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Our top choices for Shelter Island hotels

1. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
10.0 out of 10, Exceptional, (191 reviews)
"We loved our stay at Silver Sands! It was off season, so very quiet."
United States
Michael
The price is Rp3.978.700
Rp4.545.846 total
includes taxes & fees
10 Dec - 11 Dec
Silver Sands Motel & Beach Bungalows

2. The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (78 reviews)
"We enjoyed our stay!"
Australia
Nicholas
The price is Rp3.272.300
Rp3.738.603 total
includes taxes & fees
19 Nov - 20 Nov
The Chequit

3. House on Chase Creek

House on Chase Creek
2.5 star property
The Heights
9.4 out of 10, Exceptional, (87 reviews)
"Such a cute place to stay! Bill was super kind and helpful! I was only in for a quick night but I would definitely stay here again!!"
United States
Tracey
The price is Rp3.343.933
Rp3.820.397 total
includes taxes & fees
11 Nov - 12 Nov
House on Chase Creek

4. Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (446 reviews)
"Great location…thoroughly enjoyed our time."
United States
Renee
The price is Rp2.930.418
Rp3.348.002 total
includes taxes & fees
11 Nov - 12 Nov
Zey Hotel

5. The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
9.0 out of 10, Wonderful, (675 reviews)
"Such a lovely place for a getaway. Charming town and lovely water views!"
United States
Laura
The price is Rp2.690.739
Rp3.590.847 total
includes taxes & fees
15 Nov - 16 Nov
The Harbor Front Inn

6. The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (197 reviews)
"Very clean, excellent staff and excellent location. All of the shops and restaurants are within walking distance, and the wineries a very short cab ride. Really enjoyed staying here and we will absolutely be back."
United States
Daniel
The price is Rp5.551.514
Rp7.156.732 total
includes taxes & fees
1 Dec - 2 Dec
The Menhaden

7. Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (767 reviews)
"The ambience is amazing! We loved our stay!!"
United States
Christine
The price is Rp2.793.807
Rp3.708.546 total
includes taxes & fees
11 Nov - 12 Nov
Sound View Greenport

8. Oyster Estate

Oyster Estate
4.0 star property
Greenport
9.2 out of 10, Wonderful, (302 reviews)
"convenient location, clean & updated room. great stay :)"
United States
Jacqueline
The price is Rp3.400.732
Rp4.284.742 total
includes taxes & fees
15 Nov - 16 Nov
Oyster Estate

9. The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (350 reviews)
"Very clean property, beautiful view, and quiet."
United States
Masayo
The price is Rp3.355.329
Rp4.285.689 total
includes taxes & fees
11 Nov - 12 Nov
The Shoals Suites and Slips

10. Seven - A Resort Style Inn

Seven - A Resort Style Inn
2.0 star property
Shelter Island Heights
The price is Rp6.886.482
Rp7.867.806 total
includes taxes & fees
24 Nov - 25 Nov
Seven - A Resort Style Inn

11. American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (208 reviews)
"Great location, very friendly and helpful "
United States
Mary
The price is Rp4.536.721
Rp5.906.601 total
includes taxes & fees
12 Nov - 13 Nov
American Beech Hotel

12. Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (687 reviews)
"The room was nicely appointed; sufficient parking; close to downtown; and a nice variety for breakfast."
United States
Annie
The price is Rp3.961.491
Rp4.526.004 total
includes taxes & fees
11 Nov - 12 Nov
Sag Harbor Inn

13. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (299 reviews)
"Great condo. Very nice location and grounds."
United States
William
The price is Rp3.595.912
Rp6.115.348 total
includes taxes & fees
12 Nov - 13 Nov
Cliffside Resort Condominiums

14. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (73 reviews)
"Everything was perfect 💞"
United States
Altynai
The price is Rp5.810.710
Rp6.638.735 total
includes taxes & fees
19 Nov - 20 Nov
North Fork Resort

15. Faraway Sag Harbor

Faraway Sag Harbor
4.0 star property
Sag Harbor
9.0 out of 10, Wonderful, (321 reviews)
"Great location , wonderful lobby bar Cute rooms"
United States
Thomas
The price is Rp5.859.540
Rp7.364.031 total
includes taxes & fees
7 Dec - 8 Dec
Faraway Sag Harbor

16. Water's Edge Resort & Spa

Water's Edge Resort & Spa
3.5 star property
Westbrook Center
8.8 out of 10, Excellent, (1,009 reviews)
"Beautiful setting, good food, friendly staff. Will definitely stay again"
United States
cynthia
The price is Rp2.942.669
Rp3.696.104 total
includes taxes & fees
12 Nov - 13 Nov
Water's Edge Resort & Spa

