Holiday homes by the sea in Shelter Island

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FACILITIES

  • Pets Allowed
  • Wi-Fi
  • Non Smoking Only

REVIEWS

  • 9+ Exceptional
  • 8+ Fabulous
  • 7+ Very Good

DISTANCE FROM CENTRE

  • Less than 1 km
  • Less than 3 km
  • Less than 5 km

Holiday rental deals in Shelter Island

We have selected the best holiday accommodation by the sea in Shelter Island. Bluepillow allows you to save money, by finding the best rates on the main vacation rental websites in Shelter Island

  • Fordham House

    • Hotel
    10 Exceptional (48)
    Located in Greenport, Fordham House is near the beach, within a 5-minute walk of Eastern Long Island Hospital and Stony Brook Eastern Long Island Hospital. This bed & breakfast is 14.2 mi (22.8 km) from ...
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  • Beachfront

    • 4 Guests · 2Bedrooms
    10 Exceptional (4)
    Located in Southold, this apartment is on the beach. Railroad Museum of Long Island and East End Seaport Maritime Museum are local attractions and those in the mood for shopping can visit Harbes Family ...
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  • Victorian Seasons Stirling

    • Hotel
    With a stay at Victorian Seasons Stirling in Greenport, you'll be near the beach, within a 15-minute walk of Kontokosta Winery and Greenport Farmers' Market. This beach guesthouse is 1 mi (1.6 km) from ...
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  • Spacious apartment, 3 blocks to downtown and steps to fishing pier.

    • 4 Guests · 2Bedrooms
    10 Exceptional (47)
    Located in Greenport, this apartment is in the city center and near the beach. Sylvester Manor and Havens House are local landmarks, and some of the area's activities can be experienced at Greenport Carousel ...
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  • First Floor 1905 Victorian home in the heart of Greenport Village

    • 6 Guests · 2Bedrooms
    10 Exceptional (47)
    Located in Greenport, this apartment is near the beach. Railroad Museum of Long Island and East End Seaport Maritime Museum are cultural highlights, and some of the area's landmarks include Sylvester Manor ...
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  • Porch On Front~ Greenport Village 1st floor apartment, Easy Walk To Town/Jitney

    • 5 Guests · 2Bedrooms
    10 Exceptional (163)
    In the city center, this apartment is in a walkable area with good shopping. Railroad Museum of Long Island and East End Seaport Maritime Museum are cultural highlights, and some of the area's attractions ...
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  • Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

    • 6 Guests · 2Bedrooms
    9.8 Exceptional (52)
    Located in Greenport, this condo is in the city center and on the beach. Greenport Farmers' Market and Wolffer Estates Vineyard are worth checking out if shopping is on the agenda, while those wishing ...
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  • Private & Spacious Five Room Suite<br>Steps To Bay Beach and walk to Village.

    • 4 Guests · 2Bedrooms
    10 Exceptional (93)
    Located near the beach, this apartment is in Pipes Cove, a neighborhood in Greenport. Greenport Carousel and Kontokosta Winery are worth checking out if an activity is on the agenda, while those looking ...
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  • Perfect Getaway Apartment For Couples or Single Travelers

    • 2 Guests · 1Bedroom
    9.8 Exceptional (13)
    Located in East Marion, this apartment is on the waterfront. The area's natural beauty can be seen at Norman E. Klipp Marine Park and 67 Steps Beach, while East End Seaport Maritime Museum and Railroad ...
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  • Charming apartment in historic home, 1 block from village

    • 3 Guests · 4Bedrooms
    10 Exceptional (1)
    Located in Greenport, this apartment is in the city center and near the beach. 67 Steps Beach and Norman E. Klipp Marine Park reflect the area's natural beauty and area attractions include East End Seaport ...
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  • NEWLY Renovated Family Home Great Area - Beach - Greenport - Ferry - Restaurants

    • 4 Guests · 2Bedrooms
    8.8 Fabulous (56)
    This apartment is located in Greenport. East End Seaport Maritime Museum and Railroad Museum of Long Island are cultural highlights, and travelers looking to shop may want to visit Greenport Farmers' Market ...
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  • Sensational, newly remodeled waterfront Greenport condo

    • 4 Guests · 2Bedrooms
    10 Exceptional (5)
    Located in Greenport, this condo is on the waterfront. East End Seaport Maritime Museum and Railroad Museum of Long Island are local attractions and those in the mood for shopping can visit Greenport Farmers' ...
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  • Gorgeous 2 bedroom garage apartment with parking for two cars

    • 4 Guests · 2Bedrooms
    9.6 Exceptional (12)
    Located in Shelter Island, this apartment is near the beach. East End Seaport Maritime Museum and Railroad Museum of Long Island are cultural highlights, and travelers looking to shop may want to visit ...
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  • Quaint DT Greenport Apt - 2 Mi to Shelter Island!

    • 2 Guests · 1Bedroom
    9.7 Exceptional (105)
    This apartment is located in Greenport. Railroad Museum of Long Island and East End Seaport Maritime Museum are cultural highlights, and some of the area's activities can be experienced at Greenport Carousel ...
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  • Lovely second story, two bedroom unit off main St

    • 6 Guests · 2Bedrooms
    9.8 Exceptional (24)
    This apartment is located in Greenport. Sylvester Manor and Havens House are local landmarks, and some of the area's activities can be experienced at Greenport Carousel and Kontokosta Winery. East End ...
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  • The Cliffside Resort Condominiums

    • Hotel
    8.8 Fabulous (553)
    With beautiful views of the sunsets over Long Island Sound, this Greenport resort features spacious grounds and a private beach. Free Wi-Fi is available in all areas. ...
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  • Beautiful Soundfront condominium

    • 6 Guests · 2Bedrooms
    6 Pleasant (1)
    This condo is located in Greenport. Horton Point Park and Sylvester Manor are local landmarks, and the area's natural beauty can be seen at 67 Steps Beach and Norman E. Klipp Marine Park. Railroad Museum ...
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  • The Shoals

    • Hotel
    8.5 Fabulous (46)
    Located in Southold, this aparthotel is near the beach. The Old Field Vineyards and Greenport Carousel are worth checking out if an activity is on the agenda, while those wishing to experience the area's ...
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  • Charming Studio on Shelter Island

    • 3 Guests · 1Bedroom
    Located in Shelter Island Heights, this apartment is near the beach. Shelter Island Country Club and Shelter Island Whale's Tail are worth checking out if an activity is on the agenda, while those wishing ...
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Bed and breakfast offers in Shelter Island by the sea

Are you looking for an accommodation in Shelter Island and do you want to save money? Choose from 6 Bed & Breakfasts in Shelter Island

  • Seven - a boutique B&B on Shelter Island

    • Hotel
    9.8 Exceptional (63)
    Just 500 yards to the beach, this bed and breakfast is located in Shelter Island Heights. A free breakfast is served each morning. Cable TVs are provided in each room at Seven - a boutique B&B on ...
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  • The Stirling House Waterfront Inn Greenport

    • Hotel
    9.7 Exceptional (20)
    This Greenport bed and breakfast is located on the water and offers free Wi-Fi and individually decorated rooms equipped with electric fireplaces. Island’s End Golf & Country Club is 2 miles away. ...
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  • House on Chase Creek

    • Hotel
    9.2 Exceptional (212)
    Set in Shelter Island Heights, House on Chase Creek offers accommodation with free WiFi, air conditioning and access to a garden with a terrace. There is a private bathroom with shower in all units, along ...
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  • A Walk in the Woods Bed and Breakfast

    • Hotel
    8.5 Fabulous (35)
    Relax on the large wrap-around front porch of this Long Island, New York bed and breakfast. Free Wi-Fi and daily breakfast are offered. Cedar Beach is 1 mile away. ...
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  • Shorecrest Bed and Breakfast

    • Hotel
    9.5 Exceptional (64)
    Offering a private beach area, Shorecrest Bed and Breakfast is located in Greenport. Free WiFi access is available. Each room here will provide guests with a flat-screen cable TV and offer a garden or ...
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  • West Neck Guesthouse

    • Hotel
    7.4 Very Good (72)
    Situated in Shelter Island Heights, West Neck Guesthouse features free WiFi, and guests can enjoy free bikes and a garden. Every unit has a private bathroom and bath, air conditioning, a flat-screen TV ...
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Farmhouse or Hotel? Choose from the best offers

Choose the accommodation tailor-made for you for your next vacation: sleep in a farmhouse or sleep in a hotel?

Hotels in Shelter Island, our top selection just for you

Are you looking for hotels in Shelter Island? Here is a selection of the best hotels in Shelter Island

  • Southold Beach Motel

    • Hotel
    8.3 Fabulous (253)
    Located in Southold, Southold Beach Motel is on the beach. The area's natural beauty can be seen at Horton Point Park and Shell Beach, while Railroad Museum of Long Island and East End Seaport Maritime ...
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  • The Gallery Hotel

    • Hotel
    9.2 Exceptional (786)
    Located in Greenport, The Gallery Hotel is near the beach. 67 Steps Beach and Norman E. Klipp Marine Park reflect the area's natural beauty and area attractions include Railroad Museum of Long Island and ...
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  • Sound View Greenport

    • Hotel
    8.3 Fabulous (816)
    Set on the North Fork in Greenport, 157 km from New York City, Sound View Greenport features a seasonal outdoor pool and views of the Long Island Sound. Guests can enjoy a drink at the bar. All the rooms ...
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  • The Harbor Front Inn

    • Hotel
    8.9 Fabulous (774)
    Offering a seasonal outdoor swimming pool and a fitness centre, The Harbor Front Inn is centrally located near the shops and restaurants in Greenport. Free WiFi access is available. Beach access is 1.9 ...
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  • American Beech Hotel

    • Hotel
    8.8 Fabulous (301)
    American Beech Hotel has free bikes, garden, a restaurant and bar in Greenport. This 4-star hotel offers free WiFi. The property is allergy-free and is situated 42 km from Splish Splash. ...
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  • The Pridwin Hotel

    • Hotel
    8 Fabulous (95)
    Located on Crescent Beach, this Shelter Island hotel boasts an outdoor pool overlooking the bay, a private beach, free WiFi and rooms with cable TV. The North Ferry is 2 miles away. Rooms at The Pridwin ...
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  • Greenporter Hotel

    • Hotel
    8.8 Fabulous (3)
    Featuring a 1950’s retro décor, the rooms at Greenporter Hotel rooms have modern amenities like a flat-screen cable TV and a refrigerator. On weekends a continental breakfast with bagels, cereals, oatmeal, ...
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  • The Menhaden

    • Hotel
    9.2 Exceptional (120)
    Located in Greenport, The Menhaden is near the beach, within a 5-minute walk of Camera Obscura and East End Seaport Maritime Museum. This hotel is 13.5 mi (21.7 km) from Wolffer Estates Vineyard and 0.1 ...
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  • The Blue Inn At North Fork

    • Hotel
    8.5 Fabulous (417)
    When you stay at The Blue Inn At North Fork in East Marion, you'll be near the beach, within a 5-minute drive of Kontokosta Winery and Camera Obscura. This hotel is 2.6 mi (4.1 km) from Greenport Carousel ...
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  • The Chequit

    • Hotel
    8.6 Fabulous (13)
    With a stay at The Chequit in Shelter Island Heights (The Heights), you'll be within a 5-minute drive of Shelter Island Country Club and Sunset Beach. This hotel is 12 mi (19.3 km) from Wolffer Estates ...
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  • Hotel Moraine

    • Hotel
    Located in Greenport, Hotel Moraine is within a 5-minute drive of Kontokosta Winery and 67 Steps Beach. This beach hotel is 2.1 mi (3.4 km) from Greenport Carousel and 2.2 mi (3.5 km) from Safe Harbor ...
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  • Shelter Island House

    • Hotel
    8.3 Fabulous (145)
    Located in Shelter Island Heights, Shelter Island House is next to a golf course and near the beach. Sylvester Manor and Havens House are local landmarks, and some of the area's activities can be experienced ...
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  • The Chequit

    • Hotel
    8.4 Fabulous (5)
    Located near the beach, The Chequit is in The Heights, a neighborhood in Shelter Island Heights. East End Seaport Maritime Museum and Railroad Museum of Long Island are cultural highlights, and some of ...
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  • THE PRIDWIN

