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Our top choices for Shelter Island hotels

Sound View Greenport

Sound View Greenport
4.0 star property
Greenport
8.4 out of 10, Very good, (641 reviews)
"Loved our stay. Our room was gorgeous a s in the perfect location. Would recommend and plan on coming back in the future!"
United States
Tara
The price is CA $348
CA $514 total
includes taxes & fees
May 14 - May 15
Sound View Greenport

The Harbor Front Inn

The Harbor Front Inn
3.5 star property
Greenport
8.8 out of 10, Excellent, (594 reviews)
"Really nice property!"
United States
RITA
The price is CA $294
CA $406 total
includes taxes & fees
May 19 - May 20
The Harbor Front Inn

Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
4.0 star property
Greenport
9.8 out of 10, Exceptional, (152 reviews)
"Everything was excellent, best hotel on the north fork. "
United States
Dan
Silver Sands Motel & Beach Bungalows

The Pridwin Hotel

The Pridwin Hotel
4.0 star property
Shelter Island Heights
9.6 out of 10, Exceptional, (84 reviews)
"Overall the places is nice, clean and great views"
United States
Dianne
The price is CA $455
CA $572 total
includes taxes & fees
May 17 - May 18
The Pridwin Hotel

The Shoals Suites and Slips

The Shoals Suites and Slips
3.5 star property
Southold
9.4 out of 10, Exceptional, (265 reviews)
"Great rooms!"
United States
Susan
The price is CA $232
CA $299 total
includes taxes & fees
May 4 - May 5
The Shoals Suites and Slips

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.0 out of 10, Very good, (37 reviews)
"Great property! Close to beach and super clean. "
United States
Leslie
The price is CA $299
CA $342 total
includes taxes & fees
May 31 - Jun 1
West Neck Guesthouse

The Menhaden

The Menhaden
3.5 star property
Greenport
9.6 out of 10, Exceptional, (180 reviews)
"Excellent reception staff - very attentive and responsive. "
United States
David
The price is CA $505
CA $631 total
includes taxes & fees
May 3 - May 4
The Menhaden

The Chequit

The Chequit
3.0 star property
The Heights
9.0 out of 10, Wonderful, (37 reviews)
"Always a sold stay on Shelter Island"
United States
Peter
The Chequit

Harbor Knoll Bed & Breakfast

Harbor Knoll Bed & Breakfast
3.0 star property
Pipes Cove
9.2 out of 10, Wonderful, (12 reviews)
"Charming bed and breakfast in a great location right on the water…perfect for a romantic getaway!"
United States
Anthony
Harbor Knoll Bed & Breakfast

Stirling House Bed & Breakfast

Stirling House Bed & Breakfast
3.0 star property
Greenport
9.8 out of 10, Exceptional, (24 reviews)
"This was a great place to stay with old word charm. If you are looking for a quiet getaway with a beautiful view of the ocean this is it. The breakfast that we had were much better that what you could get in town. My wife and I can't wait to go back."
United States
steve
Stirling House Bed & Breakfast

American Beech Hotel

American Beech Hotel
3.5 star property
Greenport
9.0 out of 10, Wonderful, (200 reviews)
"Great location! Very clean! "
United States
Elizabeth
The price is CA $491
CA $616 total
includes taxes & fees
May 4 - May 5
American Beech Hotel

Zey Hotel

Zey Hotel
3.5 star property
Greenport
9.2 out of 10, Wonderful, (299 reviews)
"amazing stay! "
United States
Lauren
The price is CA $443
CA $506 total
includes taxes & fees
May 7 - May 8
Zey Hotel

Arbor View House B&B

Arbor View House B&B
3.5 star property
East Marion
9.2 out of 10, Wonderful, (15 reviews)
"Two mid age couples just had a good and relaxing time with great hospitality. "
United States
Michail
Arbor View House B&B

Shelter Island House

Shelter Island House
3.5 star property
Shelter Island Heights
8.4 out of 10, Very good, (57 reviews)
"One staff member was there to check us in. He was helpful in bringing our bags to our room. He also suggested several restaurants for us to try."
United States
Joseph
The price is CA $275
CA $315 total
includes taxes & fees
May 17 - May 18
Shelter Island House

Hotel Moraine

Hotel Moraine
2.0 star property
Greenport
9.8 out of 10, Exceptional, (22 reviews)
"Our 3rd stay - we love the beauty of the property and the luxurious serenity of this boutique hotel. Great views of the water; fantastic large pool and lounging areas."
United States
Amy
Hotel Moraine

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (251 reviews)
"Convenient parking and proximity to all."
United States
Rosemaria
The price is CA $275
CA $374 total
includes taxes & fees
May 31 - Jun 1
Cliffside Resort Condominiums

