Apartment vacation rentals in Bennington County

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Top-rated apartment rentals in Bennington County

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Guest favorite

Rental unit in Pownal

4.94 out of 5 average rating, 114 reviews

"The Parlors"

This beautiful, spacious, and historic property was formerly the Inn at Oak Hill. It is convenient to Williams College, Williamstown Theater Festival, Clark Art Museum, MassMOCA, FreshGrass Festival, BerkshireStock, Jiminy Peak, Bennington College, VAST snowmobile system and many other destinations in southern Vermont and western Massachusetts. Comfortably furnished with modern amenities such as Wi-Fi and satellite TV, our home also surrounds you with beautifully preserved & original features.

Guest favorite

Rental unit in Dorset

4.99 out of 5 average rating, 185 reviews

Vermont barn apartment

The Barn Apartment at Sykes Hollow Farm is in the gorgeous Mettowee Valley with 5 friendly horses, entertaining chickens, mountain views and a host who cares about you. The farm is a quiet, private, peaceful place with 30 acres to roam, but still close to Dorset and Manchester. Fields, mountains and a pond are all here. Good for couples and solo travelers who want an amazingly beautiful setting. This listing is more than a rental... it's an entire farm. Powered by solar to help the planet!

Guest favorite

Rental unit in Arlington

4.93 out of 5 average rating, 167 reviews

Spacious apartment in picturesque Arlington VT!

Come relax in this beautiful and spacious basement apartment with private entrance nestled amongst the gorgeous Green Mountains in historic Arlington, Vermont. Hiking, Ski mountains and tubing down the Battenkill river just minutes from the apartment. 10 minutes from excellent restaurants and shopping in Manchester, VT. Less than 30 minutes to Bromley. Stratton, Okemo and Mt Snow are both under an hour away. Saratoga and Albany are an hour drive. Come see why Vermont living is the best!

Guest favorite

Rental unit in Manchester

5 out of 5 average rating, 213 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.

Guest favorite

Rental unit in Wilmington

4.92 out of 5 average rating, 115 reviews

Walk To Wilmington Village

This charming apartment is on a quiet side road overlooking historic downtown Wilmington, Vermont. Hear the church bells nearby while enjoying a relaxing evening on the deck. Take a stroll downtown and visit restaurants, shops, bars, and giftshops. Easy access to Moover, free bus to Mount Snow. Brand new washer/dryer Smart TV with a variety of premium streaming services The entire covered porch, side porch, and the yard on that side is all private and for you to enjoy.

Guest favorite

Rental unit in Bennington

4.95 out of 5 average rating, 152 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.

Guest favorite

Rental unit in Stamford

4.86 out of 5 average rating, 298 reviews

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Escape to our cozy apartment in picturesque Southern Vermont! Featuring a comfortable bedroom, a well-equipped kitchenette, a private bathroom, and a charming dining area, this space has everything you need for a relaxing stay. Enjoy the perfect blend of tranquility and easy access—just a scenic 10-minute drive brings you to North Adams, MA, home to Mass MoCA, MCLA, and plenty of dining and shopping. Book now for the ideal balance of serenity and convenience!

Guest favorite

Rental unit in Wilmington

4.98 out of 5 average rating, 464 reviews

**Happy Hour! Gorgeous & Modern Downtown Retreat**

Come enjoy our beautiful apartment above our liquor store in downtown Wilmington! Lots of local shops and dining right in town! We are along a river and next to a hiking trail system! Walking distance to the serene 10+ mile lake; kayaks, stand-up paddle boards or motor boat/jet ski rentals nearby. In the winter, enjoy local trails on snowshoes or cross-country skies; only 15 minutes to Mount Snow! We look forward to meeting you!!!

Guest favorite

Rental unit in Arlington

4.87 out of 5 average rating, 134 reviews

Brian Peace of Heaven

Beautiful Mountain View 4 1/2 Acres Park your vehicle inside garage upstairs studio apt with full kitchen and Bathroom with shower. There 100 acres to the right and 40 to the left. welcome to Brian’s peace of Heaven.. There skiing 10miles a way Stratton and Bromley. Out let’s Stores in Manchester Vt . Roads are always plowed in winter. Pellet stove that you can use with Gas heat and hot water. 2 beds queen size and Full size.

Guest favorite

Rental unit in Bennington

4.93 out of 5 average rating, 620 reviews

The Octopus's Garden

Welcome to the Octopus' Garden, a warm and cozy oasis located in the heart of Bennington, VT. This relaxing one bedroom suite, infused with amenities and much love, comfortably accommodates 2 people. This peaceful space is only a 10 minute walk to art, shops and dining and is the perfect hub for a variety of activities in Southern Vermont and Western Massachusetts.

Guest favorite

Rental unit in Pownal

4.95 out of 5 average rating, 183 reviews

The Shepherd's Retreat

This in-law apartment is on the first floor of our 2 level home and has its own separate entrances. It features an open floor plan with galley kitchen and breakfast bar. This location has a peaceful relaxing atmosphere but with easy access to shopping, site seeing, hiking, and is minutes away from historic Bennington, Vt and the Berkshires (Mass Moca Museum).

Guest favorite

Rental unit in Wilmington

4.93 out of 5 average rating, 181 reviews

Quaint cozy vermont apartment

My place is close to parks, great views, restaurants and dining, art and culture. You’ll love my place because of privacy the sky lights, high ceiling, the comfy bed, the kitchen, the neighborhood, and the outdoors space. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets).