Holiday rentals in Bennington

Peaceful Get Away at Birds of a Feather Farm

Our cozy upstairs studio can accommodates up to 4 and is separate from the main house. Plush towels, linen, pillows and blankets. Kitchenette is fully stocked with everything you need for cooking. The private entrance is equipped with punch key lock to facilitate easy self check-in. A queen size sleep number bed, queen size pullout couch, table with four chairs, a dresser, one bathroom with shower, smart TV and WIFI. Heat and cooling. Spa services are available. For Booking & Fees contact host.

Birch House - lake, green trees + modern comforts

We're a little guest house near a lake in Vermont with green trees + modern comforts. Perfect for couples + individuals looking to relax + enjoy nature. Renovated, air conditioned space w/ cozy, minimalist vibes. A small modern cabin that's peaceful + private. Tucked into a quiet neighborhood. Main home is a separate building next door. Near Bennington College. 12 minutes to downtown Bennington. IG birchhousevt Please note that due to a severe allergy, it is difficult to accommodate animals

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

The Farm Cottage

Take a break and unwind at this little peaceful oasis. A little bit of the country is right beside you with the neighing horses and clucking chickens who roam our property. We are close to Bennington College, great restaurants and Robert Frost house. We are 35 minutes from Manchester where you’ll find terrific outlet shopping and a variety of restaurants. Bromley Mountain is just beyond Manchester in Peru, Vt. It is a year around resort with water slides in summer and skiing in winter .

The Hygge Loft- mid-mod cabin on 70 forested acres

The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

5BR Rustic Mountain Sanctuary Dome Home

Find connection in this secluded mountainous retreat. Enmeshed in the natural landscape, this space is only accessible via unpaved roads. Even the journey here is part of the adventure. *4WD & Snowtires are needed during winter & early spring due to the possibility of snow or mud* This property requires a lot of upkeep and the steward will likely be onsite during your stay, however the whole house will be exclusively reserved for your booking. This space will rejuvenate & inspire

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.

Cooper's Place

Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

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.

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Cozy, bright 3-bedroom Cottage with fireplace.

Cozy, spacious brook-side cottage with 3 bedrooms, 2 baths, fully-equipped kitchen, fireplace, and serene, 382-acre country setting. Colorful artwork, designer furnishings, and well-appointed kitchen and bathrooms will make you feel welcome and at home. Historic charm of Bennington ten minutes away. NYC (182 miles); Boston (118); Mt. Snow (32); Prospect Mountain (13). Close to MASS MoCA (22), Tanglewood (49) and Manchester outlets (32).

Scenic Vermont Studio

This beautiful retreat is halfway between the ski slopes of southern Vermont and the cultural centers of Williamstown and North Adams, MA. The residence is a modern, spacious, basement apartment, part of an 1860 farm house. It has its own private entrance around the back of the house at ground level. Solar garden lights and motion detector lighting will illuminate your path to the apartment.