Montauk Blue Hotel

Montauk Blue Hotel
2.0 star property
Downtown Montauk
9.2 out of 10, Wonderful, (195 reviews)
"Great view of sunrise and sunset "
United States
Christopher
The price is CA $172
CA $248 total
includes taxes & fees
May 6 - May 7
Montauk Blue Hotel

Sag Harbor Inn

Sag Harbor Inn
3.5 star property
Sag Harbor
9.4 out of 10, Exceptional, (605 reviews)
"Clean room, nice breakfast options."
United States
Annie
The price is CA $349
CA $399 total
includes taxes & fees
May 3 - May 4
Sag Harbor Inn

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
Oyster Estate

A Room At The Beach

A Room At The Beach
3.0 star property
Bridgehampton
9.2 out of 10, Wonderful, (92 reviews)
"Adorable boutique hotel!"
United States
Julianne
The price is CA $778
CA $889 total
includes taxes & fees
May 3 - May 4
A Room At The Beach
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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 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 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.

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.

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Find out more about Shelter Island

Top reasons to visit Shelter Island

  • Stunning Beaches: Enjoy picturesque beaches like Sunset Beach and Crescent Beach, perfect for relaxation and scenic views.
  • Outdoor Adventures: Experience activities such as golf, movie nights under the stars, and exploring charming parks.
  • Romantic Getaways: Ideal for couples, offering a blend of luxurious experiences and intimate retreats.
  • Cultural Exploration: Discover historic sites and local events, enriching your visit with unique island vibes.
  • Diverse Accommodations: Choose from charming bed & breakfasts to pet-friendly lodging, catering to all types of travellers.

Find great hotels near Shelter Island

Discover the charm of Shelter Island, New York, with a range of accommodations that cater to every type of traveller. From inviting bed and breakfast options to unique agritourism properties, you'll find the perfect spot for a memorable family vacation. Many hotels are pet-friendly and offer adventure-filled experiences, ensuring that your stay is both comfortable and enjoyable. Explore the diverse lodging options that Shelter Island has to offer for an unforgettable getaway.

  • Sound View Greenport: A 3.5-star hotel with an impressive guest rating of 8.4, Sound View Greenport is a delightful choice for families and pet owners seeking a beach getaway. Located 6.4km from Shelter Island, this property boasts direct beach access, making it perfect for sun-seekers and water enthusiasts. The hotel provides thoughtful amenities for children, including free cribs and window guards for safety. Pet-friendly policies ensure that your furry companions can join you on your vacation, with specific allowances for dogs and cats. With a welcoming atmosphere and family-oriented services, Sound View Greenport is an ideal destination for a memorable seaside retreat.
  • Sag Harbor Inn: Rated at 3.5 stars and with an exceptional guest rating of 9.4, Sag Harbor Inn is situated 8.0km from Shelter Island, making it an excellent base for business travellers. The hotel’s inviting atmosphere and top-notch service cater to professionals seeking comfort and convenience. While the focus is on business travel, the inn's charming surroundings and close proximity to local attractions provide a perfect balance for relaxation after a day of meetings. Guests appreciate the well-maintained facilities and attentive staff, ensuring a pleasant stay for those on the go.
  • The Harbor Front Inn: This 3.5-star inn boasts a commendable guest rating of 8.8 and is located 4.8km from Shelter Island. The Harbor Front Inn is tailored for both pet-friendly travellers and those on business trips. With amenities that allow pets in rooms and a welcoming stance towards service animals, it’s a great choice for those who wish to travel with their furry friends. The inn combines comfort with practicality, making it an ideal retreat for business guests who also want to enjoy the scenic waterfront views. With its attentive staff and quality facilities, The Harbor Front Inn promises a satisfying stay.

Where to stay near Shelter Island

Discover the charm of Shelter Island, where outdoor adventures and romantic beach vacations await. This picturesque destination boasts stunning scenery and rich history, making it perfect for family-friendly excursions or luxurious getaways. Enjoy the unique atmosphere of nearby cities and neighborhoods, offering a blend of budget-friendly options and upscale experiences. Shelter Island's traditions and convenient location make it an ideal base for exploring the best places this beautiful region has to offer.

