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Our top choices for Shelter Island hotels

1. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
John
₩380,214
₩505,152 total
includes taxes & fees
Sep 8 - Sep 9
The Harbor Front Inn

2. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
₩435,268
₩497,300 total
includes taxes & fees
Sep 1 - Sep 2
Shelter Island House

3. House on Chase Creek

House on Chase Creek
The Heights
United States
Calvin
₩338,167
₩386,353 total
includes taxes & fees
Sep 8 - Sep 9
House on Chase Creek

4. Zey Hotel

Zey Hotel
Greenport
United States
shaun
₩278,709
₩318,426 total
includes taxes & fees
Sep 8 - Sep 9
Zey Hotel

5. Oyster Estate

Oyster Estate
Greenport
United States
Jenny
₩447,998
₩564,455 total
includes taxes & fees
Sep 7 - Sep 8
Oyster Estate

6. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sol
₩543,654
₩621,128 total
includes taxes & fees
Sep 22 - Sep 23
Silver Sands Motel & Beach Bungalows

7. The Chequit

The Chequit
The Heights
United States
Kathleen
₩402,580
₩459,949 total
includes taxes & fees
Sep 8 - Sep 9
The Chequit

8. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Anna
₩738,832
₩928,527 total
includes taxes & fees
Sep 14 - Sep 15
The Pridwin Hotel

9. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Loretta
₩487,224
₩556,654 total
includes taxes & fees
Sep 20 - Sep 21
Sag Harbor Inn

10. The Menhaden

The Menhaden
Greenport
United States
Lisa
₩604,378
₩745,550 total
includes taxes & fees
Aug 30 - Aug 31
The Menhaden

11. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Maria
₩401,567
₩493,314 total
includes taxes & fees
Sep 1 - Sep 2
The Shoals Suites and Slips

12. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
Theresa
₩139,217
₩160,100 total
includes taxes & fees
Sep 27 - Sep 28
Quality Inn Old Saybrook - Westbrook

13. Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex
Saybrook Manor
United States
Egor
₩121,436
₩139,651 total
includes taxes & fees
Aug 30 - Aug 31
Pier Blue Inn Old Saybrook - Essex

14. American Beech Hotel

American Beech Hotel
Greenport
United States
kerri
₩510,347
₩638,113 total
includes taxes & fees
Sep 8 - Sep 9
American Beech Hotel

15. Sound View Greenport

Sound View Greenport
Greenport
United States
Suzanne
₩403,611
₩579,065 total
includes taxes & fees
Sep 15 - Sep 16
Sound View Greenport

16. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
₩415,696
₩597,621 total
includes taxes & fees
Sep 27 - Sep 28
Cliffside Resort Condominiums

17. Clinton Motel

Clinton Motel
Clinton
United States
Selena
₩109,095
₩125,459 total
includes taxes & fees
Aug 31 - Sep 1
Clinton Motel

18. The Captain Stannard

The Captain Stannard
Westbrook Center
United States
Deborah
₩321,953
₩357,368 total
includes taxes & fees
Aug 31 - Sep 1
The Captain Stannard

19. Water's Edge Resort & Spa

Water's Edge Resort & Spa
Westbrook Center
United States
Thomas
₩320,825
₩392,697 total
includes taxes & fees
Sep 16 - Sep 17
Water's Edge Resort & Spa

20. North Fork Resort

North Fork Resort
Greenport
United States
Lisa
₩442,218
₩505,234 total
includes taxes & fees
Sep 14 - Sep 15
North Fork Resort
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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

A clear blue sea with a wooden pier extending into the water, a sailboat in the distance, and a person standing in the water.

Wades Beach

10.0/10 (1 review)
Wades Beach offers calm, shallow waters and a broad sandy shoreline perfect for families seeking safe swimming. Lifeguards patrol in summer, and the pavilion provides a comfortable spot to enjoy the tranquil setting.
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A close-up of a beach with various shells and pebbles.

