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Villa holiday rentals in Rutland

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Top-rated villa rentals in Rutland

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
4.91 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

FamilyValueSleep quality

Superhost
A spacious entertainment area is featured, showcasing a wet bar and a pool table, with comfortable seating arranged around the space. Large windows allow natural light to fill the room, while a television is mounted on the wall. A dining table is visible in the corner.
Villa in Winhall
4.84 out of 5 average rating, 31 reviews

Stonehouse at Stratton

Create cherished memories in this unique, family-friendly haven. Designed for entertainment, enjoy a wet bar, pool table, ping pong, darts, and more. Heated floors and Bluetooth sound systems add luxury. Each bedroom has a private bath. The expansive kitchen accommodates the entire family, and a fireplace invites warmth after skiing or boarding. Revel in privacy on 4 acres, with a 2-car heated garage. Only minutes from Stratton, this home offers comfort and leisure in every detail.

LocationFamilyTV

Guest favourite
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.

LocationFamilyBiking

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!

FamilyLocationIndoor spaces

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!

AmenitiesTVCondition

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!

ValueLocationQuiet

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.

LocationHot tubComfort

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

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.

LocationCheck-inAccess

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

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.

LocationCleanlinessSleep quality

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

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

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

LocationCleanlinessAccess

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 Rutland villa rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

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

LocationSleep qualityComfort

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

LocationComfortSkiing

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

Villa with Games Room + Fitness Center Access

FamilyLocationKitchen

Superhost
A spacious entertainment area is featured, showcasing a wet bar and a pool table, with comfortable seating arranged around the space. Large windows allow natural light to fill the room, while a television is mounted on the wall. A dining table is visible in the corner.
Villa in Winhall
4.84 out of 5 average rating, 31 reviews

Stonehouse at Stratton

LocationFamilyCleanliness

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

LocationAccessBathroom

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

FamilyLocationCleanliness

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

Vermont Villa Near the Trails

KitchenHospitalityIndoor spaces

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

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

ValueFamilyCondition

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

LocationHikingAccess

Villa in Rutland

Pico F305 slope side Pool, Gym & Sauna

LocationHospitality

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

LocationHospitalityCleanliness

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

LocationFamilyGetting around

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

LocationWalkabilityComfort

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

LocationComfortHot tub

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

LocationHikingHospitality

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

Whiffletree Outdoor, Pool, Tennis, Golf

LocationFamilyWalkability

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

LocationBathroomAccess

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

FamilyLocationWalkability

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

ValueSkiingCheck-in

Villa in Rutland

Pico F305 slope side Pool, Gym & Sauna

LocationHospitality

Destinations to explore