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Check prices for these dates

Next weekend
May 29 - May 31
In two weeks
Jun 5 - Jun 7
In one month
Jun 19 - Jun 21
In two months
Jul 17 - Jul 19

Our top choices for Shelter Island bed & breakfast

Property grounds

Inn at Harbor Hill Marina

Inn at Harbor Hill Marina
3.5 star property
Niantic
9.4 out of 10, Exceptional, (1,000 reviews)
"Lovely place to stay, excellent breakfast."
United States
Mary Jo
The price is ￥33,200
￥38,180 total
includes taxes & fees
May 25 - May 26
Inn at Harbor Hill Marina
IPod dock, MP3 dock

The Captain Stannard

The Captain Stannard
3.0 star property
Westbrook Center
9.6 out of 10, Exceptional, (263 reviews)
"Very clean, easy check-in, lovely owners."
United States
GAIL
The price is ￥35,672
￥39,596 total
includes taxes & fees
Jun 1 - Jun 2
The Captain Stannard
Interior detail

Harpoon House

Harpoon House
3.0 star property
Southampton
8.4 out of 10, Very Good, (151 reviews)
"Parking was easy and secure. Check in was simple. Room was clean. Location to town center was great. Disappointed that restaurant wasn’t open for breakfast and in-room coffee machine unsatisfactory. Overall I was satisfied. "
United States
Kathie
The price is ￥41,301
￥47,186 total
includes taxes & fees
May 25 - May 26
Harpoon House
Fireplace

Westbrook Inn B&B

Westbrook Inn B&B
3.0 star property
Westbrook Center
9.8 out of 10, Exceptional, (191 reviews)
"Breakfast was amazing! Staff was so kind, and place was very clean. "
United States
Ashley
The price is ￥46,662
￥51,795 total
includes taxes & fees
Jun 4 - Jun 5
Westbrook Inn B&B
Property entrance

The Sagaponack

The Sagaponack
3.0 star property
Wainscott
8.8 out of 10, Excellent, (257 reviews)
"Room was very clean and staff very friendly!"
United States
Dawn
The price is ￥47,496
￥59,824 total
includes taxes & fees
Jun 8 - Jun 9
The Sagaponack
Deluxe Room, 1 King Bed | Premium bedding, iron/ironing board, free WiFi, bed sheets

West Neck Guesthouse

West Neck Guesthouse
3.5 star property
Shelter Island Heights
8.0 out of 10, Very Good, (37 reviews)
"Great property! Close to beach and super clean. "
United States
Leslie
The price is ￥34,772
￥39,728 total
includes taxes & fees
Jun 9 - Jun 10
West Neck Guesthouse
Interior

The Scranton Seahorse Inn

The Scranton Seahorse Inn
3.0 star property
Madison Center
9.0 out of 10, Wonderful, (242 reviews)
"We had a wonderful stay. Perfect location, great staff, and check-in process, and our room was delightful."
United States
Brian
The price is ￥53,432
￥59,310 total
includes taxes & fees
Jun 8 - Jun 9
The Scranton Seahorse Inn
Interior

Vine & Sand

Vine & Sand
3.0 star property
Southold
9.8 out of 10, Exceptional, (16 reviews)
"Wonderful stay"
United States
Judy
The price is ￥61,421
￥70,173 total
includes taxes & fees
May 25 - May 26
Vine & Sand
Front of property - evening/night

Mill House Inn

Mill House Inn
5.0 star property
Pantigo Road Historic District
9.0 out of 10, Wonderful, (84 reviews)
"The breakfast is amazing, beds super comfortable and grounds stunning. Location was perfect and staff wonderful. Also the tub in our room was incredible. Only suggestion would be for coffee in the room in the morning. Otherwise it was a literal perfect stay "
United States
Jessica
The price is ￥111,070
￥169,533 total
includes taxes & fees
May 28 - May 29
Mill House 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 ￥59,979
￥78,339 total
includes taxes & fees
May 27 - May 28
Vine + Sand--Southold, NY'S Newest B&B--Room 4--Queen Bed and Adjacent Bathroom With Rain Shower
Outdoor dining

