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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, (94 reviews)
"Stunning hotel! Will def stay again!"
United States
Anna
The price is ¥146,001
¥183,489 total
includes taxes & fees
Aug 23 - Aug 24
The Pridwin Hotel

2. West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.2 out of 10, Very Good, (42 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 ¥51,132
¥58,419 total
includes taxes & fees
Jul 27 - Jul 28
West Neck Guesthouse

3. Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very Good, (61 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 ¥51,580
¥58,931 total
includes taxes & fees
Jul 30 - Jul 31
Shelter Island House

4. The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (42 reviews)
"location!"
United States
Sharon
The price is ¥59,891
¥68,425 total
includes taxes & fees
Jul 28 - Jul 29
The Chequit

5. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (629 reviews)
"Very nice property/staff and a great location"
United States
David
The price is ¥75,948
¥95,162 total
includes taxes & fees
Aug 18 - Aug 19
The Harbor Front Inn

6. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (357 reviews)
"Great place! We really Enjoyed the room and vibe !"
United States
Zoe
The price is ¥46,239
¥52,830 total
includes taxes & fees
Aug 23 - Aug 24
Zey Hotel

7. 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 ¥76,545
¥93,982 total
includes taxes & fees
Jul 27 - Jul 28
American Beech Hotel

8. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (185 reviews)
"Staff was very accommodating and extremely nice, Great stay!"
United States
Lisa
The price is ¥100,290
¥121,106 total
includes taxes & fees
Aug 9 - Aug 10
The Menhaden

9. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (275 reviews)
"Comfortable and clean, and the beach location is amazing. The sunset was spectacular. We will definitely come back again!"
United States
Suzanne
The price is ¥81,097
¥99,740 total
includes taxes & fees
Jul 26 - Jul 27
Cliffside Resort Condominiums

10. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (160 reviews)
"Amazing!"
United States
Joseph
Silver Sands Motel & Beach Bungalows

11. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (648 reviews)
"Everything about the place was great - great value overlooking the Harbor!"
United States
Christopher
The price is ¥83,018
¥94,848 total
includes taxes & fees
Aug 10 - Aug 11
Sag Harbor Inn

12. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (299 reviews)
"It is a beautiful upscale property. The rooms are very comfortable & had all the amenities you needed. Very good location making it accessible for anything you wanted to do in the area."
United States
Sue
The price is ¥60,639
¥73,358 total
includes taxes & fees
Jul 27 - Jul 28
The Shoals Suites and Slips

13. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very Good, (667 reviews)
"Location was the best. Enjoyed using the pool. View from the room of the Long Island sound was incredible. We had dinner at Haylard restaurant. On the premises and it was delicious."
United States
rosemary
Sound View Greenport

14. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.4 out of 10, Exceptional, (34 reviews)
"Great stay & great staff!"
United States
James
The price is ¥80,422
¥91,882 total
includes taxes & fees
Aug 23 - Aug 24
North Fork Resort

15. Lamplighter Motel - Clinton, Connecticut

Lamplighter Motel - Clinton, Connecticut
2.5 star property
Clinton
6.4 out of 10, (245 reviews)
"Staff was helpful. Place is quiet. Room was a little outdated."
United States
Samantha
The price is ¥12,885
¥14,818 total
includes taxes & fees
Jul 26 - Jul 27
Lamplighter Motel - Clinton, Connecticut

16. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
2.5 star property
Old Saybrook
7.8 out of 10, Good, (1,006 reviews)
"Clean room , good breakfast"
United States
Fernando
The price is ¥20,671
¥23,772 total
includes taxes & fees
Aug 13 - Aug 14
Quality Inn Old Saybrook - Westbrook

17. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (297 reviews)
"Great location in the heart of town Walk to everything Amazing breakfast too "
United States
Michael
The price is ¥176,267
¥221,523 total
includes taxes & fees
Jul 28 - Jul 29
Faraway Sag Harbor

18. Clinton Motel

Clinton Motel
2.5 star property
Clinton
8.6 out of 10, Excellent, (325 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 ¥15,005
¥17,256 total
includes taxes & fees
Aug 23 - Aug 24
Clinton Motel

