Bed and Breakfast in Shelter Island Heights

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
20 Mar - 22 Mar
In two weeks
27 Mar - 29 Mar
In one month
10 Apr - 12 Apr
In two months
8 May - 10 May

Our top choices for Shelter Island Heights bed & breakfast

Free daily full breakfast

Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.4 out of 10, Exceptional, (1,001 reviews)
"Always a nice stay. Clean and comfortable."
United States
Shelby
The price is NZ$349
includes taxes & fees
10 Mar - 11 Mar
Inn at Harbor Hill Marina
IPod dock, MP3 dock

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (261 reviews)
"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
The Captain Stannard
Graybarn Cottage

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (81 reviews)
"Great place to stay. Very walkable, lovely room and comfortable bed. "
Australia
Alex
The price is NZ$533
includes taxes & fees
10 Mar - 11 Mar
Mill House Inn
Fireplace

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (179 reviews)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is NZ$353
includes taxes & fees
23 Mar - 24 Mar
Westbrook Inn B&B
Miss Anna James Room

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast
4.0 star property
Old Saybrook Center
9.0 out of 10, Wonderful, (23 reviews)
"Cute B&B, very nice room, check-in worked well"
United States
Isolde
The price is NZ$569
includes taxes & fees
1 Apr - 2 Apr
James Pharmacy Bed & Breakfast
Interior detail

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very good, (149 reviews)
"Great spot!"
United States
Keith
Harpoon House
Property entrance

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (226 reviews)
"The property and room was clean, easily accessible, and staff were very friendly. We would stay here again!"
United States
Daren
The price is NZ$370
includes taxes & fees
10 Mar - 11 Mar
The Sagaponack
Interior

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.6 out of 10, Exceptional, (15 reviews)
"Wonderful stay"
United States
Judy
Vine & Sand
Beach nearby

The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (105 reviews)
"Inn has been newly renovated. Room was spotless. Staff were wonderful. Had an excellent stay. Highly recommend! "
United States
Valerie
The price is NZ$711
includes taxes & fees
23 Mar - 24 Mar
The Huntting Inn
Interior

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
The price is NZ$678
includes taxes & fees
10 Mar - 11 Mar
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Room, 1 King Bed, Patio, Ground Floor (2) | Terrace/patio

The Homestead

The Homestead
3.0 star property
Madison Center
10.0 out of 10, Exceptional, (91 reviews)
"Beautiful property- wonderful staff- clean, comfortable and relaxed feeling with a lovely breakfast 😄"
United States
Anthony
The price is NZ$529
includes taxes & fees
12 Mar - 13 Mar
The Homestead
Terrace/patio

Large Room w use of pool/tennis in Spacious home

Large Room w use of pool/tennis in Spacious home
Sag Harbor
The price is NZ$1,343
includes taxes & fees
10 Mar - 11 Mar
Large Room w use of pool/tennis in Spacious home
Interior

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 review)
"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.
The price is NZ$745
includes taxes & fees
10 Mar - 11 Mar
Vine + Sand--Southold, NY'S Newest B&B--Room 1--King Bed and Ensuite Bathroom With Soaking Tub
Interior

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 review)
"Great experience. Wonderful hosts. "
United States
Mark L.
The price is NZ$678
includes taxes & fees
10 Mar - 11 Mar
Vine + Sand--Southold, NY'S Newest B&B Room--Room 3--Queen Bed and Ensuite Bathroom With Rain Shower
Interior

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
The price is NZ$745
includes taxes & fees
10 Mar - 11 Mar
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.
View all properties

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Shelter Island Heights Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

6/10 Okay
"Very welcoming staff. Average accommodations but comfortable and convenient to supermarket. "
Joseph 2-night trip
Posted 6 hours ago
Pier Blue Inn Old Saybrook - Essex

Find out more about Shelter Island Heights

Shelter Island Heights B&B information

Number of reviews
2,029
Accommodation
39 B&B
Lowest Price
NZ$349
Highest Price
NZ$1,343

Frequently asked questions

Searching for B&Bs in Shelter Island Heights?
If you want to find somewhere to stay with a small number of rooms and an intimate environment, a B&B might be a great fit for your trip to Shelter Island Heights. During your time in Shelter Island Heights, you might want to spend some time strolling along the water at Sunset Beach and Crescent Beach.
How do you know if a B&B is a good option for your stay?
With attentive service, opportunities to socialise with other guests and of course a scrumptious breakfast, B&Bs provide a one-of-a-kind setting.
What are the top B&Bs in Shelter Island Heights?
Here are some well-liked B&Bs in the area: West Neck Guesthouse: 6 rooms. 0.6 mi (1 km) from the heart of Shelter Island Heights. The Sagaponack: 10.8 mi (17.4 km) from the city centre. Harpoon House: 9 rooms. 13.7 mi (22 km) from the city centre. Enjoy the bars and unique decor. James Pharmacy Bed & Breakfast: 3 rooms. Located 14 mi (22.5 km) from the core of Shelter Island Heights. Enjoy the local cuisine breakfast and designer toiletries.
When is the best time to book my B&B in Shelter Island Heights?
When you're dreaming of a trip to Shelter Island Heights, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually August and July, with an average temperature of 21°C, while the coldest months are January and February, with an average of 3°C. Average annual precipitation for Shelter Island Heights is 1452 mm.
What is there to do in Shelter Island Heights?
Travellers looking to spend some time in nature enjoy Shelter Island Heights for its island views and beaches. Spend some time exploring Sunset Beach and Crescent Beach if you're hoping to see some of the area's natural features. You should put Shelter Island Country Club and Sylvester Manor on your list if you want to see more of the area.
How can I get to and around Shelter Island Heights?
You can plan your excursions in and around Shelter Island Heights ahead of time with these transportation options. Fly into East Hampton, NY (HTO), which is located 10.2 mi (16.4 km) away from the heart of the city. Otherwise, you can search for flights to Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.2 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.