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?

Shelter Island: Organize a holiday and find the best accommodation deals

According to whether you are trevellers in search of calm and tranquillity in the low season or whether you love the high season touristic destinations, in Shelter Island the low season period with the best offers is during the month of January, more specifically, the week from 7/01 to 14/01.
Instead, for the high season, it's possible to find more accommodation at the best price in the month of September, during the week that spans from 2/09 to 9/09.
Observing this destination at a wider spectrum, the cheapest weekend is in the month of June, from 9/06 to 11/06.
In Shelter Island it will be possible to find accommodation solutions at an average cost of 698 Australian dollars per night.

What to do in Shelter Island

Shelter Island and the time with the best weather for a holiday

Shelter Island: do you want to know which is the hottest month: the hottest month of the year is July where temperatures can reach 25°C.
If instead you are cold lovers the best month with the coldes temperatures is January, where the temperature can drop to 2°C.
On average in Shelter Island you will find an average temperature of 14°C.

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