Apartment holiday rentals in Bennington County

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Top-rated apartment rentals in Bennington County

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Guest favourite

Flat in Bennington

4.92 out of 5 average rating, 178 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 favourite

Flat in Wilmington

4.91 out of 5 average rating, 134 reviews

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

Top guest favourite

Flat in Wilmington

4.93 out of 5 average rating, 124 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. Washer/dryer Smart TV with premium streaming services The front porch, side porch, and the yard on that side is all private and for you to enjoy. Please note, I live next door, and I have a dog.

Guest favourite

Flat in Arlington

4.93 out of 5 average rating, 176 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!

Superhost

Flat in Dover

4.73 out of 5 average rating, 120 reviews

AMAZING DEAL - 2BDR - less than 1 mile from mtn

This is the downstairs unit of a top-on-bottom chalet duplex. Airbnb unit above you. You walk down a flight of stairs from the driveway and enter this unit. It has two bedrooms, and an open living and dining area with room to make your stay comfortable and memorable. The price is very reasonable considering the location, so do not expect the moon! Be reasonable. It’s comfortable & clean and you’re in VT for the outdoors. TV has apps you connect to - WE DO NOT HAVE CABLE TELEVISION

Guest favourite

Flat in Bennington

4.96 out of 5 average rating, 161 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 favourite

Flat in Stamford

4.86 out of 5 average rating, 311 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 favourite

Flat in Wilmington

4.98 out of 5 average rating, 481 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 favourite

Flat in Arlington

4.87 out of 5 average rating, 137 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 favourite

Flat in Pownal

4.94 out of 5 average rating, 190 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).

Top guest favourite

Flat in Manchester

4.97 out of 5 average rating, 101 reviews

Quiet Getaway in Equinox Valley

Newly constructed private 1-bedroom apartment in a mountain setting. Just south of Manchester Village at the base of Little Equinox Mountain. Drive by a small dairy farm and up a country lane to a second-floor walk-up with mountain view. Close to Manchester Designer Outlet shopping, restaurants, wedding venues, hiking, biking, fishing and more.

Guest favourite

Flat in Wilmington

4.93 out of 5 average rating, 180 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).