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12 Oct - 13 Oct
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13 Oct - 14 Oct
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16 Oct - 18 Oct
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23 Oct - 25 Oct

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Our top choices for Shelter Island hotels

1. The Chequit

The Chequit
The Heights
United States
Patrick
฿6,005
฿6,861 total
includes taxes & fees
1 Nov - 2 Nov
The Chequit

2. Shelter Island House

Shelter Island House
Shelter Island Heights
United States
Dorothy
฿6,748
฿7,709 total
includes taxes & fees
13 Oct - 14 Oct
Shelter Island House

3. House on Chase Creek

House on Chase Creek
The Heights
United States
Tracey
฿6,198
฿7,082 total
includes taxes & fees
2 Nov - 3 Nov
House on Chase Creek

4. Silver Sands Motel & Beach Bungalows

Silver Sands Motel & Beach Bungalows
Greenport
United States
Keith
฿9,388
฿10,726 total
includes taxes & fees
1 Nov - 2 Nov
Silver Sands Motel & Beach Bungalows

5. The Harbor Front Inn

The Harbor Front Inn
Greenport
United States
Antrii
฿6,002
฿7,815 total
includes taxes & fees
2 Nov - 3 Nov
The Harbor Front Inn

6. Zey Hotel

Zey Hotel
Greenport
United States
Renee
฿6,111
฿6,982 total
includes taxes & fees
13 Oct - 14 Oct
Zey Hotel

7. The Menhaden

The Menhaden
Greenport
United States
Daniel
฿11,585
฿14,577 total
includes taxes & fees
11 Nov - 12 Nov
The Menhaden

8. American Beech Hotel

American Beech Hotel
Greenport
United States
Mary
฿8,409
฿10,949 total
includes taxes & fees
13 Oct - 14 Oct
American Beech Hotel

9. Oyster Estate

Oyster Estate
Greenport
United States
Allison
฿7,553
฿9,516 total
includes taxes & fees
8 Nov - 9 Nov
Oyster Estate

10. The Shoals Suites and Slips

The Shoals Suites and Slips
Southold
United States
Masayo
฿8,121
฿10,116 total
includes taxes & fees
1 Nov - 2 Nov
The Shoals Suites and Slips

11. Sound View Greenport

Sound View Greenport
Greenport
United States
Irene
฿6,429
฿8,302 total
includes taxes & fees
1 Nov - 2 Nov
Sound View Greenport

12. North Fork Resort

North Fork Resort
Greenport
United States
Harold
฿8,932
฿10,205 total
includes taxes & fees
13 Oct - 14 Oct
North Fork Resort

13. Sag Harbor Inn

Sag Harbor Inn
Sag Harbor
United States
Terri
฿7,343
฿8,389 total
includes taxes & fees
1 Nov - 2 Nov
Sag Harbor Inn

14. Cliffside Resort Condominiums

Cliffside Resort Condominiums
Greenport
United States
William
฿5,667
฿10,195 total
includes taxes & fees
1 Nov - 2 Nov
Cliffside Resort Condominiums

15. Faraway Sag Harbor

Faraway Sag Harbor
Sag Harbor
United States
Miguel
฿12,674
฿15,929 total
includes taxes & fees
8 Nov - 9 Nov
Faraway Sag Harbor

16. Water's Edge Resort & Spa

Water's Edge Resort & Spa
Westbrook Center
United States
Teresa
฿5,982
฿7,458 total
includes taxes & fees
1 Nov - 2 Nov
Water's Edge Resort & Spa

17. Hyatt Place Long Island East End

Hyatt Place Long Island East End
Riverhead
United States
Susan
฿4,493
฿5,133 total
includes taxes & fees
3 Nov - 4 Nov
Hyatt Place Long Island East End

18. The Sagaponack

The Sagaponack
Wainscott
United States
Jane
฿6,730
฿9,030 total
includes taxes & fees
10 Nov - 11 Nov
The Sagaponack

19. Topping Rose House

Topping Rose House
Bridgehampton
United States
Adam
฿20,973
฿24,079 total
includes taxes & fees
13 Oct - 14 Oct
Topping Rose House

20. A Room At The Beach

A Room At The Beach
Bridgehampton
United States
Samantha
฿9,928
฿11,343 total
includes taxes & fees
13 Oct - 14 Oct
A Room At The Beach
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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.

