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B&B in Shelter Island Heights

Inn at Harbor Hill Marina

3.5 star property
Niantic
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
Old Saybrook Center
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
Westbrook Center
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

The Sagaponack

3.0 star property
Wainscott
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

East Hampton Art House Bed & Breakfast

4.0 star property
Clearwater Beach
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

Mill House Inn

5.0 star property
North Main Street Historic District
9.0 out of 10, Wonderful, (71)
"Delightful property and even more delightful staff. love staying here! "
United States
Brittany
$330 nightly
The price is $377
Dec 1 - Dec 2
Total with taxes and fees
Mill House Inn

Westbrook Inn B&B

3.0 star property
Westbrook Center
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

Vine & Sand

3.0 star property
Southold
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
$320 nightly
The price is $366
Dec 2 - Dec 3
Total with taxes and fees
Vine & Sand

The Homestead

3.0 star property
Madison Center
10.0 out of 10, Exceptional, (87)
"This is our 2nd year staying at the Homestead B & B. We absolutely love it here! Great food, amenities galore, and just an awesome getaway!"
United States
Cynthia
$298 nightly
The price is $331
Nov 9 - Nov 10
Total with taxes and fees
The Homestead

Head of Pond House

3.0 star property
Water Mill
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
Southampton
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
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
Nov 23 - Nov 24
Total with taxes and fees
The Huntting Inn

Large Room w use of pool/tennis in Spacious home

Sag Harbor
$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 Heights Hotel Reviews

Find out more about Shelter Island Heights

Shelter Island Heights B&B information

Number of reviews
1,583
Accommodation
39 B&B
Lowest Price
$183
Highest Price
$824

Frequently asked questions

What are the most popular Shelter Island Heights B&Bs?
West Neck Guesthouse is a fantastic choice for travelers seeking a serene escape in Shelter Island Heights, boasting an excellent 8.0 rating. This adults-only property provides a tranquil atmosphere great for couples looking to unwind. Guests rave about the comfortable rooms and attentive staff, ensuring a relaxing stay. The seasonal outdoor pool offers a refreshing getaway during warmer months, making it an ideal spot to soak up the sun or enjoy a leisurely swim.
What is the nightly rate for a Bed & Breakfast in Shelter Island Heights?
Prices for B&Bs in Shelter Island Heights 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 Heights 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.
Which area is best to stay in a Shelter Island Heights B&B?
The Heights is the most popular area for travelers looking to stay in a Shelter Island Heights B&B. Families will appreciate the serene environment and easy access to family-friendly activities. The nearby Crescent Beach is great for a day of sun and sand, while the Shelter Island Historical Society offers engaging exhibits that the kids will find fascinating.

For those seeking outdoor adventures, the local parks, including the beautiful Mashomack Preserve, provide numerous trails for hiking and opportunities for birdwatching. The charming local shops and restaurants add to the experience, offering a selection of tasty options for meals after a day of adventure.

Couples can enjoy the romantic ambiance of The Heights, with its scenic views of the water and lush landscapes. A leisurely stroll along the waterfront or a sunset picnic on the beach can create memorable moments together.
When is the best time to book a Bed and Breakfast in Shelter Island Heights?
The best time to book a B&B in Shelter Island Heights is during the summer months, particularly in July, when the area is alive with vibrant activities and pleasant weather. This peak season, spanning from late May to early September, attracts families and travelers looking to enjoy the serene beaches, charming boutiques, and delightful outdoor dining experiences that Shelter Island is known for.

In July, you can expect warm temperatures ranging from the mid-70s to low 80s Fahrenheit, great for a variety of outdoor activities. Whether you're taking leisurely strolls along the waterfront, indulging in water sports, or exploring the picturesque hiking trails, the inviting climate enhances every moment spent in this idyllic locale.

For those who prefer a quieter experience, the shoulder months of May and September offer a wonderful balance. These months feature milder weather and fewer crowds, allowing for more intimate encounters with the natural beauty of the island. Notably, September often showcases beautiful late-summer days, ideal for enjoying the beach before the cooler autumn air sets in.

If you're looking for a more budget-friendly option, consider visiting in December. While this is considered the low season, it provides a unique opportunity to experience the island's charm in a more tranquil setting, with cozy accommodations and a chance to unwind amidst the winter beauty.
What is the difference between a Shelter Island Heights Bed & Breakfast and a hotel?
Every Shelter Island Heights 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 Heights B&Bs.

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