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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

B&B in Shelter Island

The Sagaponack
Relax in a serene outdoor space surrounded by lush greenery and a charming house with a gabled roof.

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (165)
"The location was great, the room was clean, and the staff were very friendly and accommodating."
$376 nightly
The price is $430
Sep 1 - Sep 2
Total includes taxes and fees
The Sagaponack
Harpoon House
Relax on the porch with a comfortable chair and a view of lush greenery.

Harpoon House

3.0 star property
8.4 out of 10, Very Good, (125)
"Great location"
$272 nightly
The price is $311
Sep 4 - Sep 5
Total includes taxes and fees
Harpoon House
Inn at Harbor Hill Marina
Relax in a serene outdoor space surrounded by lush greenery and beautifully manicured lawns.

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1003)
"Really cute bed and breakfast! Great location on the marina. The food was good and the people were very friendly. "
$249 nightly
The price is $286
Sep 3 - Sep 4
Total includes taxes and fees
Inn at Harbor Hill Marina
The Huntting Inn
Relax in style on the patio, surrounded by lush greenery and comfortable seating.

The Huntting Inn

3.5 star property
8.8 out of 10, Excellent, (95)
"Great property."
$588 nightly
The price is $670
Aug 26 - Aug 27
Total includes taxes and fees
The Huntting Inn
The Hedges Inn
Cozy retreat with a four-poster bed, dresser, and nightstand, plus a large mirror and TV for a comfortable stay.

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (71)
"Great staff "
$1,042 nightly
The price is $1,190
Aug 10 - Aug 11
Total includes taxes and fees
The Hedges Inn
The Captain Stannard
Cozy up by the fireplace in this stylish living room, featuring a comfortable sofa, armchair, and decorative artwork.

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (237)
"Everything was fantastic, will stay again!"
$197 nightly
The price is $219
Sep 3 - Sep 4
Total includes taxes and fees
The Captain Stannard
Carole's Place B & B
Swimmers can enjoy a refreshing dip in the pool surrounded by a deck and lush greenery.

Carole's Place B & B

3.0 star property
9.8 out of 10, Exceptional, (47)
"It’s a very charming place and well located."
Carole's Place B & B
Mill House Inn
Stately home surrounded by lush greenery and mature trees, offering a serene and atmosphere.

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (70)
"Great experience at a wonderful property!"
$1,095 nightly
The price is $1,250
Aug 10 - Aug 11
Total includes taxes and fees
Mill House Inn
Vine & Sand
Stairs lead to a spacious interior with a polished floor, patterned wallpaper, and a modern light fixture.

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
East Hampton Art House Bed & Breakfast
Relax in a spacious outdoor area with a swimming pool surrounded by gardens and seating arrangements.

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (63)
"Very profesional, very good experiencia , the host the best , the property beatiful 100 porcent recomended"
$762 nightly
The price is $871
Sep 2 - Sep 3
Total includes taxes and fees
East Hampton Art House Bed & Breakfast
West Neck Guesthouse
Relax in this serene bedroom with a large bed, nightstand, and skylight above.

West Neck Guesthouse

3.5 star property
8.0 out of 10, Very Good, (33)
"Very convenient location next to Cresent Beach and Leon 1909 restaurant which is fantastic! "
$314 nightly
The price is $358
Aug 21 - Aug 22
Total includes taxes and fees
West Neck Guesthouse
Stirling House Bed & Breakfast
Enjoy a scenic breakfast on the deck overlooking the water, with a table set for a delicious meal.

Stirling House Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (23)
"Very comfortable king size bed. Excellent gourmet breakfast, discreet host. Older house, but all the comforts. Absolutely every need provided for. "
Stirling House Bed & Breakfast
Westbrook Inn B&B
Relax in the serene outdoor patio area, surrounded by lush greenery and comfortable seating options.

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (155)
"My granddaughter and I had a lovely stay."
$187 nightly
The price is $208
Sep 3 - Sep 4
Total includes taxes and fees
Westbrook Inn B&B
James Pharmacy Bed & Breakfast
Relax in a classic room with a four-poster bed, flat-screen TV, and comfortable armchair.

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
James Pharmacy Bed & Breakfast
434 on Main
Enjoy a peaceful view of the outdoors from this room's large window, which also illuminates the space.

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (36)
"Great hosts"
434 on Main
The Farmhouse Bed and Breakfast
Enjoy meals in this beautifully set dining area with a long table, vase, and candle holder.

The Farmhouse Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (13)
"very comfortable stay. "
The Farmhouse Bed and Breakfast
Harbor Knoll Bed & Breakfast
Relax in this open-plan living space with a high ceiling and exposed beams, featuring a dining area, seating area, and large windows.

Harbor Knoll Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (10)
"Beautiful bed and breakfast with gorgeous views. Close to shops and restaurants but far enough to be private and quiet. Will definitely be coming back"
Harbor Knoll Bed & Breakfast
The 1708 House
Two-story home with a central entrance, double doors, and a front porch supported by white columns.

The 1708 House

3.0 star property
10.0 out of 10, Exceptional, (2)
"We absolutely loved our stay here. The house is stunning, the service is fabulous. The best bed ever to sleep in! Great location and a fabulous breakfast. Thank you. "
The 1708 House
Historical Bed and breakfast<br>
Enjoy cooking in this kitchen with a central island and bar seating, featuring stainless steel appliances and large windows.

Historical Bed and breakfast<br>

8.8 out of 10, Excellent, (5)
"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>
Arbor View House B&B
Enjoy a serene beach experience with calm seas and a picturesque view.

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (15)
"Two mid age couples just had a good and relaxing time with great hospitality. "
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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Top Shelter Island Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"The room was beautiful-clean, spacious and a great view!! I would say that the prices for in-room amenities were a bit steep however. "
Linda 3-night trip
Posted 2 days ago
Saybrook Point Resort & Marina

Frequently asked questions

What is the nightly rate for a B&B in Shelter Island?
Prices for B&Bs in Shelter Island often vary, but you can find a great deal from $208 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Shelter Island B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a Bed & Breakfast in Shelter Island?
The best time to book a B&B in Shelter Island is during the summer months, particularly from June through August. This peak travel season attracts visitors seeking sunny weather and the chance to indulge in a variety of outdoor activities, such as sailing, biking, and relaxing on the beautiful beaches. The island's unique charm shines during this vibrant time, making it an ideal setting for those looking to unwind and soak in the coastal atmosphere.

July is the most popular month to visit, as the warm temperatures, typically ranging from the mid-60s to the low 80s Fahrenheit, create a great environment for both relaxation and adventure. Guests can enjoy leisurely strolls along the waterfront, explore local art galleries, or partake in seasonal events, all while mingling with fellow travelers and locals.

For those who appreciate a quieter experience, consider planning your visit in September. This month offers pleasant weather and fewer crowds, allowing you to savor the island's beauty at a more relaxed pace. Early autumn brings a lovely change in scenery, with the majority of summer visitors having departed, making it an excellent time for peaceful beach walks and exploring the nature trails.
What is the difference between a Shelter Island Bed & Breakfast and a hotel?
Every Shelter Island B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Shelter Island B&Bs.