17. Saybrook Point Resort & Marina

Saybrook Point Resort & Marina
3.5 star property
Old Saybrook Center
9.6 out of 10, Exceptional, (1,001 reviews)
"Location was amazing and restaurant was great"
United States
Jenny
The price is Rp4.865.941
Rp6.228.947 total
includes taxes & fees
18 Nov - 19 Nov
Saybrook Point Resort & Marina

18. A Room At The Beach

A Room At The Beach
3.0 star property
Bridgehampton
9.2 out of 10, Wonderful, (106 reviews)
"We loved this place! Gorgeous, well-appointed, clean, charming, staff friendly and helpful."
United States
Annabel
The price is Rp5.354.969
Rp6.117.975 total
includes taxes & fees
11 Nov - 12 Nov
A Room At The Beach

19. Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa
4.0 star property
Montauk
8.2 out of 10, Very good, (878 reviews)
"Exceptional service. Always a pleasure to visit!"
United States
Amanda
The price is Rp7.145.155
Rp9.796.052 total
includes taxes & fees
24 Nov - 25 Nov
Gurney's Montauk Resort & Seawater Spa

20. Topping Rose House

Topping Rose House
4.5 star property
Bridgehampton
9.0 out of 10, Wonderful, (165 reviews)
"Incredible stay. Going back in the fall"
United States
Adam
The price is Rp11.312.167
Rp12.987.449 total
includes taxes & fees
11 Nov - 12 Nov
Topping Rose House
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.

Where to stay in Shelter Island

Find the best Shelter Island areas 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 area 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.

Coecles Harbor

Coecles Harbour 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 area balances authentic maritime character with holiday 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.

Menantic Creek

Menantic Creek on Shelter Island offers a peaceful waterfront escape where natural beauty takes centre 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 area 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.

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 centre 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 coastal landscape with a lake, dense greenery, and a sunset sky.

Top Shelter Island Hotel Reviews

Find out more about Shelter Island

Top reasons to visit Shelter Island

  • Stunning Beaches: Shelter Island boasts picturesque beaches perfect for relaxation and romantic escapes.
  • Outdoor Activities: Enjoy a variety of outdoor adventures, including kayaking, golf, and scenic ferry rides.
  • Rich History: Visit the Shelter Island Historical Society to learn about the island's local heritage.
  • Charming Accommodation: Choose from delightful bed & breakfasts and intimate inns that cater to all types of travellers.
  • Relaxing Retreats: Experience serene atmospheres at retreats like Sunset Beach, ideal for unwinding.

Find great hotels near Shelter Island

Discover a range of delightful accommodation options on Shelter Island, New York, ideal for an unforgettable holiday. From charming bed & breakfasts to intimate inns and agritourism properties, you'll find the perfect retreat for your family vacation or adventure. Many hotels offer pet-friendly services, ensuring your furry companions are welcome too. Explore the amenities at Shelter Island House and more to create a memorable getaway in this picturesque destination.

  • Sound View Greenport: A charming 3.5-star hotel with a rating of 8.4, Sound View Greenport is an ideal choice for families and pet owners seeking a beachside retreat. Located 6km from Shelter Island, this property offers direct beach access, making it a prime spot for sun and sand. Families will appreciate the thoughtful amenities for children, such as complimentary cribs and safety features like window guards. Additionally, the hotel welcomes pets with specific policies, allowing dogs and cats to join in on the holiday fun, with waived fees for service animals.
  • Sag Harbor Inn: With a distinguished rating of 9.4, Sag Harbor Inn stands out as a premium 3.5-star accommodation, located 8km from Shelter Island. This hotel caters to business travellers, providing a professional environment with all the necessary amenities for a productive stay. Guests can expect a comfortable atmosphere, ideally suited for those on work-related trips. Its proximity to local business hubs makes it a convenient choice, while maintaining a tranquil setting away from the hustle and bustle.
  • The Harbor Front Inn: The Harbour Front Inn, rated 8.8 stars, is a delightful option located 5km from Shelter Island, appealing to both business and pet-friendly travellers. This 3.5-star property allows pets, ensuring that furry companions are welcome, with specific amenities for dogs and service animals. The Inn combines comfort with a focus on business needs, making it a practical choice for those who require a balance of work and relaxation. Guests can enjoy picturesque views and a warm atmosphere that enhances their stay.

Where to stay near Shelter Island

During your vacation on Shelter Island, New York, you'll find a charming mix of outdoor adventures and romantic beach escapes. Explore the picturesque scenery and historical sites that define the island's allure. Nearby Long Island offers family-friendly excursions and luxurious experiences, while Sunset Beach provides a serene atmosphere for relaxation. Whether you seek budget-friendly options or upscale amenities, Shelter Island promises an unforgettable getaway for all types of travellers.

