Photo by tom owens

Search Farmstay in Shelter Island from CA $718

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Browse Select Shelter Island Farmstay

Private, Charming, Lovely Farmhouse in Wainscott, East Hampton
Outdoor pool, a heated pool

Private, Charming, Lovely Farmhouse in Wainscott, East Hampton

10.0 out of 10, Exceptional, (111)
"We had an excellent stay and the host was super communicative and helpful! Can’t wait to come back again! Thank you!"
The price is CA $718
CA $1,704 total
includes taxes & fees
Jan 3 - Jan 4, 2025
Private, Charming, Lovely Farmhouse in Wainscott, East Hampton
Luxury 9 Acre Sagaponack/Sag Harbor Compound Retreat & Year-Round Spa
Outdoor pool, a heated pool

Luxury 9 Acre Sagaponack/Sag Harbor Compound Retreat & Year-Round Spa

10.0 out of 10, Exceptional, (92)
"The house was outstanding for my family. We enjoyed the hot tub and outside patio. Accommodations were perfect. Groom and groomsmen got ready at the house and photographers loved the picturesque property. I would highly recommend "
Luxury 9 Acre Sagaponack/Sag Harbor Compound Retreat & Year-Round Spa
Cutchogue Farmhouse Estate with hot tub and gardens, walk to beach & vineyards
Sun loungers, beach towels

Cutchogue Farmhouse Estate with hot tub and gardens, walk to beach & vineyards

10.0 out of 10, Exceptional, (3)
"Family get together and it was a great space for a large group."
Cutchogue Farmhouse Estate with hot tub and gardens, walk to beach & vineyards
Sprawling Modern Home Minutes from Beach
Beach

Sprawling Modern Home Minutes from Beach

9.8 out of 10, Exceptional, (10)
"Great overall stay - thanks!!"
Sprawling Modern Home Minutes from Beach
Modern farmhouse w/ heated pool, beach, horses and winery in heart of North Fork
Sun loungers, beach towels

Modern farmhouse w/ heated pool, beach, horses and winery in heart of North Fork

10.0 out of 10, Exceptional, (11)
"From booking our stay to closing the door when we left everything was spectacular. Our host was absolutely wonderful. Communication was superb. Not only was the location of the house perfect it was decorated beautifully and spotless. Even though we couldn’t use the pool due to the time of year we went it was absolutely beautiful to look at. The bed and pillows were comfortable and there was plenty of room for all of us. Instantly felt and we cannot wait to visit again I highly recommend...
Modern farmhouse w/ heated pool, beach, horses and winery in heart of North Fork
Cozy Long Island Escape
Beach nearby

Cozy Long Island Escape

10.0 out of 10, Exceptional, (2)
"Big house, lots of room for a family gathering. Mary was super friendly and accommodating. "
Cozy Long Island Escape
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Smart TV, computer monitors

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

10.0 out of 10, Exceptional, (3)
"Beautiful farmhouse with a gorgeous pool! We had a great time at the house! Robert was quick to respond if we needed anything and he met us at check in to show us around, he went above and beyond as a host! The house is well equipped for a family, kitchen has everything you need, pool toys, beach gear, etc all available for our use. Loved the location! Across the street from Dureya’s for lunch or dinner and then a short bike ride down to Orient state park beach and a beautiful nature walk...
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Sprawling Farmhouse in Private Beach Community
Smart TV, fireplace, offices

Sprawling Farmhouse in Private Beach Community

10.0 out of 10, Exceptional, (1)
"Beautiful home in East Hampton - plenty of space and amenities - two game rooms - pool. There is also a fantastic BBQ space which we took advantage of. Our host was very responsive and addressed all concerns."
Sprawling Farmhouse in Private Beach Community
Amagansett Farmhouse Short Walk to Atlantic Ave Beach
Microwave, oven, stovetop, dishwasher

Amagansett Farmhouse Short Walk to Atlantic Ave Beach

Amagansett Farmhouse Short Walk to Atlantic Ave Beach
Beautiful newly built vacation home on Shelter Island Very private
Beach

Beautiful newly built vacation home on Shelter Island Very private

Beautiful newly built vacation home on Shelter Island Very private
Luxury Beach Home Minutes to All Montauk Has to Offer
Fridge, microwave, oven, stovetop

Luxury Beach Home Minutes to All Montauk Has to Offer

Luxury Beach Home Minutes to All Montauk Has to Offer
Waterfront farmhouse with dock and south and west sunset view.
Living area

Waterfront farmhouse with dock and south and west sunset view.

Waterfront farmhouse with dock and south and west sunset view.
Farmhouse in Cutchogue
Dining

Farmhouse in Cutchogue

Farmhouse in Cutchogue
Cozy Farmhouse Secluded Community w/ Private Beach
Exterior

Cozy Farmhouse Secluded Community w/ Private Beach

10.0 out of 10, Exceptional, (1)
"We thoroughly enjoyed our stay in this home. Simple and family friendly. Lovely neighborhood and amazing beach access. The house manager was incredibly responsive and accommodating. I would definitely stay here again."
Cozy Farmhouse Secluded Community w/ Private Beach
Exquisite Historic Farmhouse
Pool

Exquisite Historic Farmhouse

Exquisite Historic Farmhouse
Stunning Historic House Nearby Beaches and Village
Interior

Stunning Historic House Nearby Beaches and Village

Stunning Historic House Nearby Beaches and Village
Historic modern Farmhouse walking distance to East Hampton Village
A heated pool

Historic modern Farmhouse walking distance to East Hampton Village

Historic modern Farmhouse walking distance to East Hampton Village
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, (1086)
"Charming and historic hotel in Montauk. Drive on up or take a taxi from the train station as there are no real sidewalks in this area. The building is beautiful and in great condition thanks to years of care and maintenance. My ground-floor suite came with a kitchenette, living room, and private patio, though I did not make use of the patio as it was 20° in December when I visited. I recommend paying a visit to Monte’s, the hotel restaurant, which appears to be popular among locals and outside...
The price is CA $188
CA $242 total
includes taxes & fees
Jan 7 - Jan 8, 2025
Montauk Manor
Montauk Oceanside Suites
Apartment | Private kitchen

Montauk Oceanside Suites

3.0 star property
8.4 out of 10, Very good, (347)
"Needs to have someone man the phones…"
The price is CA $195
CA $237 total
includes taxes & fees
Jan 2 - Jan 3, 2025
Montauk Oceanside Suites
Windward Shores Ocean Resort
View from property

Windward Shores Ocean Resort

3.0 star property
8.8 out of 10, Excellent, (264)
"Stayed for the second time at Windward and have no complaints. will book again next time I'm in Montauk!"
The price is CA $181
CA $238 total
includes taxes & fees
Jan 6 - Jan 7, 2025
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.