Shelter Island Farmstay

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Farmstay in Shelter Island

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

Sagaponack NY

Located in Sagaponack, this farm stay is by the sea, within a 5-minute drive of Wolffer Estates Vineyard and Oakland Cemetery.

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

Orient NY

With a stay at this farm stay in Orient Point, you'll be by the sea, just a 3-minute walk from Orient Point County Park and 13 minutes by foot from Little Bay.

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

Cutchogue NY

Located in Cutchogue, this farm stay is in a rural location, within a 5-minute drive of Shinn Estate Vineyards and Waters Crest Winery.

Private, Charming, Lovely Farmhouse in Wainscott, East Hampton

Wainscott NY

$1,482 nightly

$1,693 total

Jan 11 - Jan 12, 2026

Total with taxes and fees

When you stay at this farm stay in Wainscott, you'll be by the sea, within a 5-minute drive of SagPond Vineyards and Wolffer Estates Vineyard.

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

Mattituck NY

With a stay at this farm stay in Mattituck, you'll be within a 5-minute drive of Scarola Vineyards and Love Lane.

Charming 3-bedroom with WiFi and AC in lovely Southampton

Southampton NY

Located in Southampton, this farm stay is within a 5-minute drive of Shinnecock Nation Cultural Center and Museum and Shinnecock Hills Golf Course.

Sprawling Farmhouse in Private Beach Community

East Hampton NY

Located in East Hampton (Clearwater Beach), this farm stay is within a 5-minute drive of The Hamptons Beaches and Kaplan Meadows Sanctuary.

Beautiful newly built vacation home on Shelter Island Very private

Shelter Island NY

Located in Shelter Island, this farm stay is within a 5-minute drive of Sunset Beach and Shelter Island Country Club.

Amagansett Farmhouse Short Walk to Atlantic Ave Beach

Amagansett NY

With a stay at this farm stay in Amagansett, you'll be within a 5-minute drive of Atlantic Double Dunes Preserve and The Hamptons Beaches.

Cozy Farmhouse Secluded Community w/ Private Beach

East Marion NY

When you stay at this farm stay in East Marion, you'll be near the beach, within a 5-minute drive of Island's End Golf and Country Club and Kontokosta Winery.

Exquisite Historic Farmhouse

Sag Harbor NY

With a stay at this farm stay in Sag Harbor, you'll be within a 15-minute walk of Oakland Cemetery and Sag Harbor Old Burying Ground.

Historic modern Farmhouse walking distance to East Hampton Village

East Hampton NY

Located in East Hampton (East Hampton North), this farm stay is within a 15-minute walk of Old Hook Mill and East Hampton Village Nature Trail and Wildlife Sanctuary.

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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.