Shell Beach

10.0/10 (1 review)
This peaceful shoreline offers a tranquil escape with abundant shells and wildflowers framing its natural beauty. Enjoy both calm harbor waters and more dynamic waves, perfect for beachcombing and wildlife spotting.
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Shelter Island Historical Society

8.0/10 (1 review)
This historic museum preserves Shelter Island's maritime heritage through artifacts and photographs. Explore special exhibits or attend seasonal events celebrating local culture.
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Mashomack Preserve

Explore 2,039 acres of pristine wilderness across diverse ecosystems at Mashomack Preserve. The 20+ miles of trails offer intimate encounters with over 200 bird species in tidal creeks, oak forests, and marshes.
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Gardiner's Bay Country Club

This historic 1896 golf club showcases rolling fairways with stunning views of Gardiner's Bay and Coecles Harbor. Members enjoy challenging play on the Seth Raynor-influenced course and refined dining in the clubhouse.
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Menhadden Lane Beach

8.8/10 (3 reviews)
This tranquil beach on Shelter Island's east side offers serene views of Gardiner's Bay and the 'Bug' Lighthouse. Bring a blanket, find a quiet spot, and watch sailboats glide across the pristine waters.
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Havens House

Built in 1743, Havens House served as a store, tavern, school, and post office before becoming the Shelter Island Historical Society. Explore its wide plank floors and exhibits showcasing the island's unique heritage.
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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.

See all hotels in Shelter Island
A wooden gazebo by a pond with a large tree trunk nearby.

Top Shelter Island Hotel Reviews

 Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"A short stay to visit our daughter turned into a mini vacation. Lovely grounds comfortable and clean amenities, all well maintained. Did not see staff in person but responsive by text and phone."
Maria 2-night trip
Posted 3 hours ago
Hampton's Vacation Inn
Budget Host East End

Budget Host East End

10/10 Excellent
"Todo me gustó bonito lugar para ospedarse"
Walter 1-night trip
Posted 16 hours ago
Budget Host East End
Kenny's Tipperary Inn

Kenny's Tipperary Inn

10/10 Excellent
"Wonderful, friendly staff. Had given us beach passes. Loved eating breakfast in the zen garden"
Barbara 1-night trip
Posted 17 hours ago
Kenny's Tipperary Inn
Montauk Yacht Club

Montauk Yacht Club

10/10 Excellent
"All was perfect. Very family friendly. Restaurant on property was amazing. Convenient to all."
Geoff 3-night trip
Posted 20 hours ago
Montauk Yacht Club
Marram

Marram

10/10 Excellent
"none"
ITALO 1-night trip
Posted 21 hours ago
Marram
Offshore Montauk

Offshore Montauk

10/10 Excellent
"Beautiful property in an excellent location. Across the street from a beautiful beach where there are very helpful and friendly staff to set up your beach chairs and umbrellas. The hotel feels new with a beautiful wellness center with showers, a gym, saunas and cold plunges. The rooms are very clean and spacious. Worth the price"
Rosanne 2-night trip
Posted 2 days ago
Offshore Montauk
Montauk Manor

Montauk Manor

10/10 Excellent
"I really liked the hotel. They were friendly and knowledgeable. Breakfast was good and healthy. The jacuzzi was just what I needed. Shuttle service was very good. Loved the deer spotting and sunset viewing. Very good room service."
Louis 2-night trip
Posted 3 days ago
Montauk Manor
Sound View Greenport

Sound View Greenport

10/10 Excellent
"Front desk team super nice and accommodating!"
Aldo 1-night trip
Posted 3 days ago
Sound View Greenport
The Pridwin Hotel

The Pridwin Hotel

8/10 Good
"lovely place. Had an issue with my AC and there was nobody around to fix it"
Harris 2-night trip
Posted 4 days ago
The Pridwin Hotel