19. 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, (1,003 reviews)
"It was in a good location and less expensive than area hotels."
United States
David
The price is ¥16,614
¥19,106 total
includes taxes & fees
Aug 3 - Aug 4
Pier Blue Inn Old Saybrook - Essex

20. Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook
2.0 star property
Old Saybrook
7.0 out of 10, Good, (936 reviews)
"Good area and served purpose for the price. Rooms could use some cosmetic updates."
United States
Stephanie
The price is ¥13,504
¥15,995 total
includes taxes & fees
Jul 26 - Jul 27
Super 8 by Wyndham Old Saybrook
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Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Learn more about Shelter Island

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

Find out more about Shelter Island

Top reasons to visit Shelter Island

  • Stunning Beaches: Enjoy breathtaking views and sunsets at Shelter Island's beautiful beaches, perfect for relaxation and romance.
  • Outdoor Activities: Engage in various outdoor adventures, including kayaking, golfing, and exploring bird sanctuaries.
  • Rich History: Visit the Shelter Island Historical Society to learn about the island's fascinating past and cultural heritage.
  • Charming Accommodations: Choose from cozy bed & breakfasts and unique inns that offer a memorable lodging experience.
  • Scenic Ferry Rides: Take a picturesque ferry ride to soak in the stunning landscapes and connect with nearby attractions.

Find great hotels near Shelter Island

Discover the ideal lodging for your getaway on Shelter Island, New York. From charming bed & breakfasts to cozy agritourism properties, you'll find a range of accommodations to suit your needs. Whether you're seeking pet-friendly amenities or planning a family adventure, Shelter Island offers intimate inns and guest houses that provide a unique vacation experience. Explore the inviting atmosphere of the Shelter Island House and enjoy a memorable stay on this beautiful island.

  • Sound View Greenport: A charming 3.5-star hotel, Sound View Greenport offers a delightful beach getaway just 6km from Shelter Island. With a guest rating of 8.4, this family-friendly property is tailored for those looking to enjoy sun and sand. Guests appreciate the direct access to the beach, making it easy to soak in the coastal atmosphere. The hotel is equipped with amenities for children, such as free cribs and child safety features. Additionally, the property welcomes pets, adding an extra layer of convenience for families traveling with furry friends.
  • Sag Harbor Inn: Rated at 9.4, Sag Harbor Inn is a sophisticated 3.5-star lodging located 8km from Shelter Island. This inn is particularly suited for business travelers seeking a serene environment to unwind after meetings. Guests enjoy well-appointed rooms that blend comfort with functionality, making it an ideal choice for professionals on the go. The tranquil setting and proximity to local business hubs enhance its appeal, while the attentive staff ensures a pleasant stay.
  • The Harbor Front Inn: With a guest rating of 8.8, The Harbor Front Inn is a 3.5-star hotel located just 5km from Shelter Island. This property caters to both business travelers and pet owners, allowing pets in designated areas. The inn’s inviting atmosphere, combined with beautiful waterfront views, provides a relaxing retreat after a busy day. Travelers appreciate the friendly service and the convenience of being near local attractions, making it an excellent choice for those looking to explore the area.

Where to stay near Shelter Island

Discover the charm of Shelter Island, a perfect getaway for outdoor enthusiasts and couples alike. Enjoy stunning vistas and romantic sunsets at Sunset Beach, while exploring the picturesque neighborhoods that offer a family-friendly atmosphere. Venture beyond to nearby Long Island for luxury excursions and scenic landscapes. Whether you seek adventure or relaxation, Shelter Island promises an unforgettable experience that beautifully blends history and nature.

