Villa vacation rentals in Bennington

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Popular amenities for Bennington villa rentals

Private villa rentals

Guest favorite
The villa's exterior showcases a large three-story structure, adorned with white siding and multiple windows. A spacious deck leads to the front entrance, framed by greenery from surrounding trees. The sky above is partly cloudy, providing a serene backdrop.
Villa in Stockbridge
4.94 out of 5 average rating, 48 reviews

Historic Stockbridge Villa on 25 acres sleeps 16

ElizabethRating, 5 stars2 months ago
Lovely home for family and friends to stay together and enjoy puzzle time, meals and time away - easy access to many towns and restaurants etc. Great communication by host and property managers onsite.
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
4.9 out of 5 average rating, 48 reviews

5-BR Villa with Pool and Dog Friendly!

ChenghaoRating, 5 stars8 months ago
cute house and wonderful weekend
Superhost
A seating area is shown with two chairs and a small coffee table, situated beside large windows that showcase views of the lake and surrounding landscape. A television is mounted on the wall, with an open door leading to the outside deck.
Villa in Lake George
5 out of 5 average rating, 4 reviews

Cozy Villa overlooking the Lake and Mountains

CrystalRating, 5 stars9 months ago
4.5 stars This is a lakefront, standalone villa with a deck and chairs right over the water and incredible views from the living area. It was very clean and we loved starting and ending our days on the deck. This villa is at the edge of the property and feels nice and private. Unfortunately, the property next door has what sounds like a large pump right outside the bedroom window. The pump turned on/off every few minutes throughout the night, so if you are a light sleeper this may be tough for you.
Superhost
A serene lakefront scene captures a tranquil body of water bordered by lush trees and distant mountains. A dock is visible with a covered boating area, inviting peaceful moments by the lake.
Villa in Lake George
4.74 out of 5 average rating, 34 reviews

Sun Castle Resort - Luxury Lakefront Villa

NicoleRating, 5 stars3 days ago
Amazing stay! Exactly as described in the listing. It was the perfect location for us, short drive to both Lake George and Bolton Landing. We were traveling with our 10 month old and there was plenty of space for him to play. The view of the lake was 10/10!
Superhost
A view of the resort's outdoor area showcases green tennis courts surrounded by trees and grass. Multiple buildings featuring wooden exteriors are positioned in the background, with gentle hills covered in lush greenery rising beyond.
Villa in South Lee
4.78 out of 5 average rating, 124 reviews

Villa with Access to Amazing Amenities!

PamelaRating, 5 stars8 months ago
The place was great and wish i had more time there. We were just looking for a quick overnight with two bedrooms, which this was, but it seemed like a lovely place for a vacation.
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

DebbieRating, 5 stars4 months ago
Overall we had great experience at the house. The inner decorations were cozy and comfortable, and the design was awesome! The host was responsive when the new door lock had some issues. 100% recommend staying at this house!
A two-story motel exterior showcases a row of accessible guest rooms, each featuring a private entrance. The parking lot is visible in the foreground, bordered by trees, creating an open and inviting space. The clean, modern architecture is highlighted by a blue and white color scheme.
Villa in Albany
New place to stay

Sophisticated Albany Airport

JorgeRating, 5 stars2 weeks ago
Thank you Ritesh, Nice location and good communication.
The exterior of the motel features a two-story building with a small entryway and welcoming awning. Surrounding the entrance, a landscaped area includes shrubs and flowers. Parking spaces are visible in front of the building, providing easy access for guests.
Villa in Albany
New place to stay

Clean Albany Airport by Shops

TomRating, 5 stars3 weeks ago
good place

Luxury villa rentals

Guest favorite
The villa's exterior showcases a large three-story structure, adorned with white siding and multiple windows. A spacious deck leads to the front entrance, framed by greenery from surrounding trees. The sky above is partly cloudy, providing a serene backdrop.
Villa in Stockbridge
4.94 out of 5 average rating, 48 reviews

Historic Stockbridge Villa on 25 acres sleeps 16

ElizabethRating, 5 stars2 months ago
Lovely home for family and friends to stay together and enjoy puzzle time, meals and time away - easy access to many towns and restaurants etc. Great communication by host and property managers onsite.
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
4.9 out of 5 average rating, 48 reviews

5-BR Villa with Pool and Dog Friendly!

