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Check prices for these dates

Next weekend
26 Sep - 28 Sep
In two weeks
3 Oct - 5 Oct
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17 Oct - 19 Oct
In two months
14 Nov - 16 Nov

B&B in Shelter Island

Our top choices for Shelter Island bed & breakfast

The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (178)
"Great stay!"
The price is SAR 693
SAR 985 total
includes taxes & fees
13 Oct - 14 Oct
The Sagaponack
The Huntting Inn
Garden

The Huntting Inn

3.5 star property
9.0 out of 10, Wonderful, (102)
"What a wonderful place to stay! The room was beautiful. The bed was comfortable and the staff were welcoming and helpful. We loved how close it was to town. We also enjoyed the breakfast every morning. The Palm restaurant downstairs was nice to have on property and the food was great. We will definitely stay again!"
The price is SAR 1,801
SAR 2,095 total
includes taxes & fees
5 Oct - 6 Oct
The Huntting Inn
Inn at Harbor Hill Marina
Property grounds

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1000)
"Homestyle welcome in an incredibly cosy inn!"
The price is SAR 859
SAR 988 total
includes taxes & fees
1 Oct - 2 Oct
Inn at Harbor Hill Marina
Harpoon House
Porch

Harpoon House

3.0 star property
8.4 out of 10, Very Good, (140)
"Cute spot"
Harpoon House
The Captain Stannard
IPod dock, MP3 dock

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (247)
"Everything was fantastic, will stay again!"
The Captain Stannard
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, (71)
"Great staff "
The price is SAR 2,247
SAR 2,751 total
includes taxes & fees
21 Sep - 22 Sep
The Hedges Inn
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
9.8 out of 10, Exceptional, (166)
"Beautiful place and wonderful staff"
The price is SAR 816
SAR 906 total
includes taxes & fees
12 Oct - 13 Oct
Westbrook Inn B&B
James Pharmacy Bed & Breakfast
Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board

James Pharmacy Bed & Breakfast

4.0 star property
9.4 out of 10, Exceptional, (18)
"My husband and I stayed here for a quick weekend getaway and loved our experience! The location was perfect - located near restaurants, shops, and the beach - and the room was clean and charming. We will definitely be back!"
The price is SAR 1,020
SAR 1,132 total
includes taxes & fees
1 Oct - 2 Oct
James Pharmacy Bed & Breakfast
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (70)
"Great experience at a wonderful property!"
The price is SAR 1,594
SAR 2,003 total
includes taxes & fees
20 Oct - 21 Oct
Mill House Inn
Carole's Place B & B
Property grounds

Carole's Place B & B

3.0 star property
9.8 out of 10, Exceptional, (55)
"Very clean and quiet, super comfortable bed, good central location to get around on Long Island, and an great host."
The price is SAR 563
SAR 643 total
includes taxes & fees
1 Oct - 2 Oct
Carole's Place B & B
East Hampton Art House Bed & Breakfast
Aerial view

East Hampton Art House Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (64)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
The price is SAR 2,140
SAR 2,445 total
includes taxes & fees
4 Oct - 5 Oct
East Hampton Art House Bed & Breakfast
Vine & Sand
Interior entrance

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (11)
"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
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, (37)
"Great property! Close to beach and super clean. "
The price is SAR 1,176
SAR 1,343 total
includes taxes & fees
2 Oct - 3 Oct
West Neck Guesthouse
Stirling House Bed & Breakfast
Beach/ocean view

Stirling House Bed & Breakfast

3.0 star property
9.8 out of 10, Exceptional, (24)
"Our stay was only 2 nights but felt like 5. Well rested 3 days. Would return in a Heart Beat. Clay was awesome and the breakfasts were over the top !"
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, (15)
"Two mid age couples just had a good and relaxing time with great hospitality. "
Arbor View House B&B
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (36)
"Great hosts"
434 on Main
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
Harbor Knoll Bed & Breakfast
Living area

Harbor Knoll Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (10)
"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
Head of Pond House
Exterior

Head of Pond House

3.0 star property
10.0 out of 10, Exceptional, (1)
"Beautiful place with a very kind host. Highly recommend this place!"
Head of Pond House
Historical Bed and breakfast<br>
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

Historical Bed and breakfast<br>

8.8 out of 10, Excellent, (5)
"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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Top Shelter Island Hotel Reviews

The Harbor Front Inn

The Harbor Front Inn

10/10 Excellent
"Great water front hotel. Perfect location for a stay in greenport. Ask for water view rooms!"
Daniel 1-night trip
Posted 1 day ago
The Harbor Front Inn

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. Enjoy the private yard and unique décor. East Hampton Art House Bed & Breakfast: 2 rooms. 9.4 mi (15.1 km) from the heart of downtown. Enjoy the free full breakfast and fitness center. Harpoon House: 9 rooms. Located 12.7 mi (20.5 km) from the core of Shelter Island. Enjoy the bars and unique décor.
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 Gardiner's Bay Country Club and Shelter Island Historical Society 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.