    • Hotel
    The North Ferry is 2 miles and the South Ferry is 5 miles from the property-The Shelter Island Yacht Club-Sylvester Manor Educational Farm and Shelter Island Country Club are 2 miles away The Pridwin is ...
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  • Dering Harbor Inn

    • Hotel
    4.6 Pleasant (24)
    Dering Harbor Inn is located on the waterfront and in an area with good shopping. Sylvester Manor and Havens House are notable landmarks, and the area's natural beauty can be seen at Mashomack Preserve ...
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  • The Shoals Suites & Slips

    • Hotel
    8.9 Fabulous (58)
    The Shoals Suites & Slips is offering accommodation in Southold. This 4-star hotel has air-conditioned rooms with a private bathroom. Parking is free for guests, there is no extra charge. ...
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  • Silver Sands Motel & Beach Bungalows

    • Hotel
    Set in Greenport, 41 km from Splish Splash, Silver Sands Motel & Beach Bungalows offers accommodation with a garden, free private parking, a restaurant and a bar. With free WiFi, this 4-star hotel offers ...
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  • Sunset Beach Hotel

    • Hotel
    Situated in Shelter Island Heights, Sunset Beach Hotel offers 3-star accommodation with a terrace, a restaurant and a bar. The accommodation features nightclub and a concierge service. At the hotel, the ...
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The best hotels with swimming pool in Shelter Island

Book your relaxing holiday, by choosing the best deals at hotels with swimming pools in Shelter Island

  • Southold Beach Motel

    • Hotel
    8.3 Fabulous (253)
    Located in Southold, Southold Beach Motel is on the beach. The area's natural beauty can be seen at Horton Point Park and Shell Beach, while Railroad Museum of Long Island and East End Seaport Maritime ...
    Check Availability

  • The Gallery Hotel

    • Hotel
    9.2 Exceptional (786)
    Located in Greenport, The Gallery Hotel is near the beach. 67 Steps Beach and Norman E. Klipp Marine Park reflect the area's natural beauty and area attractions include Railroad Museum of Long Island and ...
    Check Availability

  • Sound View Greenport

    • Hotel
    8.3 Fabulous (816)
    Set on the North Fork in Greenport, 157 km from New York City, Sound View Greenport features a seasonal outdoor pool and views of the Long Island Sound. Guests can enjoy a drink at the bar. All the rooms ...
    Check Availability

  • The Harbor Front Inn

    • Hotel
    8.9 Fabulous (774)
    Offering a seasonal outdoor swimming pool and a fitness centre, The Harbor Front Inn is centrally located near the shops and restaurants in Greenport. Free WiFi access is available. Beach access is 1.9 ...
    Check Availability

  • American Beech Hotel

    • Hotel
    8.8 Fabulous (301)
    American Beech Hotel has free bikes, garden, a restaurant and bar in Greenport. This 4-star hotel offers free WiFi. The property is allergy-free and is situated 42 km from Splish Splash. ...
    Check Availability

  • The Pridwin Hotel

    • Hotel
    8 Fabulous (95)
    Located on Crescent Beach, this Shelter Island hotel boasts an outdoor pool overlooking the bay, a private beach, free WiFi and rooms with cable TV. The North Ferry is 2 miles away. Rooms at The Pridwin ...
    Check Availability

  • Greenporter Hotel

    • Hotel
    8.8 Fabulous (3)
    Featuring a 1950’s retro décor, the rooms at Greenporter Hotel rooms have modern amenities like a flat-screen cable TV and a refrigerator. On weekends a continental breakfast with bagels, cereals, oatmeal, ...
    Check Availability

  • The Menhaden

    • Hotel
    9.2 Exceptional (120)
    Located in Greenport, The Menhaden is near the beach, within a 5-minute walk of Camera Obscura and East End Seaport Maritime Museum. This hotel is 13.5 mi (21.7 km) from Wolffer Estates Vineyard and 0.1 ...
    Check Availability

  • The Blue Inn At North Fork

    • Hotel
    8.5 Fabulous (417)
    When you stay at The Blue Inn At North Fork in East Marion, you'll be near the beach, within a 5-minute drive of Kontokosta Winery and Camera Obscura. This hotel is 2.6 mi (4.1 km) from Greenport Carousel ...
    Check Availability

