Photo by tom owens

Find a Bed and Breakfast in Shelter Island from CA $190

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Check prices for these dates

Next weekend
Apr 11 - Apr 13
In two weeks
Apr 18 - Apr 20
In one month
May 2 - May 4
In two months
May 30 - Jun 1

Browse Select Shelter Island B&B

The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (144)
"Sara at the front desk was helpful. I had a cottage and it was noisy. I could hear the persons television next door and the cars from the street all night. There was snacks at night. The breakfast was just continental. "
The price is CA $258
CA $367 total
includes taxes & fees
Apr 6 - Apr 7
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)
"Loved my solo weekend at Inn at Harbor Hill. No detail was left unattended to. Beautiful property and amazing staff. I felt like family. It was my first of many trips to Niantic (because of my experience with your hotel) so thank you for making it so special. Not only is the hotel amazing but I found the citizens of Niantic to be among the friendliest I've encountered. Diane O'Toole"
The price is CA $224
CA $257 total
includes taxes & fees
Apr 6 - Apr 7
Inn at Harbor Hill Marina
The Captain Stannard
Standard Room, 1 Bedroom, Private Bathroom

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (217)
"Clean, classic, charming seaside New England inn. Unique in that it isn’t really staffed in the traditional sense but provided much more than we expected - 24 hour guest pantry, beautiful common spaces to relax, fresh cookies upon arrival, and basic breakfast. This will be our new go-to when we’re in the area. "
The price is CA $236
CA $262 total
includes taxes & fees
Apr 6 - Apr 7
The Captain Stannard
Harpoon House
Porch

Harpoon House

3.0 star property
8.2 out of 10, Very good, (115)
"Place was great! Love the area and place was also very clean and quiet. Great stay and would definitely come back."
The price is CA $505
CA $578 total
includes taxes & fees
Apr 7 - Apr 8
Harpoon House
Carole's Place B & B
Property grounds

Carole's Place B & B

3.0 star property
9.6 out of 10, Exceptional, (67)
"We stayed with Carole for two nights, and we absolutely loved her place! The location was perfect for us—central and convenient. From the moment we arrived, we felt right at home. She has created such a warm and cozy space, and her hospitality made all the difference. We truly appreciated her kindness and how welcoming she was. Without a doubt, we’ll be staying with her again the next time we visit Long Island!"
The price is CA $190
CA $217 total
includes taxes & fees
Apr 7 - Apr 8
Carole's Place B & B
Mill House Inn
Front of property - evening/night

Mill House Inn

5.0 star property
9.0 out of 10, Wonderful, (68)
"What a lovely space and wonderful thoughtful staff! Absolutely loved everything about it, and the breakfast was beyond excellence! Hats off to the chef you can tell she cooked with ❤️ love. Highly Recommend you experience it for yourself. "
The price is CA $458
CA $575 total
includes taxes & fees
Apr 6 - Apr 7
Mill House Inn
The Scranton Seahorse Inn
Staircase

The Scranton Seahorse Inn

3.0 star property
9.0 out of 10, Wonderful, (236)
"Amazing and too short. Loveliest little B&B with one of the best breakfasts I've ever had. Incredibly clean with updated bathroom(s). So quiet, even though almost full. Will be going back, regularly!"
The price is CA $365
CA $405 total
includes taxes & fees
Apr 21 - Apr 22
The Scranton Seahorse Inn
Westbrook Inn B&B
Terrace/patio

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (148)
"Westbrook Inn is a very quaint and clean Inn, much attention to detail and very warm and friendly atmosphere, will definitely be coming back!"
The price is CA $261
CA $290 total
includes taxes & fees
Apr 7 - Apr 8
Westbrook Inn B&B
The 1708 House
Exterior

The 1708 House

3.0 star property
10.0 out of 10, Exceptional, (1)
The price is CA $423
CA $494 total
includes taxes & fees
Apr 26 - Apr 27
The 1708 House
The Huntting Inn
Exterior

The Huntting Inn

3.5 star property
8.6 out of 10, Excellent, (87)
"One of the very few options in East Hampton that offered a one night stay, most have a 2-night minimum. An old, charming inn that was very welcoming and clean. Our king bed room was spacious enough and decorated nicely. The bathroom was very clean and modernized. We did have to walk up a flight of stairs with our luggage which wasn’t difficult for us but may be for some."
The price is CA $579
CA $675 total
includes taxes & fees
May 4 - May 5
The Huntting 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
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
The Hedges Inn
Room One: Large Queen Guestroom

The Hedges Inn

3.5 star property
9.6 out of 10, Exceptional, (68)
"Super friendly staff, very accommodating! We can’t wait to return. "
The Hedges Inn
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)
"What a beautiful, quiet, peaceful place to stay, even in the dead of winter. The home itself is modern, welcoming, bright, everything you could dream of. The hosts are very active and successful artists who all but gave us a private master class in how their work is imagined and created. I don’t know when we’ve had a more delightful weekend. The walks to the beach were lovely, too. "
The price is CA $595
CA $679 total
includes taxes & fees
Apr 7 - Apr 8
East Hampton Art House Bed & Breakfast
434 on Main
Reception hall

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main
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. "
The price is CA $471
CA $539 total
includes taxes & fees
Apr 7 - Apr 8
Stirling House Bed & Breakfast
James Pharmacy Bed & Breakfast
Garden

James Pharmacy Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (14)
"We loved staying in the historic pharmacy. We stayed in the Ann Petry room and it is well appointed, clean and charming. The property sits on the town's main street and is very walkable to shopping and dining. We look forward to our next stay. "
The price is CA $426
CA $641 total
includes taxes & fees
Apr 6 - Apr 7
James Pharmacy Bed & Breakfast
Arbor View House B&B
Exterior

Arbor View House B&B

3.5 star property
9.2 out of 10, Wonderful, (13)
"This house was old but beautiful and decorated nicely inside. "
Arbor View House B&B
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>
Large Room w use of pool/tennis in Spacious home
Outdoor dining

Large Room w use of pool/tennis in Spacious home

The price is CA $317
CA $513 total
includes taxes & fees
Apr 7 - Apr 8
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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Other property types in Shelter Island

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
Outdoor pool, a heated pool

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!

10.0 out of 10, Exceptional, (41)
"This is the most magical property with a gorgeous pool, beautiful large trees, a pond and a badmitten court. My two children loved it. The property was a 3-4 minute drive from everything and yet felt totally isolated and removed from everything. I will say that the house was more cozy than we expected as the bedrooms upstairs were a steep walk and there was only one bathroom for the entire house. But we made do and had a lovely time."
The price is CA $1,138
CA $2,039 total
includes taxes & fees
Apr 30 - May 1
Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!
Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1149)
"the location is great and price is reasonable. "
The price is CA $209
CA $266 total
includes taxes & fees
Apr 21 - Apr 22
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (368)
"Had a great stay here . Staff was friendly and check in and out was a breeze . Was very clean and comfortable. Only complaint was I couldn’t get a hot shower . Otherwise place is excellent. Shops , restaurants and bars are all a short walk . "
The price is CA $192
CA $234 total
includes taxes & fees
Apr 9 - Apr 10
Montauk Oceanside Suites
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?
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 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.