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House vacation rentals in Bennington County

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Top-rated house rentals in Bennington County

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Home in Readsboro

4.86 out of 5 average rating, 124 reviews

Relax 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 Wilmington

4.99 out of 5 average rating, 187 reviews

Vermont Sugar House Retreat

Stay at this unique rustic Vermont getaway. Nestled on a quiet hill in Wilmington, this private retreat will serve as the perfect home base for your Vermont adventures. You'll have the house to yourself without a neighbor in sight. While very private and surrounded by beautiful forest, this house is still only a short 5 minute drive from downtown Wilmington. The house is built around an enormous one-of-a-kind natural stone fireplace that was formed atop the old foundations of a sugar house.

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, 194 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, 234 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, 118 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 Jamaica

4.86 out of 5 average rating, 277 reviews

Yellow Sweetie at the Base of Stratton

Our adorable home, The Yellow Sweetie, is located in a quiet setting at the base of Stratton Mountain, just 1 minute to the Stratton Resort access road and 8 mins to the slopes. Explore Vermont's many historic towns with classic architecture and covered bridges, as well as its breathtaking mountains, rivers and lakes. The Yellow Sweetie offers stylish country living-meets-shabby chic comfort and coziness. Escape to the fresh Vermont mountain air where life feels a little bit simpler!

Home in Wilmington

4.94 out of 5 average rating, 259 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, 114 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 Shaftsbury

4.99 out of 5 average rating, 276 reviews

Quintessential Vermont Country Home on 140 acres.

Lovingly restored Vermont historic home. Surrounded by 140 acres of private, wooded trails, natural stone fire pit, streams, apple orchard, gardens and vistas for you to enjoy. Very bright home inside, with lovely views, fully furnished. Location is convenient to ski mountains, hiking, the famous Battenkill River for fishing, restaurants, Manchester, VT premium outlet shopping, museums, etc.

Home in Bennington

4.99 out of 5 average rating, 268 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.

Vacation rentals for every style

Get the amount of space that is right for you

Chalets

Adventure-ready homes with après-ski style

Cabins

Kick off your hiking boots at these rustic lodgings

Apartments

Convenient locations with everyday essentials

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, 44 reviews

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

Home in Wilmington

5 out of 5 average rating, 12 reviews

Silver Moose Lodge (Mt Snow)

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

4.77 out of 5 average rating, 52 reviews

Chimney Hill Home w/ New Hot Tub & Amenity Center!

Home in Wilmington

4.83 out of 5 average rating, 40 reviews

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

Home in Dover

4.97 out of 5 average rating, 39 reviews

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

Weekly house rentals

Home in Dorset

4.98 out of 5 average rating, 55 reviews

Home in the Heart of Dorset Village

Home in Wardsboro

4.95 out of 5 average rating, 99 reviews

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

Home in Dorset

4.83 out of 5 average rating, 12 reviews

Heavenly sunsets and nature

Home in Shaftsbury

4.99 out of 5 average rating, 67 reviews

VT Mountain House Epic Views 350 Acre Farm Hot Tub

Home in Manchester

4.95 out of 5 average rating, 38 reviews

Gather and Relax with Friends & Family

Home in Arlington

5 out of 5 average rating, 21 reviews

New Charming Waterfront Cottage Retreat

Home in Manchester

5 out of 5 average rating, 22 reviews

Cozy & Modern Village Cottage

Home in Shaftsbury

4.89 out of 5 average rating, 100 reviews

Cozy Renovated Barn-one of a kind experience

Private house rentals

Home in Arlington

5 out of 5 average rating, 4 reviews

The Riverside Treehouse

Home in Dover

4.93 out of 5 average rating, 82 reviews

Cozy Riverfront Home, 1mi to Mt Snow, On Moover

Home in Manchester

4.94 out of 5 average rating, 49 reviews

The (Manchester) Center of it all!

Home in Manchester

4.98 out of 5 average rating, 54 reviews

Greybourne House former B&B sleeps 12-14!

Home in Arlington

4.85 out of 5 average rating, 93 reviews

Quaint Pink House on The Battenkill River

Home in Dover

4.92 out of 5 average rating, 76 reviews

New Hot Tub! Gas Fireplace! 2 min to Mt Snow

Home in Bennington

4.99 out of 5 average rating, 68 reviews

Stylish dreamy VT cabin with fast & reliable wifi

Home in Manchester

5 out of 5 average rating, 19 reviews

The Village Cottage

Destinations to explore