such an amazing stay! The house was beautiful, comfortable, and very clean. It is an easy walk to grab a great cup of coffee, which we loved. One of our favorite parts was sitting on the two Adirondack chairs on the water. The owner could not have been nicer and had great restaurant recommendations. We really loved it and will absolutely rebook soon!"
United States
Jeanine
The price is NT$12,889
NT$14,726 total
includes taxes & fees
Sep 3 - Sep 4
House on Chase Creek

4. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (279 reviews)
"Great place!"
United States
Christine
The price is NT$10,867
NT$15,296 total
includes taxes & fees
Aug 5 - Aug 6
Cliffside Resort Condominiums

5. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very Good, (43 reviews)
"It was great! The location was perfect, plenty of amenities close by as well. Easy ferry access depending on time of day. Room was very clean. Will be staying again!"
United States
Allie
The price is NT$10,128
NT$11,571 total
includes taxes & fees
Aug 9 - Aug 10
West Neck Guesthouse

6. The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (42 reviews)
"It’s a beautiful property with a fun bar and delicious restaurant . The rooms were beautiful and the bed was super comfortable"
United States
Kristin
The price is NT$12,357
NT$14,118 total
includes taxes & fees
Aug 24 - Aug 25
The Chequit

7. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (366 reviews)
"Fantastic location and hugely helpful staff. I would absolutely stay again."
United States
Alex
The price is NT$7,889
NT$9,013 total
includes taxes & fees
Sep 3 - Sep 4
Zey Hotel

8. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (653 reviews)
"Everything about the place was great - great value overlooking the Harbor!"
United States
Christopher
The price is NT$16,444
NT$18,787 total
includes taxes & fees
Aug 10 - Aug 11
Sag Harbor Inn

9. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (311 reviews)
"Great stay"
United States
Connor
The price is NT$11,541
NT$13,998 total
includes taxes & fees
Sep 1 - Sep 2
The Shoals Suites and Slips

10. Oyster Estate

Oyster Estate
2.0 star property
Greenport
9.2 out of 10, Wonderful, (284 reviews)
"Great location, great hotel, great staff! "
United States
Jenny
The price is NT$15,555
NT$19,599 total
includes taxes & fees
Sep 1 - Sep 2
Oyster Estate

11. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (634 reviews)
"Very nice property/staff and a great location"
United States
David
The price is NT$13,350
NT$16,914 total
includes taxes & fees
Aug 31 - Sep 1
The Harbor Front Inn

12. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (44 reviews)
"This is the most thoughtfully designed and maintained hotel Everything was excellent"
United States
Lisa
The price is NT$23,260
NT$26,575 total
includes taxes & fees
Aug 25 - Aug 26
North Fork Resort

13. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (187 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
The price is NT$16,176
NT$19,774 total
includes taxes & fees
Aug 6 - Aug 7
The Menhaden

14. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (675 reviews)
"Great in town getaway"
United States
Yveline
The price is NT$23,123
NT$29,200 total
includes taxes & fees
Sep 4 - Sep 5
Sound View Greenport

15. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (203 reviews)
"The hotel doesn’t reception doesn’t open till 9am. For early risers we had to leave the hotel just to get coffee. 9am is unheard of for a hotel"
United States
kerri
The price is NT$12,567
NT$15,650 total
includes taxes & fees
Aug 5 - Aug 6
American Beech Hotel

16. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (300 reviews)
"Great location in the heart of town Walk to everything Amazing breakfast too "
United States
Michael
The price is NT$34,729
NT$43,646 total
includes taxes & fees
Aug 5 - Aug 6
Faraway Sag Harbor

17. Arbor View House B&B

Arbor View House B&B
3.5 star property
East Marion
9.4 out of 10, Exceptional, (16 reviews)
"Wonderful stay! Will definitely be back!"
United States
Lekecia
The price is NT$19,746
NT$23,259 total
includes taxes & fees
Sep 3 - Sep 4
Arbor View House B&B

18. Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (327 reviews)
"It was a nice motor lodge with chairs for sitting outside. There’s also a pool out back that was great."
United States
David
The price is NT$2,714
NT$3,121 total
includes taxes & fees
Aug 5 - Aug 6
Clinton Motel

19. The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (273 reviews)
"This is a very tastefully decorated B&B in an idyllic location. 6 minute walk to West Beach and near all the famous CT shoreline restaurants and attractions."
United Kingdom
Jessica
The price is NT$7,557
NT$8,388 total
includes taxes & fees
Aug 5 - Aug 6
The Captain Stannard

20. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,003 reviews)
"Very friendly staff, easy parking, great breakfast, and clean towels and beds made daily. Great place to stay."
United States
John
The price is NT$3,268
NT$3,758 total
includes taxes & fees
Aug 30 - Aug 31
Quality Inn Old Saybrook - Westbrook
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.

