Villa vacation rentals in Bennington

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Popular amenities for Bennington villa rentals

Private villa rentals

Guest favorite
Villa in Stockbridge
4.94 out of 5 average rating, 47 reviews

Historic Stockbridge Villa on 25 acres sleeps 16

TracyRating, 5 stars1 month ago
This was a return visit of a group of medical professionals taking continuing education class in the area. Villa favorita is perfect for our large group. Lots of space for everyone to have their own bedroom but also to come together for group dinners and class discussion.
Guest favorite
The exterior of the house features a multi-story design with a large wooden deck overlooking the surrounding greenery. A circular fire pit with seating is visible in the backyard, complemented by a fenced area and a mature tree. The sky is partially cloudy with blue hues.
Villa in Coxsackie
4.89 out of 5 average rating, 47 reviews

5-BR Villa with Pool and Dog Friendly!

DeliaRating, 5 stars6 months ago
The villa is exactly as promised. It’s on a hill overlooking the Hudson with great views and outdoor space. It’s dog friendly with a fenced in yard, a wonderful feature for dogs and people. We were there for a family wedding so did not make full use of the outdoor spaces, but the pool and fire pit are very inviting. The bedrooms were comfortable and we enjoyed lounging in the living room with tv football games. The location is a short walk from downtown Coxsackie for coffee and treats. You should know that access to front door is up about 12 or so steps but there was a railing if anyone has mobility issues. We would return if we were to come back to the area. Lakpa is super responsive.
Guest favorite
An indoor pool area is featured, with a spacious swimming pool lined by blue lounge chairs. Large windows allow natural light to fill the room, enhancing the bright atmosphere. The covered structure showcases a high ceiling, ensuring a comfortable swimming experience year-round.
Villa in Brownsville
4.82 out of 5 average rating, 22 reviews

Villa with Pool + Fitness Center Access

JayRating, 5 stars2 months ago
Such a great deal considering the price and amenities. The location was quite a drive from our destination but it was close to other places like Okemo and Woodstock. Beautiful surroundings. A warm full size pool in the winter time is unbeatable. Place was clean when we arrived. The building was quiet and peaceful. No issues with noise nor difficulty with checking in.
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
4.71 out of 5 average rating, 28 reviews

Sun Castle Resort - Luxury Lakefront Villa

JennaRating, 5 stars8 months ago
We had a great stay! Location was great with pool and lake access
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 stars2 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 wooden lodge is set among lush green trees, with a gravel driveway leading to it. A two-car garage is visible to the left, and a spacious deck extends from the lodge. Large windows and skylights allow natural light to fill the space.
Villa in Wilmington
4.95 out of 5 average rating, 22 reviews

Dancing Bear Lodge The Charm of Chimney Hill

EmilyRating, 5 stars2 months ago
We had a great stay at Marlene’s guest house. 15 min drive to Mount Snow and 5 min drive to the grocery store. We had plenty of space for two families with bunk beds for the 4 kids on the lower level. The air hockey table and access to the clubhouse swimming pool was a big hit. There were two tvs and board games to keep the group occupied after a long day of skiing. Host was also very responsive to any questions we had. Place was very clean and well stocked. Would highly recommend this place.
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 stars1 month 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
Villa in Pownal
4.94 out of 5 average rating, 69 reviews

Vermont Vacation Villa—Grapevine Getaway

CindyRating, 5 stars2 months ago
lovely stay for my group’s annual ski trip! beautiful home - would love to stay here again :)

Luxury villa rentals

Guest favorite
The exterior of the house features a multi-story design with a large wooden deck overlooking the surrounding greenery. A circular fire pit with seating is visible in the backyard, complemented by a fenced area and a mature tree. The sky is partially cloudy with blue hues.
Villa in Coxsackie
4.89 out of 5 average rating, 47 reviews

5-BR Villa with Pool and Dog Friendly!

DeliaRating, 5 stars6 months ago
The villa is exactly as promised. It’s on a hill overlooking the Hudson with great views and outdoor space. It’s dog friendly with a fenced in yard, a wonderful feature for dogs and people. We were there for a family wedding so did not make full use of the outdoor spaces, but the pool and fire pit are very inviting. The bedrooms were comfortable and we enjoyed lounging in the living room with tv football games. The location is a short walk from downtown Coxsackie for coffee and treats. You should know that access to front door is up about 12 or so steps but there was a railing if anyone has mobility issues. We would return if we were to come back to the area. Lakpa is super responsive.
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 stars1 month 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
Villa in Pownal
4.94 out of 5 average rating, 69 reviews

Vermont Vacation Villa—Grapevine Getaway

CindyRating, 5 stars2 months ago
lovely stay for my group’s annual ski trip! beautiful home - would love to stay here again :)
A game room features a classic billiard table at the center, surrounded by slate flooring. The space includes large windows providing natural light, along with bookshelves filled with books and various wall art. Accessories like cue sticks and a guitar are visible, enhancing the playful atmosphere.
Villa in Rupert
4.32 out of 5 average rating, 59 reviews

Gorgeous Victorian-Style House w/ Hilltop Pool!

