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19 Aug - 20 Aug
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20 Aug - 21 Aug
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21 Aug - 23 Aug
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28 Aug - 30 Aug

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Our top choices for Shelter Island hotels

Pet-friendly
Hotel
Reserve now, pay later
Breakfast included
Pool

1. The Pridwin Hotel

The Pridwin Hotel
Shelter Island Heights
United States
Anna
฿17,693
฿22,236 total
includes taxes & fees
13 Sept - 14 Sept
The Pridwin Hotel

2. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
฿10,396
฿11,877 total
includes taxes & fees
17 Sept - 18 Sept
Shelter Island House

3. West Neck Guesthouse

West Neck Guesthouse
Shelter Island Heights
United States
Allie
฿10,305
฿11,774 total
includes taxes & fees
17 Sept - 18 Sept
West Neck Guesthouse

4. House on Chase Creek

House on Chase Creek
The Heights
United States
Calvin
฿8,137
฿9,296 total
includes taxes & fees
9 Sept - 10 Sept
House on Chase Creek

5. The Chequit

The Chequit
The Heights
United States
Kristin
฿9,615
฿10,985 total
includes taxes & fees
14 Sept - 15 Sept
The Chequit

6. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
Christine
฿10,075
฿14,441 total
includes taxes & fees
20 Sept - 21 Sept
Cliffside Resort Condominiums

7. Zey Hotel

Zey Hotel
Greenport
United States
shaun
฿6,657
฿7,605 total
includes taxes & fees
17 Sept - 18 Sept
Zey Hotel

8. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Sol
฿15,450
฿17,651 total
includes taxes & fees
20 Sept - 21 Sept
Silver Sands Motel & Beach Bungalows

9. The Menhaden

The Menhaden
Greenport
United States
Lisa
฿17,165
฿20,935 total
includes taxes & fees
25 Aug - 26 Aug
The Menhaden

10. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Connor
฿9,630
฿11,830 total
includes taxes & fees
1 Sept - 2 Sept
The Shoals Suites and Slips

11. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
John
฿9,148
฿12,154 total
includes taxes & fees
8 Sept - 9 Sept
The Harbor Front Inn

12. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Christopher
฿11,637
฿13,295 total
includes taxes & fees
20 Sept - 21 Sept
Sag Harbor Inn

13. Oyster Estate

Oyster Estate
Greenport
United States
Jenny
฿10,779
฿13,581 total
includes taxes & fees
7 Sept - 8 Sept
Oyster Estate

14. American Beech Hotel

American Beech Hotel
Greenport
United States
kerri
฿12,978
฿16,142 total
includes taxes & fees
7 Sept - 8 Sept
American Beech Hotel

15. Sound View Greenport

Sound View Greenport
Greenport
United States
Yveline
฿8,913
฿13,000 total
includes taxes & fees
15 Sept - 16 Sept
Sound View Greenport

16. North Fork Resort

North Fork Resort
Greenport
United States
Lisa
฿10,562
฿12,067 total
includes taxes & fees
20 Sept - 21 Sept
North Fork Resort

17. Arbor View House B&B

Arbor View House B&B
East Marion
United States
Lekecia
฿20,142
฿23,725 total
includes taxes & fees
3 Sept - 4 Sept
Arbor View House B&B

18. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Joseph
฿22,353
฿28,093 total
includes taxes & fees
15 Sept - 16 Sept
Faraway Sag Harbor

19. The Captain Stannard

The Captain Stannard
Westbrook Center
United Kingdom
Jessica
฿7,689
฿8,535 total
includes taxes & fees
23 Aug - 24 Aug
The Captain Stannard

20. Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook
Old Saybrook
United States
John
฿3,325
฿3,824 total
includes taxes & fees
13 Sept - 14 Sept
Quality Inn Old Saybrook - Westbrook
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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.

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.

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.

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

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 harbour waters and more dynamic waves, perfect for beachcombing and wildlife spotting.
See properties
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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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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Shelter Island Historical Society

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

North Fork Resort

North Fork Resort

10/10 Excellent
"THERE WAS ONLY ONE THING. THE LAST MORNING THERE WAS NO HOT H2O HOWEVER THE PROBLEM WAS FIXED."
KATHLEEN 2-night trip
Posted 2 hours ago
North Fork Resort
Sound View Greenport

Sound View Greenport

8/10 Good
"Stayed here for 2 nights mid-August. Pool was nice (could have been a little cleaner). Restaurant, excellent. Valet staff, excellent. Front desk staff, good. Bar, nice. Breakfast included, very nice. Room, a bit dated but nicely renovated. Through the years I always wanted to stay here - glad I did. The view (and sunset) of the Long Island Sound from the shared balcony cannot be beat. Breathtaking."
Barbara 2-night trip
Posted 4 hours ago
Sound View Greenport
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

8/10 Good
"Clean and comfortable room. Very dated furniture."
Leon 1-night trip
Posted 7 hours ago
Pier Blue Inn Old Saybrook - Essex
Water's Edge Resort & Spa

