House holiday rentals in Bennington County

Stylish VT Barn+Guest Favorite Leaf Peaking Season

Unwind in a stylish “one of a kind" refurbished barn with a cozy and relaxing vintage vibe. A Guest Favorite. Perfect for Family Travel, friends or a couple’s getaway all year long 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. Nearby attractions: swimming, hiking, skiing, fishing, biking, shops,golf, museums, restaurants, local or a drive away.

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.

Warm Brook Farm | Farmhouse & Gardens | Hot Tub

Step into the timeless charm of Warm Brook Farm, a beautifully restored 18th-century farmhouse in Southern Vermont. Once a lively inn and stagecoach stop in the early 1800s, this elegant retreat combines historic character with modern luxury. Enjoy a genuine chef's kitchen, award-winning gardens, and upscale amenities throughout. We cover your Airbnb service fees — the price you see is what you pay. An inviting getaway to relax, explore, and create lasting memories with family and friends.

Ski and Play in Manchester Center!

Fully renovated 2000 sf 5 bedroom/2 bathroom house in the heart of Manchester Center, VT! 6 miles to Bromley, 15 miles to Stratton, 6 miles to the Vermont Summer Festival horse show, and less than a mile to all of the shops and restaurants Manchester Center has to offer! You cannot beat this location no matter the season! The house is set back off the road and surrounded by woodlands so even with all of these amenities at your fingertips, you feel like you're far off the beaten path!

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!

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.

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!

The Vermont Farmhouse|Hiking|Dog Trails|Village

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.

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.

Wilmington. In Town Village Home

Beautifully renovated bright, 125 year 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.

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.

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!