Find a Bed and Breakfast in Shelter Island from CA $271

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Our top choices for Shelter Island bed & breakfast

Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.4 out of 10, Exceptional, (1,001 reviews)
"Always a nice stay. Clean and comfortable."
United States
Shelby
The price is CA $236
CA $271 total
includes taxes & fees
Apr 13 - Apr 14
Inn at Harbor Hill Marina

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (183 reviews)
"Delicious breakfast, wonderful service and beautiful accommodations."
United States
Beth
The price is CA $310
CA $344 total
includes taxes & fees
Apr 7 - Apr 8
Westbrook Inn B&B

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (24 reviews)
"Cute B&B, very nice room, check-in worked well"
United States
Isolde
The price is CA $358
CA $397 total
includes taxes & fees
Apr 9 - Apr 10
James Pharmacy Bed & Breakfast

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.6 out of 10, Exceptional, (263 reviews)
"Very clean, easy check-in, lovely owners."
United States
GAIL
The price is CA $278
CA $309 total
includes taxes & fees
May 6 - May 7
The Captain Stannard

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (82 reviews)
"It is a very nice place, the staff is very friendly and the breakfast is very good. Also they have delicious teas, coffee, hot cider and snacks. We definitely recommend this hotel "
United States
Eliane
The price is CA $453
CA $570 total
includes taxes & fees
Apr 8 - Apr 9
Mill House Inn

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (150 reviews)
"Room was clean. Bathroom was refinished. "
United States
robert
The price is CA $340
CA $388 total
includes taxes & fees
Apr 11 - Apr 12
Harpoon House

The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.0 out of 10, Wonderful, (240 reviews)
"Great stay and will be back!"
United States
David
The price is CA $288
CA $320 total
includes taxes & fees
Apr 7 - Apr 8
The Scranton Seahorse Inn

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (237 reviews)
"Really comfortable stay - wonderful property, staff and amenities."
Canada
Anne
The price is CA $237
CA $320 total
includes taxes & fees
Apr 27 - Apr 28
The Sagaponack

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (16 reviews)
"Wonderful stay"
United States
Judy
The price is CA $493
CA $564 total
includes taxes & fees
Apr 7 - Apr 8
Vine & Sand

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
Southold
The price is CA $482
CA $622 total
includes taxes & fees
Apr 7 - Apr 8
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower

The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (105 reviews)
"Inn has been newly renovated. Room was spotless. Staff were wonderful. Had an excellent stay. Highly recommend! "
United States
Valerie
The price is CA $602
CA $701 total
includes taxes & fees
May 3 - May 4
The Huntting Inn

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Southold
10.0 out of 10, Exceptional, (1 review)
"Must like historical houses and little sausage-shaped dogs. A seamless blend of old and mod. Room is meticulously shiny clean. Substantial bedding designed for a good night’s sleep. High-end details (furnishings, footed tub with heat lamp and fluffy robes), culture (gallery), included breakfast is simple perfection due to high-quality ingredients/sourcing (fresh pastries, eggs, butter, fruit). Pool and hot tub divine. Our hosts are upbeat and fun and really went beyond for us. There are great...
United States
Jessica P.
The price is CA $540
CA $699 total
includes taxes & fees
Apr 7 - Apr 8
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Southold
10.0 out of 10, Exceptional, (1 review)
"Great experience. Wonderful hosts. "
United States
Mark L.
The price is CA $482
CA $622 total
includes taxes & fees
Apr 7 - Apr 8
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower

Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Southold
The price is CA $540
CA $699 total
includes taxes & fees
Apr 7 - Apr 8
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite 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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Top Shelter Island Hotel Reviews

Find out more about Shelter Island

Shelter Island B&B information

Number of reviews
2,063
Accommodation
38 B&B
Lowest Price
CA $271
Highest Price
CA $701

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.Harpoon House: 9 rooms. 12.7 mi (20.5 km) from the downtown core. Enjoy the bars and unique décor. Mill House Inn: 10 rooms. 10.7 mi (17.2 km) from the heart of downtown. 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 Gardiner's Bay Country Club 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.

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