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Villa vacation rentals in Rutland

Find and book unique villas on Airbnb

Top-rated villa rentals in Rutland

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, 46 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

ValueLocationAccuracy

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.

LocationFamilyLayout

Guest favorite
Villa in Brownsville
4.8 out of 5 average rating, 79 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.

FamilyLocationCleanliness

Top guest favorite
The unique house features a modern design with large glass windows allowing for natural light. It is surrounded by lush greenery, with a wooden deck visible on the upper level. Trees and foliage provide a serene, private setting.
Villa in Ludlow
4.93 out of 5 average rating, 57 reviews

Modern 3 Bedroom 4 Bath Villa w HotTub/ back trail

This unique house has a style all its own. with floor to ceiling windows and doors throughout There are 3 levels. top floor has 2 bedrooms with full baths and Hot Tub on the balcony middle level entry; plus Great room: with kitchen, dining, living, activity area with a big table, fireplace and 75 inch television bottom level has 2 bedrooms and 2 full baths

ValueLocationRiver

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!

ValueLocationOutdoor spaces

Villa in Brownsville
4.5 out of 5 average rating, 4 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!

LocationConditionTV

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!

FamilyLocationAmenities

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.

LocationPoolComfort

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.

LocationSkiingComfort

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

An indoor swimming pool area is illuminated by natural light filtering through high windows. The spacious pool features clear blue water, while a hot tub is situated nearby. The room showcases a modern design with wooden beams and tiled flooring.
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.

LocationFamilyCleanliness

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.

FamilyLocationSkiing

Popular amenities for Rutland villa rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Private villa rentals

Villa in Brownsville
New place to stay

2BR Duplex Villa w/ Balcony | Game Room + Fire Pit

Top guest favorite
The unique house features a modern design with large glass windows allowing for natural light. It is surrounded by lush greenery, with a wooden deck visible on the upper level. Trees and foliage provide a serene, private setting.
Villa in Ludlow
4.93 out of 5 average rating, 57 reviews

Modern 3 Bedroom 4 Bath Villa w HotTub/ back trail

ValueLocationWalkability

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

LocationFamilyHeating

An indoor swimming pool area is illuminated by natural light filtering through high windows. The spacious pool features clear blue water, while a hot tub is situated nearby. The room showcases a modern design with wooden beams and tiled flooring.
Villa in Killington
4.69 out of 5 average rating, 13 reviews

Base of Killington with Sports center access Golf

FamilyLocationSkiing

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

LocationSleep qualitySkiing

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

ValueLocationSleep quality

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

Villa with Games Room + Fitness Center Access

ValueLocationHeating

Villa in Brownsville
4.5 out of 5 average rating, 4 reviews

Vermont Villa Near the Trails

LocationAmenitiesHospitality

Luxury villa rentals

Top guest favorite
The unique house features a modern design with large glass windows allowing for natural light. It is surrounded by lush greenery, with a wooden deck visible on the upper level. Trees and foliage provide a serene, private setting.
Villa in Ludlow
4.93 out of 5 average rating, 57 reviews

Modern 3 Bedroom 4 Bath Villa w HotTub/ back trail

ValueLocationHot tub

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 aroundCleanlinessSkiing

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

LocationAccessHospitality

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

ValueLocationCleanliness

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

ValueHospitalityPets

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

Whiffletree Outdoor, Pool, Tennis, Golf

FamilyValueCondition

An indoor swimming pool area is illuminated by natural light filtering through high windows. The spacious pool features clear blue water, while a hot tub is situated nearby. The room showcases a modern design with wooden beams and tiled flooring.
Villa in Killington
4.69 out of 5 average rating, 13 reviews

Base of Killington with Sports center access Golf

FamilyLocationHot tub

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

LocationCleanlinessSkiing

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

ValueFamilyWalkability

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

DecorCleanlinessGetting around

Villa in Killington
4.75 out of 5 average rating, 4 reviews

Sunrise East Glade C8 Ski on Ski off

LocationHot tubSkiing

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

LocationBathroomHospitality

Destinations to explore