House holiday rentals in Bennington County

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Top-rated house rentals in Bennington County

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Guest favourite

A cozy fire pit is surrounded by stone, situated in the foreground of a spacious lawn. In the background, a modern chalet features large windows and a combination of wood and stone siding, framed by colorful autumn foliage.

Home in Winhall

4.95 out of 5 average rating, 168 reviews

Summit View Ski and Golf Retreat w/hot tub & Sauna

Summit View Chalet @ Stratton is the ideal VT retreat, Minutes from Manchester, directly across the entrance from Stratton's 27 Hole Championship Golf Course. Beautifully remodeled! Relax in the hot tub on the deck with direct summit views in any season. Enjoy shuttle access to lifts, minutes from snowmobiling, hiking, fine dining and shopping. Comfortable accommodations for 6 adults and 5 children. Perfect for 2 families to enjoy any season in Southern Vermont's beautiful Green Mountains!

Top Guest favourite

The colonial home features a classic white exterior with black shutters and a welcoming front porch. An American flag is displayed prominently, and soft outdoor lighting highlights the entrance. The well-maintained lawn includes neatly trimmed bushes, creating a warm first impression.

Home in Sandgate

4.99 out of 5 average rating, 126 reviews

Country Colonial Home with rolling fields & stream

This wonderful colonial home offers wide open space on 21 acres of rolling fields with paths leading to the Green River. In the summer build your own dam or in the winter cross country ski along the edges of the stream and get a full view of the West Arlington valley. Swearing Hill is located within a mile of an old country store for all types of immediate supplies. The town of Arlington is 5 miles away, and Manchester, Vt. Is 14 miles, offering golfing, shopping, and wonderful restaurants.

Guest favourite

A modern interior is showcased with wooden walls and flooring, featuring a cozy bed positioned near large windows. A compact dining area is visible, with a small table and two chairs. An air conditioning unit is installed on the wall, contributing to the space's comfort.

Home in Winhall

4.94 out of 5 average rating, 319 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Superhost

An open-concept living area features a dining table set for six, with a gas fireplace framed by a white brick mantel. A television is positioned on a stand nearby, with comfortable seating arranged around the room. Natural light filters in through adjacent windows.

Home in Dover

4.9 out of 5 average rating, 115 reviews

Private Hot Tub, 2 Min to Mt Snow, Cozy Fireplace!

Newly renovated house, available all year, only 2 min from Mt Snow! New beds, mattresses, heat baseboards, dining table and chairs. To top it off a brand new outdoor hot tub in the backyard! Fully equipped kitchen and linens provided. Essentials as a starter kit provided for the first couple days. Families and friends will enjoy an open concept living with bar counter overlooking a dining area with fireplace and TV lounge. One pet allowed but must be disclosed at reservation (fee applies).

Superhost

A charming yellow house is nestled among snow-covered trees, framed by tall evergreens. A snow-blanketed driveway leads up to the entrance, inviting visitors into a serene winter retreat in a wooded setting.

Home in Stratton

4.82 out of 5 average rating, 117 reviews

Stay mins from Mt. Snow & Stratton w/ EV charger

Enjoy the ultimate ski getaway in this private home that sits on 1 acre of beautiful wooded land. Park your car in the detached garage (w/Tesla charger). The spacious house comfortably sleeps 8 guests and sits between Stratton Mountain and Mount Snow with hiking trails and lakes just minutes away. Sit outside on the deck to enjoy serene views, warm sunshine and sounds of nature. Leave your worries and just relax, BBQ and enjoy the fire pit for cozy evenings with friends & family.

Top Guest favourite

The exterior of a charming house features a gabled roof and a welcoming front porch with a wooden rocking chair. Lush green grass surrounds the home, and neatly trimmed shrubs are visible, complemented by tall trees in the background against a partly cloudy sky.

Home in Bennington

4.99 out of 5 average rating, 346 reviews

Southern Vermont Home

Beautiful home that offers privacy on over one acre of land. It is only a short drive to the conveniences of downtown shopping, restaurants, Bennington College, and much more. This house is 35 minutes from Manchester's famous outlets, 20 minutes from Williamstown, MA, and 45 minutes from Albany, NY. Bromley and Mount Snow ski areas are 40 minutes. The home has wonderful finishes and you will feel right at home upon arrival. Please come explore Vermont from our country escape!

