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Find a Bed and Breakfast in Shelter Island from CA $214

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Browse Select Shelter Island B&B

The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (126)
"I really liked the manager Shelby. She went above and beyond to make us feel welcome. She was hospitable, warm and friendly. The room was new, however the bathroom was very small and it was challenging to adjust the water temperature in the shower .But overall it exceeded my expectations. "
The price is CA $229
CA $311 total
includes taxes & fees
Dec 30 - Dec 31
The Sagaponack
Inn at Harbor Hill Marina
Property grounds

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1001)
"Lovely stay - beautiful view. Well appointed though small room. Appreciated the cooked to order breakfast and happy hour. Will stay again. Easy walk to restaurants and shops downtown. "
The price is CA $214
CA $246 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Inn at Harbor Hill Marina
The Scranton Seahorse Inn
Staircase

The Scranton Seahorse Inn

3.0 star property
9.0 out of 10, Wonderful, (234)
"This was a one night stay. The property is an older house in the city center. We were here to help a friend celebrate a birthday. The B&B was very close to the party making it easy to come and go. The room was small but comfortable. The bed was very comfortable. Breakfast was fantastic. "
The price is CA $388
CA $431 total
includes taxes & fees
Dec 30 - Dec 31
The Scranton Seahorse Inn
The Huntting Inn
Exterior

The Huntting Inn

3.5 star property
8.6 out of 10, Excellent, (87)
"One of the very few options in East Hampton that offered a one night stay, most have a 2-night minimum. An old, charming inn that was very welcoming and clean. Our king bed room was spacious enough and decorated nicely. The bathroom was very clean and modernized. We did have to walk up a flight of stairs with our luggage which wasn’t difficult for us but may be for some."
The price is CA $514
CA $601 total
includes taxes & fees
Jan 9 - Jan 10, 2025
The Huntting Inn
Harpoon House
Porch

Harpoon House

3.0 star property
8.2 out of 10, Very good, (109)
"The place and the room were great and extremely well equipped. This was an independent stay, but staff was very efficient and friendly in checking us in."
The price is CA $234
CA $267 total
includes taxes & fees
Jan 26 - Jan 27, 2025
Harpoon House
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
8.8 out of 10, Excellent, (60)
"Lovely building. Our room was great. Staff were very nice and accommodating. We would definitely return."
The price is CA $359
CA $410 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Mill House Inn
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (142)
"If you're looking for a quaint New England B & B, this is your place! Beautifully appointed, it's a few minutes drive to parks, shopping, the shoreline, and historic sites. "
The price is CA $308
CA $342 total
includes taxes & fees
Jan 9 - Jan 10, 2025
Westbrook Inn B&B
Carole's Place B & B
Property grounds

Carole's Place B & B

3.0 star property
9.6 out of 10, Exceptional, (67)
"We stayed with Carole for two nights, and we absolutely loved her place! The location was perfect for us—central and convenient. From the moment we arrived, we felt right at home. She has created such a warm and cozy space, and her hospitality made all the difference. We truly appreciated her kindness and how welcoming she was. Without a doubt, we’ll be staying with her again the next time we visit Long Island!"
Carole's Place B & B
The Captain Stannard B&B Country Inn
Front of property

The Captain Stannard B&B Country Inn

3.0 star property
9.6 out of 10, Exceptional, (214)
"We had a wonderful time and the owner was great. We had a fun time talking about history of both inn’s. Look forward to returning and doing more next time"
The price is CA $287
CA $318 total
includes taxes & fees
Jan 2 - Jan 3, 2025
The Captain Stannard B&B Country Inn
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
West Neck Guesthouse
Deluxe Room, 1 King Bed

West Neck Guesthouse

3.5 star property
8.0 out of 10, Very good, (32)
"Very convenient location next to Cresent Beach and Leon 1909 restaurant which is fantastic! "
West Neck Guesthouse
The Hedges Inn
Room One: Large Queen Guestroom

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (68)
"Super friendly staff, very accommodating! We can’t wait to return. "
The Hedges Inn
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (60)
"Beautiful grounds, pool and hot tub! Beautiful breakfast!"
The price is CA $606
CA $692 total
includes taxes & fees
Dec 30 - Dec 31
East Hampton Art House Bed & Breakfast
The Baker House 1650
Indoor pool, seasonal outdoor pool, sun loungers

The Baker House 1650

4.5 star property
9.4 out of 10, Exceptional, (33)
"Absolutely best place to stay in East Hampton! Charming B&B with incredible staff. "
The Baker House 1650
Vine & Sand
Interior entrance

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (6)
"My husband and I escaped to Long Island for a beautiful fall weekend and thoroughly enjoyed our stay at Vine + Sand. The hosts were very friendly and helpful with restaurant reservations and offered great tips for local activities. The accommodations were eco-friendly, modern and super comfortable and the breakfast in the morning offered delicious pastries and other homemade foods from local bakeries and markets which were a great touch. The location was private yet close enough to get to town...
Vine & Sand
James Pharmacy Bed & Breakfast
Garden

James Pharmacy Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (14)
"We loved staying in the historic pharmacy. We stayed in the Ann Petry room and it is well appointed, clean and charming. The property sits on the town's main street and is very walkable to shopping and dining. We look forward to our next stay. "
James Pharmacy Bed & Breakfast
Historical Bed and breakfast<br>
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

Historical Bed and breakfast<br>

8.6 out of 10, Excellent, (4)
"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>
Harbor Knoll Bed & Breakfast
Living area

Harbor Knoll Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (9)
"We stayed here for our mini moon and couldn't have asked for a better weekend! We loved hanging out at the inn and getting to know Leueen and the other guests. The inn is walking distance to the main streets and the train. Will definitely visit again!"
Harbor Knoll Bed & Breakfast
The Farmhouse Bed and Breakfast
Garden

The Farmhouse Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (10)
"Lovely B&B run by a lovely couple"
The Farmhouse Bed and Breakfast
Arbor View House 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
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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Other property types in Shelter Island

Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1087)
"Charming and historic hotel in Montauk. Drive on up or take a taxi from the train station as there are no real sidewalks in this area. The building is beautiful and in great condition thanks to years of care and maintenance. My ground-floor suite came with a kitchenette, living room, and private patio, though I did not make use of the patio as it was 20° in December when I visited. I recommend paying a visit to Monte’s, the hotel restaurant, which appears to be popular among locals and outside...
The price is CA $188
CA $242 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (347)
"Needs to have someone man the phones…"
The price is CA $195
CA $237 total
includes taxes & fees
Jan 1 - Jan 2, 2025
Montauk Oceanside Suites
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (264)
"Stayed for the second time at Windward and have no complaints. will book again next time I'm in Montauk!"
The price is CA $181
CA $238 total
includes taxes & fees
Jan 6 - Jan 7, 2025
Windward Shores Ocean Resort
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.

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: Harpoon House: 9 rooms. Situated 12.7 mi (20.5 km) from the heart of Shelter Island. Enjoy the bars and unique décor. East Hampton Art House Bed & Breakfast: 2 rooms. 9.4 mi (15.1 km) from the heart of downtown. Enjoy the free full breakfast and fitness center. Mill House Inn: 10 rooms. Located 10.7 mi (17.2 km) from the core of Shelter Island. Enjoy the free cooked breakfast and designer toiletries.
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 Historical Society and Mashomack Preserve 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.