
Villa holiday 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.

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

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.

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!

Private suite in a country house (Private Office)
Cozy Private Suite in Troy | Private Bath + Office | Quiet & Safe Relax in this quiet, private suite featuring a queen bed, private bathroom, and personal office — perfect for business travelers or remote work. Enjoy fast Wi-Fi, heating/AC, coffee corner, and free parking in a peaceful, safe neighborhood. Only 5 min to Russell Sage College, 10 min to Downtown Troy, and 15 min to Albany. Ideal for short or extended stays — no smoking, no parties.

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

Cozy Villa overlooking the Lake and Mountains
For a private Adirondack vacation lakeside, look no further than our only 1-bedroom villa! Includes occupancy for up to 4 guests with 1 king bedroom, 1 queen pull-out sofa sleeper, and a kitchenette. Lake George Village is 1.25 miles from the property

Sun Castle Resort - Luxury Lakefront Villa
Reminisce about vacationing on the Lake in one of our luxury Villas. Includes occupancy of up to 4 guests with two king bedrooms one queen pull out sofa sleeper and a kitchenette. Lake George Village is 1.25 miles from the property

Cozy home in the capital of New York state
Enjoy a warm stay at this home centrally located.
Popular amenities for Bennington villa rentals
Private villa rentals

Modern 4 Bedroom 4 Bath Villa w HotTub/ back trail

Vermont Vacation Villa—Grapevine Getaway

Cozy Villa overlooking the Lake and Mountains

Sun Castle Resort - Luxury Lakefront Villa

Private City Line Compound

Stonehouse at Stratton
Destinations to explore
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- John Boyd Thacher State Park
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- West Mountain Ski Resort
- Saratoga Spa State Park
- Norman Rockwell Museum
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Beartown State Forest
- Lake George Expedition Park
- Albany Center Gallery
- Peebles Island State Park
- Berkshire Botanical Garden
- Hildene, The Lincoln Family Home
- Dorset Field Club
- National Museum of Racing and Hall of Fame