Water's Edge Resort & Spa

8/10 Good
"I booked through Expedia because I believed the price I was quoted would be the final cost other than incidentals. Additional resort fees and tax were added to the final bill. Over 130.00 in unexpected cost. Be aware when booking."
Debra 1-night trip
Posted 10 hours ago
Water's Edge Resort & Spa
Montauk Blue Hotel

Montauk Blue Hotel

10/10 Excellent
"Great hotel"
Maria 1-night trip
Posted 23 hours ago
Montauk Blue Hotel
Offshore Montauk

Offshore Montauk

8/10 Good
"We had a fabulous time at Offshore for two nights midweek. The only negative was the construction next to the pool, but we spent our time at the beach anyway. I know they're building a restaurant next to the pool, and we would happily stay there again and look forward to the new addition. The only other minor issue is the grounds could be kept up a bit better around the front parking lot."
Anthony 2-night trip
Posted 1 day ago
Offshore Montauk
 Hampton's Vacation Inn

Hampton's Vacation Inn

10/10 Excellent
"Great place to stay. The closing of the pool at 7pm is a bit early."
Theresa 4-night trip
Posted 1 day ago
Hampton's Vacation Inn
Zey Hotel

Zey Hotel

10/10 Excellent
"James was amazing"
ROBIN 3-night trip
Posted 2 days ago
Zey Hotel
Ocean Resort Inn

Ocean Resort Inn

10/10 Excellent
"It was a great stay!"
Tynan 2-night trip
Posted 2 days ago
Ocean Resort Inn

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
฿3,143
฿3,615 total
10 Sept - 11 Sept
includes taxes & fees
8/10 Very good! (1,011 reviews)
Pier Blue Inn Old Saybrook - Essex
Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

100 Essex Rd Old Saybrook CT
฿3,325
฿3,824 total
13 Sept - 14 Sept
includes taxes & fees
7.8/10 Good! (1,007 reviews)
Quality Inn Old Saybrook - Westbrook
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
฿4,109
฿4,695 total
25 Aug - 26 Aug
includes taxes & fees
Budget Host East End
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
฿5,597
฿7,222 total
7 Sept - 8 Sept
includes taxes & fees
The Bentley Hotel Southampton
 Hampton's Vacation Inn

Hampton's Vacation Inn

177 West Montauk Highway Hampton Bays NY
฿6,706
฿7,662 total
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (379 reviews)
Hampton's Vacation Inn
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
฿6,527
฿8,285 total
8 Sept - 9 Sept
includes taxes & fees
The Atlantic Hotel

Find out more about Shelter Island

Top reasons to visit Shelter Island

  • Stunning Beaches: Enjoy pristine sandy shores and breathtaking sunsets at scenic spots like Sunset Beach.
  • Outdoor Adventures: Engage in activities like golfing, kayaking, and exploring lush landscapes.
  • Rich History: Visit the Shelter Island Historical Society for a glimpse into the island's heritage.
  • Charming Accommodations: Choose from intimate inns and agritourism properties for a cosy stay.
  • Serene Retreats: Experience relaxation at local retreats and bird sanctuaries amidst nature.

Find great hotels near Shelter Island

For an unforgettable stay on Shelter Island, you'll discover a delightful array of accommodations, including charming agritourism properties and intimate inns. Many hotels cater to families and pet lovers alike, ensuring a welcoming atmosphere for all travellers. Whether you prefer the comfort of a guest house or the unique charm of a bed and breakfast, Shelter Island offers a myriad of options to enhance your vacation experience amidst its stunning natural beauty.

  • Sound View Greenport: Nestled just 6km away from Shelter Island, Sound View Greenport offers a delightful beachside retreat with a 3.5-star rating and a commendable guest score of 8.4 out of 10. This family-friendly establishment is ideal for those seeking a blend of relaxation and adventure, featuring direct access to the beach. Families will appreciate the thoughtful amenities for children, including complimentary cribs and safety window guards. The hotel's inviting atmosphere and proximity to the shore create a charming environment for both leisure and business travellers.
  • Sag Harbor Inn: Located 8km from Shelter Island, Sag Harbor Inn is a distinguished 3.5-star lodging option boasting a remarkable guest rating of 9.4 out of 10. This hotel caters specifically to business travellers, providing a tranquil atmosphere and convenient access to local amenities. The elegant décor and professional services ensure a productive stay, while its serene setting allows guests to unwind after a busy day. The Sag Harbor Inn is a refined choice for those looking to blend work with leisure in a picturesque locale.
  • The Harbor Front Inn: Situated merely 5km from Shelter Island, The Harbor Front Inn is a welcoming 3.5-star property with a notable guest rating of 8.8 out of 10. This inn stands out for its pet-friendly policy, allowing guests to bring their furry companions along for their stay. With amenities tailored for pets, including a maximum weight allowance and waived fees for service animals, it is perfect for travellers who wish to enjoy their getaway with their pets. The Harbour Front Inn also offers a blend of comfort and professional service for business travellers.

