Photo by tom owens

Search B&B in Shelter Island

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

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

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (136)
"We had an unexpected trip to sag harbor and had to reserve quickly. The property was clean very pretty and quaint. The room was comfortable and quaint as well. "
The price is SAR 522
SAR 727 total
includes taxes & fees
23 Feb - 24 Feb
The Sagaponack

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1005)
"We really enjoyed our stay! This was our second time staying on the property - in the same room. We love the fireplace and the bathroom was great too! Beautiful view of the marina and the water beyond. Breakfast was absolutely delicious every morning as well! "
The price is SAR 456
SAR 525 total
includes taxes & fees
23 Feb - 24 Feb
Inn at Harbor Hill Marina

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (67)
"What a lovely space and wonderful thoughtful staff! Absolutely loved everything about it, and the breakfast was beyond excellence! Hats off to the chef you can tell she cooked with ❤️ love. Highly Recommend you experience it for yourself. "
The price is SAR 938
SAR 1,177 total
includes taxes & fees
23 Feb - 24 Feb
Mill House Inn

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 SAR 881
SAR 977 total
includes taxes & fees
24 Feb - 25 Feb
The Scranton Seahorse Inn

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

3.0 star property
10.0 out of 10, Exceptional, (144)
"The host was very friendly and helpful. The property was well maintained. It is quite and we enjoyed our stay. "
The price is SAR 806
SAR 895 total
includes taxes & fees
24 Feb - 25 Feb
Westbrook Inn B&B

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 SAR 1,728
SAR 2,009 total
includes taxes & fees
24 Mar - 25 Mar
The Huntting Inn

Harpoon House

3.0 star property
8.2 out of 10, Very Good, (111)
"We were told to check in at a restaurant that was closed, but we decided to try going in the house and there was a small reception deal and a number to call. The host answered immediately and we were quickly taken to our room. The room was very inviting, clean, and elegant. My only complaint is the bathroom was freezing cold! A small space heater in NY in February would have made all the difference! The room had a great heating system, but leaving the bathroom door wide open all the time let in...
The price is SAR 469
SAR 535 total
includes taxes & fees
23 Feb - 24 Feb
Harpoon House

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 SAR 673
SAR 747 total
includes taxes & fees
27 Feb - 28 Feb
The Captain Stannard B&B Country Inn

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main

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

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

4.0 star property
9.6 out of 10, Exceptional, (61)
"What a beautiful, quiet, peaceful place to stay, even in the dead of winter. The home itself is modern, welcoming, bright, everything you could dream of. The hosts are very active and successful artists who all but gave us a private master class in how their work is imagined and created. I don’t know when we’ve had a more delightful weekend. The walks to the beach were lovely, too. "
The price is SAR 1,584
SAR 1,808 total
includes taxes & fees
24 Feb - 25 Feb
East Hampton Art House Bed & Breakfast

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

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 SAR 1,256
SAR 1,433 total
includes taxes & fees
24 Feb - 25 Feb
Stirling House Bed & Breakfast

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

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (7)
"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

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

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

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.
Don't see what you're looking for?
See all available properties in Shelter Island
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Shelter Island

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1116)
"We loved the manor, it had great amenities and an excellent experience. highly recommend! "
The price is SAR 491
SAR 634 total
includes taxes & fees
24 Feb - 25 Feb
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very Good, (362)
"I didn’t realize the property was mobile check-in and that all communication would be automated in the winter season. if you guys had that more clear on the Expedia it would be awesome. Otherwise the stay was great, clean room, no hassle to get in, right by the beach. "
The price is SAR 421
SAR 518 total
includes taxes & fees
27 Feb - 28 Feb
Montauk Oceanside Suites

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (273)
"Everything Was Great The Only Issues Were The Fridge Was Not Getting Cold And The Bed Was Not Comfortable But Property was Great "
The price is SAR 494
SAR 645 total
includes taxes & fees
20 Mar - 21 Mar
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. Enjoy the outdoor pool and free beach shuttle. 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. 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 Shelter Island Historical Society 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.