
Villa vacation rentals in Bennington
Find and book unique villas on Airbnb
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
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.

5-BR Villa with Pool and Dog Friendly!
cute house and wonderful weekend

Cozy Villa overlooking the Lake and Mountains
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.

Sun Castle Resort - Luxury Lakefront Villa
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!

Villa with Access to Amazing Amenities!
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.

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!

Sophisticated Albany Airport
Thank you Ritesh, Nice location and good communication.

Clean Albany Airport by Shops
good place
Luxury villa rentals

Historic Stockbridge Villa on 25 acres sleeps 16
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.

5-BR Villa with Pool and Dog Friendly!
cute house and wonderful weekend

Gatehouse Villa at Blue Water Manor w/pool, lake
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 !!!

Gorgeous Victorian-Style House w/ Hilltop Pool!
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.

Sun Castle Resort - Luxury Lakefront Villa
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!

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!

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
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.
Villa rentals with a pool

Villa with Pool + Fitness Center Access
This was a perfect spot for us as we attended a graduation. It was clean, had plenty of room and then goodness had coffee and a filter for the pot! Would highly recommend.

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

Villa Near Biking and Hiking Trails
The hosts were very responsive and checked in with us. The staff at the Airbnb were very helpful and friendly.

Villa with a Fireplace Near the Trails
Really nice place it had lots of fun amenities! My only complaint is that there were some basics that were missing from the kitchen (salt, pepper, olive oil, cutting board etc.).
Destinations to explore
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Six Flags Great Escape Lodge & Indoor Water park
- John Boyd Thacher State Park
- Jiminy Peak Mountain Resort
- Albany Center Gallery
- Stratton Mountain Resort
- West Mountain Ski Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Norman Rockwell Museum
- Lake George Expedition Park
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Naumkeag
- Hildene, The Lincoln Family Home
- Bromley Mountain Ski Resort
- Fox Run Golf Club