More cheap stays in Shelter Island

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

1430 Boston Post Rd Old Saybrook CT
₩121,436
₩139,651 total
Aug 30 - Aug 31
includes taxes & fees
8/10 Very Good! (1,002 reviews)
Pier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT
₩139,217
₩160,100 total
Sep 27 - Sep 28
includes taxes & fees
Quality Inn Old Saybrook - Westbrook
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
₩169,161
₩193,266 total
Sep 10 - Sep 11
includes taxes & fees
6.8/10 (868 reviews)
Budget Host East End
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
₩204,581
₩268,143 total
Sep 28 - Sep 29
includes taxes & fees
The Bentley Hotel Southampton
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
₩246,502
₩316,035 total
Sep 28 - Sep 29
includes taxes & fees
7.2/10 Good! (1,000 reviews)
The Atlantic Hotel
 Hampton's Vacation Inn

Hampton's Vacation Inn

177 West Montauk Highway Hampton Bays NY
₩279,642
₩319,496 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (388 reviews)
Hampton's Vacation Inn

Find out more about Shelter Island

Top reasons to visit Shelter Island

  • Stunning Beaches: Enjoy beautiful beaches like Sunset Beach, perfect for relaxation and breathtaking views.
  • Outdoor Adventures: Engage in various outdoor activities such as golfing, kayaking, and exploring urban parks.
  • Rich History: Visit the Shelter Island Historical Society to learn about the island's fascinating past.
  • Scenic Ferry Rides: Take a scenic ferry ride for a unique perspective of the island and surrounding waters.
  • Charming Accommodations: Choose from cozy inns and bed & breakfasts for a comfortable stay amidst nature.

Find great hotels near Shelter Island

Discover the charm of Shelter Island, New York, where a variety of accommodations await you. From cozy bed & breakfasts to intimate inns and agritourism properties, you’ll find the perfect spot for your getaway. Many hotels offer pet-friendly options and cater to families seeking adventure and relaxation. Explore the amenities at the Shelter Island House and enjoy a serene escape amidst nature's beauty.

  • Sound View Greenport: Nestled just 6km from Shelter Island, Sound View Greenport is a charming 3.5-star hotel that emphasizes a relaxed beach vacation experience. Rated 8.4 out of 10, this property is ideal for families and pet owners, offering direct beach access and amenities catered to children, such as complimentary cribs and window guards for safety. Guests can enjoy the scenic views of the waterfront while taking advantage of the pet-friendly policies, making it a great choice for those traveling with furry companions.
  • Sag Harbor Inn: Located 8km from Shelter Island, the Sag Harbor Inn boasts a 3.5-star rating and an impressive guest rating of 9.4 out of 10. This hotel is tailored for business travelers seeking a comfortable retreat with modern conveniences. The inn features a cozy atmosphere and is well-equipped to meet the needs of professionals on the go. Its proximity to local businesses and meeting facilities makes it a smart choice for those blending work and leisure during their stay.
  • The Harbor Front Inn: A mere 5km from Shelter Island, The Harbor Front Inn is another 3.5-star accommodation, rated at 8.8 out of 10. This property is a blend of business and leisure, allowing pets to accompany guests, with specific amenities for furry friends. The inn's location offers stunning waterfront views and a tranquil setting, making it suitable for both business trips and family vacations. With a welcoming atmosphere and essential facilities, it is a delightful choice for travelers looking to unwind.

Where to stay near Shelter Island

Discover the charm of Shelter Island, a picturesque getaway perfect for outdoor adventures and romantic beach vacations. Explore the stunning scenery, rich history, and family-friendly atmosphere that this unique destination offers. Don't miss Sunset Beach for breathtaking views and a relaxing vibe. Nearby, Long Island invites you to experience luxury and excursions, ensuring a memorable stay filled with diverse experiences. Whether you seek tranquility or excitement, Shelter Island has something for everyone.

