Guest house holiday rentals in Bennington County

"The Library Suite"

This beautiful and spacious property is located at the former Inn at Oak Hill and Cherry Court. It's convenient to Williams College, Williamstown Theatre Festival, Clark Art Museum, MassMOCA, Fresh Grass Festival, Jiminy Peak, Bennington College, and many other destinations in southern Vermont and western Massachusetts. Comfortably furnished with modern amenities such as Wi-Fi and satellite TV, this innovative space also surrounds you with beautifully preserved and rustic architectural features.

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

Romantic Barn Guesthouse in Village Center

Keep it simple at our peaceful and centrally-located hideaway. This rustic and cozy two-story barn guesthouse with fireplace is located on four acres of a 1768 historic homestead right in Manchester Center. Enjoy the pond and mountain views from the bedroom and living room windows; the guesthouse faces a peaceful meadow and wildlife pond which abuts 70 acres of preserved land with hiking trails, yet it's also just steps from Main Street and all of the dining and shopping of Manchester Village.

Mount Snow-Cozy 2BR-The Streif

Enjoy your Green Mountain getaway at our cozy & private 2 bedroom guesthouse located less than one mile from Mount Snow’s North Access Road. All the amenities you need for a relaxing and comfortable Vermont escape including: a full kitchen with breakfast bar, gas fireplace, WiFi high speed internet, 2nd floor deck with beautiful mountain views, backyard patio & fire pit, private hiking/cross country skiing trails, direct VAST snowmobile trail access, all the privacy you need and much more.

Cozy, charming cottage 7 mins from Mt Snow & Lake

Take a deep breath & relax at this cozy, design-forward mountain cottage. Less than 10-minute drive from both Mt. Snow and two lakes, it's an idyllic getaway all year round. You'll stay in the guest cottage next to the main house. -Bunk bed handmade locally -Three outdoor fire pits -Nespresso w/ lots of coffee options -Aesop products -65in 4K TV w/ Sonos surround sound system -Fiber WiFi -Peloton -Weber grill with side burner -Sustainably sourced furniture -Local art & handmade goods

Cozy Log Cabin Suite [100+ Reviews 4.98 Rating]

Welcome to a cozy log cabin loft on private property. Our 600+ square foot suite is consistently upgraded for our guest. You'll enjoy high end accommodations, solid wood flooring, AC, 50" TV with Cable, wireless internet, premium King size bed, fridge and kitchen. Cleanliness has always been a top priority for our guests. We are proud to hold a 5-star rating. As a Registered Nurse in our local hospital, I can assure you we are cleaning and disinfecting following the CDC guidelines.

Guest Cottage with Mountain View - Close to skiing

Stay in a renovated cottage in the heart of Old Bennington. Overlooking a 3-acre yard with mountain views, enjoy New England foliage/skiing/hiking and history steps away. The Bennington Monument, First Church, Robert Frost's grave, and the Bennington Museum are 2 mins away, as are Bennington restaurants and shopping. Williamstown, North Adams museums, Manchester shopping and nordic and downhill skiing are all within a scenic 25 min drive.

In Town Manchester Studio w/ Loft Bedroom.

The Barn, situated behind our house, is located just a few minutes walk to the center of Manchester. It is a working studio setting with general living area on the main floor and a bedroom above in a loft. There is hot tub available to barn guest and a shared (with house) outdoor space. Very clean, very fun space with ample room, comfortable bedding. Perfect for two. (Note: Bedroom Loft is only accessible via a spiral staircase).

New! remodeled Barn. min from Lake, Ski, Hot tub

Just remodeled old barn with original wood beams and floors. All new Kitchen/bathroom/furniture and appliances. Attached to main house but private entrance and driveway. Minutes from the beautiful town of Wilmington. 15 Minutes from MT snow Skiing and 5 minutes to beautiful Wards beach at Lake Whitingham. New Hot tub and deck to enjoy the after a long hike or watching the amazing stars. Just added a firepit. wood provided

Green River Escape

Welcome to Green River Escape, your peaceful getaway nestled on 8 acres of open land along the Green River and 30 acres of woods cut with the gentle flow of Hopper Creek. Our charming escape with a deck was built at the confluence of the Green River and Hopper Creek, perched above a heated two-car garage. It is the perfect place to unwind and reconnect with nature (your furry friends are welcome, too!).

Carriage House

This renovated carriage house is one block from Main Street in historic Manchester Center and a 5 minute walk to a variety of restaurants, shopping and outdoor activities. Historic Manchester Village is a 5 minute drive. Bromley is a 10 minute drive and Stratton is a 25 minute drive. Guest privacy is respected by the hosts, who live in the original farm house and can quickly address guest concerns.

Home in Dover – 5 Min to Mt Snow

Just minutes from Mount Snow, this cozy and private home offers easy access to skiing and tubing, as well as local favorite bars and restaurants - all conveniently located on the bus route. Enjoy breathtaking views from the wraparound deck, three spacious bedrooms, two pull-out couches, and all the comforts of home for a relaxing mountain getaway!