Photo by Erisa Dilo

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

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Browse Select Shelter Island Heights B&B

The Sagaponack

3.0 star property
8.8 out of 10, Excellent, (146)
"It’s okay for a night or two not a first or second choice however. The cosmetic upgrade for this property is okay in comparison to the cost of the stay. The doors only have a button lock on some cottages and seems like the original handle, it was loose and the key was sticking. Though I was accommodated with a different cottage that had a padlock as well, there was a visible mold and moisture issue causing the laminate floors to bubble. Some groundskeeping opportunities with pathways and the...
The price is CA $287
CA $399 total
includes taxes & fees
Apr 27 - Apr 28
The Sagaponack

Inn at Harbor Hill Marina

3.5 star property
9.4 out of 10, Exceptional, (1001)
"Our stay for just one evening was excellent. The bed was so comfortable. Had no aches in the morning. Forgot to ask the type/name if you can let me know. Very clean which is so important and smelled nice. Food and service excellent as well. Will stay again when in area. Thanks for everything. Lisa and Tom. "
The price is CA $248
CA $285 total
includes taxes & fees
Apr 28 - Apr 29
Inn at Harbor Hill Marina

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

3.0 star property
8.2 out of 10, Very good, (116)
"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 $498
CA $570 total
includes taxes & fees
Apr 29 - Apr 30
Harpoon House

Carole's Place B & B

3.0 star property
9.6 out of 10, Exceptional, (68)
"Excellent experienced bed-and-breakfast host. And she goes above and beyond! I left my wedding ring in the bathroom and she called me immediately and sent it overnight back to me. Highly recommend!"
Carole's Place B & B

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 $520
CA $653 total
includes taxes & fees
Apr 28 - Apr 29
Mill House Inn

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 Scranton Seahorse Inn

Westbrook Inn B&B

3.0 star property
10.0 out of 10, Exceptional, (149)
"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 $285
CA $317 total
includes taxes & fees
Apr 29 - Apr 30
Westbrook Inn B&B

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

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

The Homestead

3.0 star property
10.0 out of 10, Exceptional, (77)
"Charming in every aspect. Highly recommend, Hosts are wonderful people."
The price is CA $390
CA $433 total
includes taxes & fees
Apr 29 - Apr 30
The Homestead

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

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

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

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 $577
CA $659 total
includes taxes & fees
May 12 - May 13
East Hampton Art House Bed & Breakfast

434 on Main

4.0 star property
10.0 out of 10, Exceptional, (35)
"Great hosts"
434 on Main

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

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 29 - Apr 30
James Pharmacy Bed & Breakfast

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>

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>
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 Heights

Montauk Manor

3.5 star property
9.2 out of 10, Wonderful, (1162)
"Above and beyond what we expected for an off-season stay! Beautifully maintained property, gorgeous view from our room's balcony, kind and helpful staff. Will definitely be back in the near future."
The price is CA $210
CA $267 total
includes taxes & fees
May 12 - May 13
Montauk Manor

Montauk Oceanside Suites

3.0 star property
8.6 out of 10, Excellent, (371)
"Perfect for a quick getaway. The location can’t be beat. Loved the beach-themed decor also."
The price is CA $189
CA $231 total
includes taxes & fees
Apr 28 - Apr 29
Montauk Oceanside Suites

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (282)
"Condo was great, family of 5 , clean, no hassle"
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.