Villa vacation rentals in Bennington

WILDINGS on Hudson - River Estate w amazing views

Hudson River Estate w breathtaking pool featured in House Beautiful mag only 7 min from Hudson town in Catskill,NY Enjoy the best of the Hudson Valley & Catskills region staying in fully renovated historic home right on the Hudson w storybook vistas of the RVW bridge & Olana 4 bed/3 bth, beautiful rooms and huge kitchen to create wonderful memories with friends & fam Discover one of the best corners of the nation and discover its restaurants, shops + natural wonders. No events allowed. Thanks

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 30-day & seasonal stays, and a 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. Staff onsite. Experience more.

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.

4 TH of July Get Away, Dog Friendly, Big Back Yard

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!

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.

Villa Santa Lucia ....Piece of Italy in Upstate NY

Enjoy a beautiful home decorated like an Italian villa..each room represents a different part of Italy ..most photos were taken when we went to Italy and many items in home were brought back from Italy ! The villa sits on a 5 acre piece of land..overlooking the helderbergs mountains ! Enjoy a stunning outdoor kitchen..pergola...and gazebo complete with amazing landscaping and a stone waterfall! For more photos check out our Facebook book page.

1 Mi to Race Course！6BR/4BA Heated Pool & Sauna

🌟Ultimate Saratoga Retreat! 6BR/4BA home just 5 mins to the Race Course. Highlights: 🏠Outdoor Oasis: Private fenced yard with heated pool, spa, brand-new sauna, and gazebo with grill & string lights. 🅿️Groups Welcome: Fun game room, chef’s kitchen, and rare parking for up to 6 cars! 🐶🐱Pet Friendly: Bring your furry friends to this quiet, spacious getaway. 🚗Minutes from downtown shops & dining. Perfect for large families!

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.