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

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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

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Villa in Ticonderoga

Expansive Eagle Lake Escape w/ Boathouse + Beach

7,000 Sq Ft | Renovated Stagecoach Stop | 3 Kitchens | Kayaks, Rowboat & Canoe A unique stay awaits at this historic mansion on Eagle Lake! This impressive Ticonderoga villa is a true Adirondack gem, boasting multiple gathering spaces for your crew and private lakefront access with a sandy beach. Launch a canoe from your backyard or explore local favorites such as Lake Champlain and Lake George. Wind down with s’mores by the fire under a starlit sky. Your mountain escape is calling!

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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.

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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.

LocationValueSleep quality

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!

FamilyLocationOutdoor 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!

HospitalityKitchenIndoor spaces

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!

LocationValueQuiet

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.

LocationComfortSkiing

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.

LocationCleanlinessSkiing

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 favourite