Top Guest favourite

A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.

Home in Bennington

5 out of 5 average rating, 106 reviews

Vermont Farmhouse •Walk to Village & Hiking Trails

Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

Guest favourite

Home in Wilmington

4.9 out of 5 average rating, 165 reviews

4BR Cabin w/ Hot Tub & Pools –15 mins to Mt Snow

Family-friendly cabin in Chimney Hill, just 15 min to Mount Snow & 35 to Stratton! Relax in our 4BR, 2BA home with a hot tub, indoor and outdoor pools, fire pit, clubhouse gym, fully equipped kitchen & cozy living spaces. Sleeps 8 comfortably (King, Queen, Full + trundle, 2 Twin Bunks) with a Pack ’n Play for little ones. Perfect for skiing, hiking, or unwinding year-round. Enjoy mountain charm, modern comfort, and easy access to trails, lakes, and Wilmington’s shops & dining.

Guest favourite

A sunroom is featured with large windows allowing natural light to fill the space. Wooden furniture adds a warm touch, while a woven rug covers the floor. A small side table is positioned next to a seating area, overlooking a green landscape outside.

Home in Manchester

4.78 out of 5 average rating, 235 reviews

The Equinox Cottage

The Equinox Cottage is a quick 3 minute drive to the Equinox Hotel and the heart of Historic Manchester Village. Enjoy the shops, outlets, restaurants, cafes, golfing, and relaxed summer vibe. The Cottage is also an easy walk to the trails in the Equinox Pond preserve. Enjoy this pristine wilderness oasis, plus hiking up Equinox Mountain and surrounding trail system without having to step into your car. This peaceful, spacious, serene spot is ideal for summer relaxation.

Superhost

A sprawling grassy yard is surrounded by trees, providing natural shade. A wooden deck and seating area are positioned in the background, inviting outdoor relaxation. The white house is visible beyond the tree line, contributing to the serene countryside setting.

Home in Readsboro

4.86 out of 5 average rating, 132 reviews

Snowy Cozy Vermont Winter Escape

Our home is nestled in the Green mtns, with quick access to the road. A babbling brook lulls you from the master bedroom, a clawfoot soaking tub, stocked home. Hiking, antiques, shops, lakes, ski, snowboard, covered bridges, local inns, mountain views! Scenic roads, ski nearby Mt. Snow, VAST snowmobile trails, Mt.Greylock, Mass MOCA museum, N.Adams, MA, Berkshires, Bennington, Wilmington. Great location! PEACEFUL PERFECT ROMANTIC Vermont getaway! ☺

Top Guest favourite

An open dining area features a large wooden table surrounded by white chairs. Natural light fills the space from multiple windows, highlighting rustic wooden beams above. A cozy seating nook with plants and a decorative fireplace creates a welcoming ambiance.

Home in Dover

4.89 out of 5 average rating, 268 reviews

Mt Snow retreat, ski & summer

Warm and welcoming space for relaxation and play, your home base for VT recreation. 7 min. drive to Mount Snow, convenient location. Easy access to hiking, mountain biking, x-c skiing, golf course, and more! Sleeps 5 easily. ~10 min. walk to Moover, 7-11, restaurants. INTERNET - There is a fiber optic connection and the plan speed is 50Mbps down / 30Mbps up. LGBTQ+ friendly 🌈💞

Top Guest favourite

A mid-century retreat is illuminated at dusk, surrounded by snow-covered trees. Floor-to-ceiling windows create a warm glow, inviting guests into the living space. The landscape features a serene atmosphere with gently falling snow, enhancing the peaceful setting of the property.

Home in Winhall

4.98 out of 5 average rating, 413 reviews

Stunning mid-century house on 2.5 private acres

Stay at our relaxing, mid-century retreat! The house was built in the 60s but has modern amenities. A 4-wheel-drive vehicle is recommended. Our house is conveniently located 7 miles from Stratton and 12 miles from the outlets/restaurants in Manchester. Floor to ceiling windows provide a stunning view of the property. Please note, the house has a non-working fireplace.