
Villa vacation rentals in Bennington
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Top-rated villa rentals in Bennington
Guests agree: these villas are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Bennington villa rentals
Private villa rentals

Historic Stockbridge Villa on 25 acres sleeps 16
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.

5-BR Villa with Pool and Dog Friendly!
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.

Villa with Pool + Fitness Center Access
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.

Sun Castle Resort - Luxury Lakefront Villa
We had a great stay! Location was great with pool and lake access

Stonehouse at Stratton
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!

Dancing Bear Lodge The Charm of Chimney Hill
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.

Modern 4 Bedroom 4 Bath Villa w HotTub/ back trail
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.

Vermont Vacation Villa—Grapevine Getaway
lovely stay for my group’s annual ski trip! beautiful home - would love to stay here again :)
Luxury villa rentals

5-BR Villa with Pool and Dog Friendly!
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.

Modern 4 Bedroom 4 Bath Villa w HotTub/ back trail
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.

Vermont Vacation Villa—Grapevine Getaway
lovely stay for my group’s annual ski trip! beautiful home - would love to stay here again :)

Gorgeous Victorian-Style House w/ Hilltop Pool!
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!

Stumble Abode - 3
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

Historic Stockbridge Villa on 25 acres sleeps 16
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.

5-BR Villa with Pool and Dog Friendly!
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.

Villa with Pool + Fitness Center Access
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.

Gorgeous Victorian-Style House w/ Hilltop Pool!
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!

Sun Castle Resort - Luxury Lakefront Villa
We had a great stay! Location was great with pool and lake access

Dancing Bear Lodge The Charm of Chimney Hill
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.

Vermont Vacation Villa—Grapevine Getaway
lovely stay for my group’s annual ski trip! beautiful home - would love to stay here again :)

Vermont Villa Near the Trails
Great stay, lots of room. Front desk was super friendly.
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