Holiday homes by the sea in Shelter Island
Choose the right place for you
FACILITIES
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Pets Allowed
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Wi-Fi
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Non Smoking Only
REVIEWS
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9+ Exceptional
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8+ Fabulous
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7+ Very Good
DISTANCE FROM CENTRE
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Less than 1 km
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Less than 3 km
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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
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Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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' ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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. ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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 ...Check Availability -
Shelter Island - United States
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 ...Check Availability
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
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Shelter Island - United States
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 ... -
Shelter Island - United States
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. ... -
Shelter Island - United States
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 ... -
Shelter Island - United States
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. ... -
Shelter Island - United States
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 ... -
Shelter Island - United States
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 ...Check Availability
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?
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![Farmstays in Shelter Island]()
Farmstays in Shelter Island -
![Hotels in Shelter Island]()
Hotels in Shelter Island
Shelter Island: the best offers for the best accommodation and holiday homes
How much doeas it cost to stay in Shelter Island? The more economical accommodation in Shelter Island has an average cost of 651 Canadian dollars per night.
If you want to organize a holiday in Shelter Island during the low season, where you can enjoy the destination without the hectic turism, January is the best month. The week with the highes amount of accommodation available at the best price is from 01-07 to 01-14.
If instead you are looking for the high season, the highest amount of accommodation available with the lowest price is in the month of September, during the week that spans from 09-02 to 09-09.
What to do in Shelter Island
The weather forcast in Shelter Island
Shelter Island: during the year, the average temperature throughout the year is around 14°C. The coldest period of the year is in the month of January where the temperature can drop to 2°C. The hottest month of the year is instead in July where the maximum temperature can reach 25°C.