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

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

Top Shelter Island Hotel Reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

10/10 Excellent
"Beautiful place. Staff were very helpful and polite."
Deborah 1-night trip
Posted 12 hours ago
Water's Edge Resort & Spa
The Bentley Hotel Southampton

The Bentley Hotel Southampton

10/10 Excellent
"Very Very Clean!!! Staff was excellent!!!"
John 2-night trip
Posted 15 hours ago
The Bentley Hotel Southampton
Sun N Sound

Sun N Sound

10/10 Excellent
"Perfect in every way. The view is spectacular. Amazing sunsets. Well equipped kitchen if you are eating in. Plenty of parking. The housekeepers keep the place super clean. Wonderful place to just enjoy the ocean breeze."
Anna 5-night trip
Posted 20 hours ago
Sun N Sound
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

10/10 Excellent
"Exceptional service. Always a pleasure to visit!"
Amanda 1-night trip
Posted 21 hours ago
Gurney's Montauk Resort & Seawater Spa
Ocean Vista Resort

Ocean Vista Resort

10/10 Excellent
"Ocean Vista was a very well-maintained property. Staff was very welcoming and pleasant as well as professional. Enjoyed our stay we’ll go back."
JEAN-LUC 2-night trip
Posted 2 days ago
Ocean Vista Resort
Faraway Sag Harbor

Faraway Sag Harbor

10/10 Excellent
"We were pleased with the excellent location to Sag Harbor's Main Street and the Zagaya restaurant *upstairs. It was superb! The staff was very friendly and helpful. The rooms were small and the baths particularly small so just a heads up on that although the toiletries were really nice. The hotel has a great vibe at night with live music in the bar area on Thursday evenings. The weather was cool...absolutely gorgeous for early October so we didn't use the pool/cabanas (although it was heated). I did peek in the fitness room and it was very nice. Not enough time to check out the spa but there's always next time!"
SUSAN 4-night trip
Posted 3 days ago
Faraway Sag Harbor
Ocean Surf Resort

Ocean Surf Resort

10/10 Excellent
"Perfect for weekend stay"
DAWN 1-night trip
Posted 8 days ago
Ocean Surf Resort

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
฿2,868
฿3,298 total
14 Oct - 15 Oct
includes taxes & fees
Pier Blue Inn Old Saybrook - Essex
Budget Host East End

Budget Host East End

30 Lake Avenue Riverhead NY
฿2,984
฿3,409 total
13 Oct - 14 Oct
includes taxes & fees
6.8/10 (898 reviews)
Budget Host East End
The Atlantic Hotel

The Atlantic Hotel

1655 County Road 39 Southampton NY
฿3,591
฿4,941 total
28 Oct - 29 Oct
includes taxes & fees
The Atlantic Hotel
The Bentley Hotel Southampton

The Bentley Hotel Southampton

161 Hills Station Rd Southampton NY
฿4,795
฿5,478 total
28 Oct - 29 Oct
includes taxes & fees
9.6/10 Exceptional! (598 reviews)
The Bentley Hotel Southampton
Ocean Surf Resort

Ocean Surf Resort

84 South Emerson Avenue Montauk NY
฿3,655
฿5,634 total
18 Oct - 19 Oct
includes taxes & fees
8.6/10 Excellent! (329 reviews)
Ocean Surf Resort
The Hampton Maid

The Hampton Maid

259 E Montauk Hwy Hampton Bays NY
฿7,092
฿8,102 total
13 Oct - 14 Oct
includes taxes & fees
9.2/10 Wonderful! (803 reviews)
The Hampton Maid

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 Gurney's Montauk Resort & Seawater Spa and Offshore Montauk. 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?
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.

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