
House vacation rentals in Bennington
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Top-rated house rentals in Bennington
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One of kind VT Renovated Barn for every season
Unwind in a stylish “one of a kind" refurbished barn with a cozy and relaxing vintage vibe. Perfect for Family Travel, friends or a couple’s getaway and Holidays. The barn has 2 bedrooms plus an extra sleep area upstairs. Gather in the living room area with the fireplace or enjoy the yard views with a campfire and sounds of the babbling brook. Enjoy excursions swimming, hiking, skiing, fishing, biking, shopping, golf, breweries, museums, restaurants, local or a drive away. Fun Lasting Memories.

Warm Brook Farm+Holiday Escape+HotTub+Dogs Welcome
Step into the timeless charm of Warm Brook Farm, a beautifully restored 18th-century farmhouse nestled in Southern Vermont. Once a lively inn and stagecoach stop in the early 1800s, this elegant retreat seamlessly combines historic character with modern luxury. Surrounded by the stunning Green Mountains, enjoy upscale amenities, a stunning chef's kitchen, and award-winning gardens. Warm Brook Farm offers an inviting getaway to relax, explore, and create lasting memories with family & friends.

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.

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

A paradise in the woods, minutes from MASS MoCA
Stay and wake up to the magic Berkshire sunlight ! Nestled on a quiet hill on the back of MassMoca, this house is only 3 minute drive from downtown. It was renovated in 2021 with brand new wood floors in the living room and master bedroom, and an updated bathroom with hot tub. This is a second home to the owners, who sometimes come to the area for work, the arts, and the outdoors. They treat every corner of the house with love and care, and want to share this serene experience with you.

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!

Steps to MoCA private house + SAUNA!
In North Adams—one of the Berkshires’ prime destinations for fall colors— Chase Hill sits on a hilltop oasis just above MoCA (3 minutes by walk). Once home to the owners of the factory that became MASS MoCA, the whimsically restored house is part of this private historic estate. Only 10 minutes’ drive to Williams College & The Clark, and steps to downtown restaurants. ✨ Your stay enables us to host refugee & immigrant musicians pro bono year-round. More info on @chasehillartistretreat.

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.

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.

North Adams Getaway-walk to MASS MoCA
BRAND NEW! Ready for guests to enjoy all the Berkshires has to offer! Whether you are visiting for work or pleasure, with family or friends this is a perfect place for you. Located in downtown North Adams you are surrounded by breath taking mountains and foliage, nestled between award winning museums, access to great food, and a short drive to ski resorts, breweries, Tanglewood, the highest peak in MA, and more. A true outdoorsman paradise. BOOK NOW!

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.

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.
Popular amenities for Bennington house rentals
House rentals with a pool

Magical Farm Getaway - a must visit!

The 1770 House

Adams Farm-"The Little Farmhouse"

The Brick House on Washington Street

HotTub/Pool, king bed, between Lk George/Saratoga

Historic Home on 17 acres of land. Go escape!

Hollywood Bungalow in the Berkshires #C0191633410

The Vermont Barn (Mount Snow)
Weekly house rentals

Charming Vermont Schoolhouse

Memes High Mountain Lake House

River view cottage

Comfortable Entire Farmhouse close to North Adams

3-bedroom country home with mountain views

Vermont Mirror House

Bright airy cottage w/ lake view

Green Mountain Getaway
Private house rentals

The Birdhouse Retreat w/Hot Tub

The Barn @ Blackberry Steep

Enjoy Summer & Private, Peace and Relaxation

Buskirk School House

Sugar Shack Lodge

Vermont Historic Farmhouse Ski/Hike/River

Upper level of Waterfront Home Incredible Sunsets

Historic Stone Church in The Berkshires
Quick stats about house rentals in Bennington
Total rentals
10 properties
Nightly prices starting at
$56 CAD before taxes and fees
Total number of reviews
460 reviews
Family-friendly rentals
10 properties are a good fit for families
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Destinations to explore
- Stratton Mountain
- Okemo Mountain Resort
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Berkshire East Mountain Resort
- Six Flags Great Escape Lodge & Indoor Water park
- John Boyd Thacher State Park
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Saratoga Spa State Park
- West Mountain Ski Resort
- Norman Rockwell Museum
- Bousquet Mountain Ski Area
- Mount Snow Ski Resort
- Mount Sugarloaf State Reservation
- Beartown State Forest
- Lake George Expedition Park
- Albany Center Gallery
- Peebles Island State Park
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Berkshire Botanical Garden
- National Museum of Racing and Hall of Fame