Photo by Brian V. Rowe

Book Shelter Island Bed & Breakfast

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Our top choices for Shelter Island bed & breakfast

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (215)
"Clean & amenities, staff friendly Thank you "
United States
Archil
$172 nightly
The price is $197
Dec 29 - Dec 30
Total with taxes and fees
The Sagaponack

Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.4 out of 10, Exceptional, (1001)
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
$159 nightly
The price is $183
Dec 29 - Dec 30
Total with taxes and fees
Inn at Harbor Hill Marina

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (259)
"The Inn and staff were warm and welcoming, the facility exceptionally clean. Breakfast exceeded my expectations for a continental breakfast! Would absolutely stay again! "
United States
Lisa
$238 nightly
The price is $264
Dec 30 - Dec 31
Total with taxes and fees
The Captain Stannard

East Hampton Art House Bed & Breakfast

East Hampton Art House Bed & Breakfast
4.0 star property
Clearwater Beach
9.6 out of 10, Exceptional, (65)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
United States
Dan
$437 nightly
The price is $499
Dec 25 - Dec 26
Total with taxes and fees
East Hampton Art House Bed & Breakfast

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (75)
"the rooms are outdated and the front desk staff was overbearing the location is great but it’s noisy the breakfast was awesome as was the chef "
United States
Sharon
$578 nightly
The price is $660
Dec 29 - Dec 30
Total with taxes and fees
Mill House Inn

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (177)
"Our stay was amazing! All the staff were so accommodating and kind. The inn has a rustic charm and was so festive for the holidays! Rooms are a good size, clean, and have everything you need. The breakfast was delicious and they even had free tea/coffee/cookies for all guests to enjoy :) "
United States
Chewon
$222 nightly
The price is $247
Dec 29 - Dec 30
Total with taxes and fees
Westbrook Inn B&B

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (13)
"This B&B, and its hosts, were simply amazing. I cannot recommend this place enough."
United States
Sandra
$324 nightly
The price is $371
Jan 7 - Jan 8, 2026
Total with taxes and fees
Vine & Sand

Head of Pond House

Head of Pond House
3.0 star property
Water Mill
10.0 out of 10, Exceptional, (3)
"Beautiful place with a very kind host. Highly recommend this place!"
United States
Michèle
$495 nightly
The price is $566
Jan 5 - Jan 6, 2026
Total with taxes and fees
Head of Pond House

Stirling House Bed & Breakfast

Stirling House Bed & Breakfast
3.0 star property
Greenport
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 !"
United States
Adam
$335 nightly
The price is $383
Jan 23 - Jan 24, 2026
Total with taxes and fees
Stirling House Bed & Breakfast

The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (104)
"Staff and management was very welcoming!"
United States
Sanailer
$393 nightly
The price is $447
Jan 6 - Jan 7, 2026
Total with taxes and fees
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)
"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.
$376 nightly
The price is $430
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very Good, (148)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
United States
Karissa
$298 nightly
The price is $341
Jan 5 - Jan 6, 2026
Total with taxes and fees
Harpoon House

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)
"Great experience. Wonderful hosts. "
United States
Mark L.
$340 nightly
The price is $389
Jan 4 - Jan 5, 2026
Total with taxes and fees
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower

Large Room w use of pool/tennis in Spacious home

Large Room w use of pool/tennis in Spacious home
Sag Harbor
$722 nightly
The price is $824
Dec 25 - Dec 26
Total with taxes and fees
Large Room w use of pool/tennis in Spacious home

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
$350 nightly
The price is $400
Jan 1 - Jan 2, 2026
Total with taxes and fees
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 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
$376 nightly
The price is $430
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Shelter Island Hotel Reviews

Find out more about Shelter Island

Shelter Island B&B information

Number of reviews
1,539
Accommodation
38 B&B
Lowest Price
$183
Highest Price
$823

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 $183 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.

Explore a world of travel with Expedia