Farmstay vacation rentals in Windsor County

Find and book unique farmstay rentals on Airbnb

Top-rated farmstay rentals in Windsor County

Guests agree: these farmstay rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A spacious living area features a central stone fireplace, surrounded by cozy seating. Large windows frame scenic views of the trees outside, filling the space with natural light. The rustic wooden beams and walls add warmth, while the open layout connects to the kitchen and loft above.

Barn in Andover

Fat Cat Barn - Close Okemo & Magic, Vermont

Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

4.99 out of 5 average rating, 156 reviews

Top guest favorite

A modern kitchen features a central island with a wooden countertop, surrounded by two stools. White cabinetry and ample counter space are present, with large windows providing natural light and garden views. A variety of appliances and kitchen tools are visible, enhancing functionality.

Home in Hartford

Quechee Ski Haus: Hot Tub, Sauna, & Mtn Views

Hathaway House: an 1850s barn perched on a hill & made into a stunning modern farm-house with panoramic mountain views west, hot tub, sauna, huge kitchen, study, deck, screened porch & fiber internet. Play on the sprawling lawn or ping pong & foosball in the barn. Enjoy dinner by the great room’s fire or grill and eat al fresco on the deck w/ hot tub, surrounded by gardens & woods. Your private retreat, yet 5 min to Quechee, 15 to Hanover, Saskedena, & Woodstock; 30 to Sunapee & Killington base.

4.97 out of 5 average rating, 131 reviews

Top guest favorite

A charming red exterior defines the recently built house, surrounded by lush greenery and a clear sky. The spacious porch features rustic columns, while comfortable seating invites relaxation. Large windows ensure natural light fills the interior, offering a connection to the serene outdoor environment.

Home in Windsor

Custom cabin on Mt Ascutney, Fall and Winter Days…

Combining sweeping views of distant hills with privacy and wraparound porches, the Red House is a custom cabin built for couples and smaller families getting away from busy lives. Glorious colors and quiet winter evenings. Within easy reach of trailheads to hike or bike Mt Ascutney, or to visit Woodstock, Hanover, Ludlow and the Upper Valley, the Red House sits among some of the best restaurants in Vermont. It awaits the discerning traveler who can do absolutely nothing, yet experience it all!

4.97 out of 5 average rating, 138 reviews

Guest favorite

A vibrant garden is showcased, filled with an array of colorful flowers in various hues, surrounded by lush greenery. A charming wooden structure with a metal roof is partially visible in the background, illuminated by gentle sunlight filtering through the trees.

Townhouse in Fairlee

Garden Retreat, Lake Fairlee, Dartmouth & Ski-way

Set in a lovely 3 acre garden setting, our Airbnb is 1/4 mile from the lake and 23 minutes from Dartmouth College or the Ski-way. This private, comfortable apartment is built onto our house with its own entrance, hardwood floors, radiant heat, large windows, full kitchen and bath, & gorgeous garden views. The wrap around loft has 3 generous semi-private sleeping areas with 2 queens + 1 twin. A queen futon is downstairs. Rental includes pass to Treasure Island Recreation area & beach: 1.5 mi..

4.98 out of 5 average rating, 285 reviews

Top guest favorite

Home in Rochester

Bill’s Barn Rochester Vermont 3 Bdrm entire house

Our place is a 1980's barn/woodshop that never housed animals that has been converted into a lovely three bedroom home.We are 20 minutes from Rikert 2019 hosts of the Bill Koch Festival and the Middlebury College Snow Bowl.The place is light and airy with southern and eastern sun.The main living room has 13 foot ceilings with lots of couches, arm chairs and places to hang out, read and or relax.We are in the heart of the Green Mountains with skiing and colleges, an easy drive from the house.

4.97 out of 5 average rating, 112 reviews

Guest favorite

A snow-covered landscape surrounds the historic farmhouse and attached barn. The yellow house features a rounded wall and is partially obscured by snowdrifts. The red barn is visible to the right, under a clear blue sky, creating a serene winter scene.

Home in Chester

Vermont 1828 Reunion House, near Okemo

The Vermont 1828 Reunion House, close to Okemo is a spacious historic vintage ski lodge and farmhouse with 2 kitchens, 8 bedrooms, 4 baths, & a quintessential Vermont character. Excellent for gatherings & family reunions. Linens & towels provided, beds made. 10 acres, meadow & hidden pond. . A new automatic sprinkler system was installed in 2024 & the house complies with all safety regulations & certified by the town of Chester. Must be 25 years to rent. Long term rentals possible.

4.8 out of 5 average rating, 101 reviews

Top guest favorite

The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.

Cottage in Windsor

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

4.97 out of 5 average rating, 471 reviews

Top guest favorite

Home in Clarendon

Killington Retreat | Deck-Fire Pit-Mountain Views!

Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

4.95 out of 5 average rating, 351 reviews

Top guest favorite

Cottage in Hartland

Cottage 5 miles from Woodstock-Dog Friendly w/FIOS

Just 5 miles from Woodstock, the Cottage at StillwoodVT is a bright and cozy two-story home set on a peaceful 20-acre oasis of woods, pasture, and hill views. Two bedrooms (queen upstairs, full downstairs), one bath with shower, and open kitchen/living/dining area. Private, quiet, and surrounded by nature. One-bedroom use receives 10% back after checkout (not combinable with other discounts).

4.94 out of 5 average rating, 177 reviews

Top guest favorite

A bright interior is featured, showcasing a mix of seating options including a blue sofa and an upholstered armchair. A small dining table is complemented by wooden chairs. The kitchen area is visible, equipped with diverse utensils, while large windows on two sides allow natural light to fill the space.

Apartment in Andover

Private Hilltop farm apartment

Our cozy apartment is located on a beautiful hilltop farm with views out from the porch across horse pasture and to the mountains as far away as New Hampshire. There are over 100 acres of field to walk through as well as a mile long trail running down through our property. We are 15 minutes from Chester, Ludlow and Weston. We also have very fast internet!

4.97 out of 5 average rating, 480 reviews

Guest favorite

A wooden porch is framed by weathered gray walls, leading to a solid wooden door. A small bench sits nearby, while a potted plant with white flowers adds a touch of greenery to the rustic setting.

Farm stay in South Royalton

Corncrib Tiny House Glamping Cabin

Queen-sized bed in historic corncrib cabin in the heart of Vermont with gorgeous views of fields and forest. We also have several other rooms available. The tiny house comes with a queen sized bed in the loft. It has a private full bathroom with clawfoot tub and shower, tiny living room, dining area and full kitchen. It can accommodate one or two people.

4.84 out of 5 average rating, 226 reviews

Top guest favorite

A large farmhouse is set against a backdrop of vibrant autumn foliage. The structure features a modern design with a metal roof and expansive glass windows, allowing for abundant natural light. A spacious lawn complements the serene rural setting.

Home in Rochester

Modern Farmhouse on 25 Acres - Superb Views

This Truex Cullins designed Farmhouse is inspired by the iconic old farmsteads found throughout northern New England. Embracing the dramatic beauty of Rochester's north hollow the house is a serene retreat where connection to your partner, family and the environment will thrive. Unplug, recharge, renew and enjoy all that mountain living has to offer.

4.97 out of 5 average rating, 157 reviews