  • Hamptons: Located a mere 14km from Shelter Island, the Hamptons is a renowned summer getaway that offers a blend of stunning beaches and outdoor activities. The area attracts visitors primarily from June to August, drawn by its romantic atmosphere and vibrant beach culture. Enjoy a round of golf, take in the scenic views from the local lakes, or unwind at family-friendly beaches. The Hamptons is a perfect destination for those looking to indulge in a mix of relaxation and adventure, with a variety of dining and entertainment options that reflect its upscale charm.
  • Greenport: Just 5km from Shelter Island, Greenport is a picturesque village that exudes a quaint charm. Known for its outdoor activities and romantic settings, this vibrant city sees a seasonal influx of tourists, particularly between June and August. Stroll along the waterfront, enjoy musical concerts, and explore the local parks, which offer ample space for picnicking and recreation. With its beautiful beaches and inviting atmosphere, Greenport is the ideal spot for a leisurely escape, where you can immerse yourself in the natural beauty and community spirit of the area.
  • Sag Harbor: Located 8km from Shelter Island, Sag Harbor is a historic whaling village that combines rich history with modern allure. It attracts visitors seasonally, especially during the summer months, thanks to its stunning beaches and outdoor experiences. Visitors can indulge in various activities, from golfing to enjoying the serene lakeside views. The town is also known for its charming streets lined with shops and eateries, making it a delightful destination for those seeking both relaxation and cultural exploration amidst a romantic backdrop.

Things to do near Shelter Island

Shopping

For shopping on Shelter Island, visit local boutiques like The Islander for unique gifts and handmade items. If you're up for a drive, check out the Greenport Village area, where you’ll find charming shops and galleries showcasing local art and crafts.

Recreation

On Shelter Island, the Spa at the Chequit offers rejuvenating treatments amidst a serene atmosphere, ideal for relaxation. For outdoor enthusiasts, the Shelter Island Tennis Club provides a vibrant environment for recreational play, while the Ram’s Head Inn features scenic views perfect for leisurely strolls and unwinding by the water.

Adventure

Experience the thrill of motor racing at Riverhead Raceway, located 35km from Shelter Island, where the excitement of speed and competition fills the air. Alternatively, visit Waterford Speedbowl, 39km away, to immerse yourself in another exhilarating motor racing venue with a vibrant sports atmosphere.

Nightlife

Experience Shelter Island's nightlife at the lively Sunset Beach, where you can enjoy cocktails by the shore. Alternatively, visit the charming Chequit Inn for a cosy atmosphere and local brews, perfect for unwinding after a day of exploration.

*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 Shelter Island

Shelter Island is an idyllic destination for outdoor enthusiasts and romantic beach getaways. Visitors can explore a variety of attractions, including scenic beaches, urban parks, and historic buildings, offering a rich blend of culture and nature. A visit to the Shelter Island Historical Society is also recommended for those keen on local history. This charming locale provides an enriching experience for all travellers seeking a delightful escape.

  • Gardiner's Bay Country Club: Nestled within Shelter Island, this golf course offers stunning views of Gardiner's Bay. Enjoy a leisurely round of golf amidst lush greenery and serene landscapes, making it a delightful experience for both seasoned players and novices alike.
  • Shell Beach: A charming beach on Shelter Island, Shell Beach invites visitors to unwind and soak up the sun. With its soft sands and tranquil waters, it's an idyllic spot for leisurely strolls or simply basking in the beach vibes.
  • Mashomack Preserve: This expansive urban park features diverse landscapes perfect for outdoor adventures. Families can explore scenic trails, observe wildlife, and enjoy the natural beauty, providing a refreshing escape from city life.

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 MonthTemperaturePrecipitationCloudinessOccupancyPricing
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 from the major airports is quite easy. New York, NY (JFK-John F. Kennedy Intl.) is situated 130km away, with excellent hotel options like The William Vale and Arlo Williamsburg, both 18km from the airport. Another option is New York, NY (LGA-LaGuardia), located 134km away, where you may consider staying at Hilton Club The Quin New York or The Plaza, A Fairmont Hotel, both 5 to 10km from the airport. Additionally, White Plains, NY (HPN-Westchester County) is 114km away, with top hotels such as The Opus Westchester and Sonesta White Plains Downtown, just 6km from HPN, offering convenient transport services.

Frequently Asked Questions

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: Resort, 13-minute walk from The Hamptons Beaches. Offers a seasonal outdoor pool, an indoor pool and a private beach. Offshore Montauk and Water's Edge Resort & Spa 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 101 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 Mashomack Preserve, Sunset Beach and Wades Beach. A couple of additional sights to add to your itinerary are Shelter Island Historical Society and Crescent Beach. 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.

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 traveller data. Other good choices for your stay in the area are Gurney's Montauk Resort & Seawater Spa and Offshore Montauk. See all available top hotels, or vacation rentals in Shelter Island.