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Check prices for these dates

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Sep 5 - Sep 7
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Sep 12 - Sep 14
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Sep 26 - Sep 28
In two months
Oct 24 - Oct 26

B&B in Shelter Island

Our top choices for Shelter Island bed & breakfast

The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (171)
"Great stay!"
The price is ￥41,337
￥53,116 total
includes taxes & fees
Sep 24 - Sep 25
The Sagaponack
Harpoon House
Porch

Harpoon House

3.0 star property
8.4 out of 10, Very Good, (131)
"Pop Up Rocco was excellent—bed was crisp & comfortable "
Harpoon House
The Huntting Inn
Garden

The Huntting Inn

3.5 star property
8.8 out of 10, Excellent, (99)
"Great property."
The price is ￥85,122
￥98,725 total
includes taxes & fees
Sep 11 - Sep 12
The Huntting Inn
The Captain Stannard
IPod dock, MP3 dock

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (244)
"Everything was fantastic, will stay again!"
The Captain Stannard
Inn at Harbor Hill Marina
Property grounds

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1003)
"Love this place!!! Beautiful view ! "
The price is ￥38,143
￥43,864 total
includes taxes & fees
Sep 2 - Sep 3
Inn at Harbor Hill Marina
The Hedges Inn
Room One: Large Queen Guestroom | Egyptian cotton sheets, premium bedding, in-room safe

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (71)
"Great staff "
The price is ￥66,139
￥82,779 total
includes taxes & fees
Sep 2 - Sep 3
The Hedges Inn
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (160)
"Charming, beautiful inn; excellent food and service."
The price is ￥32,034
￥35,557 total
includes taxes & fees
Sep 23 - Sep 24
Westbrook Inn B&B
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (63)
"Very profesional, very good experiencia , the host the best , the property beatiful 100 porcent recomended"
The price is ￥93,310
￥106,607 total
includes taxes & fees
Sep 28 - Sep 29
East Hampton Art House Bed & Breakfast
Carole's Place B & B
Property grounds

Carole's Place B & B

3.0 star property
9.8 out of 10, Exceptional, (51)
"That is our second time there and we had a blast again , Carole’s is so kind , and always make sure we are okay with what she will offer for breakfast, great location , so clean and the property has a good care , definitely coming back again ! "
Carole's Place B & B
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (70)
"Great experience at a wonderful property!"
The price is ￥87,626
￥110,123 total
includes taxes & fees
Sep 9 - Sep 10
Mill House Inn
James Pharmacy Bed & Breakfast
Miss Anna James Room | 1 bedroom, individually decorated, individually furnished

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Beautiful property in a great location, convenient to everything.Our room was clean and comfortable."
The price is ￥52,048
￥57,774 total
includes taxes & fees
Sep 8 - Sep 9
James Pharmacy Bed & Breakfast
West Neck Guesthouse
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets

West Neck Guesthouse

3.5 star property
8.2 out of 10, Very Good, (36)
"Great property! Close to beach and super clean. "
The price is ￥46,169
￥52,749 total
includes taxes & fees
Sep 2 - Sep 3
West Neck Guesthouse
Vine & Sand
Interior entrance

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (9)
"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport. "
Vine & Sand
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (36)
"Great hosts"
434 on Main
Harbor Knoll Bed & Breakfast
Living area

Harbor Knoll Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (10)
"Beautiful bed and breakfast with gorgeous views. Close to shops and restaurants but far enough to be private and quiet. Will definitely be coming back"
Harbor Knoll Bed & Breakfast
Arbor View House B&B
Exterior

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (15)
"Two mid age couples just had a good and relaxing time with great hospitality. "
Arbor View House B&B
Stirling House Bed & Breakfast
Beach/ocean view

Stirling House Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (24)
"Our stay was only 2 nights but felt like 5. Well rested 3 days. Would return in a Heart Beat. Clay was awesome and the breakfasts were over the top !"
Stirling House Bed & Breakfast
The 1708 House
Exterior

The 1708 House

3.0 star property
10.0 out of 10, Exceptional, (2)
"We absolutely loved our stay here. The house is stunning, the service is fabulous. The best bed ever to sleep in! Great location and a fabulous breakfast. Thank you. "
The 1708 House
Head of Pond House
Exterior

Head of Pond House

3.0 star property
Head of Pond House
Historical Bed and breakfast<br>
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

Historical Bed and breakfast<br>

8.8 out of 10, Excellent, (5)
"Very great house , Owner was amazing and was very easy to contact and gave us early check in . Would definitely do it agian"
Historical Bed and breakfast<br>
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Shelter Island Hotel Reviews

Find out more about Shelter Island

Find out more about Shelter Island

Shelter Island B&B information

Number of reviews
1,347
Accommodation
38 B&B
Lowest Price
￥32,034
Highest Price
￥93,310

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Searching for B&Bs in Shelter Island?
If you want to find a place to stay with a small number of rooms and an intimate environment, a bed and breakfast might be a great fit for your trip to Shelter Island. During your time in Shelter Island, you might want to spend some time strolling along the water at Sunset Beach and Crescent Beach.
How do you know if a B&B is a good option for your stay?
B&Bs all have a unique charm. Whether it's a cozy reading space or a sunlit breakfast nook, the quaint details are what make bed and breakfasts a fun place to get away.
What are the top B&Bs in Shelter Island?
Here are some B&Bs in the area: The Sagaponack: 9.4 mi (15.2 km) from the heart of Shelter Island.Harpoon House: 9 rooms. Situated 12.7 mi (20.5 km) from the heart of Shelter Island. Enjoy the bars and unique décor. The Captain Stannard: 11 rooms. 16 mi (25.8 km) from the heart of downtown. Enjoy the private yard and unique décor. East Hampton Art House Bed & Breakfast: 2 rooms. Located 9.4 mi (15.1 km) from the core of Shelter Island. Enjoy the free full breakfast and fitness center.
When should I book my B&B in Shelter Island?
When you're dreaming of a escape to Shelter Island, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually August and July with an average temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Shelter Island is 57 inches.
What is there to do in Shelter Island?
Spend some time exploring Sunset Beach and Crescent Beach if you're hoping to see some of the area's natural features. You might put Shelter Island Whale's Tail and Wades Beach on your list if you want to see more of the area.
How can I get to and around Shelter Island?
Planning your excursions in and around Shelter Island is easier with these transportation options. Fly into East Hampton, NY (HTO), which is located 8.8 mi (14.2 km) away from the city center. Otherwise, look for flights into Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.1 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip.