Photo by Erisa Dilo

Find a Bed and Breakfast in Shelter Island Heights

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Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

Browse Select Shelter Island Heights B&B

The Chequit
Outdoor dining

The Chequit

3.0 star property
8.8 out of 10, Excellent, (28)
"Excellent "
The price is CA $455
CA $520 total
includes taxes & fees
Feb 1 - Feb 2
The Chequit
The Pridwin Hotel
Seasonal outdoor pool, pool umbrellas, sun loungers

The Pridwin Hotel

4.0 star property
9.6 out of 10, Exceptional, (57)
"Fantastic property. Rooms are beautifully appointed, decor is super chic and comfortable. Gorgeous views and amenities. Absolutely enjoyed our second stay at The Pridwin!"
The Pridwin Hotel
House on Chase Creek
View from property

House on Chase Creek

2.5 star property
9.4 out of 10, Exceptional, (67)
"Everything you need for a stay on the island"
The price is CA $150
CA $171 total
includes taxes & fees
Feb 3 - Feb 4
House on Chase Creek
The Rams Head Inn
Exterior

The Rams Head Inn

4.0 star property
7.6 out of 10, Good, (18)
"Beautiful views and lovely service "
The price is CA $756
CA $863 total
includes taxes & fees
Feb 13 - Feb 14
The Rams Head Inn
West Neck Guesthouse
Deluxe Room, 1 King Bed

West Neck Guesthouse

3.5 star property
8.0 out of 10, Very good, (32)
"Very convenient location next to Cresent Beach and Leon 1909 restaurant which is fantastic! "
West Neck Guesthouse
Shelter Island House
Terrace/patio

Shelter Island House

3.5 star property
8.4 out of 10, Very good, (56)
"Everything was excellent. However, it would have been nice if there had been something offered for breakfast."
Shelter Island House
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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Other property types in Shelter Island Heights

Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1104)
"The King size bed was very nice to sleep on for my back "
The price is CA $189
CA $243 total
includes taxes & fees
Feb 6 - Feb 7
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (359)
"Perfect for a short stay. Very warm, clean and comfortable. Very close to shops and beach. Check in and check out was super easy. Only critique would be that the walls were thin and you could very easily hear the conversation of the guests in the room next door. "
The price is CA $196
CA $238 total
includes taxes & fees
Feb 1 - Feb 2
Montauk Oceanside Suites
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (268)
"Was a winter wonderland. Quiet and clean. Staff were very helpful and kind!"
The price is CA $190
CA $248 total
includes taxes & fees
Feb 2 - Feb 3
Windward Shores Ocean Resort
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.

Frequently asked questions

Searching for B&Bs in Shelter Island Heights?
If you want to find a place to stay with fewer rooms than the traditional hotel and a cozy 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 the right choice for your stay?
With attentive service, opportunities to meet guests from other places, and tasty breakfasts, B&Bs offer a truly 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: The Sagaponack: 10.8 mi (17.4 km) from the heart of Shelter Island Heights.Mill House Inn: 10 rooms. Situated 12.1 mi (19.5 km) from the heart of Shelter Island Heights. Enjoy the free cooked breakfast and designer toiletries. The Baker House 1650: 13 rooms. 12.2 mi (19.7 km) from the heart of downtown. Enjoy the free full breakfast and designer toiletries.
What's the best time of year to book my B&B in Shelter Island Heights?
When you’re dreaming of a stay in 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 temp of 70°F, while the coldest months are January and February with an average of 38°F. Average annual precipitation for Shelter Island Heights is 57 inches.
What is there to do in Shelter Island Heights?
Travelers 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 might 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?
Planning your excursions in and around Shelter Island Heights is easier with these transportation options. Fly into East Hampton, NY (HTO), which is located 10.2 mi (16.4 km) away from the city center. You can also search for flights into 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.