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Villa holiday rentals in Windsor County

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Top-rated villa rentals in Windsor County

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

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Guest favourite

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

4.9 out of 5 average rating, 42 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

A game room is highlighted by a foosball table and several pool tables. Green pendant lights hang above the pool tables, providing illumination. The floor features wood-like flooring, enhancing the spacious feel of the area. Walls are painted in neutral tones, contributing to a relaxed atmosphere.

Villa in Brownsville

4.79 out of 5 average rating, 72 reviews

Villa with a Fireplace Near the Trails

Dreaming of a cozy villa with a fireplace? 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!

The exterior view showcases an inviting multi-unit building with a unique architectural design. Angled roofs and large windows create an airy feel, while well-kept landscaping and gravel pathways enhance the property’s natural setting.

Villa in Killington

Whiffletree base of Killington outdoor pool

Whiffletree I2 Take the shuttle to the mountain and ski home at the end of the day.

Villa in Killington

4.8 out of 5 average rating, 5 reviews

Whiffletree base of Killington outdoor pool

Whiffletree F6 is on the shuttle bus route with a ski back trail

Guest favourite

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 access

Trail Creek 12, Lovely 1 bedroom close to Mountain

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

Base of Killington with Sports center access

Trail Creek 52 on the Shuttle with ski back trail

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

4.67 out of 5 average rating, 12 reviews

Base of Killington with Sports center access

Trail Creek 70, Fantastic 3 bed close to Mountain

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

Trail Creek, Lovely 2 bedroom close to Mountain

A spacious living area features comfortable seating arrangements, including a patterned armchair and a large sofa. Natural light fills the room through large windows, with drapes that complement the decor. A rustic coffee table and side tables accompany a welcoming fireplace, enhancing a cozy ambiance.

Villa in Rutland

4.25 out of 5 average rating, 4 reviews

Pico C103 located at the base of Pico Mountain

Pico C103 located at the base of Pico Mountain

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 is on a ski home trail

Trail Creek 11 is on a ski home trail

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 out of 5 average rating, 3 reviews

Pico D305 located slope side at Pico quiet area

Pico D305 located slope side at Pico.

Villa in Rutland

Pico F305 slope side Pool, Gym & Sauna

Pico F305 located slope side at Pico

Popular amenities for villa rentals in Windsor County

Free parking on premises

Air conditioning

Private villa rentals

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 is on a ski home trail

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 out of 5 average rating, 3 reviews

Pico D305 located slope side at Pico quiet area

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

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

The exterior view showcases an inviting multi-unit building with a unique architectural design. Angled roofs and large windows create an airy feel, while well-kept landscaping and gravel pathways enhance the property’s natural setting.

Villa in Killington

Whiffletree base of Killington outdoor pool

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

4.67 out of 5 average rating, 12 reviews

Base of Killington with Sports center access

A spacious living area features comfortable seating arrangements, including a patterned armchair and a large sofa. Natural light fills the room through large windows, with drapes that complement the decor. A rustic coffee table and side tables accompany a welcoming fireplace, enhancing a cozy ambiance.

Villa in Rutland

4.25 out of 5 average rating, 4 reviews

Pico C103 located at the base of Pico Mountain

Villa in Rutland

Pico F305 slope side Pool, Gym & Sauna

Luxury villa rentals

Villa in Killington

4.3 out of 5 average rating, 10 reviews

Whiffletree base of Killington outdoor 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 base of Killington outdoor pool

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

4.67 out of 5 average rating, 12 reviews

Base of Killington with Sports center access

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

Villa rentals with a pool

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 out of 5 average rating, 3 reviews

Pico D305 located slope side at Pico quiet area

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

An indoor pool area is featured, with a spacious swimming pool lined by blue lounge chairs. Large windows allow natural light to fill the room, enhancing the bright atmosphere. The covered structure showcases a high ceiling, ensuring a comfortable swimming experience year-round.

Villa in Brownsville

4.83 out of 5 average rating, 23 reviews

Villa with Pool + Fitness Center Access

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

The exterior view showcases an inviting multi-unit building with a unique architectural design. Angled roofs and large windows create an airy feel, while well-kept landscaping and gravel pathways enhance the property’s natural setting.

Villa in Killington

Whiffletree base of Killington outdoor pool

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

Base of Killington with Sports center access

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

4.67 out of 5 average rating, 12 reviews

Base of Killington with Sports center access

An indoor pool area is highlighted by clear blue water under a high, metallic ceiling. Surrounding the pool, multiple lounge chairs are arranged for relaxation. Large windows provide natural light, creating a bright atmosphere throughout the space.

Villa in Brownsville

4.67 out of 5 average rating, 3 reviews

Vermont Villa Near the Trails

Destinations to explore