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Aug 29 - Aug 31
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Sep 5 - Sep 7
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Sep 19 - Sep 21
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Browse Select Shelter Island Farmstay

Our top choices for Shelter Island farmstays

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Smart TV, fireplace, computer monitors

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

10.0 out of 10, Exceptional, (7)
"We had such a nice weekend here. Check-in was super easy and flexible. The hosts were welcoming and available for any questions. The home is beautiful and well stocked. Can’t beat the location"
Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach
Modern farmhouse w/ heated pool, beach, horses and winery in heart of North Fork
3 bedrooms, iron/ironing board, travel crib, WiFi

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

10.0 out of 10, Exceptional, (17)
"We had a wonderful stay and the owners were very responsive. We would love to come back!"
Modern farmhouse w/ heated pool, beach, horses and winery in heart of North Fork
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
Charming 2-bedroom farmhouse in Lyme just 5 minutes from I-95
Interior

Charming 2-bedroom farmhouse in Lyme just 5 minutes from I-95

Charming 2-bedroom farmhouse in Lyme just 5 minutes from I-95
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, (101)
"Beautiful clean well decorated house with lots of activities to do. Highly recommend this house for your next group Hamptons trip! Host was responsive and so nice!!!"
Luxury 9 Acre Sagaponack/Sag Harbor Compound Retreat & Year-Round Spa
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
Exquisite Historic Farmhouse
Pool

Exquisite Historic Farmhouse

Exquisite Historic Farmhouse
Farmhouse in Cutchogue
Dining

Farmhouse in Cutchogue

Farmhouse in Cutchogue
Stunning Historic House Nearby Beaches and Village
Interior

Stunning Historic House Nearby Beaches and Village

Stunning Historic House Nearby Beaches and Village
Charming 3-bedroom with WiFi and AC in lovely Southampton
Dining

Charming 3-bedroom with WiFi and AC in lovely Southampton

Charming 3-bedroom with WiFi and AC in lovely Southampton
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
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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Top Shelter Island Hotel Reviews

The Atlantic Hotel

The Atlantic Hotel

10/10 Excellent
"Nice staff and the hotel is fine. "
Granger 2-night trip
Posted 15 hours ago
The Atlantic Hotel