Holiday homes by the sea in Shelter Island

search
B&B and Vacation Rentals
B&B and Vacation Rentals
B&B and Vacation Rentals
Choose the right place for you

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

  • The Cliffside Resort Condominiums

    • Hotel
    11.4 Exceptional (634)
    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

  • Fordham House

    • Hotel
    13.3 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 0.5 mi (0.9 km) from ...
    Check Availability

  • 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

  • Lagoon Lodge North Fork Charming 3Br Waterfront wifi on beach G

    • 8 Guests · 3Bedrooms
    13.1 Exceptional (24)
    Located in East Marion in the New York State region, Lagoon Lodge North Fork Charming 3Br Waterfront wifi on beach G has a balcony. ...
    Check Availability

  • Charming Greenport Gem 1, 1 Mile to Ferry!

    • 6 Guests · 2Bedrooms
    13.3 Exceptional (15)
    Charming Greenport Gem 1, 1 Mile to Ferry! is situated in Greenport. Free WiFi is available throughout the property and Splish Splash is 42 km away. ...
    Check Availability

  • Bright 2nd-Floor Apt - half Mi to Greenport Harbor!

    • 2 Guests · 1Bedroom
    9.6 Exceptional (57)
    Located in Greenport in the New York State region, Bright 2nd-Floor Apt - half Mi to Greenport Harbor! features a patio. Free WiFi is available throughout the property and Splish Splash is 43 km away. ...
    Check Availability

  • Cottage fields of Lavender by the Sea 5min Greenport Shelter Isl

    • 6 Guests · 3Bedrooms
    13.3 Exceptional (6)
    Cottage fields of Lavender by the Sea 5min Greenport Shelter Isl is located in East Marion, 44 km from Splish Splash, in an area where skiing can be enjoyed. ...
    Check Availability

  • Sensational, newly remodeled waterfront Greenport condo

    • 4 Guests · 2Bedrooms
    10 Exceptional (5)
    Located in Greenport, this condo is on the waterfront. Sylvester Manor and Havens House are local landmarks, and some of the area's activities can be experienced at Greenport Carousel and Kontokosta Winery. ...
    Check Availability

  • Greenport Village Vacationer's Delight

    • 7 Guests · 3Bedrooms
    12 Exceptional (6)
    Situated in Greenport, 41 km from Splish Splash, Greenport Village Vacationer's Delight features air-conditioned accommodation with a patio and free WiFi. This holiday home features a garden. ...
    Check Availability

  • Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

    • 6 Guests · 2Bedrooms
    13.1 Exceptional (207)
    Located in Greenport, this condo is in a rural area and on the beach. Railroad Museum of Long Island and East End Seaport Maritime Museum are cultural highlights, and some of the area's attractions include ...
    Check Availability

  • Spacious apartment, 3 blocks to downtown and steps to fishing pier.

    • 4 Guests · 2Bedrooms
    10 Exceptional (62)
    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

  • Private & Spacious Five Room Suite<br>Steps To Bay Beach and walk to Village.

    • 4 Guests · 2Bedrooms
    10 Exceptional (145)
    Located near the beach, this apartment is in Pipes Cove, a neighborhood in Greenport. Sylvester Manor and Havens House are local landmarks, and some of the area's attractions include Railroad Museum of ...
    Check Availability

  • First Floor 1905 Victorian home in the heart of Greenport Village

    • 6 Guests · 2Bedrooms
    9.8 Exceptional (68)
    Located in Greenport, this apartment is near the beach. Sylvester Manor and Havens House are local landmarks, and the area's natural beauty can be seen at 67 Steps Beach and Norman E. Klipp Marine Park. ...
    Check Availability

  • Perfect Getaway Apartment For Couples or Single Travelers

    • 2 Guests · 1Bedroom
    9.8 Exceptional (15)
    Located in East Marion, this apartment is on the waterfront. The area's natural beauty can be seen at Truman's Beach and Norman E. Klipp Marine Park, while East End Seaport Maritime Museum and Railroad ...
    Check Availability

  • 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 Hidden Waterfront

    • 8 Guests · 1Bedroom
    10 Exceptional (8)
    Shelter Island Hidden Waterfront is set in Shelter Island. The air-conditioned accommodation is 2.1 km from Wades Beach, and guests can benefit from complimentary WiFi and private parking available on ...
    Check Availability

  • 'Treetop' Harborview Studio, with Balcony, in the Heart of Shelter Island

    • 2 Guests · 1Bedroom
    Located in Shelter Island Heights, this apartment is in the city center and on the waterfront. Sylvester Manor and Havens House are local landmarks, and the area's natural beauty can be seen at Sunset ...
    Check Availability

