Photo by tom owens

Find a Bed and Breakfast in Shelter Island from CA $248

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Check prices for these dates

Next weekend
May 2 - May 4
In two weeks
May 9 - May 11
In one month
May 23 - May 25
In two months
Jun 20 - Jun 22

Browse Select Shelter Island B&B

The Sagaponack
Exterior

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (146)
"Great experience at a great resort. We loved our cottage and will be back!"
The price is CA $287
CA $399 total
includes taxes & fees
Apr 27 - Apr 28
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)
"It was very quaint very cozy .I will stay again great experience."
The price is CA $248
CA $285 total
includes taxes & fees
Apr 28 - Apr 29
Inn at Harbor Hill Marina
The Captain Stannard
LED TV

The Captain Stannard

3.0 star property
9.6 out of 10, Exceptional, (219)
"Wonderful welcome and impeccable property. We will plan to go again!"
The price is CA $273
CA $303 total
includes taxes & fees
Apr 29 - Apr 30
The Captain Stannard
Harpoon House
Porch

Harpoon House

3.0 star property
8.2 out of 10, Very good, (116)
"Our stay was spectacular!"
The price is CA $498
CA $570 total
includes taxes & fees
Apr 29 - Apr 30
Harpoon House
Carole's Place B & B
Property grounds

Carole's Place B & B

3.0 star property
9.6 out of 10, Exceptional, (68)
"Great location and excellent breakfast!"
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)
"Great experience at a wonderful property!"
The price is CA $520
CA $653 total
includes taxes & fees
Apr 27 - Apr 28
Mill House Inn
The Scranton Seahorse Inn
Staircase

The Scranton Seahorse Inn

3.0 star property
9.0 out of 10, Wonderful, (236)
"Great stay and will be back!"
The Scranton Seahorse Inn
Westbrook Inn B&B
Front of property

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (149)
"It is beautiful and comfortable. The breakfast was great. And the bed was extremely comfortable."
The price is CA $285
CA $317 total
includes taxes & fees
Apr 29 - Apr 30
Westbrook Inn B&B
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
The Huntting Inn
Exterior

The Huntting Inn

3.5 star property
8.8 out of 10, Excellent, (88)
"Very reasonably priced, clean, friendly, but basic."
The price is CA $564
CA $658 total
includes taxes & fees
May 11 - May 12
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
Seasonal outdoor pool

Vine & Sand

3.0 star property
10.0 out of 10, Exceptional, (7)
"Bedding, linen breakfasts "
Vine & Sand
The Hedges Inn
Room One: Large Queen Guestroom

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 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)
"The hosts were really nice and the breakfast is excellent!"
The price is CA $577
CA $659 total
includes taxes & fees
May 12 - May 13
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
Property grounds

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
James Pharmacy Bed & Breakfast
Miss Anna James Room

James Pharmacy Bed & Breakfast

4.0 star property
9.6 out of 10, Exceptional, (15)
"Great and historic. "
The price is CA $419
CA $631 total
includes taxes & fees
Apr 28 - Apr 29
James Pharmacy Bed & Breakfast
Arbor View House B&B
1 bedroom, Frette Italian sheets, premium bedding, pillowtop beds

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
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>
Harbor Knoll Bed & Breakfast
Living area

Harbor Knoll Bed & Breakfast

3.0 star property
9.0 out of 10, Wonderful, (9)
"Charming bed and breakfast in a great location right on the water…perfect for a romantic getaway!"
Harbor Knoll Bed & Breakfast
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

Montauk Manor
Front of property - evening/night

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1162)
"Beautiful hotel."
The price is CA $210
CA $267 total
includes taxes & fees
May 20 - May 21
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (371)
"Good for a short stay "
The price is CA $189
CA $230 total
includes taxes & fees
Apr 27 - Apr 28
Montauk Oceanside Suites
Windward Shores Ocean Resort
Ocean View 2BD Corner King and Queen | Private kitchen

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (282)
"Love the ocean view from the balcony"
The price is CA $198
CA $256 total
includes taxes & fees
Apr 27 - Apr 28
Windward Shores Ocean Resort
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.