  • Hamptons: Located 14km from Shelter Island, the Hamptons is a world-renowned summer destination known for its stunning beaches and charming villages. The area attracts visitors seeking outdoor adventures, romantic getaways, and beach relaxation. Peak travel season from June to August brings vibrant beach scenes, while the quieter winter months offer a chance to enjoy peaceful lakes and scenic golf courses. Popular activities include golfing and skiing, making it a versatile destination year-round. With family-friendly beaches and picturesque landscapes, the Hamptons provide a perfect backdrop for memorable vacations.
  • Greenport: Just 5km away from Shelter Island, Greenport is a quaint waterfront town that captivates visitors with its small-town charm and outdoor activities. With peak tourist season from June to August, Greenport is popular for those seeking romantic retreats and beach days. The town boasts recreational areas, music concerts, and beautiful parks, adding to the vibrant local culture. Visitors can enjoy family-friendly beaches and explore the inviting downtown with its unique shops and eateries. Greenport's laid-back atmosphere makes it an ideal spot for relaxation and exploration.
  • Sag Harbor: Situated 8km from Shelter Island, Sag Harbor is a historic village that combines maritime heritage with modern attractions. This charming city is popular among travelers seeking outdoor experiences and romantic beach settings, especially during the peak season from June to August. With access to golf courses, skiing, and beautiful family beaches, Sag Harbor offers a little something for everyone. The picturesque surroundings, including serene lakes, make it a favored destination for those looking to unwind and enjoy the coastal lifestyle. The vibrant arts scene and local dining options add to its allure.

Things to do near Shelter Island

Shopping

Shelter Island offers charming local shops like the Shelter Island Craft Shop, where you can find unique handmade items and souvenirs. If you're up for a drive, visit the nearby Greenport Village, about 16km away, featuring boutiques, galleries, and specialty shops for a broader shopping experience.

Recreation

On Shelter Island, the Spa at the Chequit offers a serene atmosphere with rejuvenating treatments that incorporate local ingredients. Nearby, the Shelter Island Yoga Studio hosts classes in serene settings, helping you find balance and tranquility amidst nature’s beauty.

Adventure

Experience the thrill of motor racing at Riverhead Raceway, situated 35km from Shelter Island, where the adrenaline rush of high-speed competition awaits. Alternatively, head 39km to Waterford Speedbowl, where the vibrant atmosphere and exciting races create an unforgettable adventure for motorsport enthusiasts.

Nightlife

For a lively evening on Shelter Island, visit the Sunset Beach for beachside cocktails and a vibrant atmosphere. Alternatively, the Chequit offers a cozy spot with live music, while the Islander serves up a relaxed vibe with local brews and tasty bites to enjoy with friends.

*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 is perfect for outdoor and romantic beach vacations, featuring attractions like beautiful beaches, urban parks, and historic buildings. Visitors can immerse themselves in local culture and enjoy a variety of outdoor experiences. A must-see is the Shelter Island Historical Society, which offers insights into the island's rich history. Whether you're seeking relaxation or adventure, Shelter Island has something for everyone.

  • Gardiner's Bay Country Club: Nestled on Shelter Island, this charming golf course offers a serene environment for golf enthusiasts. With its well-maintained greens and stunning views of Gardiner's Bay, it's an ideal spot for both novice and experienced players looking to enjoy a leisurely round of golf.
  • East Hampton Main Beach: Located 19km away, this popular beach invites visitors to soak up the sun and enjoy the vibrant beach atmosphere. With soft sands and gentle waves, it's a great place to relax, swim, or take a leisurely stroll along the coastline.
  • Mashomack Preserve: Situated within Shelter Island, this urban park boasts diverse trails and scenic landscapes. It's an excellent destination for families and outdoor enthusiasts to explore nature, hike, and observe local wildlife in a peaceful setting.

Best time to go to Shelter Island

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

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 with several major airports nearby. John F. Kennedy International Airport (JFK) is located 130km away, with luxurious hotel options such as The William Vale, Arlo Williamsburg, and The Boro Hotel, all around 18km from the airport. LaGuardia Airport (LGA) is 134km from Shelter Island and features upscale accommodations like Hilton Club The Quin New York and The Plaza, A Fairmont Hotel, within 10km. Additionally, Bradley International Airport (BDL) in Hartford, CT, is 100km away, with comfortable stays at DoubleTree by Hilton Hartford and Marriott Hartford Downtown nearby.

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 Water's Edge Resort & Spa. 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. Water's Edge Resort & Spa and Offshore Montauk 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. In Shelter Island, there are 102 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, Crescent Beach, and Mashomack Preserve. A couple of additional sights to add to your agenda are Shelter Island Historical Society and Havens House. 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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