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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 38 B&B in Shelter Island with updated reviews, rates, and availability.

The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (154)
"Cute spot close to Sag and Wolfer Esate."
The price is AED 732
AED 1,025 total
includes taxes & fees
2 Jun - 3 Jun
The Sagaponack
Inn at Harbor Hill Marina
Property grounds

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1001)
"Very clean, great location and staff"
The price is AED 988
AED 1,136 total
includes taxes & fees
2 Jun - 3 Jun
Inn at Harbor Hill Marina
The Captain Stannard
LED TV

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (224)
"Wonderful welcome and impeccable property. We will plan to go again!"
The price is AED 925
AED 1,027 total
includes taxes & fees
4 Jun - 5 Jun
The Captain Stannard
Carole's Place B & B
Property grounds

Carole's Place B & B

3.0 star property
10.0 out of 10, Exceptional, (33)
"Loved our visit."
Carole's Place B & B
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (150)
"Beautiful bed and breakfast with plush robes and slippers, super clean, would stay again!"
The price is AED 841
AED 933 total
includes taxes & fees
5 Jun - 6 Jun
Westbrook Inn B&B
Harpoon House
Porch

Harpoon House

3.0 star property
8.2 out of 10, Very Good, (116)
"Our stay was spectacular!"
The price is AED 1,581
AED 1,807 total
includes taxes & fees
2 Jun - 3 Jun
Harpoon House
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (61)
"The hosts were really nice and the breakfast is excellent!"
The price is AED 2,799
AED 3,198 total
includes taxes & fees
2 Jun - 3 Jun
East Hampton Art House Bed & Breakfast
The Huntting Inn
Iron/ironing board, free WiFi, bed sheets

The Huntting Inn

3.5 star property
8.8 out of 10, Excellent, (89)
"Very reasonably priced, clean, friendly, but basic."
The price is AED 2,123
AED 2,462 total
includes taxes & fees
15 Jun - 16 Jun
The Huntting Inn
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (69)
"I loved The Mill House Inn! Kenny, the general manager was so amazing! He was so kind and accommodating, and went above and beyond to make my stay wonderful! He is a gem! I got a free upgrade as it was a slow weekend in early spring. My room was large and amazing and so comfortable. Can’t wait to stay here again on my next visit! Thank you Kenny!🙏"
The price is AED 1,745
AED 2,885 total
includes taxes & fees
2 Jun - 3 Jun
Mill House Inn
West Neck Guesthouse
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets

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! "
The price is AED 804
AED 919 total
includes taxes & fees
8 Jun - 9 Jun
West Neck Guesthouse
James Pharmacy Bed & Breakfast
Garden

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (16)
"Great and historic. "
The price is AED 1,514
AED 2,121 total
includes taxes & fees
9 Jun - 10 Jun
James Pharmacy Bed & Breakfast
Vine & Sand
Interior entrance

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (7)
"We enjoyed an amazing wine weekend at Vine and Sand. Beautiful home and relaxing, enjoyable stay. Great location for visiting vineyards as well as the villages of Southold and Greenport. "
Vine & Sand
Harbor Knoll Bed & Breakfast
Living area

Harbor Knoll Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (9)
"Beautiful bed and breakfast with gorgeous views. Close to shops and restaurants but far enough to be private and quiet. Will definitely be coming back"
Harbor Knoll Bed & Breakfast
The Hedges Inn
Room One: Large Queen Guestroom | Egyptian cotton sheets, premium bedding, in-room safe

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (68)
"Absolutely fabulous homely and beautifully decorated Conveniently located between downtown and the beach so easy to walk"
The price is AED 2,200
AED 2,694 total
includes taxes & fees
2 Jun - 3 Jun
The Hedges Inn
The 1708 House
Exterior

The 1708 House

3.0 star property
10.0 out of 10, Exceptional, (2)
"We absolutely loved our stay here. The house is stunning, the service is fabulous. The best bed ever to sleep in! Great location and a fabulous breakfast. Thank you. "
The 1708 House
Stirling House Bed & Breakfast
Dock

Stirling House Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (23)
"Very comfortable king size bed. Excellent gourmet breakfast, discreet host. Older house, but all the comforts. Absolutely every need provided for. "
Stirling House Bed & Breakfast
Arbor View House B&B
Exterior

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (13)
"Two mid age couples just had a good and relaxing time with great hospitality. "
Arbor View House B&B
The Farmhouse Bed and Breakfast
Garden

The Farmhouse Bed and Breakfast

4.0 star property
10.0 out of 10, Exceptional, (10)
"Lovely B&B run by a lovely couple"
The Farmhouse Bed and Breakfast
Historical Bed and breakfast<br>
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

Historical Bed and breakfast<br>

8.6 out of 10, Excellent, (4)
"Very great house , Owner was amazing and was very easy to contact and gave us early check in . Would definitely do it agian"
Historical Bed and breakfast<br>
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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Frequently asked questions

Searching for B&Bs in Shelter Island?
If you want to find a place to stay with a small number of rooms and an intimate environment, a bed and breakfast might be a great fit for your trip to Shelter Island. During your time in Shelter Island, 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?
B&Bs all have a unique charm. Whether it’s a cozy reading space or a sunlit breakfast nook, the quaint details are what make bed and breakfasts a fun place to get away.
What are the top B&Bs in Shelter Island?
Here are some B&Bs in the area: The Sagaponack: 9.4 mi (15.2 km) from the heart of Shelter Island.The Captain Stannard: 11 rooms. Situated 16 mi (25.8 km) from the heart of Shelter Island. Mill House Inn: 10 rooms. 10.7 mi (17.2 km) from the heart of downtown. Enjoy the free cooked breakfast and designer toiletries. East Hampton Art House Bed & Breakfast: 2 rooms. Located 9.4 mi (15.1 km) from the core of Shelter Island. Enjoy the free full breakfast and fitness center.
When should I book my B&B in Shelter Island?
When you’re dreaming of a escape to Shelter Island, 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 is 57 inches.
What is there to do in Shelter Island?
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 Whale’s Tail and Wades Beach on your list if you want to see more of the area.
How can I get to and around Shelter Island?
Planning your excursions in and around Shelter Island is easier with these transportation options. Fly into East Hampton, NY (HTO), which is located 8.8 mi (14.2 km) away from the city center. Otherwise, look for flights into Fishers Island, NY (FID-Elizabeth Field), which is 20.6 mi (33.1 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.