Where to stay near Shelter Island

Embark on a delightful journey to Shelter Island, New York, where scenic beauty and historical charm intertwine. This idyllic destination offers a perfect blend of outdoor adventures, romantic beach escapes, and family-friendly excursions. Explore the picturesque landscapes, enjoy stunning sunsets at Sunset Beach, and discover the luxurious yet budget-friendly experiences nearby on Long Island. Shelter Island promises a memorable vacation filled with relaxation and exploration for every type of traveller.

  • Hamptons: Situated 14km from Shelter Island, the Hamptons are renowned for their picturesque beaches and vibrant outdoor lifestyle. This charming region attracts visitors primarily during the summer months from June to August, offering a romantic escape with a plethora of activities. Enjoy a round of golf, indulge in a relaxing day at the beach, or explore the scenic lakes. The local atmosphere is filled with a blend of luxury and nature, making it a perfect destination for families and couples alike. Don't miss the chance to experience local seafood restaurants and boutique shopping.
  • Greenport: Just 5km away from Shelter Island, Greenport is a delightful village that presents a perfect mix of outdoor adventures and romantic settings. With its peak tourist season from June to August, visitors flock to enjoy its beautiful beaches and parks. The vibrant local culture features music concerts and recreational areas, inviting you to immerse yourself in the community spirit. Stroll along the charming streets, sample fresh seafood, and take in the stunning waterfront views that make Greenport a must-visit destination.
  • Sag Harbor: Located 8km from Shelter Island, Sag Harbor is a historic whaling village that offers a unique blend of outdoor activities and beach experiences. With peak visitor numbers from June to August, this quaint town invites couples and families to enjoy its inviting beaches and serene lakes. Engage in golfing or simply relax along the scenic waterfront. The rich history and charming architecture add to Sag Harbor's allure, making it an excellent spot for leisurely exploration, dining, and cultural experiences.

Things to do near Shelter Island

Shopping

In Shelter Island, you can find charming local shops offering unique gifts and souvenirs. For a wider selection, if you're up for a drive, visit the Tanger Outlets in Riverhead, located about 24km away, featuring a range of brand-name retailers at discounted prices.

Recreation

Experience the tranquil ambiance of the Shelter Island Wellness Centre, where you can indulge in rejuvenating massages and holistic therapies. For outdoor enthusiasts, the nearby Mashomack Preserve offers scenic trails for hiking and birdwatching, allowing you to connect with nature while enjoying the peaceful surroundings.

Adventure

At Riverhead Raceway, located 35km from Shelter Island, immerse yourself in the thrilling atmosphere of motor racing, where speed and excitement reign. Alternatively, head to Waterford Speedbowl, 39km away, for another exhilarating racing experience that captures the spirit of adventure on the track.

Nightlife

Shelter Island boasts a relaxed nightlife atmosphere with venues like The Chequit, offering intimate cocktails and live music, while the Sunset Beach provides stunning waterfront views and vibrant social scenes. Enjoy the laid-back charm and warm hospitality at local bars and eateries throughout the island.

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

Find the best attractions in Shelter Island

Whether you're seeking a romantic getaway or an outdoor adventure, Shelter Island, New York, offers a delightful mix of beach relaxation and cultural exploration. With popular attractions such as pristine beaches, urban parks, and historic buildings, visitors can immerse themselves in the local charm. Don’t miss the Shelter Island Historical Society for a glimpse into the island's rich heritage, ensuring a memorable holiday experience for all types of travellers.

  • Gardiner's Bay Country Club: Nestled in the heart of Shelter Island, this golf club offers a serene golfing experience with stunning bay views. The meticulously maintained course caters to golfers of all skill levels, providing a relaxed atmosphere amidst lush landscapes.
  • Shell Beach: Renowned for its tranquil beach vibes, Shell Beach invites you to unwind on its sandy shores. Whether you prefer sunbathing, swimming, or simply enjoying a leisurely stroll, this charming beach offers a perfect escape into nature.
  • Mashomack Preserve: This expansive urban park features scenic trails and diverse wildlife, ideal for families and outdoor enthusiasts. Enjoy hiking or picnicking while surrounded by the beauty of nature, providing a refreshing retreat from urban life.

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

To reach Shelter Island, New York, you can fly into several major airports. New York, NY (JFK-John F. Kennedy Intl.) is located 130km away, with nearby hotels such as The William Vale and Arlo Williamsburg, both 18km from the airport. Providence, RI (PVD-T.F. Green) is 105km away, offering options like the Omni Providence Hotel, only 11km from the airport. Lastly, White Plains, NY (HPN-Westchester County) is 114km away, with excellent hotels like The Opus Westchester, just 6km from the airport, and convenient transportation services available to and from these hotels.

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 traveller data. Other good choices for your stay in the area are Sound View Greenport and The Atlantic Hotel. 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! 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?
Sound View Greenport: Offers a private beach, a seasonal outdoor pool and 2 bars. The Atlantic Hotel 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 103 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 Sunset Beach, Crescent Beach and Mashomack Preserve. A couple of additional sights to add to your itinerary are Shelter Island Historical Society and Gardiner's Bay Country Club. 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.

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