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Find a Bed and Breakfast in Shelter Island Heights from CA $244

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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

Browse Select Shelter Island Heights B&B

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, (166)
"The location was great, the room was clean, and the staff were very friendly and accommodating."
The price is CA $443
CA $562 total
includes taxes & fees
Sep 9 - Sep 10
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, (126)
"Great location"
The price is CA $379
CA $434 total
includes taxes & fees
Sep 8 - Sep 9
Harpoon House
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."
The price is CA $795
CA $922 total
includes taxes & fees
Aug 26 - Aug 27
The Huntting Inn
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. "
The price is CA $342
CA $393 total
includes taxes & fees
Sep 8 - Sep 9
Inn at Harbor Hill Marina
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!"
The price is CA $244
CA $271 total
includes taxes & fees
Sep 8 - Sep 9
The Captain Stannard
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 "
The price is CA $989
CA $1,198 total
includes taxes & fees
Aug 10 - Aug 11
The Hedges Inn
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
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"
The price is CA $944
CA $1,078 total
includes taxes & fees
Sep 2 - Sep 3
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
8.2 out of 10, Very good, (34)
"Great property! Close to beach and super clean. "
The price is CA $431
CA $492 total
includes taxes & fees
Sep 8 - Sep 9
West Neck Guesthouse
The Homestead
Relax in a spacious room with a large bed, seating area, and cozy fireplace.

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (82)
"Best breakfast. The little things that were provided (warm bathroom towels, comfortable bed, patio outside our room just for us to enjoy) added to our wonderful 3 day get away in Madison. Don't want to forget the freshly made popcorn in the evening we so enjoyed. "
The Homestead
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, (9)
"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
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. "
The price is CA $567
CA $795 total
includes taxes & fees
Aug 10 - Aug 11
James Pharmacy Bed & Breakfast
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!"
The price is CA $1,369
CA $1,721 total
includes taxes & fees
Aug 10 - Aug 11
Mill House Inn
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, (156)
"My granddaughter and I had a lovely stay."
The price is CA $283
CA $314 total
includes taxes & fees
Sep 2 - Sep 3
Westbrook Inn B&B
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
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
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>
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
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
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
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 Heights Hotel Reviews

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

10/10 Excellent
"Friendly staff, good restaurant "
Barbara 5-night trip
Posted 2 days ago
Saybrook Point Resort & Marina