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Most frequently booked hotels in Shelter Island

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Private Hamptons Cottage

Private Hamptons Cottage

94 S Ferry Rd, Shelter Island, NY
During your stay at this holiday home, you'll be within walking distance of Wades Beach. Enjoy your stay with amenities like a private pool and a kitchen in the holiday home.
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Waterfront House With Dock And Private Beach

Waterfront House With Dock And Private Beach

18 Thompson Road, Shelter Island, NY
Our customers tell us they enjoy this holiday home's beach location. During your stay, you'll be within walking distance of Wades Beach. Enjoy your stay with amenities like a kitchen and 2 bathrooms in the holiday home.
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Heavenly 4 Bedroom Beach Home! Perfect Retreat/grand Piano, Pond, Deck, Grounds

Heavenly 4 Bedroom Beach Home! Perfect Retreat/grand Piano, Pond, Deck, Grounds

4 Peppermill Lane, Shelter Island, NY
During your stay at this holiday home, you'll be within walking distance of Shelter Island Historical Society. Enjoy your stay with amenities like a kitchen and 2.5 bathrooms in the holiday home.
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NEW LISTING: Farmhouse renovated w/ Convenience + Comfort, Stylish and...

NEW LISTING: Farmhouse renovated w/ Convenience + Comfort, Stylish and...

53 North Cartwright Road, Shelter Island, NY
During your stay at this holiday home, you'll be within walking distance of Shelter Island Whale's Tail. Enjoy features like a hot tub. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.
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Brand New House in Beach Community on Shelter Island, NY

Brand New House in Beach Community on Shelter Island, NY

3 Conrad Rd, Shelter Island, NY
During your stay at this holiday home, you'll be close to Wades Beach. Enjoy your stay with amenities like a private pool and a kitchen in the holiday home.
£82
Montauk Manor

Montauk Manor

3.5 out of 5.0 236 Edgemere St., Montauk, NY
Our customers tell us that they can't get enough of the comfortable beds at Montauk Manor. During your stay, you're just a quick walk from Shadmoor State Park. Features include free WiFi in public areas, free self-parking and a free area shuttle. Built in 1927, this 3.5-star condominium resort has 140 condos over 4 floors. Enjoy your stay with amenities like free WiFi and a kitchen in each condo.
£379
Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4.0 out of 5.0 290 Old Montauk Highway, Montauk, NY
The clean rooms at Gurney's Montauk Resort & Seawater Spa get good marks from our customers. During your stay, you'll be close to Shadmoor State Park. Free WiFi in public areas, free self-parking and 2 restaurants are available. This 4-star resort has 152 rooms. Free WiFi and flat-screen TVs are available in all rooms.
£206
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5.0 2 Bridge St, Old Saybrook, CT
Our customers tell us that they can't get enough of the helpful staff at Saybrook Point Resort & Marina. During your stay, you'll be within walking distance of General William Hart House. You'll find features such as free WiFi in public areas, free self-parking and a free area shuttle. This 3.5-star hotel has 100 rooms over 3 floors. Enjoy your stay with amenities like free WiFi and cable TV channels in each room.
£146
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5.0 1525 Boston Post Road, Westbrook, CT
Our customers tell us they enjoy Water's Edge Resort & Spa 's beach location. During your stay, you'll be within walking distance of Westbrook Town Beach. Features include free WiFi in public areas and free valet parking, plus 3 restaurants. This 3.5-star resort has 190 rooms. Enjoy your stay with amenities like free WiFi and a flat-screen TV in each room.
£123
Sag Harbor Inn

Sag Harbor Inn

3.5 out of 5.0 45 West Water Street, Sag Harbor, NY
During your stay at Sag Harbor Inn, you're just a quick walk from Sag Harbor Whaling and Historical Museum. Free breakfast, free self-parking and an outdoor pool are available. Built in 1989, this 3.5-star inn has 42 rooms over 3 floors. All rooms offer free WiFi and balconies/patios.
£129
Southampton Inn

