We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

House vacation rentals in Bennington County

Find and book unique houses on Airbnb

Top-rated house rentals in Bennington County

Guests agree: these houses are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Home in Readsboro

4.86 out of 5 average rating, 124 reviews

December in Peaceful Vermont (Pet Friendly)

Beautiful Country Home, nestled in Vermont's Green mountains, panoramic views, with good access by the road. A babbling brook to lull you asleep from the master bedroom, and a clawfoot soaking tub, fully stocked house. Hiking, antiques, shops, lakes, picnics, covered bridges, cozy local inns, mountain views! Enjoy Vermont! Scenic roads, Mt. Snow, VAST trails, Mt.Greylock, Mass MOCA museum, nearby N.Adams, MA, Berkshires. Bennington Wilmington & Mt. Snow. PEACEFUL & PERFECT Vermont getaway! ☺

Home in Sandgate

4.99 out of 5 average rating, 104 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.

Home in Winhall

4.95 out of 5 average rating, 196 reviews

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Just minutes to skiing at Stratton Mountain, Bromley and Magic. Explore 27+ acres of forest with trails, river, sculpture gardens and private pond. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. A short drive to Manchester with shops and restaurants. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

Home in Sunderland

4.97 out of 5 average rating, 236 reviews

MOUNTAIN NEST, views, Manchester, hot tub,

Convenient to downtown Manchester's outlet stores and restaurants,golf (equinox golf course 3 miles away) hiking, kayaking and fishing (battenkill river)skiing-Stratton or Bromley, hot tub on full deck with close-up views of Mount Equinox, these mountain views will either make you weep or sing for joy, dines 8 easy, master on main (king bed). This home was intended to bring INSIDE the natural beauty you see OUTSIDE. Complete with vaulted living area and exposed timber beams throughout!

Home in Shaftsbury

4.85 out of 5 average rating, 119 reviews

Quaint One-Story Vermont House with Mountain View

From our quaint one-story house, you can see a variety of scenery, from the bright changing colors of the leaves in the autumn to the soft piles of snow in the winter. Experience the quiet of the nearby woods, and see roaming animals such as deer or turkey. Make sure to stop at one of the nearby lakes, each of which offers a variety of amenities, and lush scenery. In the winter, keep warm in the cozy living room next to the fireplace, while having a chat with your friends and family.

Home in Arlington

4.95 out of 5 average rating, 100 reviews

Southern Vermont Cottage

Cozy but not small, this home is in a peaceful location with plenty of beds to house your family as you visit beautiful Vermont for skiing, hiking, swimming or shopping. Manchester Center, Dorset and Bennington are all within a 20 minute drive. Southern VT boasts many of the state's best restaurants and shopping, & the Southern Vermont Arts Center. Also nearby - Dorset Theater Playhouse, Dorset Quarry, Mt Equinox, Bromley Mountain, Mt. Snow and Stratton! Trampoline is now allowed

Home in Wilmington

4.94 out of 5 average rating, 260 reviews

Wilmington. Easy walk to center of town.

Beautifully renovated bright, 120year old home in town. House thoroughly cleaned and sanitized after each stay. Touchless flushing toilets. Mini-Split air conditioning in each bedroom and on the main level. Minutes to MT Snow. Easy walk to town for food and shopping. Deerfield river directly across the street. 2 min from the lake. Valley hiking trails within sight. There is a 2 car limit. A request for additional vehicles needs to be made prior to check-in.

Home in Bennington

4.99 out of 5 average rating, 124 reviews

The Gate House--Experience Vermont!

The Gate House is a historic property located at the foothills of Mt Anthony. Built in 1865, the original structure of the house served as the gate house to the Colgate Estate, one of the most beautiful properties in Southwestern Vermont. Our home is just a few short miles to downtown where you can find local restaurants and breweries. We are not far from some of the best skiing/riding in the Northeast at Mt Snow, Bromley, Stratton and Prospect Mountains.

Home in Londonderry

4.98 out of 5 average rating, 115 reviews

Modern 3-bedroom A-frame in Londonderry w/ Pond

This 1970s A-Frame has been newly renovated and is ready to host guests. This home is located on a 2.6 acre property complete with a swimmable pond , outdoor firepit (snow dependent) and dining al fresco. It's located only a few minutes away from amenities such as Londonderry Market, Pingree Park, Lowell Lake and several restaurants. For skiing, this home is in proximity to Magic (8min), Bromley (9min), Okemo (25 min) and Stratton (20 min).