PeterRating, 5 stars3 months ago
Our stay at the house was amazing! Place is very spacious so our guests were very comfortable! Plenty rooms and beds to sleep in. Kitchen is stocked up. There is everything you need ti make meals. We absolutely loved it!! Our group had people whi ski and hike . Everyone had plenty to do!! Definitely recommend that place! If we ever go back to Vermont we’ll stay there for sure!! Thank you so much for having us!
Superhost
A fenced tennis court is visible, featuring a well-maintained playing surface under a clear blue sky. Lush greenery surrounds the area, and a single player is seen mid-game, while a large tree adds to the natural backdrop.
Villa in Lake George
4.75 out of 5 average rating, 52 reviews

Stumble Abode - 3

GigiRating, 5 stars6 months ago
We visited Stumble Abode over a long weekend. The beautiful cottage was clean and cozy. It was perfect for two adults and two small children. Parking was easy and close by. It had all the amenities we needed and more. We hope to visit again soon, and definitely recommend others to stay there!

Villa rentals with a pool

Guest favorite
Villa in Stockbridge
4.94 out of 5 average rating, 47 reviews

Historic Stockbridge Villa on 25 acres sleeps 16

TracyRating, 5 stars1 month ago
This was a return visit of a group of medical professionals taking continuing education class in the area. Villa favorita is perfect for our large group. Lots of space for everyone to have their own bedroom but also to come together for group dinners and class discussion.
Guest favorite
The exterior of the house features a multi-story design with a large wooden deck overlooking the surrounding greenery. A circular fire pit with seating is visible in the backyard, complemented by a fenced area and a mature tree. The sky is partially cloudy with blue hues.
Villa in Coxsackie
4.89 out of 5 average rating, 47 reviews

5-BR Villa with Pool and Dog Friendly!

DeliaRating, 5 stars6 months ago
The villa is exactly as promised. It’s on a hill overlooking the Hudson with great views and outdoor space. It’s dog friendly with a fenced in yard, a wonderful feature for dogs and people. We were there for a family wedding so did not make full use of the outdoor spaces, but the pool and fire pit are very inviting. The bedrooms were comfortable and we enjoyed lounging in the living room with tv football games. The location is a short walk from downtown Coxsackie for coffee and treats. You should know that access to front door is up about 12 or so steps but there was a railing if anyone has mobility issues. We would return if we were to come back to the area. Lakpa is super responsive.
Guest favorite
The exterior of the resort is set amidst landscaped greenery and natural stone features. A spacious parking area is visible, with modern architecture showcasing a welcoming entrance. The backdrop includes the mountains and a partly cloudy sky, enhancing the natural setting.
Villa in Brownsville
4.82 out of 5 average rating, 22 reviews

Villa with Pool + Fitness Center Access

JayRating, 5 stars2 months ago
Such a great deal considering the price and amenities. The location was quite a drive from our destination but it was close to other places like Okemo and Woodstock. Beautiful surroundings. A warm full size pool in the winter time is unbeatable. Place was clean when we arrived. The building was quiet and peaceful. No issues with noise nor difficulty with checking in.
A game room features a classic billiard table at the center, surrounded by slate flooring. The space includes large windows providing natural light, along with bookshelves filled with books and various wall art. Accessories like cue sticks and a guitar are visible, enhancing the playful atmosphere.
Villa in Rupert
4.32 out of 5 average rating, 59 reviews

Gorgeous Victorian-Style House w/ Hilltop Pool!

PeterRating, 5 stars3 months ago
Our stay at the house was amazing! Place is very spacious so our guests were very comfortable! Plenty rooms and beds to sleep in. Kitchen is stocked up. There is everything you need ti make meals. We absolutely loved it!! Our group had people whi ski and hike . Everyone had plenty to do!! Definitely recommend that place! If we ever go back to Vermont we’ll stay there for sure!! Thank you so much for having us!
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
4.71 out of 5 average rating, 28 reviews

Sun Castle Resort - Luxury Lakefront Villa

JennaRating, 5 stars8 months ago
We had a great stay! Location was great with pool and lake access
Guest favorite
Villa in Wilmington
4.95 out of 5 average rating, 22 reviews

Dancing Bear Lodge The Charm of Chimney Hill

EmilyRating, 5 stars2 months ago
We had a great stay at Marlene’s guest house. 15 min drive to Mount Snow and 5 min drive to the grocery store. We had plenty of space for two families with bunk beds for the 4 kids on the lower level. The air hockey table and access to the clubhouse swimming pool was a big hit. There were two tvs and board games to keep the group occupied after a long day of skiing. Host was also very responsive to any questions we had. Place was very clean and well stocked. Would highly recommend this place.
Guest favorite
Villa in Pownal
4.94 out of 5 average rating, 69 reviews

Vermont Vacation Villa—Grapevine Getaway

CindyRating, 5 stars2 months ago
lovely stay for my group’s annual ski trip! beautiful home - would love to stay here again :)
Superhost
An indoor pool area is highlighted by clear blue water under a high, metallic ceiling. Surrounding the pool, multiple lounge chairs are arranged for relaxation. Large windows provide natural light, creating a bright atmosphere throughout the space.
Villa in Brownsville
4.67 out of 5 average rating, 3 reviews

Vermont Villa Near the Trails

DavidRating, 5 stars50 months ago
Great stay, lots of room. Front desk was super friendly.

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