  • Hamptons: Nestled 14.5km from Shelter Island, the Hamptons are a renowned getaway known for their stunning beaches and vibrant outdoor scene. This region sees a surge in visitors from June to August, drawn by its romantic ambiance and various activities. Golf enthusiasts can enjoy local courses, while winter visitors can embrace the ski fields. With charming family beaches and picturesque lakes, the Hamptons offer a diverse range of experiences, ensuring relaxation and adventure for all types of travellers.
  • Greenport: Located a mere 4.8km from Shelter Island, Greenport is a charming city that captures the essence of coastal living. The visitor influx peaks during the summer months, offering outdoor enthusiasts a plethora of activities. With beautiful parks and family-friendly beaches, it's an ideal spot for picnics or leisurely strolls. Music concerts and recreational areas enhance the cultural experience, making Greenport a delightful blend of romance and relaxation amidst its scenic backdrop.
  • Noyack: Just 8.0km from Shelter Island, Noyack is a picturesque village perfect for those seeking an outdoor escape. Like its neighbours, Noyack enjoys a seasonal influx of visitors, especially during the summer. With access to beautiful beaches and serene lakes, it’s a romantic getaway that also caters to golf lovers and winter sports enthusiasts. The village's laid-back vibe combined with its scenic beauty makes Noyack a must-visit for a tranquil yet engaging holiday experience.

Things to do in Shelter Island

Discover the charm of Shelter Island, New York, perfect for outdoor and romantic beach getaways. Enjoy activities like golfing, windsurfing, and tennis. Take a scenic boat tour or experience the excitement of Splish Splash water park. Don't miss wellness packages to relax and rejuvenate during your visit, and keep an eye out for lively music concerts that add to the island's vibrant atmosphere.

Shopping

In Shelter Island, visit local shops like the Shelter Island Craft Shop for unique handmade gifts and souvenirs. For a broader shopping experience, if you're up for a drive, check out The Shops at East Wind, located 24.1km away, featuring various boutiques and specialty stores.

Recreation

Experience tranquility at the Shelter Island Meditation Retreat, where guided sessions enhance mindfulness amid serene nature. For rejuvenation, visit the Spa at Shelter Island, offering holistic treatments like massages and facials, perfect for unwinding after a day of exploring the island's beautiful beaches and lush trails.

Adventure

Explore the picturesque landscapes of Shelter Island by kayaking through its serene waters or hiking the trails of Mashomack Preserve, where you can encounter diverse wildlife. For a thrilling experience, try stand-up paddleboarding, offering a unique view of the island’s natural beauty.

Nightlife

The nightlife on Shelter Island offers a relaxed yet vibrant atmosphere. Enjoy cocktails at the charming Sunset Beach Hotel, or unwind at the rustic Islander, where live music often creates a lively backdrop for an enjoyable evening out. Each venue embodies the island's unique coastal charm.

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

Booking tips and Expedia advantages for Shelter Island

  • 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 Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to refine your preferences, such as your budget, desired location, and the type of hotel you envision. For instance, selecting the Eco-certified option will showcase sustainable and environmentally friendly hotels currently available. To find the best prices and offers, simply sort the price filter from lowest to highest.
  • Consider bundling your trip: You can save some money by combining your Shelter Island hotel reservation with your flights and activities by booking a package through Expedia.

Find the best attractions in Shelter Island

Whether you're seeking a romantic getaway or an adventurous outdoor experience, Shelter Island offers a perfect blend of beach vacations and cultural exploration. You can enjoy stunning locations such as Sunset Beach, Crescent Beach, and Indian Wells Beach, along with scenic waterfront views and historic sites. With its charming urban parks and beautiful landscapes, Shelter Island caters to every traveler's desire for relaxation and adventure.

  • Gardiner's Bay Country Club: Experience the elegance of this picturesque golf course, nestled within Shelter Island. With stunning views of Gardiner's Bay, it's an ideal spot for both seasoned golfers and beginners looking to enjoy a round amidst beautiful landscapes.
  • Shell Beach: Relax and soak up the sun at Shell Beach, where you can enjoy the calming beach vibes. Perfect for sunbathing, swimming, or beachcombing, it's a serene escape for those looking to unwind by the water.
  • Mashomack Preserve: Explore the natural beauty of Mashomack Preserve, an urban park that offers a blend of family-friendly activities and outdoor adventures. Wander through its scenic trails and enjoy birdwatching and picnicking in this peaceful haven.

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.

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

Visiting Shelter Island, New York, is convenient with major airports like JFK and LaGuardia. JFK Airport, located 130.4km away, offers luxurious accommodations such as Arlo Williamsburg, The William Vale, and The Boro Hotel, all within 17.7km. LaGuardia Airport is slightly farther at 133.6km, with top hotels nearby including The Plaza - A Fairmont Managed Hotel and The Pierre, both 5-star rated just 8.0km away. Lastly, Bradley International Airport in Hartford, CT, is 99.8km from Shelter Island, featuring options like the DoubleTree by Hilton and Simsbury 1820 House, making your travel seamless and enjoyable.