Home in Wardsboro

4.95 out of 5 average rating, 100 reviews

Hot Tub & Game Room - Ski Mt. Snow/Stratton

Welcome to Three Bears Mountain House - your Southern Vermont getaway! We're located 10 minutes from Mount Snow and 15 minutes from Stratton. We designed our cabin to be inviting and cozy, a place you'll never want to leave. Come for a fun-filled weekend on the mountains skiing or a relaxing getaway in nature. End your day with a relaxing soak in our 7-person hot tub. Visit the local breweries and farms for an authentic Vermont experience!

Home in Bennington

4.99 out of 5 average rating, 269 reviews

Cozy Modern Sugar House with spectacular views.

This beautiful Vermont home sits on 25 acres with spectacular views. We moved this sugar house structure to this land and had an architect adapt it to its surroundings. It has three walls of windows that display the amazing views. The house is surrounded by Mount Anthony hiking trails and a gorgeous pond. The location is a 5 minute drive to town or a lovely 20 minute walk.

Home in Winhall

4.98 out of 5 average rating, 368 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.

Vacation rentals for every style

Get the amount of space that is right for you

Apartments

Convenient locations with everyday essentials

Chalets

Adventure-ready homes with après-ski style

Cabins

Kick off your hiking boots at these rustic lodgings

Popular amenities for Bennington County house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Home in Cambridge

4.97 out of 5 average rating, 39 reviews

Country hideaway

Home in Wardsboro

5 out of 5 average rating, 45 reviews

Minutes to Mt. Snow/Stratton! Hot Tub + Game Room

Home in Wilmington

4.88 out of 5 average rating, 163 reviews

Adams Farm-"The Little Farmhouse"

Home in Dorset

4.95 out of 5 average rating, 20 reviews

Idyllic Dorset Home: Serene Escape w/amazing views

Home in Wilmington

5 out of 5 average rating, 12 reviews

Stylish Chimney Hill Home - Close to Mt. Snow!

Home in Dover

4.98 out of 5 average rating, 40 reviews

3bd Mt.Snow condo: Fireplace and ski off trail.

Home in Wilmington

4.83 out of 5 average rating, 42 reviews

Mountain Paradise 4 Bed w/ Hot Tub Mins to Mt Snow

Home in Wilmington

4.83 out of 5 average rating, 162 reviews

The Vermont Barn (Mount Snow)

Weekly house rentals

Home in Dover

4.9 out of 5 average rating, 69 reviews

Timber Frame Contemporary w/ Hot Tub at Mount Snow

Home in Dorset

4.98 out of 5 average rating, 55 reviews

Home in the Heart of Dorset Village

Home in Manchester

4.95 out of 5 average rating, 38 reviews

Gather and Relax with Friends & Family

Home in Shaftsbury

4.99 out of 5 average rating, 67 reviews

VT Mountain House Epic Views 350 Acre Farm Hot Tub

Home in Arlington

5 out of 5 average rating, 22 reviews

New Charming Waterfront Cottage Retreat

Home in Manchester

5 out of 5 average rating, 22 reviews

Cozy & Modern Village Cottage

Home in Woodford

4.92 out of 5 average rating, 26 reviews

Green Mountains Lake Retreat - Hidden Gem

Home in Bennington

4.99 out of 5 average rating, 68 reviews

Stylish dreamy VT cabin with fast & reliable wifi

Private house rentals

Home in Dover

4.96 out of 5 average rating, 49 reviews

Good Vibes & Comforts of Home @Ellis Brook Retreat

Home in Whitingham

4.97 out of 5 average rating, 91 reviews

Ski Season! Play Area, Crib, 11 Acre Farmhouse

Home in Sandgate

5 out of 5 average rating, 18 reviews

Pet Friendly Hillside Getaway

Home in Manchester

5 out of 5 average rating, 15 reviews

School Street House

Home in Arlington

4.85 out of 5 average rating, 93 reviews

Quaint Pink House on The Battenkill River

Home in Manchester

5 out of 5 average rating, 19 reviews

The Village Cottage

Home in Wardsboro

4.86 out of 5 average rating, 22 reviews

The Perch

Home in Dover

5 out of 5 average rating, 21 reviews

The Rosewood Lodge at Mt Snow

Destinations to explore