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Check prices for these dates

Next weekend
Jun 27 - Jun 29
In two weeks
Jul 4 - Jul 6
In one month
Jul 18 - Jul 20
In two months
Aug 15 - Aug 17

Compare 38 B&B in Shelter Island with updated reviews, rates, and availability.

The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (156)
"The location was great, the room was clean, and the staff were very friendly and accommodating."
$364 nightly
The price is $416
Jun 22 - Jun 23
Total includes taxes and fees
The Sagaponack
Harpoon House
Porch

Harpoon House

3.0 star property
8.2 out of 10, Very Good, (117)
"Great location"
$244 nightly
The price is $279
Jun 24 - Jun 25
Total includes taxes and fees
Harpoon House
Inn at Harbor Hill Marina
Property grounds

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1000)
"Wonderfully maintained old home. Aesthetically pleasing. Absolute piece of heaven. "
$269 nightly
The price is $309
Jun 23 - Jun 24
Total includes taxes and fees
Inn at Harbor Hill Marina
The Captain Stannard
LED TV

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (227)
"Very nice place and the owners are super people and treat their customers very well! I loved it here and would definitely stay here again!"
$252 nightly
The price is $280
Jun 22 - Jun 23
Total includes taxes and fees
The Captain Stannard
Carole's Place B & B
Property grounds

Carole's Place B & B

3.0 star property
10.0 out of 10, Exceptional, (35)
"WE HAD A GOOD EXPERIENSE. "
Carole's Place B & B
The Huntting Inn
Garden

The Huntting Inn

3.5 star property
8.8 out of 10, Excellent, (90)
"Best place to stay in East Haven! Location is perfect, attention can’t "
$588 nightly
The price is $670
Jul 7 - Jul 8
Total includes taxes and fees
The Huntting Inn
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (69)
"Great experience at a wonderful property!"
$875 nightly
The price is $999
Jun 23 - Jun 24
Total includes taxes and fees
Mill House Inn
West Neck Guesthouse
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets

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! "
$219 nightly
The price is $250
Jun 23 - Jun 24
Total includes taxes and fees
West Neck Guesthouse
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
Stirling House Bed & Breakfast
Beach/ocean view

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 Hedges Inn
Room One: Large Queen Guestroom | Egyptian cotton sheets, premium bedding, in-room safe

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (68)
"Absolutely fabulous homely and beautifully decorated Conveniently located between downtown and the beach so easy to walk"
$942 nightly
The price is $1,076
Jun 22 - Jun 23
Total includes taxes and fees
The Hedges Inn
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (61)
"The hosts were really nice and the breakfast is excellent!"
$762 nightly
The price is $871
Jun 23 - Jun 24
Total includes taxes and fees
East Hampton Art House Bed & Breakfast
Vine & Sand
Interior entrance

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
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (150)
"Beautiful bed and breakfast with plush robes and slippers, super clean, would stay again!"
$276 nightly
The price is $307
Jun 26 - Jun 27
Total includes taxes and fees
Westbrook Inn B&B
The Farmhouse Bed and Breakfast
Living area

The Farmhouse Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (11)
"Lovely B&B run by a lovely couple"
The Farmhouse Bed and Breakfast
Harbor Knoll Bed & Breakfast
Living area

Harbor Knoll Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (9)
"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
Exterior

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
James Pharmacy Bed & Breakfast
Miss Anna James Room | 1 bedroom, individually decorated, individually furnished

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
$532 nightly
The price is $578
Jun 22 - Jun 23
Total includes taxes and fees
James Pharmacy Bed & Breakfast
Arbor View House B&B
Exterior

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (14)
"Two mid age couples just had a good and relaxing time with great hospitality. "
Arbor View House B&B
Historical Bed and breakfast<br>
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

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>
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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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 $250 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.