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Villa vacation rentals in Windsor County

Find and book unique villas on Airbnb

Top-rated villa rentals in Windsor County

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

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Guest favorite
The Windsor Mansion is positioned at the top of a hillside, surrounded by a lush landscape of trees in various shades of green and hints of autumn colors. The elegant white of the mansion’s exterior contrasts with the natural setting, creating a striking visual.
Private room in Windsor
4.91 out of 5 average rating, 45 reviews

Private Wing of largest Colonial Mansion in US

Built in 1902 and comprehensively renovated in late 2016, the Windsor Mansion is an incredibly well preserved example of Colonial Revival Architecture. Filled with elegance & history, Three US Presidents have slept here. Our 17 Rooms/Suites are individually decorated each with private bathroom & free wireless internet. Set on 14 acres with a tiered terrace offering spectacular views & a custom fire pit. Lots to see in area including Saint-Gaudens Nat'l Park, Quechee Falls, Dartmouth College, etc

FamilyLocationIndoor spaces

A large white house with multiple sections stands against a backdrop of lush greenery. The property features a covered porch and numerous windows, providing a welcoming appearance. Attached garages can be seen, indicating ample space for vehicles. The blue sky and scattered clouds contribute to the serene setting.
Villa in Woodstock
3.67 out of 5 average rating, 3 reviews

❤Luxe Prime Woodstock❤Private Pond❤ 25 Acres❤Spa❤

⚜ Gorgeous family home on a 25-acre estate in a picturesque natural setting. ⚜ Large, lush house that sleeps up to 8 adults (plus 2 extra children). Luxurious, immaculate and well-equipped home. ⚜ Private swimming pond ⚜ Top of the line Organic mattresses and bedding ⚜Separate guest house available to accommodate 12 guests total ➨ Suicide Six 5 min ➨ Killington 20 min ➨ Okemo 30 min ➨ Woodstock Inn 5 min ➨ Woodstock boutiques 5 min ➨ Boston 2 hours ➨ $295 pet fee, prior approval

LocationValueComfort

Guest favorite
Villa in Brownsville
4.79 out of 5 average rating, 77 reviews

2-Bedroom Villa w/ King, Queen & Private Balcony

Set among the forested hills of southern Vermont, this two-bedroom villa is the perfect mountain escape for families and small groups. A fully equipped kitchen, dedicated dining area, and a private balcony invite you to unwind after a day in the Green Mountains. On-site amenities include a fitness center, movie theater, game room, and outdoor fire pits — everything you need for a memorable Vermont getaway.

LocationFamilyCheckout

Top guest favorite
Aerial view of a large purple house set against a backdrop of rolling hills and trees. The expansive lawn surrounds the property, showcasing natural greenery and a gravel driveway with parked vehicles. The scene is illuminated by bright daylight, highlighting the serene rural atmosphere.
Villa in Fairlee
4.95 out of 5 average rating, 279 reviews

The Upper Valley Retreat

Upper Valley Retreat: A 20-Acre Vermont Symphony of Light, Land, and Legacy Tucked into the gentle embrace of the Upper Valley, where rolling meadows meet the ancient hush of Brushwood Forest, stands the Upper Valley Retreat — a magnificent 20-acre estate and working apple orchard that feels like a poem written in wood, stone, and sky.

LocationValueHeating

Villa in Brownsville
4.82 out of 5 average rating, 11 reviews

Villa Near Biking and Hiking Trails

This villa is perfect for your group! Enjoy stunning views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

FamilyValueCheck-in

Villa in Brownsville
4.67 out of 5 average rating, 3 reviews

Vermont Villa Near the Trails

You'll be able to enjoy panoramic views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

TVHospitalityKitchen

Villa in Brownsville
4.83 out of 5 average rating, 29 reviews

Villa with Games Room + Fitness Center Access

Enjoy stunning views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!

FamilyLocationAccuracy

A cozy living area is enhanced by a large brick fireplace. Two plaid sofas face each other, complemented by a wooden coffee table in the center. A large window allows natural light to fill the space, framed by blue curtains and adorned with seasonal decor.
Villa in Killington
4.75 out of 5 average rating, 4 reviews

Sunrise East Glade C8 Ski on Ski off

SUNRISE CHAIR PROVIDES SKI TO/FROM TO KILLINGTON TRAILS. EXCEPTIONAL SPORTS CENTER WITH FULL GYM, WINTER INDOOR POOL AND HOT TUB, SUMMER OUTDOOR POOL AND BARBECUE GRILL. Hiking and snowshoe/cross country trails.