  • Charming Studio on Shelter Island

    • 2 Guests · 1Bedroom
    Located in Shelter Island, this apartment is near the beach. Mashomack Nature Preserve and Sunset Beach reflect the area's natural beauty and area attractions include Shelter Island Whale's Tail and East ...
    Check Availability

  • Water front Home Sailors rest Boat Dock w Jacuzzi

    • 7 Guests · 3Bedrooms
    Boasting a spa bath, Water front Home Sailors rest Boat Dock w Jacuzzi is set in East Marion. The air-conditioned accommodation is 2.4 km from Greenport. ...
    Check Availability

  • Beach house Sailors Delight Vineyards, Farm Stands, North Fork P

    • 10 Guests · 4Bedrooms
    Boasting air-conditioned accommodation with a balcony, Beach house Sailors Delight Vineyards, Farm Stands, North Fork P is located in East Marion. It is set 44 km from Splish Splash and provides a 24-hour ...
    Check Availability
Discover all the offers >

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

  • House on Chase Creek

    • Hotel
    11.6 Exceptional (235)
    Set in Shelter Island Heights, House on Chase Creek offers 4-star accommodation with a garden and a terrace. The property has sea and lake views. The bed and breakfast offers rooms with air conditioning, ...
    Check Availability

  • Shorecrest Bed and Breakfast

    • Hotel
    11.7 Exceptional (83)
    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 ...
    Check Availability

  • West Neck Guesthouse

    • Hotel
    10.1 Exceptional (72)
    Situated in Shelter Island Heights, West Neck Guesthouse features free bikes and garden. This bed and breakfast features free private parking and a housekeeping service. The bed and breakfast has family ...
    Check Availability

  • Seven - a boutique B&B on Shelter Island

    • Hotel
    9.8 Exceptional (63)
    Just 450 metres 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 ...
    Check Availability

  • 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. ...
    Check Availability

  • 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. ...
    Check Availability
Discover all the offers >

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?

  • Farmstays in Shelter Island
    Farmstays in Shelter Island
  • Hotels in Shelter Island
    Hotels in Shelter Island

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

  • The Pridwin Hotel

    • Hotel
    10 Exceptional (146)
    The Pridwin is a waterfront resort located on Shelter Island with 33 well-appointed guest rooms and 16 private cottages an all-American restaurant and lively lounge with water views a full service spa-scenic ...
    Check Availability

  • Sound View Greenport

    • Hotel
    10.8 Exceptional (1460)
    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
    11 Exceptional (1315)
    Offering a seasonal outdoor swimming pool and a fitness center, 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
    11.6 Exceptional (498)
    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 Shoals Suites & Slips

    • Hotel
    12.6 Exceptional (178)
    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

  • Cliffside Resort Condominiums

    • Hotel
    11.4 Exceptional (634)
    When you stay at Cliffside Resort Condominiums in Greenport, you'll be near the beach, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach. This beach aparthotel is 2 mi (3.2 km) from Eastern ...
    Check Availability

  • The Menhaden Hotel

    • Hotel
    12.8 Exceptional (270)
    Situated 41 km from Splish Splash, The Menhaden Hotel in Greenport has a terrace and bar. With free bikes, the 4-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. ...
    Check Availability

  • Southold Beach Motel

    • Hotel
    10.9 Exceptional (381)
    Set in Southold and within 36 km of Splish Splash, Southold Beach Motel has a garden, non-smoking rooms, and free WiFi throughout the property. Boasting family rooms, this property also provides guests ...
    Check Availability

  • Shelter Island House

    • Hotel
    11.1 Exceptional (147)
    Shelter Island House features a seasonal outdoor swimming pool, garden, a shared lounge and restaurant in Shelter Island Heights. Featuring a bar, the 4-star hotel has air-conditioned rooms with free WiFi, ...
    Check Availability

  • The Chequit

    • Hotel
    8.2 Fabulous (34)
    Offering a sun terrace and views of the sea, The Chequit is located in Shelter Island Heights, 44 km from Mystic. Guests can enjoy the on-site restaurant. Free WiFi is available throughout the property ...
    Check Availability

  • The Blue Inn At North Fork

    • Hotel
    11.2 Exceptional (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

  • Hotel Moraine

    • Hotel
    13.4 Exceptional (24)
    Located in Greenport, 39 km from Splish Splash, Hotel Moraine provides accommodation with free bikes, free private parking, a seasonal outdoor swimming pool and a fitness centre. A sun terrace, an on-site ...
    Check Availability