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.

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.

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.

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.

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

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.

A wooden gazebo by a pond with a large tree trunk nearby.

Top Shelter Island Hotel Reviews

More cheap stays in Shelter Island

Hotels in Shelter Island with star-rating

Find out more about Shelter Island

Top reasons to visit Shelter Island

  • Scenic Beaches: Enjoy the serene beauty of Shelter Island's picturesque beaches, perfect for relaxation and sunset views.
  • Outdoor Activities: Engage in golfing, kayaking, and nature walks, catering to both adventure seekers and couples.
  • Rich History: Visit the Shelter Island Historical Society to explore the area's captivating past and cultural heritage.
  • Charming Accommodations: Choose from cozy bed & breakfasts and unique agritourism properties for a memorable stay.
  • Ferry Rides: Experience scenic ferry rides that connect you to the beauty of nearby Long Island.

Find great hotels near Shelter Island

Discover a delightful selection of accommodations on Shelter Island, where you can choose from charming agritourism properties and cozy bed & breakfasts. Whether you're seeking a pet-friendly getaway, a family-friendly adventure, or an intimate inn experience, Shelter Island offers a variety of options to make your stay memorable. Explore the unique amenities of local guest houses and the renowned Shelter Island House for a perfect vacation retreat.

  • Sound View Greenport: This 3.5-star hotel is a delightful beachside retreat located 6km from Shelter Island. With a guest rating of 8.4 out of 10, Sound View Greenport is perfect for families and pet owners seeking a relaxing getaway. The property boasts direct beach access, allowing guests to enjoy sun-soaked days by the water. Families will appreciate the amenities tailored for children, including complimentary cribs and window guards for safety. Pet lovers can also bring their furry friends along, with policies in place to accommodate dogs and cats. The friendly atmosphere and beach vibe make it a great choice for a memorable vacation.
  • Sag Harbor Inn: Situated 8km from Shelter Island, Sag Harbor Inn is a 3.5-star hotel with an impressive guest rating of 9.4 out of 10, ideal for business travelers. The inn blends professional convenience with a cozy atmosphere, ensuring comfort during your stay. Guests can expect well-appointed rooms and essential amenities tailored for those on business trips. Its proximity to local attractions and meeting spaces makes it a practical choice for professionals looking to balance work with leisure while enjoying the charm of Sag Harbor.
  • The Harbor Front Inn: Located 5km from Shelter Island, The Harbor Front Inn is another 3.5-star option that garners a guest rating of 8.8 out of 10. This property caters to both business travelers and pet owners, offering a unique blend of services. Guests can unwind in comfortable accommodations while enjoying views of the harbor. With policies that allow pets, including dogs of certain weights, travelers can rest easy knowing their furry companions are welcome. The Harbor Front Inn provides a great base for exploring the local area while ensuring a pleasant and accommodating experience.

Where to stay near Shelter Island

Embark on a charming getaway to Shelter Island, New York, where outdoor enthusiasts and romantic souls can revel in breathtaking scenery and serene beaches. Discover the quaint allure of Shelter Island, indulge in luxury experiences, or enjoy family-friendly excursions. Don't miss the picturesque sunset at Sunset Beach, and explore the nearby splendors of Long Island for a perfect blend of adventure and relaxation on your vacation.

  • Hamptons: Located 14km from Shelter Island, the Hamptons is a premier vacation destination renowned for its beautiful beaches and upscale lifestyle. This charming area attracts visitors primarily from June to August, where outdoor activities abound, from relaxing on sandy shores to golfing at scenic courses. The Hamptons also offers romantic dining experiences and vibrant nightlife. Local landmarks include stunning beaches, picturesque family-friendly spots, and serene lakes, making it a versatile location for all types of travelers.
  • Greenport: Just 5km away from Shelter Island, Greenport is a quaint village that combines charming maritime history with modern amenities. This destination experiences seasonal visitor peaks from June to August, drawing couples and outdoor enthusiasts alike. Visitors can enjoy recreational parks, local music concerts, and beautiful beaches perfect for sunbathing or picnicking. With its inviting atmosphere and close-knit community, Greenport is a delightful stop for anyone looking to immerse themselves in the local culture and enjoy the natural beauty of Long Island.
  • Sag Harbor: Located 8km from Shelter Island, Sag Harbor is a historic whaling town that offers a unique blend of artsy charm and coastal beauty. Seasonal tourism peaks from June to August, attracting those seeking outdoor and romantic experiences. Visitors can explore local golf courses, stunning beaches, and serene lakes. Sag Harbor's vibrant arts scene, coupled with its rich history, creates an inviting backdrop for leisurely strolls along the waterfront and delightful dining at local eateries.

