Book Shelter Island Bed & Breakfast

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 30 B&B in Shelter Island with updated reviews, rates, and availability.

Library
Westbrook Inn B&B
3.0 star property
10.0 out of 10, Exceptional, (134)
"Very sweet hosts who served us great breakfast!! Felt so comfortable "
The price is $215
$239 total
includes taxes & fees
May 6 - May 7
Westbrook Inn B&B
Reception hall
434 on Main
4.0 star property
10.0 out of 10, Exceptional, (34)
"Great hosts"
434 on Main
Garden
The Farmhouse Bed and Breakfast
3.5 star property
10.0 out of 10, Exceptional, (5)
"The Farmhouse was a perfect stay for a relaxing weekend in beautiful surroundings. The Farmhouse is charming and impeccably kept. The hosts are friendly and amazing cooks. Added plus : a destination charger for our Tesla! Definitely recommend!"
The Farmhouse Bed and Breakfast
Save an average of 15% on thousands of hotels when you're signed in
Exterior
Fordham House
3.0 star property
10.0 out of 10, Exceptional, (16)
"Fantastic couple runs this B&B. Very nice, helpful and accommodating!!!!!!! Beautiful House, Great Breakfast, Nice Area & Wonderful Hosts!"
Fordham House
Aerial view
East Hampton Art House Bed & Breakfast
4.0 star property
9.8 out of 10, Exceptional, (53)
"Beautiful property and Michael and Rosealind are some the nicest hosts we have ever encountered. "
The price is $416
$475 total
includes taxes & fees
May 6 - May 7
East Hampton Art House Bed & Breakfast
Flat-screen TV, fireplace, pay movies
Harbor Knoll Bed & Breakfast
3.0 star property
9.8 out of 10, Exceptional, (6)
"Beautiful, private oceanfront property right next to all the restaurants in town. "
The price is $330
$377 total
includes taxes & fees
May 6 - May 7
Harbor Knoll Bed & Breakfast
Dock
Stirling House Bed & Breakfast
3.0 star property
9.8 out of 10, Exceptional, (21)
"This was a great place to stay with old word charm. If you are looking for a quiet getaway with a beautiful view of the ocean this is it. The breakfast that we had were much better that what you could get in town. My wife and I can't wait to go back."
Stirling House Bed & Breakfast
Garden
Shorecrest Bed and Breakfast
3.5 star property
9.8 out of 10, Exceptional, (18)
"We had a really nice, two night stay! The breakfasts were delicious and accommodations were really nice!"
Shorecrest Bed and Breakfast
Exterior
North Fork Guest House
3.5 star property
9.8 out of 10, Exceptional, (10)
"This is a lovely inn with even lovelier hosts! Absolutely exceeded my expectations."
North Fork Guest House
Front of property
Captain Stannard B&B Country Inn
3.0 star property
9.6 out of 10, Exceptional, (168)
"Excellent place. We had a good time. "
The price is $179
$199 total
includes taxes & fees
May 5 - May 6
Captain Stannard B&B Country Inn
Property grounds
The Hedges Inn
3.5 star property
9.6 out of 10, Exceptional, (66)
"Beautiful location and lovely accommodation."
The Hedges Inn
Indoor pool, seasonal outdoor pool, sun loungers
The Baker House 1650
4.5 star property
9.4 out of 10, Exceptional, (32)
"Absolutely best place to stay in East Hampton! Charming B&B with incredible staff. "
The price is $460
$525 total
includes taxes & fees
May 8 - May 9
The Baker House 1650
Garden
James Pharmacy Bed & Breakfast
4.0 star property
9.4 out of 10, Exceptional, (7)
"quiet and safe, close to everything yet off the 'main' part of the road. bright and airy, loved the room and decor was gorgeous. we were already at the beach, didn't need to see more beach decor. pass to harveys beach was nice, but the beach was gross. breakfast voucher was great, restaurant was quick and delicious"
The price is $286
$438 total
includes taxes & fees
May 5 - May 6
James Pharmacy Bed & Breakfast
Property grounds
Inn at Harbor Hill Marina
3.5 star property
9.2 out of 10, Wonderful, (1003)
"Very quiet place "
The price is $199
$229 total
includes taxes & fees
May 5 - May 6
Inn at Harbor Hill Marina
Property grounds
Carole's Place B & B
3.0 star property
9.2 out of 10, Wonderful, (39)
"It's a cozy house, beautifuly decorated and with a lovely lady serving us a delicious breakfast. I will definitely recommend it to my friends."
Carole's Place B & B
Exterior
Arbor View House B&B
3.5 star property
9.2 out of 10, Wonderful, (13)
"This house was old but beautiful and decorated nicely inside. "
Arbor View House B&B
Staircase
The Scranton Seahorse Inn
3.0 star property
9.0 out of 10, Wonderful, (215)
"We enjoyed our stay, Michael was helpful and a delight to converse with and gave excellent suggestions for the area. "
The price is $223
$248 total
includes taxes & fees
May 6 - May 7
The Scranton Seahorse Inn
Front of property - evening/night
Mill House Inn
5.0 star property
8.8 out of 10, Excellent, (49)
"This place feels like home away from home. Very nice staff. "
The price is $375
$471 total
includes taxes & fees
May 5 - May 6
Mill House Inn
Front of property
The Wainscott Inn
3.0 star property
8.6 out of 10, Excellent, (91)
"The best was incredibly comfy the staff was so nice and over all I couldn’t have found a better place to stay"
The price is $175
$235 total
includes taxes & fees
May 5 - May 6
The Wainscott Inn
Exterior
The Huntting Inn
3.5 star property
8.6 out of 10, Excellent, (71)
"This is the East Hampton we remember from many years ago, My spouse and I have been long time home owners in the East Hampton area and found ourselves staying at the Huntting Inn as we were in the process of moving back into our newly renovated home. Our stay covered three nights and it could not have been a better experience. The room was immaculate, very upto date--clearly they have invested in the property. The staff was thoughtful and very helpful ranging from the modified continental...
The price is $383
$447 total
includes taxes & fees
May 16 - May 17
The Huntting Inn
Don't see what you're looking for?
See all available properties in Shelter Island
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.

Other property types in Shelter Island

Front of property - evening/night
Montauk Manor
3.5 star property
9.2 out of 10, Wonderful, (1012)
"It’s a great place to stay, with beautiful views"
The price is $168
$211 total
includes taxes & fees
May 7 - May 8
Montauk Manor
View from property
Windward Shores Ocean Resort
3.0 star property
8.8 out of 10, Excellent, (233)
"Everything was just as described!"
The price is $159
$203 total
includes taxes & fees
May 5 - May 6
Windward Shores Ocean Resort
On the beach, white sand
The Surf Club
3.5 star property
8.6 out of 10, Excellent, (218)
"Very nice location and nice condo"
The price is $211
$295 total
includes taxes & fees
May 5 - May 6
The Surf Club
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.

Shelter Island B&B information

Number of reviews
1,231
Accommodation
30 B&B
Lowest Price
$175
Highest Price
$460

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 Wainscott Inn: 9.4 mi (15.2 km) from the heart of Shelter Island.Captain Stannard B&B Country Inn: 11 rooms. 16 mi (25.8 km) from the downtown core. Harpoon House: 9 rooms. 12.7 mi (20.5 km) from the heart of downtown. Enjoy the bars 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 Shell Beach and Gardiner’s Bay Country Club 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.

Recent reviews of Shelter Island hotels
Expedia verified reviews