Villa vacation rentals in Bennington

Private Wing of largest Colonial Mansion in US

Built in 1902 and comprehensively renovated in late 2016, the Windsor Mansion is an incredibly well preserved example of Colonial Revival Architecture. Filled with elegance & history, Three US Presidents have slept here. Our 17 Rooms/Suites are individually decorated each with private bathroom & free wireless internet. Set on 14 acres with a tiered terrace offering spectacular views & a custom fire pit. Lots to see in area including Saint-Gaudens Nat'l Park, Quechee Falls, Dartmouth College, etc

5-BR Villa with Pool and Dog Friendly!

Welcome to Hudson View Villa! Relax with family or friends at a hilltop property overlooking The Hudson and Berkshires. Hudson View House offers over 2900 sq ft of gorgeous luxury space with views of the Hudson and Berkshires virtually from every room. The scenic views of the surroundings, breathtaking sunrises and sunsets will want you never to go home! Heated swimming pool now Open ( May - Sep/October). Propane grill on back deck overlooking Hudson River. Tesla charging- bring own adapter

Hot tub -Dog Friendly-Back Yard -2 night minimum

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 55” Outdoor TV and seating area All amenities For a vacation stay. No Garage

Elegant Suite / Free Parking/Near RPI

Welcome to this thoughtfully designed sanctuary infused with the essence of nature. We offer workshops on Chinese ink wash painting and paper flower crafting; please feel free to ask Lily for details if you are interested. Tranquil Private Suite | Minutes to RPI & Research Hubs • Private Suite in Troy w/ Reserved Parking & Fast Wi-Fi • Scholar & Pro Retreat: Quiet Suite near RPI/Albany • Dedicated Workspace • Free Parking on Premises • Fast Wi-Fi (The homeowner lives on the second floor)

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.

Luxury Private Suite on a Historic Estate

Stay in a beautifully restored 1860 historic estate set on 3.5 peaceful acres. Enjoy a private guest suite with an en-suite bath and office and thoughtfully appointed amenities for a comfortable stay. Guests have access to well-maintained common spaces, including kitchens, laundry facilities, sitting areas, a bright sunroom, and indoor garage parking. Conveniently located minutes from shopping, dining, and everyday essentials, while downtown Albany is only a 10–12 minute drive away.

The Mansion at Rebecca’s Fountain near Saratoga NY

The Mansion at Rebecca’s Fountain, a private hilltop estate overlooking the Mohawk River, marina, and surrounding mountains. Designed for travel & seasonal stays, is the top choice for business travelers, executives, & private groups. Ideally located near Saratoga Springs & the Racetrack, Lake George, Albany NY. 11-bed luxury retreat on 3 acres with pond, hot tub, outdoor amenities, and curated services including Private Hibachi Chef, catering, & in-home wellness. Experience more.

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!

Historic Stockbridge Villa on 25 acres

At the end of a tree-lined driveway, this huge private eleven bedroom villa sits by the edge of a field with garden and blackberry patch surrounded by 25 acres of woods. Walking paths reveal rocky knolls and paths circling through pine and maple trees. The private estate has ample space for a retreat, a workshop, a grand party or just family togetherness in a beautiful place, far from the madding crowd but close to highways, shopping, spas and everything you might need.

Mountain-View Retreat @ Hudson

Experience breathtaking mountain views from this designer-decorated home in the heart of Hudson.. Inside, enjoy a full game room, in-house laundry, and on-premise parking. The fenced property offers complete privacy with a security system. Walk to downtown Hudson (5 minutes drive), access nearby track and tennis courts, or take a short drive to Catskills trails, Bash Bish Falls, and Hunter Mountain. Ideal for relaxation and adventure, with easy Amtrak access nearby.

Woodland Retreat on Robert Frost Trail

Escape to this serene home nestled on a private one-acre wooded lot with its own exclusive trail connecting to the iconic Robert Frost Trail. This peaceful retreat offers stunning views, a fully stocked kitchen, and cozy, inviting spaces to make you feel right at home. Located just 8-10 minutes from Amherst College, UMass, and downtown Amherst, you'll enjoy the perfect balance of nature and convenience. There is an additional dwelling unit in the property.

Large Updated Mt Snow Villa Jacuzzi/Hot Tub/GameRm

Relax at Mt Snow Villas!! Welcome to our gorgeous mountain villa duplex nestled in the heart of breathtaking West Dover just 1/2 mile from Mount Snow! If you're seeking a peaceful escape from the hustle and bustle of everyday life, this spacious villa offers a perfect blend of warmth, elegance and modern comfort, making it the ideal getaway for couples, families, or groups of friends.