Farmstay vacation rentals in Windsor County

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Top-rated farmstay rentals in Windsor County

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Top guest favorite

A serene sauna environment is highlighted by warm wooden walls and benches. A soft glow from a wall-mounted light enhances the intimate atmosphere. A wooden bucket and ladle are positioned on a bench, suggesting a traditional sauna experience.

Home in Hartford

4.97 out of 5 average rating, 106 reviews

Luxury Barn Home w/Hot Tub, Sauna, Gardens MtnView

Escape to a luxurious reinvention of an 1850s barn perched atop a hill, w/ hot tub, in house sauna, panoramic views, chef's kitchen, 4 bedrooms & bathrooms, backup generator & fiber optic internet. After a hot tub, make dinner before the fire and mtns on the deck al fresco. Play ping pong, foosball, darts, games. You are surrounded by peace & nature, but close to restaurants, shops, Upper Valley. 5 min to Quechee, White River; 15 to Hanover, Woodstock, Lebanon; 35 to Killington & Lake Sunapee

Top guest favorite

Barn in Andover

4.98 out of 5 average rating, 130 reviews

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

Top guest favorite

A distinctive round house with a metal roof is surrounded by snow-covered ground, showcasing rustic wooden details. Warm light emanates from multiple windows, creating a welcoming contrast against the evening sky and rugged landscape, which features gentle hills in the background.

Home in Tunbridge

4.97 out of 5 average rating, 384 reviews

The Barnbrook House

Come relax in the serenity of the quiet countryside. This home boasts beautiful views, a large stone fireplace, and stained glass windows throughout the home. Enjoy the comforts of home with a full kitchen, amenities, and beds with 1500 thread count sheets while exploring the interesting features of this one of a kind house. Sit by the spring fed pond overlooking the property laced with apple trees. The home has direct access to short walking trails and is close to VAST trails for snowmobiling.

Top guest favorite

An expansive view of rolling hills showcases a vibrant tapestry of colorful autumn foliage. The serene landscape reveals a distant farm with several buildings nestled among the trees, set against a backdrop of mountains under a clear blue sky.

Guest suite in Royalton

4.96 out of 5 average rating, 257 reviews

Private Guest Suite on 155 Acre Royalton Town Farm

1 Bed, 1 Bath apartment attached to historic farm house. This cozy space is the perfect spot for a weekend getaway or a long family vacation on a historic Vermont Farm. Equipped with all the linens and dishes you will need and even a few extras like farm fresh eggs in the fridge and hot chocolate. Close to I-89 and 30 minutes of Ski Resorts like Saskadena Six. Property of 155 acres has trails, sledding hills and our farm animals you can enjoy. Check our reviews, you won't be disappointed!

Top guest favorite

The exterior of a two-story cabin is displayed, featuring a wooden façade with large windows. A covered porch is seen in the foreground, furnished with two Adirondack chairs facing the open lawn. The sky is partly cloudy, complementing the natural setting.

Farm stay in Windsor

4.98 out of 5 average rating, 124 reviews

Fat Sheep Farm & Cabins - Sunrise Cabin

The Boston Globe referred to Fat Sheep Farm & Cabins as a "magical place," with "five stunning cabins [that] are spotless, spacious, and perfectly placed to provide access to incredible views." Enjoy a unique lodging experience while staying on our working farm. Our guests can enjoy our cheese, produce, eggs from our chickens and a visit with the farm animals. The farm feels secluded but is only 10 minutes from I91, about 11 miles from both Woodstock and Quechee, and 6 miles from the GMHA.

Top guest favorite

Yurt in Randolph

5 out of 5 average rating, 129 reviews

Howling Wolf Farm Yurt--A Magical Glamping Retreat

Our 88-acre farm spreads up a steep hillside above the village of Randolph, one mile away. The land is a mixture of open areas where we rotate our sheep flock daily, and wooded land with trails and old stone walls. You might hear the occasional car or truck on a nearby road, but more likely you'll hear our sheep baaing to one another or the cows across the valley trumpeting, or the abundance of birdsong. The energy here is calming and peaceful--we know you will love it as much as we do.

Top guest favorite

The spacious living area showcases soaring wooden beams and a rustic charm. A selection of comfortable seating arrangements surrounds a large coffee table, while vintage rugs add warmth to the wooden floors. Natural light floods in through multiple windows, enhancing the cozy ambiance.

Barn in Woodstock

4.99 out of 5 average rating, 153 reviews

Stunning Converted Barn Home 3-bed 2 bath

Stunning renovated barn, surrounded by fenced pastures, this beautiful authentic barn home provides guests with a unique experience, in a beautiful 3-bedroom, 2 bath rustic barn. Fully equipped, beautifully decorated with high end furnishings, antique rugs, comfortable beds, cook in the chef's kitchen, relax by the stone fireplace, sit on the deck with amazing views, walk the fields, and enjoy thethe firepit. An original classic barn, you won't forget. Sorry, we can no longer accept pets.

Top guest favorite

A serene pond is framed by lush greenery and wildflowers, with a wooden dock extending into the water. Two simple wooden chairs are positioned at the edge of the dock, inviting relaxation and enjoyment of the peaceful natural surroundings.

Cottage in Windsor

4.97 out of 5 average rating, 389 reviews

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.

Superhost

Home in Sharon

4.92 out of 5 average rating, 112 reviews

Authentic farm house - experience the VT farm life

Your cozy, authentic Vermont country stay awaits! We invite you stay in our farmhouse to relax and unwind. We're located only 10 minutes from exit 2 off of 89. It's easy to get here (other than mud season of course). Enjoy our beautiful valley and our historic farm rich in natural resources. Our farm is well known in the Upper Valley for its round barn, a 10 sided remarkable structure built as a dairy barn in the early 1900's. Follow and tag us on IG: @windingbrookfarmvt

Guest favorite

A loft-style bedroom area is visible, featuring a spacious bed with white linens. Natural light enters through a window framed by wooden beams, enhancing the coziness of the space. A small bookshelf is positioned nearby, while wooden stairs lead down to the lower level.

Home in Rochester

4.98 out of 5 average rating, 204 reviews

The Guest House at Sky Hollow

This quiet hilltop house on an 1800's farm turned homestead at the end of a dirt road offers high speed internet, hiking and mountain bike trails, a swimming pond, X-C ski, and sauna. Only miles from renowned New England ski resorts, and featuring 2 bedrooms, 1.5 baths, a full kitchen, an open floor plan, and a small backyard right beside a brook, the guest house is quiet and private, the perfect retreat for a cozy weekend with outdoor adventures and creature comforts!

Top guest favorite

A wooden deck area is presented, featuring two white chairs placed beside planters. A decorative planter with a Buddha head design holds tall green plants. Glass doors reflect the natural light, enhancing the inviting and open ambiance of the space.

Farm stay in Plainfield

4.97 out of 5 average rating, 224 reviews

Renovated 1817 Hobby Farm Close to Dartmouth

Come stay at PRIVATE GUEST QUARTERS on our hobby farm in Plainfield Village! Experience country living with a 20-minute proximity to Dartmouth University. You can see gorgeous views of Mount Ascutney from your window, hike to the French Ledges, visit St. Gaudens Park, or J.D. Sallingers farm. Every season is beautiful here! Or learn how to make macarons :) if you are brave enough.

Top guest favorite

Apartment in Andover

4.98 out of 5 average rating, 427 reviews

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!