Things to do near Shelter Island

Shopping

In Shelter Island, enjoy local shops offering unique gifts and souvenirs, showcasing handmade crafts and artisanal products. If you're up for a drive, visit the nearby Southold Marketplace, about 19km away, featuring a variety of boutiques and specialty stores for a broader shopping experience.

Recreation

Experience the serene atmosphere at Shelter Island's wellness retreats, where you can indulge in yoga classes and meditation sessions. Explore nature trails for hiking or biking, and unwind with spa treatments that feature local ingredients, providing a refreshing escape from everyday life.

Adventure

Experience the thrill of motorsport at Riverhead Raceway, located 35km from Shelter Island, where you can enjoy thrilling races and a vibrant atmosphere. Alternatively, head to Waterford Speedbowl, 39km away, for more exciting racing action amidst a lively backdrop of camaraderie and competition.

Nightlife

Enjoy the laid-back vibe at the Shelter Island Wine Company, where you can sample local wines. For a lively atmosphere, visit the Sunset Beach Bar for cocktails and beachside views. If you're in the mood for dancing, the Tavern at Shelter Island offers great music and a fun crowd.

*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 trip to Shelter Island, visit between January and March for the lowest hotel rates, and consider booking your stay on a Tuesday. Avoid Fridays for the highest prices. Use Expedia to find deals by filtering for your budget and preferences, and look for Eco-certified hotels for sustainable options. Combining your hotel, flight, and activities into one package can lead to great savings. Lastly, explore the island on foot to enjoy free activities and avoid transportation costs.

  • 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: Utilize Expedia's search tool to tailor your results according to your preferences, such as your budget, desired location, and the type of hotel you're looking for. For instance, selecting the Eco-certified option will highlight sustainable and environmentally friendly hotels that are currently available. To find the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can save money by combining your Shelter Island hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in Shelter Island

Shelter Island offers a perfect blend of outdoor activities, romance, and beach relaxation. Visitors can explore beautiful beaches, urban parks, and historic buildings, making it an ideal destination for those seeking culture and adventure. Don't miss the Shelter Island Historical Society for a deeper dive into the area's rich past. Enjoy the serene environment and various attractions that cater to all types of travelers looking for a memorable experience.

  • Gardiner's Bay Country Club: Nestled in Shelter Island, this golf course offers stunning views of Gardiner’s Bay. Enjoy a round of golf surrounded by lush landscapes and well-maintained greens. The club's welcoming atmosphere makes it an ideal spot for both beginners and seasoned golfers alike.
  • Shell Beach: Experience the laid-back beach vibes at Shell Beach, where you can relax on the sandy shores and soak up the sun. The calm waters are perfect for swimming, making it a popular spot for families and friends looking to enjoy a day by the sea.
  • Mashomack Preserve: This urban park provides a serene escape into nature with hiking trails and diverse wildlife. Ideal for families, Mashomack Preserve is great for outdoor activities, picnicking, and exploring the natural beauty of Shelter Island.

Best time to go to Shelter Island

The best time to visit Shelter Island can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Shelter Island falls in August, when visitor numbers are high and weather is mostly sunny with light rain. The coolest average temperature in Shelter Island falls in January, visitor numbers are average and weather is mostly sunny with light rain.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
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

Traveling to Shelter Island, New York, is convenient via several major airports. John F. Kennedy International Airport (JFK) is located 130km away, with excellent hotel options such as The William Vale, Arlo Williamsburg, and The Boro Hotel, all about 18km from the airport. LaGuardia Airport (LGA) is 134km from Shelter Island, offering luxury stays at Hilton Club The Quin New York, The Plaza, and The Luxury Collection Hotel Manhattan Midtown, all within 10km of the airport. Additionally, Bradley International Airport (BDL) is 100km away, with nearby accommodations including DoubleTree by Hilton and Marriott Hartford Downtown, providing easy access to transportation services for your journey.

Frequently asked questions

Where is the best place to stay in Shelter Island?
Located 15.5 mi (24.9 km) from the heart of Shelter Island, Pier Blue Inn Old Saybrook - Essex is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are Sound View Greenport 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, 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?
Sound View Greenport: Offers a private beach, a seasonal outdoor pool, and 2 bars. Montauk Yacht Club and Gurney's Montauk Resort & Seawater Spa 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. A top sight in the area is The Hamptons Beaches. In Shelter Island, there are 105 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, Wades Beach, and Mashomack Preserve. Additionally, you'll find The Hamptons Beaches in the area. 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.

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