Stirling House Bed & Breakfast

Stirling House Bed & Breakfast
3.0 star property
Greenport
9.8 out of 10, Exceptional, (24 reviews)
"This was a great place to stay with old word charm. If you are looking for a quiet getaway with a beautiful view of the ocean this is it. The breakfast that we had were much better that what you could get in town. My wife and I can't wait to go back."
United States
steve
The price is ￥79,993
￥91,394 total
includes taxes & fees
May 29 - May 30
Stirling House Bed & Breakfast
Beach nearby

The Huntting Inn

The Huntting Inn
3.5 star property
Egypt Lane Historic District
9.0 out of 10, Wonderful, (105 reviews)
"Rooms are wonderful, quiet and the location cannot be beat. "
United States
Sophie
The price is ￥95,698
￥110,924 total
includes taxes & fees
Jun 7 - Jun 8
The Huntting Inn
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 ￥59,979
￥78,339 total
includes taxes & fees
May 26 - May 27
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 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 ￥78,334
￥102,217 total
includes taxes & fees
Jun 1 - Jun 2
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 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 ￥64,487
￥84,218 total
includes taxes & fees
May 26 - May 27
Vine + Sand--Southold, NY'S Newest B&B--Room 2--King Bed and Ensuite Bathroom With Rain Shower
Beach nearby, sun loungers, beach umbrellas, beach towels

The Hedges Inn

The Hedges Inn
3.5 star property
East Hampton
9.6 out of 10, Exceptional, (73 reviews)
"Excellent place"
United States
Miguel
The price is ￥114,229
￥138,290 total
includes taxes & fees
Jun 11 - Jun 12
The Hedges Inn
Sport court

Pool tennis gym Bikes all included & <2m’s fr/ all

Pool tennis gym Bikes all included & <2m’s fr/ all
Southampton
The price is ￥78,631
￥174,954 total
includes taxes & fees
Jun 15 - Jun 16
Pool tennis gym Bikes all included & <2m’s fr/ all
1 bedroom, iron/ironing board, free WiFi, bed sheets

Home 2 mins. from Shinnecock Golf town SH beaches

Home 2 mins. from Shinnecock Golf town SH beaches
Southampton
The price is ￥78,631
￥159,710 total
includes taxes & fees
Jun 15 - Jun 16
Home 2 mins. from Shinnecock Golf town SH beaches
Outdoor dining

Free ride to Shinnecock Golf, SH Town or SH beache

Free ride to Shinnecock Golf, SH Town or SH beache
Southampton
The price is ￥150,908
￥186,753 total
includes taxes & fees
Jun 16 - Jun 17
Free ride to Shinnecock Golf, SH Town or SH beache
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

Montauk Blue Hotel

Montauk Blue Hotel

10/10 Excellent
"Right off the beach; beautiful views Sound of ocean so peaceful Friendly helpful staff Steps from town We will be returning next year"
Elizabeth 3-night trip
Posted 11 hours ago
Montauk Blue Hotel

Find out more about Shelter Island

Shelter Island B&B information

Number of reviews
2,361
Accommodation
39 B&B
Lowest Price
￥38,180
Highest Price
￥186,753

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.Harpoon House: 9 rooms. 12.7 mi (20.5 km) from the downtown core. Enjoy the bars and unique décor. The Huntting Inn: 19 rooms. 10.8 mi (17.4 km) from the heart of downtown. Enjoy the fireplace in the lobby and bar/lounge. Mill House Inn: 10 rooms. Located 10.7 mi (17.2 km) from the core of Shelter Island. Enjoy the free cooked breakfast and designer toiletries.
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 Mashomack Preserve 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.