Villa vacation rentals in Bennington

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Top-rated villa rentals in Bennington

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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

4.9 out of 5 average rating, 39 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

Guest favorite

The outdoor heated swimming pool is framed by a stone patio, with a shaded pergola alongside. Sunlight reflects off the clear water, capturing the serenity of the surrounding landscape and distant hills at sunset.

Villa in Coxsackie

4.91 out of 5 average rating, 57 reviews

5-BR Villa with Pool and Dog Friendly!

Welcome to Hudson View Villa! Relax with family or friends at a hilltop property overlooking The Hudson and Berkshires. Hudson View House offers over 2900 sq ft of gorgeous luxury space with views of the Hudson and Berkshires virtually from every room. The scenic views of the surroundings, breathtaking sunrises and sunsets will want you never to go home! Heated swimming pool now Open ( May - Sep/October). Propane grill on back deck overlooking Hudson River. Tesla charging- bring own adapter

Guest favorite

The exterior of a turn-of-the-century home is depicted, featuring a textured white facade and multiple arched entryways. A shaded porch is accentuated by hanging lights and comfortable seating, while lush greenery surrounds the property, providing a serene and inviting atmosphere.

Villa in Bolton

4.93 out of 5 average rating, 68 reviews

100 yrs old 2024! Historic Musician's Villa Bolton

This truly intriguing turn-of-the century home transports guests to the inspiring mood & enduring character of the great & gracious. Built by a legendary musician’s family w/focus on elegant entertaining, this 100 yr old home is ready for guests after 3 yrs of restoration. Remaining true to original form, guests find showpiece architectural acoustics in great room, elevated framework throughout w/timeless archways, dramatic stairway w/ornate balustrade, romantic rounded walls, relaxing patios.

The house is set on a grassy lot, featuring a screened porch and large windows. Well-kept shrubs line the property, and mature trees provide shade. The structure's exterior displays a soft neutral tone, with a distinct architectural style that offers charm and character.

Villa in Queensbury

5 out of 5 average rating, 3 reviews

Private City Line Compound

2 Bedroom,s sleep 4, Walk to Coffee Shop, Breakfast, locations, Restaurants, Grocery Market, medical. West Mountain Ski Area 5 miles away. Summer activities there . Bike path to lake George accessibility from house. 2 car secure garage . 6 person Hot Tub on outdoor porch, with 43” TV. 63’ TV in Living , Room, Sonos Theatre sound system 43” TV’s in Bed Rooms . WiFi/internet/cable Outdoor gas grill Breakfast Nook 65" Outdoor TV and seating area All amenities For a vacation stay. No Garage

Guest favorite

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

4.91 out of 5 average rating, 23 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.

Guest favorite

An aerial view captures the spacious villa surrounded by vibrant autumn foliage and rolling hills. The property features a pool nestled among trees, with expansive lawns and a gravel driveway leading up to the home, offering a serene retreat in nature.

Villa in Pownal

4.94 out of 5 average rating, 85 reviews

Vermont Vacation Villa—Grapevine Getaway

Nestled in the stunning natural beauty of Vermont, this striking villa offers the perfect escape from the hustle and bustle of everyday life. Surrounded by rolling hills, and picturesque countryside, this home is a paradise. Whether exploring the area's cultural institutions, immersing yourself in the natural beauty of Vermont, or relaxing and unwinding with family and friends, this vacation home is the perfect retreat. Experience the magic of this beautiful area for yourself!

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, 45 reviews

Modern 4 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

Villa in Dover

The Myrtle house Heated Pool-Hot Tub-Tennis &More

The Timbercrest Mansions, The Myrtle House Welcome to our newly renovated retreat, just 3 minutes from Mount Snow! This spacious home is designed for an unforgettable family experience, offering the perfect mix of adventure and relaxation. With 6 bedrooms, 9 beds, 5 bathrooms and an abundance of common areas, it comfortably accommodates 16+ guests.

Superhost

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!

Superhost

An indoor pool area features a long, rectangular swimming pool surrounded by multiple lounge chairs. The high, vaulted ceiling is supported by metal beams, and large windows provide natural light to the space, creating a bright and inviting atmosphere.

Villa in Brownsville

4.8 out of 5 average rating, 10 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!