Search B&B in Shelter Island

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
In two months
16 Jan - 18 Jan

B&B in Shelter Island

Terrace/patio
Westbrook Inn B&B

Westbrook Inn B&B

3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (175)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is SAR 536
SAR 595 total
includes taxes & fees
2 Dec - 3 Dec
Westbrook Inn B&B
Property grounds
Inn at Harbor Hill Marina

Inn at Harbor Hill Marina

3.5 star property
Niantic
9.4 out of 10, Exceptional, (1001)
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
The price is SAR 539
SAR 620 total
includes taxes & fees
23 Nov - 24 Nov
Inn at Harbor Hill Marina
IPod dock, MP3 dock
The Captain Stannard

The Captain Stannard

3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (256)
"Amazing stay! Everything was perfect and it is clear that the owners love their jobs and their inn. Can't wait to go back! "
United States
Julie
The price is SAR 569
SAR 632 total
includes taxes & fees
30 Nov - 1 Dec
The Captain Stannard
Exterior
The Sagaponack

The Sagaponack

3.0 star property
Wainscott
8.8 out of 10, Excellent, (207)
"An absolute gem of a place to stay. The rooms are full of character and charm, it’s The Hamptons all the way. Great location, too. "
United States
Brad
The price is SAR 632
SAR 872 total
includes taxes & fees
1 Dec - 2 Dec
The Sagaponack
Front of property - evening/night
Mill House Inn

Mill House Inn

5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (73)
"We stayed at the Inn for our anniversary last weekend. We are devotees of bed and breakfast hotels and loved this one. We arrived to find a huge, and I mean, huge, bouquet of the most beautiful white roses waiting for us in the suite that they upgraded us to. Totally unexpected. These folks could not do enough for us. Breakfast was extremely nice, cooked to order with quality ingredients. Bed was extremely warm and comfortable. The management, the staff, can't say anything negative about...
United States
margaret
The price is SAR 1,125
SAR 1,414 total
includes taxes & fees
1 Dec - 2 Dec
Mill House Inn
Aerial view
East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast

4.0 star property
Clearwater Beach
9.6 out of 10, Exceptional, (65)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
United States
Dan
The price is SAR 1,474
SAR 1,684 total
includes taxes & fees
4 Dec - 5 Dec
East Hampton Art House Bed & Breakfast
Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board
James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4.0 star property
Old Saybrook Center
9.2 out of 10, Wonderful, (20)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
United States
Rachel
The price is SAR 1,133
SAR 1,257 total
includes taxes & fees
23 Nov - 24 Nov
James Pharmacy Bed & Breakfast
Interior entrance
Vine & Sand

Vine & Sand

3.0 star property
Southold
9.6 out of 10, Exceptional, (13)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
United States
Sandra
Vine & Sand
Seasonal outdoor pool
Head of Pond House

Head of Pond House

3.0 star property
Water Mill
10.0 out of 10, Exceptional, (2)
"Beautiful place with a very kind host. Highly recommend this place!"
United States
Michèle
The price is SAR 1,975
SAR 2,256 total
includes taxes & fees
3 Dec - 4 Dec
Head of Pond House
Porch
Harpoon House

Harpoon House

3.0 star property
Southampton
8.4 out of 10, Very Good, (148)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
United States
Karissa
Harpoon House
Garden
The Huntting Inn

The Huntting Inn

3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (104)
"Staff and management was very welcoming!"
United States
Sanailer
The price is SAR 1,434
SAR 1,676 total
includes taxes & fees
4 Dec - 5 Dec
The Huntting Inn
Outdoor dining
Large Room w use of pool/tennis in Spacious home

Large Room w use of pool/tennis in Spacious home

Sag Harbor
The price is SAR 2,143
SAR 3,091 total
includes taxes & fees
22 Nov - 23 Nov
Large Room w use of pool/tennis in Spacious home
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.
View all properties

White Friday Sale

Limited-time deals: Save up to 50% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shelter Island Hotel Reviews

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

10/10 Excellent
"Staff was kind. Easy, comfortable stay."
Jake 3-night trip
Posted 2 days ago
Quality Inn Old Saybrook - Westbrook

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. Harpoon House: 9 rooms. 12.7 mi (20.5 km) from the heart of downtown. Enjoy the bars and unique décor. The Captain Stannard: 11 rooms. Located 16 mi (25.8 km) from the core of Shelter Island. Enjoy the private yard 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 Shelter Island Whale's Tail 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.