Southampton Inn

3.0 out of 5.0 91 Hill Street, Southampton, NY
Our customers tell us that they enjoy the comfortable beds at Southampton Inn. During your stay, you're just a quick walk from Agawam Park. Enjoy features like free WiFi in public areas and a free beach shuttle, plus 2 bars. Built in 1998, this 3-star hotel has 90 rooms over 2 floors. All rooms offer free WiFi and Tempur-Pedic beds.
£210
Sound View Greenport

Sound View Greenport

3.0 out of 5.0 58775 Route 48, Greenport, NY
Our customers tell us they enjoy Sound View Greenport's beach location. During your stay, you'll be close to East End Seaport Maritime Museum. You'll find features such as free breakfast, free WiFi in public areas and free self-parking. This 3-star hotel has 55 rooms over 2 floors. Enjoy your stay with amenities like free WiFi and a balcony/patio in each room.
£131
The Harborfront Inn

The Harborfront Inn

3.5 out of 5.0 209 Front St, Greenport, NY
During your stay at The Harborfront Inn , you're just a quick walk from Camera Obscura. Features include free breakfast and free WiFi in public areas, plus a 24-hour fitness centre. This 3.5-star hotel has 35 rooms. All rooms offer free WiFi and flat-screen TVs.
£282
Marram

Marram

4.0 out of 5.0 21 Oceanview Terrace, Montauk, NY
Marram's great location gets high marks from our customers. During your stay, you're just a quick walk from South Edison Beach. Features include free breakfast, free WiFi in public areas and free self-parking. This 4-star hotel has 96 rooms. Free WiFi and fridges are available in all rooms.
£154
Sea Crest Resort

Sea Crest Resort

2.5 out of 5.0 2166 Montauk Hwy, Amagansett, NY
Our customers tell us they enjoy Sea Crest Resort's good location. During your stay, you're just a quick walk from Napeague State Park. Free WiFi in public areas, an outdoor pool and laundry facilities are available. This 2.5-star hotel has 50 rooms over 2 floors. All rooms offer free WiFi and kitchens.

Finding Shelter Island Hotels

So, you're considering a holiday to Shelter Island? If you want to find accommodation that's located near the sights, you can enter your holiday dates and then use the filters next to your hotel search results to find somewhere to stay near the area's attractions. You can choose among 27 Shelter Island hotels and accommodation options to find a place to stay.

Top Hotels and Other Accommodation Options in Shelter Island

When you're deciding where to stay in Shelter Island, you'll be able to quickly and easily search ebookers for hotels offering services such as high-speed Internet, free airport transport or a swimming pool. You can use the filters to narrow down your search for accommodation, so you get the services that are important to you, such as air conditioning or an in-room kitchen.

The following Shelter Island hotel is liked by guests for the swimming pool:

  • Perfect Family Summer Vacation Home Close to beach 18x42 pool

Exploring Shelter Island

The city of Shelter Island has some interesting things to see and do. Popular attractions in and around Shelter Island include:

  • Mashomack Preserve
  • Havens House
  • Shelter Island Historical Society
  • Wades Beach
  • Sylvester Manor
  • Cooper's Beach
  • Bay Street Theatre

When making plans for your holiday in Shelter Island, you can also use ebookers to find a convenient flight to Islip, NY (ISP-MacArthur) Airport. You can narrow down your search by number of stops, airline or departure time to identify one that works best for you.

When is the Best Time to Explore Shelter Island?

If you're curious when is the best time of year to explore Shelter Island, you might find this info about seasonal weather useful when you are planning your trip. The warmest months in Shelter Island are typically July and August, whereas the coldest months are usually January and February. The months with the most rain are March and April, whereas February and December have the least.

Here's an overview on how much rain you can expect and what the temperatures are going to be like:

  • From January to March, the average daytime temperature is 11°C and at night it is -7°C. Seasonal average rainfall is 282 mm.
  • If you visit between April and June, you can expect an average temp of 26°C during the day and -1°C at night. Average rainfall during this season is 321 mm.
  • The daytime average temp from July to September is 27°C and the night-time average is 8°C. Average precipitation for this season is 293 mm.
  • Between October and December, the average temp during the day is 20°C and -6°C at night. Seasonal average rain is 295 mm.
  • The annual rainfall average in Shelter Island is 1190 mm.
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.