LocationComfortCheck-in

The living area features a comfortable blue sofa paired with a cozy armchair, illuminated by warm table lamps. A wooden coffee table sits at the center, and large windows with blue drapes provide a view of the surrounding landscape, creating a welcoming atmosphere.
Villa in Rutland
5.0 out of 5 average rating, 3 reviews

Pico D305 located slope side at Pico quiet area

SKI IN/OUT Conveniently located at the base of Pico. Access to the Pico Fitness Center and lane pool. Close to Killington Road and Rutland. Next to Appalachian Trail.

LocationComfortAccuracy

Villa in Rutland

Pico F305 slope side Pool, Gym & Sauna

SKI IN/OUT Conveniently located at the base of Pico. Access to the Pico Fitness Center and lane pool. Close to Killington Road and Rutland. Next to Appalachian Trail.

LocationHospitality

Guest favorite
A comfortable living area features a gray sectional sofa and a pull-out sofa bed, positioned beside a circular coffee table. Large windows with sheer curtains allow natural light into the space, while a wooden ceiling adds warmth. A small fireplace and bear-themed wall art enhance the ambiance.
Villa in Killington
4.83 out of 5 average rating, 6 reviews

Base of Killington with Sports center, golf

EXCEPTIONAL LOCATION ON SKI BACK TRAIL AND SHUTTLE TO MOUNTAIN, SPORTS CENTER WITH POOL, JACUZZI, GYM EQUIPMENT, POOL TABLE AND GAMES.

ValueFamilySkiing

A spacious living area is highlighted by large windows allowing natural light to fill the space. Comfortable dark sofas are arranged around a rustic coffee table in front of a fireplace. A staircase leads to an upper level, enhancing the open feel of the room.
Villa in Killington
4.69 out of 5 average rating, 13 reviews

Base of Killington with Sports center access Golf

EXCEPTIONAL LOCATION ON SKI BACK TRAIL AND SHUTTLE TO MOUNTAIN, SPORTS CENTER WITH POOL, JACUZZI, GYM EQUIPMENT, POOL TABLE AND GAMES.

FamilyLocationWalkability

Popular amenities for Windsor County villa rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

Top guest favorite
Aerial view of a large purple house set against a backdrop of rolling hills and trees. The expansive lawn surrounds the property, showcasing natural greenery and a gravel driveway with parked vehicles. The scene is illuminated by bright daylight, highlighting the serene rural atmosphere.
Villa in Fairlee
4.95 out of 5 average rating, 279 reviews

The Upper Valley Retreat

ValueLocationDecor

Guest favorite
Villa in Brownsville
4.79 out of 5 average rating, 77 reviews

2-Bedroom Villa w/ King, Queen & Private Balcony

LocationFamilyCheckout

Villa in Brownsville
4.82 out of 5 average rating, 11 reviews

Villa Near Biking and Hiking Trails

LocationValueCleanliness

Guest favorite
A comfortable living area features a gray sectional sofa and a pull-out sofa bed, positioned beside a circular coffee table. Large windows with sheer curtains allow natural light into the space, while a wooden ceiling adds warmth. A small fireplace and bear-themed wall art enhance the ambiance.
Villa in Killington
4.83 out of 5 average rating, 6 reviews

Base of Killington with Sports center, golf

FamilyValueAmenities

Villa in Brownsville
4.67 out of 5 average rating, 3 reviews

Vermont Villa Near the Trails

TVKitchenAmenities

Villa in Brownsville
4.83 out of 5 average rating, 29 reviews

Villa with Games Room + Fitness Center Access

FamilyLocationSleep quality

A spacious living area is highlighted by large windows allowing natural light to fill the space. Comfortable dark sofas are arranged around a rustic coffee table in front of a fireplace. A staircase leads to an upper level, enhancing the open feel of the room.
Villa in Killington
4.69 out of 5 average rating, 13 reviews

Base of Killington with Sports center access Golf

LocationFamilySleep quality

A living area features a large sectional sofa facing a stone fireplace with a wooden mount displaying the Killington logo. A television is positioned above a console, while a large window offers views of the outdoors. Natural light brightens the room.
Villa in Killington
4.8 out of 5 average rating, 5 reviews

Whiffletree F6 Outdoor, Pool, Tennis, Golf

Getting aroundHospitalitySkiing

Luxury villa rentals

A comfortable living area is furnished with a spacious sofa and a wooden coffee table. Natural light floods the room through large windows, providing views of the outdoors. Artwork is displayed on the walls, while a lamp adds subtle illumination beside the seating.
Villa in Killington
4.33 out of 5 average rating, 3 reviews

Sunrise Timberline I7 Ski on Ski off

LocationComfortHiking

A spacious living area features a colorful floral sofa alongside two brown leather chairs. A wooden coffee table sits in front of the seating. A wood-burning fireplace is located against a textured wall, with vintage skis displayed above it. Large windows allow natural light to enter.
Villa in Killington

