Villa holiday rentals in Bennington

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

100 yrs old 2024! Historic Musician's Villa Bolton

This truly intriguing turn-of-the century home transports guests to the inspiring mood & enduring character of the great & gracious. Built by a legendary musician’s family w/focus on elegant entertaining, this 100 yr old home is ready for guests after 3 yrs of restoration. Remaining true to original form, guests find showpiece architectural acoustics in great room, elevated framework throughout w/timeless archways, dramatic stairway w/ornate balustrade, romantic rounded walls, relaxing patios.

Mansion @Rebeccas Fountain w/Chef near Saratoga NY

30 day & Seasonal Rental. Escape the city & discover luxury- The Hilltop Mansion @ Rebecca's Fountain, a hidden gem near Saratoga overlooking the Mohawk River & Marina. 11 bed oasis on 3 acres offers pond, Hot Tub, outdoor games add extras like Private Hibachi Chef, Masseur & more. Perfectly located for Albany, Saratoga, Lake George, boating, ski & all Capital Region adventures. ALB International Airport 12min. Create lifelong memories. Ask us cost for additional services of our On-site staff.

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.

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.

Historic Stockbridge Villa on 25 acres sleeps 16

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 or just family togetherness in a beautiful place, far from the madding crowd but close to highways, shopping, spas and everything you might need.

The Myrtle house Heated Pool-Hot Tub-Tennis &More

The Timbercrest Mansions, The Myrtle House Welcome to our newly renovated retreat, just 3 minutes from Mount Snow! This spacious home is designed for an unforgettable family experience, offering the perfect mix of adventure and relaxation. With 6 bedrooms, 9 beds, 5 bathrooms and an abundance of common areas, it comfortably accommodates 16+ guests.

Villa with Access to Amazing Amenities!

Sleeps 4 up to 6 people (Max 5 Adults) - Large and small outdoor pool - Two indoor pools: Open - Hot Tub - 2 on-site Bar - *18-hole mini golf course - *Sports courts - *Barbecue grills - *Fitness center - *Parking - *Wi-Fi - *Fitness gyms - Hiking Trail - Game Room: arcade-style games - On-site Café and Marketplace grab & go

Villa with a Fireplace Near the Trails

Dreaming of a cozy villa with a fireplace? You'll be able to enjoy panoramic views from the top of Mt. Ascutney State Park right outside your door when you stay in this fantastic location. With an awesome fitness centre, a restaurant, and more on-site, you'll have access to a number of great amenities!