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B&B in Shelter Island

Our top choices for Shelter Island bed & breakfast

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (178)
"Great stay!"
$246 nightly
The price is $282
Oct 13 - Oct 14
Total with taxes and fees
The Sagaponack

The Huntting Inn

3.5 star property
9.0 out of 10, Wonderful, (102)
"What a wonderful place to stay! The room was beautiful. The bed was comfortable and the staff were welcoming and helpful. We loved how close it was to town. We also enjoyed the breakfast every morning. The Palm restaurant downstairs was nice to have on property and the food was great. We will definitely stay again!"
$490 nightly
The price is $559
Oct 6 - Oct 7
Total with taxes and fees
The Huntting Inn

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1000)
"Homestyle welcome in an incredibly cosy inn!"
$229 nightly
The price is $263
Oct 1 - Oct 2
Total with taxes and fees
Inn at Harbor Hill Marina

Harpoon House

3.0 star property
8.4 out of 10, Very Good, (140)
"Cute spot"
$296 nightly
The price is $339
Oct 22 - Oct 23
Total with taxes and fees
Harpoon House

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (247)
"Everything was fantastic, will stay again!"
$238 nightly
The price is $264
Sep 25 - Sep 26
Total with taxes and fees
The Captain Stannard

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (71)
"Great staff "
$442 nightly
The price is $505
Sep 25 - Sep 26
Total with taxes and fees
The Hedges Inn

Westbrook Inn B&B

3.0 star property
9.8 out of 10, Exceptional, (167)
"Beautiful place and wonderful staff"
$220 nightly
The price is $245
Sep 23 - Sep 24
Total with taxes and fees
Westbrook Inn B&B

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (18)
"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!"
$272 nightly
The price is $302
Oct 1 - Oct 2
Total with taxes and fees
James Pharmacy Bed & Breakfast

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (70)
"Great experience at a wonderful property!"
$468 nightly
The price is $534
Oct 20 - Oct 21
Total with taxes and fees
Mill House Inn

Carole's Place B & B

3.0 star property
9.8 out of 10, Exceptional, (55)
"Very clean and quiet, super comfortable bed, good central location to get around on Long Island, and an great host."
$150 nightly
The price is $171
Oct 1 - Oct 2
Total with taxes and fees
Carole's Place B & B

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (64)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
$634 nightly
The price is $724
Sep 29 - Sep 30
Total with taxes and fees
East Hampton Art House Bed & Breakfast

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (11)
"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

West Neck Guesthouse

3.5 star property
8.0 out of 10, Very Good, (37)
"Great property! Close to beach and super clean. "
$314 nightly
The price is $358
Oct 2 - Oct 3
Total with taxes and fees
West Neck Guesthouse

Stirling House Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (24)
"Our stay was only 2 nights but felt like 5. Well rested 3 days. Would return in a Heart Beat. Clay was awesome and the breakfasts were over the top !"
Stirling House Bed & Breakfast

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

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (36)
"Great hosts"
434 on Main

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

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

Head of Pond House

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful place with a very kind host. Highly recommend this place!"
Head of Pond House

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>
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

Find out more about Shelter Island

Shelter Island B&B information

Number of reviews
1,694
Accommodation
38 B&B
Lowest Price
$171
Highest Price
$724

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 $171 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.

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