Trail Creek 11 Sports Center near Golf

LocationSkiingGetting around

Top guest favorite
Aerial view of a large purple house set against a backdrop of rolling hills and trees. The expansive lawn surrounds the property, showcasing natural greenery and a gravel driveway with parked vehicles. The scene is illuminated by bright daylight, highlighting the serene rural atmosphere.
Villa in Fairlee
4.95 out of 5 average rating, 279 reviews

The Upper Valley Retreat

ValueLocationAccuracy

A spacious living area is highlighted by large windows allowing natural light to fill the space. Comfortable dark sofas are arranged around a rustic coffee table in front of a fireplace. A staircase leads to an upper level, enhancing the open feel of the room.
Villa in Killington
4.69 out of 5 average rating, 13 reviews

Base of Killington with Sports center access Golf

FamilyLocationCondition

A comfortable living area is featured, showcasing a soft beige couch and a light gray armchair positioned around a wooden coffee table. Natural light filters through large windows, highlighting the wooden ceiling and creating a cozy ambiance.
Villa in Killington
4.6 out of 5 average rating, 5 reviews

Base of Killington with Sports center access Golf

LocationValueCleanliness

A large white house with multiple sections stands against a backdrop of lush greenery. The property features a covered porch and numerous windows, providing a welcoming appearance. Attached garages can be seen, indicating ample space for vehicles. The blue sky and scattered clouds contribute to the serene setting.
Villa in Woodstock
3.67 out of 5 average rating, 3 reviews

❤Luxe Prime Woodstock❤Private Pond❤ 25 Acres❤Spa❤

ValueFamilyHot tub

Villa in Rutland

Pico F305 slope side Pool, Gym & Sauna

LocationHospitality

Villa rentals with a pool

A cozy living area is accented by wooden paneling and a gas fireplace. Two comfortable chairs are positioned with cushions, while a sofa and a wooden side table complement the seating arrangement. Natural light enters through sliding glass doors, revealing a view of the outdoors.
Villa in Killington
2.67 out of 5 average rating, 3 reviews

Whiffletree G1 Outdoor, Pool, Tennis, Golf

ValueHospitalityCleanliness

Villa in Killington
4.3 out of 5 average rating, 10 reviews

Whiffletree Outdoor, Pool, Tennis, Golf

LocationValueHospitality

Guest favorite
A comfortable living area features a gray sectional sofa and a pull-out sofa bed, positioned beside a circular coffee table. Large windows with sheer curtains allow natural light into the space, while a wooden ceiling adds warmth. A small fireplace and bear-themed wall art enhance the ambiance.
Villa in Killington
4.83 out of 5 average rating, 6 reviews

Base of Killington with Sports center, golf

ValueLocationCondition

A spacious living area is highlighted by large windows allowing natural light to fill the space. Comfortable dark sofas are arranged around a rustic coffee table in front of a fireplace. A staircase leads to an upper level, enhancing the open feel of the room.
Villa in Killington
4.69 out of 5 average rating, 13 reviews

Base of Killington with Sports center access Golf

FamilyLocationAccuracy

A living area features a large sectional sofa facing a stone fireplace with a wooden mount displaying the Killington logo. A television is positioned above a console, while a large window offers views of the outdoors. Natural light brightens the room.
Villa in Killington
4.8 out of 5 average rating, 5 reviews

Whiffletree F6 Outdoor, Pool, Tennis, Golf

HospitalityCleanlinessDecor

The living area features a comfortable blue sofa paired with a cozy armchair, illuminated by warm table lamps. A wooden coffee table sits at the center, and large windows with blue drapes provide a view of the surrounding landscape, creating a welcoming atmosphere.
Villa in Rutland
5.0 out of 5 average rating, 3 reviews

Pico D305 located slope side at Pico quiet area

LocationCleanlinessAccuracy

A cozy living area is enhanced by a large brick fireplace. Two plaid sofas face each other, complemented by a wooden coffee table in the center. A large window allows natural light to fill the space, framed by blue curtains and adorned with seasonal decor.
Villa in Killington
4.75 out of 5 average rating, 4 reviews

Sunrise East Glade C8 Ski on Ski off

LocationSkiingHot tub

A spacious living area is centered around a stone fireplace, complemented by a wooden ceiling. Two armchairs and a sofa provide comfortable seating, while a coffee table occupies the center. Natural light enters through a large window, offering a view of the outdoors.
Villa in Killington
4.67 out of 5 average rating, 3 reviews

Base of Killington with Sports center access Golf

LocationCleanlinessHospitality

Destinations to explore