Frequently asked questions

What is the best area to stay in Shelter Island?
The best area to stay on Shelter Island is the main village of Shelter Island Heights for its convenience and access to amenities.

Shelter Island Heights is the island's commercial centre, offering a mix of shops, restaurants, and hotels. It's well-connected by ferry to Greenport on the North Fork, making it an ideal base for exploring both sides of the Peconic Bay. The area is very walkable, with most establishments clustered around the main streets leading from the ferry terminal.

For couples seeking a refined and relaxed getaway, Shelter Island Heights offers elegant boutique hotels and fine dining options. You'll find art galleries and charming local shops, great for leisurely strolls. The easy access to the ferry also makes day trips to Greenport's vineyards and breweries very straightforward.

Families will also appreciate Shelter Island Heights for its practical location. There are ice cream parlours and family-friendly eateries within easy reach.
What are the best family hotels in Shelter Island?
For families visiting Shelter Island, the Sunset Beach Hotelis an excellent choice.

This highly-rated hotel, with a 9.2 review score, is particularly well-suited for families. It offers a range of family-friendly amenities including complimentary cots, beach toys, and games for children. There is also onsite babysitting and childcare services available, providing convenience for parents. The hotel is incredibly well-located, being just 0.1 km from Sunset Beach and 0.5 km from Crescent Beach, making it easy to enjoy the local surroundings. Find more child-friendly accommodations in Shelter Island
What are the best spa hotels in Shelter Island?
For a top-rated spa hotel in Shelter Island, the Sunset Beach Hotelis an excellent choice.

This hotel, with a superb 9.2 rating, offers a wonderful range of amenities to enhance your spa experience. Guests can enjoy massages on the beach, as well as general massage services, and the rooms feature designer toiletries, Frette Italian sheets, luxurious bathrobes, and comfortable premium bedding. The hotel also provides champagne service and air conditioning for added comfort. It is conveniently located just 0.5 km from Crescent Beach and 0.7 km from Shelter Island Country Club. See all spa hotels in Shelter Island
What are the top pet-friendly hotels in Shelter Island?
For a top pet-friendly hotel in Shelter Island, the Sunset Beach Hotelis an outstanding choice.

The Sunset Beach Hotel, with an excellent rating of 9.2, is highly recommended for travellers with pets. It not only permits pets but also provides thoughtful amenities such as food and water bowls, ensuring your furry companions are well catered for. The hotel is wonderfully located, just 0.1 km from Sunset Beach and 0.5 km from Crescent Beach, offering easy access for walks and seaside enjoyment. Guests can also indulge in massages on the beach, adding to a relaxing stay for both you and your pet. See more pet-friendly hotels in Shelter Island
What are the best budget hotels in Shelter Island?
For a budget-friendly hotel in Shelter Island, the Sunset Beach Hotelis an excellent choice.

This hotel, with a superb 9.2 rating, offers complimentary WiFi and free self-parking, which adds to its value. Guests can also enjoy massages directly on the beach, providing a relaxing experience. Its location is a key highlight, being just 0.1 km from Sunset Beach and 0.5 km from Crescent Beach, making it very convenient for beach lovers. View all budget hotels in Shelter Island
What are the best hotels in Shelter Island near Crescent Beach?
For a wonderful stay near Crescent Beach in Shelter Island, the Sunset Beach Hotelis an excellent choice.

This highly-rated hotel, with a superb 9.2 review score, is conveniently located just 0.5 km from Crescent Beach. It is also only 0.1 km from Sunset Beach. Guests with families will like the range of amenities, including free cribs, beach toys, and other toys and games specifically for children. On-site babysitting and childcare services are also available, providing added convenience for parents.
When is the best time to go to Shelter Island?
The best time to visit Shelter Island is during the summer months, from June to August, when the weather is warm and all the island's amenities are in full swing.

For those seeking a classic summer holiday experience, July and August offer the warmest temperatures, superb for enjoying the beaches and water activities. You'll find all the restaurants and shops open, and there's a lively, yet relaxed, atmosphere across the island. This period is ideal for families and couples looking for a traditional seaside escape with plenty of sunshine.

If you prefer a slightly quieter visit with pleasant weather and fewer crowds, late May and early June, or early September, are also excellent choices. The weather is still lovely, most establishments are open, and you can experience the island's natural beauty with a bit more tranquility.
Can I cancel my hotel reservation on Expedia?
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Shelter Island.
How can I save on a Shelter Island hotel booking with Expedia?
Members always get our best prices. Find our best Shelter Island hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings.
How much is the nightly rate at a Shelter Island hotel?
Prices for hotels in Shelter Island often vary, but you can find a great deal from CA $109 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.

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