Vacation rentals in Windham County

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Top-rated vacation rentals in Windham County

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Superhost

Cabin in Londonderry

4.82 out of 5 average rating, 473 reviews

Stunning Rustic Apple Barn - hot tub & sauna

VT’s #1 dream cabin with an overall 5 star rating. Brand new 4 person private hot tub, sauna & outdoor shower! Clawfoot tubs inside & out! Originally a horse barn & tack room…We salvaged and restored to it's original beauty! The rustic charm is 100% intentional & every barn board and nail is back in place! This is upscale rustic:) Xcountry/snowshoe our groomed trails out your front door. Minutes to Magic, Bromley, Stratton, Okemo & Mnt Snow! FAST WIFI, & beautiful new appliances! @bentapplefarm

Superhost

Two wooden Adirondack chairs are positioned facing a circular stone fire pit, where flames are seen glowing amidst glowing embers. Two glasses filled with a light beverage rest on the ground nearby. A stack of firewood is arranged in the background, surrounded by greenery.

Cabin in Wardsboro

4.88 out of 5 average rating, 133 reviews

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Top guest favorite

A spacious screened-in porch features several chairs arranged for relaxation. The wooden flooring complements the vertical wood panels of the wall. A door leads into the cabin, while a view of the yard and a distant structure can be seen through the screen.

Cabin in Jamaica

5 out of 5 average rating, 242 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Guest favorite

A vibrant garden blooms with various flowers, including orange daylilies, purple asters, and white daisies. Yellow coneflowers add contrast, while lush green grass stretches into the background. The image captures the natural beauty of the Vermont countryside under a clear sky.

Guesthouse in Jamaica

4.95 out of 5 average rating, 156 reviews

The Chick Inn

This is a two-story, renovated barn adjacent to the chicken coop in rural Vermont with views of the forests. It has brand new floors, a new kitchenette, and fresh look. (Some renovation is still taking place.) The chicken coop is just next door but the birds are free-range and range they will. Enjoy a private, hot shower in the garden, just outside. This listing is only suitable for people comfortable with dogs, cats, and chickens which will undoubtedly greet you outside during your stay.

Top guest favorite

A fire pit surrounded by large, smooth rocks is centered in the image. Two wooden Adirondack chairs are positioned nearby, offering a place to relax. Lush green ferns frame the scene, creating a natural setting for warmth and gathering.

Tiny home in Dover

4.99 out of 5 average rating, 181 reviews

Rustic Cabin in foothills of Green Mountains

Rennsli Cabin is off grid + nestled on a forested plateau in the foothills of the Green Mountains. You will feel like you are in the middle of nowhere, unplugged and able to regenerate. Kitchen is equipped with cooking essentials+ hosts provide water, coffee, tea, milk, fresh eggs + homemade soap. There is an indoor compostable toilet + outhouse + outdoor shower. Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

Superhost

A bathtub is positioned beside a large window, offering views of the surrounding greenery. Natural light filters through sheer curtains, illuminating the tub and a neatly rolled towel placed nearby.

Cottage in Putney

4.82 out of 5 average rating, 271 reviews

The Cottage, a house built for guests.

In the village there is a wonderful farm to table restaurant, the Gleanery. A local pub, friendly, great food with indoor and outdoor dining & pub. The General Store, is the oldest continually run general store in Vt. The Next Stage, Yellow Barn, Sandglass Theater, these places provide an amazing collection of visual, musical, spoken word and world renowned art and artist to experience. These cultural event locations are but a mile away for the Cottage I hope you choose for your stay.

Guest favorite

The compact kitchen features modern appliances, including a microwave and refrigerator, paired with wooden cabinetry and a dining area. Light-colored wood flooring extends throughout, and a staircase leads to the sleeping loft above. Decor elements include framed artwork and a vase of flowers positioned on the counter.

Tiny home in Brattleboro

4.87 out of 5 average rating, 157 reviews

Sweet Vermont Tiny Home Get Away

Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

Guest favorite

A night sky displays a gradient of purple and dark blue tones, with stars scattered across the expanse. Silhouettes of power lines extend from the foreground into the distance, contrasting against the celestial backdrop.

Camper/RV in Guilford

4.93 out of 5 average rating, 136 reviews

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for up to two adults and one kid (63" long fold down couch).

Guest favorite

A snow-covered mountain is visible in the distance, with skiing trails marked by white lines. Soft clouds drift across the peak, bathed in the warm colors of sunset. Surrounding trees are silhouetted in front of the mountain, adding depth to the natural landscape.

Tiny home in Jamaica

4.94 out of 5 average rating, 1,265 reviews

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

Top guest favorite

Barn in Marlboro Township

4.96 out of 5 average rating, 314 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

Guest favorite

A stone wall is partially visible along the base of a wooden structure, showcasing weathered wood and a lush green fern growing nearby. Natural sunlight highlights the textures of the stones and wood, creating a serene outdoor atmosphere.

Apartment in Newfane

4.87 out of 5 average rating, 144 reviews

Apartment at Five Ferns

A cozy spot perfect for quick romantic getaways and an equally comfortable base for longer adventures. Views out your windows show perennial flower gardens and trees. Queen mattress in a spacious bedroom, en-suite bathroom (shower), and a living/dining area with an equipped kitchen are all at your service. Enjoy our yard and trails along the river. We are an easy 5 minute drive to a fantastic restaurant and many more within 15 minutes of driving.

Guest favorite

A serene private pool is framed by natural stone, surrounded by lush greenery and a few lounge chairs. The inviting water reflects the sunlight, providing a tranquil space for relaxation. Umbrellas are positioned nearby for shade.

Barn in Newfane

4.97 out of 5 average rating, 150 reviews

Beautiful rustic woods and fields retreat.

Within the Fritz Conference Center, tucked into the beauty of the Vermont Countryside, is this charming apartment. Part of a renovated 19th century barn it is the perfect getaway. It sits on over 33 acres of fields, woods, apple orchard and Mountain View’s. 2 miles from historic Newfane Vermont, you are able to enjoy privacy, while close to the many attractions of the area. We are also dog friendly. There is an extra fee of $80 per trip per dog