ChenghaoRating, 5 stars8 months ago
cute house and wonderful weekend
Superhost
A sandy beach area features several lounge chairs arranged in rows, with umbrellas providing shade. The serene lake view is framed by green trees in the background. A dock with boats is visible, enhancing the tranquil atmosphere of the lakeside setting.
Villa in Bolton
4.53 out of 5 average rating, 17 reviews

Gatehouse Villa at Blue Water Manor w/pool, lake

TracyRating, 5 stars9 months ago
We had an excellent experience… best way for our family to spend summer vacation. The home was a perfect fit for all 6 of us in terms of space and layout. We enjoyed the porch, pool , lake and all town had to offer. We will be back. Thank you, Michelle for being an excellent host !!!
The Victorian home is framed by lush greenery and features a wraparound porch with black shutters. The white exterior is complemented by a decorative top turret. A stone wall borders the entrance, leading to a welcoming approach.
Villa in Rupert
4.33 out of 5 average rating, 60 reviews

Gorgeous Victorian-Style House w/ Hilltop Pool!

SilenaRating, 5 stars1 month ago
Beautiful old home full of an eclectic art collection. It served my group's needs well. Never did find the lockbox for the keys. Had to get them from the on-site groundskeeper, which was a difficult task given we had a significant language barrier. The outside of the house could use some maintenance, so if that is important to you, this may not be the place for you. My one complaint is that they expect you replace the paper towels and toilet paper you use. I would expect those to be included at any price, but especially for the price you pay for this location. Overall, it was a great stay for two nights and we had fun exploring the house.
Superhost
A serene lakefront scene captures a tranquil body of water bordered by lush trees and distant mountains. A dock is visible with a covered boating area, inviting peaceful moments by the lake.
Villa in Lake George
4.74 out of 5 average rating, 34 reviews

Sun Castle Resort - Luxury Lakefront Villa

NicoleRating, 5 stars3 days ago
Amazing stay! Exactly as described in the listing. It was the perfect location for us, short drive to both Lake George and Bolton Landing. We were traveling with our 10 month old and there was plenty of space for him to play. The view of the lake was 10/10!
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

DebbieRating, 5 stars4 months ago
Overall we had great experience at the house. The inner decorations were cozy and comfortable, and the design was awesome! The host was responsive when the new door lock had some issues. 100% recommend staying at this house!
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
4.95 out of 5 average rating, 42 reviews

Modern 4 Bedroom 4 Bath Villa w HotTub/ back trail

RebeccaRating, 5 stars3 months ago
Great stay- so nice to be so close to okemo which made skiing really seamless. The house matched the pics perfectly. Kids had a good bunk room and the 3 adult couples all had their own rooms with en suite bathrooms. The hot tub on the upper deck was a nice bonus. Easy in and out, and Nicholas was very easy to communicate with. We had one minor hiccup with the fridge but Nicholas was responsive and accommodating. Thanks for the great weekend away.
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, 72 reviews

Vermont Vacation Villa—Grapevine Getaway

ChristopherRating, 5 stars3 weeks ago
Anthony's house was an excellent venue for the weekend of our son's wedding in Williamstown. It easily fit the eight family members staying there with plenty of privacy on three floors and great gathering spaces on the main floor, deck, and pool deck. We're grateful the pool was open; the kids loved it on a hot afternoon of our stay. If you are looking at this house, don't let the backroads approaching it look like a liability. They are well maintained and allow easy access to Williamstown and the southern Vermont towns along route 7, yet the quiet location will insure you sleep well.

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