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Search B&B in Shelter Island

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Check prices for these dates

Next weekend
31 Jan - 2 Feb
In two weeks
7 Feb - 9 Feb
In one month
21 Feb - 23 Feb
In two months
21 Mar - 23 Mar

Compare 31 B&B in Shelter Island with updated reviews, rates, and availability.

The Sagaponack
Room

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 AED 585
AED 796 total
includes taxes & fees
26 Jan - 27 Jan
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)
"We stay this and all night kept hearing someone walking back and forth. I would go back and stay on the second floor. Place is beautiful. "
The price is AED 465
AED 535 total
includes taxes & fees
23 Jan - 24 Jan
Inn at Harbor Hill Marina
Mill House Inn
Front of property

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (63)
"Greeting was so welcoming n informative "
The price is AED 918
AED 1,153 total
includes taxes & fees
23 Jan - 24 Jan
Mill House Inn
The Scranton Seahorse Inn
Front of property

The Scranton Seahorse Inn

3.0 star property
9.0 out of 10, Wonderful, (235)
"Amazing experience!"
The price is AED 983
AED 1,091 total
includes taxes & fees
6 Feb - 7 Feb
The Scranton Seahorse Inn
Carole's Place B & B
Front of property

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
Dock

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 AED 789
AED 876 total
includes taxes & fees
26 Jan - 27 Jan
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 AED 1,315
AED 1,538 total
includes taxes & fees
10 Feb - 11 Feb
The Huntting Inn
Harpoon House
Reception

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 AED 527
AED 602 total
includes taxes & fees
3 Feb - 4 Feb
Harpoon House
The Captain Stannard B&B Country Inn
Exterior

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 AED 776
AED 862 total
includes taxes & fees
13 Feb - 14 Feb
The Captain Stannard B&B Country Inn
434 on Main
Front of property

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
West Neck Guesthouse
Property grounds

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
Front of property

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 AED 1,551
AED 1,771 total
includes taxes & fees
23 Jan - 24 Jan
East Hampton Art House Bed & Breakfast
The Baker House 1650
Exterior

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
Room

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
Room

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 AED 1,272
AED 1,852 total
includes taxes & fees
9 Feb - 10 Feb
James Pharmacy Bed & Breakfast
Historical Bed and breakfast<br>
Exterior

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
Exterior

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
Front of property

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
Room

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
Exterior

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1095)
"I love the hotel ! Fireplace in the room ! Kitchenet! Great restaurant ar the hotel ! We wil be back "
The price is AED 481
AED 621 total
includes taxes & fees
27 Jan - 28 Jan
Montauk Manor
Montauk Oceanside Suites
Front of property

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very Good, (354)
"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 AED 500
AED 607 total
includes taxes & fees
24 Jan - 25 Jan
Montauk Oceanside Suites
Windward Shores Ocean Resort
Property grounds

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (267)
"Perfect location for a peaceful winter weekend getaway. We’ve stayed here before and definitely will again. "
The price is AED 464
AED 609 total
includes taxes & fees
26 Jan - 27 Jan
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.East Hampton Art House Bed & Breakfast: 2 rooms. 9.4 mi (15.1 km) from the downtown core. Enjoy the free full breakfast and fitness center. Mill House Inn: 10 rooms. 10.7 mi (17.2 km) from the heart of downtown. Enjoy the free cooked breakfast and designer toiletries. Harpoon House: 9 rooms. Located 12.7 mi (20.5 km) from the core of Shelter Island. Enjoy the bars and unique décor.
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 Shell 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.