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Find a Bed and Breakfast in Shelter Island

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Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

Browse Select Shelter Island B&B

The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (130)
"We had a wonderful stay! We will definitely be back!"
The price is CA $229
CA $312 total
includes taxes & fees
Feb 2 - Feb 3
The Sagaponack
Inn at Harbor Hill Marina
Property grounds

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1000)
"This was our first time staying and the decor, attention to details, the coziness and atmosphere of the Inn along with the wonderful staff...and the beautiful location...it was a wonderful visit. Highly recommend!"
The price is CA $195
CA $224 total
includes taxes & fees
Feb 9 - Feb 10
Inn at Harbor Hill Marina
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (65)
"A beautiful house with super friendly staff that's prompt and ready to serve. House was quiet. Our room had a wonderful view of the windmill across the street. Complimentary breakfast was outstanding. Highly recommended."
The price is CA $360
CA $452 total
includes taxes & fees
Feb 10 - Feb 11
Mill House Inn
The Scranton Seahorse Inn
Staircase

The Scranton Seahorse Inn

3.0 star property
9.0 out of 10, Wonderful, (235)
"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 $389
CA $432 total
includes taxes & fees
Feb 10 - Feb 11
The Scranton Seahorse Inn
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
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (143)
"Beautiful bed and breakfast with plush robes and slippers, super clean, would stay again!"
The price is CA $309
CA $344 total
includes taxes & fees
Feb 2 - Feb 3
Westbrook Inn B&B
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 $516
CA $603 total
includes taxes & fees
Feb 13 - Feb 14
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 $207
CA $236 total
includes taxes & fees
Feb 10 - Feb 11
Harpoon House
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 $304
CA $338 total
includes taxes & fees
Feb 13 - Feb 14
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 $608
CA $694 total
includes taxes & fees
Feb 3 - Feb 4
East Hampton Art House Bed & 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
Stirling House Bed & Breakfast
Dock

Stirling House Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (22)
"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."
The price is CA $402
CA $458 total
includes taxes & fees
Feb 10 - Feb 11
Stirling House Bed & Breakfast
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. "
The price is CA $499
CA $726 total
includes taxes & fees
Feb 10 - Feb 11
James Pharmacy Bed & Breakfast
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
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>
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--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Exterior

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
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, (1103)
"The King size bed was very nice to sleep on for my back "
The price is CA $189
CA $243 total
includes taxes & fees
Feb 3 - Feb 4
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (359)
"Perfect for a short stay. Very warm, clean and comfortable. Very close to shops and beach. Check in and check out was super easy. Only critique would be that the walls were thin and you could very easily hear the conversation of the guests in the room next door. "
The price is CA $196
CA $238 total
includes taxes & fees
Feb 2 - Feb 3
Montauk Oceanside Suites
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (268)
"Was a winter wonderland. Quiet and clean. Staff were very helpful and kind!"
The price is CA $190
CA $248 total
includes taxes & fees
Feb 2 - Feb 3
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: The Sagaponack: 9.4 mi (15.2 km) from the heart of Shelter Island.Mill House Inn: 10 rooms. Situated 10.7 mi (17.2 km) from the heart of Shelter Island. Enjoy the free cooked breakfast and designer toiletries. The Baker House 1650: 13 rooms. 10.8 mi (17.4 km) from the heart of downtown. Enjoy the free full 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 Mashomack Preserve if you’re hoping to see some of the area’s natural features. You might put Shelter Island Whale’s Tail and Crescent 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.