  • The Chequit

    • Hotel
    8.6 Fabulous (13)
    With a stay at The Chequit in Shelter Island Heights (The Heights), you'll be within a 5-minute drive of Shelter Island Country Club and Sunset Beach. This hotel is 12 mi (19.3 km) from Wolffer Estates ...
    Check Availability

  • Hotel Moraine

    • Hotel
    Located in Greenport, Hotel Moraine is within a 5-minute drive of Kontokosta Winery and 67 Steps Beach. This beach hotel is 2.1 mi (3.4 km) from Greenport Carousel and 2.2 mi (3.5 km) from Safe Harbor ...
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  • Shelter Island House

    • Hotel
    8.3 Fabulous (145)
    Located in Shelter Island Heights, Shelter Island House is next to a golf course and near the beach. Sylvester Manor and Havens House are local landmarks, and some of the area's activities can be experienced ...
    Check Availability

  • The Chequit

    • Hotel
    8.4 Fabulous (5)
    Located near the beach, The Chequit is in The Heights, a neighborhood in Shelter Island Heights. East End Seaport Maritime Museum and Railroad Museum of Long Island are cultural highlights, and some of ...
    Check Availability

  • THE PRIDWIN

    • Hotel
    The North Ferry is 2 miles and the South Ferry is 5 miles from the property-The Shelter Island Yacht Club-Sylvester Manor Educational Farm and Shelter Island Country Club are 2 miles away The Pridwin is ...
    Check Availability

  • Dering Harbor Inn

    • Hotel
    4.6 Pleasant (24)
    Dering Harbor Inn is located on the waterfront and in an area with good shopping. Sylvester Manor and Havens House are notable landmarks, and the area's natural beauty can be seen at Mashomack Preserve ...
    Check Availability

  • The Shoals Suites & Slips

    • Hotel
    8.9 Fabulous (58)
    The Shoals Suites & Slips is offering accommodation in Southold. This 4-star hotel has air-conditioned rooms with a private bathroom. Parking is free for guests, there is no extra charge. ...
    Check Availability

  • Silver Sands Motel & Beach Bungalows

    • Hotel
    Set in Greenport, 41 km from Splish Splash, Silver Sands Motel & Beach Bungalows offers accommodation with a garden, free private parking, a restaurant and a bar. With free WiFi, this 4-star hotel offers ...
    Check Availability

  • Sunset Beach Hotel

    • Hotel
    Situated in Shelter Island Heights, Sunset Beach Hotel offers 3-star accommodation with a terrace, a restaurant and a bar. The accommodation features nightclub and a concierge service. At the hotel, the ...
    Check Availability
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Shelter Island: where to stay

Where to stay in Shelter Island? Accommodations? If you are a lone traveller, a small or large family or even a group, in Shelter Island you can find multiple types of accommodation.
The accommodation in this area have had positive reviews from the tourists a total of 13,784 times, 9,144 reviews with a score of 10.0 Excellent and 2,066 reviews with a score of 8.0 Very Good.
In Shelter Island you can find 530 apartments, 37 hotels, 38 b&bs, 487 independent homes, 48 villas, 4 farmhouses and much more.
Every need can be fulfilled thanks to the multitude of services that are available for you. Pets Allowed, Pool, Kitchen, Spa and Parking are the best features in the accommodation in Shelter Island.

Shelter Island and the best offers per the best accommodation

Shelter Island is a touristic destination where the accommodation has an average cost of 576 pounds per night.

What to do in Shelter Island

In Shelter Island, the best accommodation near the sea can also be found near the major interest points.

Only a few km from the sea you can find 636 accommodation options available at the best price: 530 Apartments, 38 B&Bs, 37 Hotels, and much more. Below you can find the best apartments near the beaches.
A Shelter Island, furthermore, much of the best accommodation is close to the best beaches in the area: 148 Apartments, B&Bs, Hotels, and much more.

Shelter Island: What's the weather like?

Shelter Island: are you wondering about the weather you might find during your holiday? Befor organizing a holiday we always think about the wheather we might find when we get there. In Shelter Island the average yearly temperature is 14°C. During the hottest month, which in this case is July, the temperature can get up to 25°C.
Instead the coldest month is January, reaching a minimum temperature of 2°C.

Top Regions in Shelter Island

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