House holiday rentals in Bennington

Vermont Farmhouse •Walk to Village & Hiking Trails

Experience the magic of this lovingly restored 1860s Vermont farmhouse, where historic charm blends seamlessly with modern living. Set on 1 acre with 1700 sq ft of thoughtfully designed space, enjoy 2 cozy bedrooms, 2.5 baths, and sun-filled common areas made for unwinding. Sip coffee in Adirondack rockers on the expansive front deck, explore 280 acres of woodland trails steps away, stroll into the village, then gather at the fire pit for s'mores under the stars. Welcome to The Vermont Farmhouse

Lawrence Cottage

Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

Renovated Barn +Four-Season Getaway +Near Skiing

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 live stream. Enjoy excursions swimming, hiking, skiing, fishing, biking, shopping, golf, breweries, museums, restaurants, local or a drive away. Fun Lasting Memories.

Warm Brook Farm+Entertainers Dream+Hot Tub+Ski VT

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.

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.

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.

Charming Carriage House in Saratoga Springs

Charming carriage house that has been completely renovated but still has some original character. The carriage house is one bedroom, one bathroom, and full kitchen with 2 off street parking spaces. There are two outdoor areas to enjoy in the front and back of the house. The location is walking distance to Beekman street arts district and Broadway downtown Saratoga Springs. Saratoga spa state park, performing arts center, casino and Saratoga race track are all a short car ride away.

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.

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! ☺

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!

Steps to MoCA private house + SAUNA! Near SKI

Take advantage of our off season prices! This home is tucked away at a private historical estate in central North Adams. Outdoor sauna, fire pits, gardens. Just a 5-minute walk to MASS MoCA, 10 mins by car to Williams & Clark. Important: all proceeds from your stay sponsor pro bono residencies for refugee & immigrant musicians. Nearest ⛷️ SKI resorts: Jiminy Peak, Berkshire East Mountain and many others.

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.