  • Hamptons: Located 14km from Shelter Island, the Hamptons is a renowned vacation spot famous for its stunning beaches and vibrant outdoor activities. The area attracts a seasonal influx of travelers, peaking from June to August, making it a lively summer retreat. Visitors enjoy romantic beach outings, golfing, and various outdoor adventures, including skiing in the winter months. Iconic landmarks like picturesque family beaches and serene lakes make the Hamptons a perfect destination for relaxation and recreation.
  • Greenport: Just 5km away from Shelter Island, Greenport is a charming village that offers a delightful blend of outdoor and romantic experiences. With visitor numbers peaking from June to August, this city is ideal for beach lovers and those seeking a peaceful getaway. Enjoy activities such as golfing, exploring parks, and attending music concerts. Greenport's scenic beaches and family-friendly parks provide a beautiful backdrop for leisurely strolls and memorable moments, making it a must-visit spot on your vacation.
  • Sag Harbor: Situated 8km from Shelter Island, Sag Harbor is a picturesque town known for its rich maritime history and vibrant arts scene. The peak travel season runs from June to August, drawing visitors eager for outdoor adventures and beach experiences. Enjoy activities like golfing and skiing while taking in the beauty of local beaches and scenic lakes. With its charming streets lined with boutiques and eateries, Sag Harbor offers a unique mix of relaxation and culture, perfect for a romantic escape or family outing.

Things to do near Shelter Island

Shopping

For unique gifts, explore local shops like the Shelter Island Craft Shop, offering handmade items and art. If you're up for a drive, head to the nearby Greenport Village, where you’ll discover charming boutiques and markets for a wider selection of souvenirs.

Recreation

At the Shelter Island Wellness Center, indulge in rejuvenating spa treatments and yoga classes designed to enhance relaxation. Explore the serene nature trails at Mashomack Preserve for a peaceful hike and connect with the natural beauty of the island while enjoying fresh air and tranquility.

Adventure

Experience the thrill of motor racing at Riverhead Raceway, located 35km from Shelter Island, where you can enjoy exciting races and a lively atmosphere. Alternatively, head to Waterford Speedbowl, 39km away, for more adrenaline-pumping racing events and an energetic vibe that will keep you on your toes.

Nightlife

Visit the Sunset Beach for a beachfront bar experience featuring cocktails and stunning views. For a laid-back vibe, check out the Shelter Island Craft Brewery to sample local brews. If you're in the mood for dancing, head over to the Tavern on the Green for a lively atmosphere.

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

Find the best attractions in and around Shelter Island

Shelter Island offers a perfect getaway for outdoor enthusiasts and couples seeking a romantic beach vacation. Visitors can explore beautiful beaches, urban parks, and historic buildings, making it an ideal destination for those interested in culture and outdoor activities. Don't miss the Shelter Island Historical Society for a glimpse into the island's rich history. Enjoy your time soaking up the sun and exploring the unique attractions that Shelter Island has to offer.

  • East Hampton Main Beach: Located 19km from Shelter Island, this beach offers a quintessential seaside experience with golden sands and refreshing ocean waves. Enjoy sunbathing, beach volleyball, or a leisurely stroll along the shore while soaking up the vibrant beach vibes.
  • Gardiner's Bay Country Club: Nestled within Shelter Island, this golf course features stunning views of Gardiner's Bay. Golf enthusiasts can enjoy a challenging round of golf amidst beautifully manicured greens and a tranquil atmosphere, making it a perfect spot to unwind.
  • Mashomack Preserve: This urban park on Shelter Island provides a serene escape into nature with family-friendly trails and outdoor activities. Explore diverse habitats and enjoy birdwatching, hiking, or simply relaxing in a peaceful setting that highlights the beauty of the area.

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 is convenient with access through several major airports. John F. Kennedy International Airport (JFK), located 130km away, offers nearby hotels such as The William Vale and Arlo Williamsburg, both rated 5 stars and just 18km from the airport. LaGuardia Airport (LGA) is 134km from Shelter Island, with luxury options like The Plaza, A Fairmont Hotel and Hilton Club The Quin New York, both around 5 to 10km away. Additionally, Bradley International Airport (BDL) in Hartford, CT is 100km distant, featuring hotels like DoubleTree by Hilton Hartford, just 2km from the airport, providing great access for travelers.

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 Gurney's Montauk Resort & Seawater Spa and Montauk Yacht Club. See all available top hotels, or vacation rentals in Shelter Island.
What's the top vacation rental that Shelter Island has to offer?
The Hampton Sack a cheerful relaxing beach cottage: Visitors like this Shelter Island vacation home rental. It is equipped with a barbecue grill, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop. See all 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. Offers a seasonal outdoor pool, an indoor pool, and a private beach. Montauk Yacht Club 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. 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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