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B&B in Shelter Island

Inn at Harbor Hill Marina
3.5 star property
9.4 out of 10, Exceptional, (1002)
"Clean great staff great breakfast quiet guests beautiful scenery 10/10"
United States
Trey
$159 nightly
The price is $183
Dec 1 - Dec 2
Total with taxes and fees
Inn at Harbor Hill Marina
James Pharmacy Bed & Breakfast
4.0 star property
9.2 out of 10, Wonderful, (20)
"Beautiful property in a great location, convenient to everything.Our room was clean and comfortable."
United States
Ray
$302 nightly
The price is $335
Nov 9 - Nov 10
Total with taxes and fees
James Pharmacy Bed & Breakfast
The Captain Stannard
3.0 star property
9.6 out of 10, Exceptional, (255)
"Clean, friendly and delicious continental breakfast "
United States
Miriam
$238 nightly
The price is $264
Nov 10 - Nov 11
Total with taxes and fees
The Captain Stannard
East Hampton Art House Bed & Breakfast
4.0 star property
9.6 out of 10, Exceptional, (65)
"The hosts were really nice and the breakfast is excellent!"
United States
IVAN
$422 nightly
The price is $482
Nov 10 - Nov 11
Total with taxes and fees
East Hampton Art House Bed & Breakfast
The Sagaponack
3.0 star property
8.8 out of 10, Excellent, (198)
"The room was spotless and had everything that you would need. Would stay here again."
United States
Marjorie
$195 nightly
The price is $223
Nov 12 - Nov 13
Total with taxes and fees
The Sagaponack
Mill House Inn
5.0 star property
9.0 out of 10, Wonderful, (71)
"Delightful property and even more delightful staff. love staying here! "
United States
Brittany
$468 nightly
The price is $534
Nov 25 - Nov 26
Total with taxes and fees
Mill House Inn
Vine & Sand
3.0 star property
9.6 out of 10, Exceptional, (13)
"My husband and I escaped to Long Island for a beautiful fall weekend and thoroughly enjoyed our stay at Vine + Sand. The hosts were very friendly and helpful with restaurant reservations and offered great tips for local activities. The accommodations were eco-friendly, modern and super comfortable and the breakfast in the morning offered delicious pastries and other homemade foods from local bakeries and markets which were a great touch. The location was private yet close enough to get to town...
United States
Heather
Vine & Sand
Westbrook Inn B&B
3.0 star property
9.8 out of 10, Exceptional, (174)
"Beautiful place and wonderful staff"
United States
Rebecca
$209 nightly
The price is $233
Dec 7 - Dec 8
Total with taxes and fees
Westbrook Inn B&B
Head of Pond House
3.0 star property
10.0 out of 10, Exceptional, (2)
"Beautiful place with a very kind host. Highly recommend this place!"
United States
Michèle
$527 nightly
The price is $603
Nov 9 - Nov 10
Total with taxes and fees
Head of Pond House
Harpoon House
3.0 star property
8.4 out of 10, Very Good, (147)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
United States
Karissa
$248 nightly
The price is $284
Nov 14 - Nov 15
Total with taxes and fees
Harpoon House
The Huntting Inn
3.5 star property
9.0 out of 10, Wonderful, (104)
"Staff and management was very welcoming!"
United States
Sanailer
$393 nightly
The price is $447
Nov 20 - Nov 21
Total with taxes and fees
The Huntting Inn
Large Room w use of pool/tennis in Spacious home
$722 nightly
The price is $824
Nov 8 - Nov 9
Total with taxes and fees
Large Room w use of pool/tennis in Spacious home
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

Shelter Island B&B information

Number of reviews
1,496
Accommodation
38 B&B
Lowest Price
$183
Highest Price
$824

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.

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