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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

B&B in Shelter Island

Exterior
The Sagaponack
The Sagaponack
3.0 star property
8.8 out of 10, Excellent, (194)
"The room was spotless and had everything that you would need. Would stay here again."
United States
Marjorie
The price is AED 574
AED 803 total
includes taxes & fees
26 Oct - 27 Oct
The Sagaponack
Property grounds
Inn at Harbor Hill Marina
Inn at Harbor Hill Marina
3.5 star property
9.4 out of 10, Exceptional, (1001)
"Homestyle welcome in an incredibly cosy inn!"
United Kingdom
Clive
The price is AED 621
AED 714 total
includes taxes & fees
2 Nov - 3 Nov
Inn at Harbor Hill Marina
Property grounds
Carole's Place B & B
Carole's Place B & B
3.0 star property
9.8 out of 10, Exceptional, (60)
"Small B&B with a charming old school vibe. Second time we’ve stayed there and we will return."
United States
Frank
The price is AED 551
AED 629 total
includes taxes & fees
26 Oct - 27 Oct
Carole's Place B & B
IPod dock, MP3 dock
The Captain Stannard
The Captain Stannard
3.0 star property
9.6 out of 10, Exceptional, (252)
"Amazing stay! Everything was perfect and it is clear that the owners love their jobs and their inn. Can't wait to go back! "
United States
Julie
The Captain Stannard
Front of property - evening/night
Mill House Inn
Mill House Inn
5.0 star property
9.0 out of 10, Wonderful, (70)
"Great experience at a wonderful property!"
United States
Brian
The price is AED 1,194
AED 1,500 total
includes taxes & fees
27 Oct - 28 Oct
Mill House Inn
Terrace/patio
Westbrook Inn B&B
Westbrook Inn B&B
3.0 star property
9.8 out of 10, Exceptional, (173)
"Charming, beautiful inn; excellent food and service."
United States
Michael
The price is AED 807
AED 896 total
includes taxes & fees
30 Oct - 31 Oct
Westbrook Inn B&B
Aerial view
East Hampton Art House Bed & Breakfast
East Hampton Art House Bed & Breakfast
4.0 star property
9.6 out of 10, Exceptional, (65)
"Roz and Michael built a beautiful paradise that they enjoy sharing with you. Everything is amazing. "
United States
Dan
The price is AED 1,395
AED 1,594 total
includes taxes & fees
27 Oct - 28 Oct
East Hampton Art House Bed & Breakfast
Miss Anna James Room | Individually decorated, individually furnished, iron/ironing board
James Pharmacy Bed & Breakfast
James Pharmacy Bed & Breakfast
4.0 star property
9.2 out of 10, Wonderful, (19)
"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!"
United States
Rachel
The price is AED 1,110
AED 1,232 total
includes taxes & fees
26 Oct - 27 Oct
James Pharmacy Bed & Breakfast
Garden
The Huntting Inn
The Huntting Inn
3.5 star property
9.0 out of 10, Wonderful, (103)
"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!"
United States
Dena
The price is AED 1,405
AED 1,642 total
includes taxes & fees
6 Nov - 7 Nov
The Huntting Inn
Porch
Harpoon House
Harpoon House
3.0 star property
8.4 out of 10, Very Good, (146)
"Very cute location- rooms are very spacious. We were able to walk into town. Would definitely stay again. "
United States
Karissa
The price is AED 1,196
AED 1,366 total
includes taxes & fees
31 Oct - 1 Nov
Harpoon House
Outdoor dining
Large Room w use of pool/tennis in Spacious home
Large Room w use of pool/tennis in Spacious home
The price is AED 2,099
AED 3,028 total
includes taxes & fees
25 Oct - 26 Oct
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 Hotel Reviews

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

10/10 Excellent
"Very nice staff, amenities great, an older place, but well kept. Wish there was more than 1 window, a bit stuffy. Felt safe in parking lot and in my room."
Michelle 3-night trip
Posted 3 days ago
Pier Blue Inn Old Saybrook - Essex

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.East Hampton Art House Bed & Breakfast: 2 rooms. Situated 9.4 mi (15.1 km) from the heart of Shelter Island. Enjoy the free full breakfast and fitness center. Mill House Inn: 10 rooms. 10.7 mi (17.2 km) from the heart of downtown. Enjoy the free cooked breakfast and designer toiletries. 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 Mashomack Preserve and Gardiner's Bay Country Club 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.