  • Greenporter Hotel

    • Hotel
    12.2 Exceptional (119)
    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 Chequit

    • Hotel
    16.4 Exceptional (17)
    Located near the beach, The Chequit is in The Heights, a neighborhood in Shelter Island Heights. Sylvester Manor and Havens House are local landmarks, and the area's natural beauty can be seen at Sunset ...
    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

  • Silver Sands Motel & Beach Bungalows

    • Hotel
    13.3 Exceptional (50)
    Set in Greenport, 41 km from Splish Splash, Silver Sands Motel & Beach Bungalows offers accommodation with free bikes, free private parking, a garden and a restaurant. With free WiFi, this 4-star hotel ...
    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
Discover all the offers >

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

  • The Pridwin Hotel

    • Hotel
    10 Exceptional (146)
    The Pridwin is a waterfront resort located on Shelter Island with 33 well-appointed guest rooms and 16 private cottages an all-American restaurant and lively lounge with water views a full service spa-scenic ...
    Check Availability

  • Sound View Greenport

    • Hotel
    10.8 Exceptional (1460)
    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
    11 Exceptional (1315)
    Offering a seasonal outdoor swimming pool and a fitness center, 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
    11.6 Exceptional (498)
    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 Shoals Suites & Slips

    • Hotel
    12.6 Exceptional (178)
    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

  • Cliffside Resort Condominiums

    • Hotel
    11.4 Exceptional (634)
    When you stay at Cliffside Resort Condominiums in Greenport, you'll be near the beach, within a 5-minute drive of Kontokosta Winery and 67 Steps Beach. This beach aparthotel is 2 mi (3.2 km) from Eastern ...
    Check Availability

  • The Menhaden Hotel

    • Hotel
    12.8 Exceptional (270)
    Situated 41 km from Splish Splash, The Menhaden Hotel in Greenport has a terrace and bar. With free bikes, the 4-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. ...
    Check Availability

  • Southold Beach Motel

    • Hotel
    10.9 Exceptional (381)
    Set in Southold and within 36 km of Splish Splash, Southold Beach Motel has a garden, non-smoking rooms, and free WiFi throughout the property. Boasting family rooms, this property also provides guests ...
    Check Availability

  • Shelter Island House

    • Hotel
    11.1 Exceptional (147)
    Shelter Island House features a seasonal outdoor swimming pool, garden, a shared lounge and restaurant in Shelter Island Heights. Featuring a bar, the 4-star hotel has air-conditioned rooms with free WiFi, ...
    Check Availability

  • The Chequit

    • Hotel
    8.2 Fabulous (34)
    Offering a sun terrace and views of the sea, The Chequit is located in Shelter Island Heights, 44 km from Mystic. Guests can enjoy the on-site restaurant. Free WiFi is available throughout the property ...
    Check Availability

  • The Blue Inn At North Fork

    • Hotel
    11.2 Exceptional (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

  • Hotel Moraine

    • Hotel
    13.4 Exceptional (24)
    Located in Greenport, 39 km from Splish Splash, Hotel Moraine provides accommodation with free bikes, free private parking, a seasonal outdoor swimming pool and a fitness centre. A sun terrace, an on-site ...
    Check Availability

  • Greenporter Hotel

    • Hotel
    12.2 Exceptional (119)
    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 Chequit

    • Hotel
    16.4 Exceptional (17)
    Located near the beach, The Chequit is in The Heights, a neighborhood in Shelter Island Heights. Sylvester Manor and Havens House are local landmarks, and the area's natural beauty can be seen at Sunset ...
    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

  • Silver Sands Motel & Beach Bungalows

    • Hotel
    13.3 Exceptional (50)
    Set in Greenport, 41 km from Splish Splash, Silver Sands Motel & Beach Bungalows offers accommodation with free bikes, free private parking, a garden and a restaurant. With free WiFi, this 4-star hotel ...
    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
Discover all the offers >

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 numerous 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

Nearby cities

Hyde Park
Kenmore
Long Island City
Dunkirk
Syracuse
Albany
Shirley
Ithaca
White Plains
Greenwich Village
Queens
Rocky Point
Queensbury
Buffalo
Harlem
Woodhaven
Sag Harbor
Mount Vernon
Millbrook
Jackson Heights
Averill Park
Bolton Landing
Branchport
Brewster
Amityville
Babylon
Bridgehampton
Baldwinsville
Broad Channel
Broadalbin
Allegany
Angola-on-the-Lake
Ballston Spa
Brockport