Vacation rentals in Bennington County

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Top-rated vacation rentals in Bennington County

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Top guest favorite

A welcoming porch features two white Adirondack chairs positioned around a small wooden table, adorned with a floral centerpiece. Potted plants provide a splash of color near the entrance, while warm light emanates from the cabin interior, hinting at a cozy atmosphere inside.

Cabin in Londonderry

4.94 out of 5 average rating, 346 reviews

Stone Fence Cabin

Cute, Cozy & Charming, our rustic, Studio Cabin is on 5 private acres near scenic Gale Meadows Pond. We are close to Stratton, Bromley & Manchester and you’ll enjoy beautiful scenery & hiking right outside your front door. The Cabin has an open floor plan with a full bath, galley kitchen & dining/living area with pullout futon couch that converts into a 2nd bed. The sleeping loft is accessible by ladder. Our place is a great fit for couples and solo adventurers looking to get away from it all!

Superhost

Two wooden Adirondack chairs are positioned facing a circular stone fire pit, where flames are seen glowing amidst glowing embers. Two glasses filled with a light beverage rest on the ground nearby. A stack of firewood is arranged in the background, surrounded by greenery.

Cabin in Wardsboro

4.88 out of 5 average rating, 133 reviews

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Top guest favorite

A red covered bridge is seen spanning over a quiet road. The bridge features a slatted wooden design, allowing glimpses of nature beyond. Autumn foliage varies in color, and fallen leaves are scattered along the pathway, suggesting the changing season.

Guest suite in Shaftsbury

4.99 out of 5 average rating, 163 reviews

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.

Guest favorite

Apartment in Bennington

4.92 out of 5 average rating, 181 reviews

Escape the City- Vermont Studio

Our studio apartment is located minutes from Bennington College, and sits on 7 acres of land in the Grn. Mtn. National Forest. It's on the second floor of our home (above the garage) through a private entrance with a personal deck and outdoor seating. Take an afternoon stroll to the Mile Around Woods, or day hike to the white rocks! Walk the Ninja trail from the college to see the historic covered bridges, or drive 20-30 miles N to enjoy Vermont's best skiing, and shopping at designer outlets!

Top guest favorite

Guesthouse in North Bennington

4.99 out of 5 average rating, 252 reviews

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 animal

Top guest favorite

A spacious screened-in porch features several chairs arranged for relaxation. The wooden flooring complements the vertical wood panels of the wall. A door leads into the cabin, while a view of the yard and a distant structure can be seen through the screen.

Cabin in Jamaica

5 out of 5 average rating, 242 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

Top guest favorite

An airy living space showcases vaulted ceilings with exposed wooden beams. A wood-burning fireplace features a dark surround, with a light area rug beneath a round coffee table. Bright natural light streams through strategically placed windows, illuminating the modern kitchen and dining area.

Cabin in Shaftsbury

4.99 out of 5 average rating, 266 reviews

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!

Top guest favorite

A wooden door with a rustic finish is positioned at the top of a carpeted staircase. The door features a handle and a small window, allowing light to filter through. Soft lighting illuminates the stairway, leading to a welcoming entrance.

Apartment in Manchester

4.99 out of 5 average rating, 252 reviews

Private two-bedroom suite within a two-story house

This is a private suite located on the second floor of a house. Separate entrance. The owners live downstairs. Great location with mountain views. Please note: 1) Our kitchen is fully equipped, but it has a hot plate instead of the traditional stove. 2) Instead of a full-size living room there is a small sitting area with a TV in the same area where the kitchen is located. 3) Guests don't have access to the backyard/patio, but you can enjoy the outside seating set in front of the house.

Top guest favorite

A wooden horse silhouette is displayed on the wall above, showcasing a trotting design in dark green and natural wood tones. Exposed wooden beams add a rustic charm to the space, contributing to the overall tranquil atmosphere.

Farm stay in Bennington

4.98 out of 5 average rating, 172 reviews

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 of horses and the clucking of chickens who roam our property. We are close to Bennington College and great restaurants and Robert Frost house. We are 35 minutes from Manchester that has some great restaurants and shopping. Bromley ski resort is just beyond Manchester in Peru Vermont . It is a year around resort with water slides in summer and skiing in winter .

Guest favorite

A view from the cabin features a spacious lawn bordered by trees under a partly cloudy sky. A gravel pathway leads through the landscape, inviting exploration. This outdoor area is surrounded by greenery, emphasizing the tranquil rural setting.

Guesthouse in Arlington

4.98 out of 5 average rating, 161 reviews

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.

Top guest favorite

Cottage in Shaftsbury

4.99 out of 5 average rating, 689 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 350 acre property.

Guest favorite

A cozy corner features a tan leather chair with a fluffy white throw draped over its back. A small round table holds a stack of books beside a modern lamp. A potted plant adds a touch of greenery, while a woven basket stores assorted magazines.

Apartment in Bennington

4.95 out of 5 average rating, 164 reviews

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.