Apartment holiday rentals in Bennington County

4.91 out of 5 average rating, 154 reviews

A cozy living space features a sectional sofa and a wooden entertainment unit with a large TV. In the background, a kitchen area is visible, equipped with wooden cabinets and essential appliances. A round dining table with chairs is seen, illuminated by soft overhead lighting.

Flat in Wilmington

Walk To Wilmington Village 420 Friendly

420 friendly apartment, keep this in mind if your sensitive to the smell of cannabis I live next door. I have 3 kids and a dog. Expect normal household noise Located on a quiet side road overlooking historic downtown Wilmington, Vermont. Hear the church bells nearby while enjoying a relaxing evening on the deck. Stroll downtown and visit restaurants, shops, bars, and giftshops. Easy access to the Moover Washer/dryer Smart TV Front porch, side porch, and the yard on that side is all private

4.89 out of 5 average rating, 336 reviews

A cozy living area features a dark sofa adorned with colorful throw pillows. Natural light enters through a window, illuminating the space. A coffee table rests in front, complemented by a comfortable side chair and ottoman. Wall décor includes vintage items, enhancing the inviting atmosphere.

Flat in Wilmington

Globetrotter Retreat - Minutes to the Mountain

Newly renovated, fully furnished apt 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 sleeps 4 people in comfort. Private balcony overlooks rolling river. Steps from many restaurants, bars & shopping. Supermarket is a short walk. FreeMoover bus stop across the street - leave your car parked & ride for free to local destinations! No guest under 18 years old.

4.93 out of 5 average rating, 221 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!

A well-lit bedroom features a spacious bed dressed in grey bedding with orange accent pillows. Natural light enters through a skylight, illuminating the wooden floor. A bedside table is positioned beside the bed, accompanied by a woven basket and a door leading to another space.

4.93 out of 5 average rating, 105 reviews

Cozy Loft steps from VT Downtown

This third floor loft apartment is walking distance from Historic Old Bennington and the downtown proper. Enjoy local shops and restaurants. Located a few minutes from the highway, giving you access to any number of ski slopes. This space offers high vaulted ceilings, sky lights and modern furnishings. A large bay window sitting area for plenty of natural light and a private balcony with views of Mount Anthony and the Monument. The space also has fiber Wi-Fi internet, Chromecast - YouTubeTV.

4.94 out of 5 average rating, 214 reviews

A large, two-story house is set amidst greenery, showcasing a wide front porch and multiple gabled roofs. A gravel driveway leads to a spacious parking area lined with trees and shrubs, while a wooden fence borders the property.

Flat in Arlington

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!

A cozy living area features a light grey sofa paired with a wooden coffee table. An accent chair with a textured throw sits beside a basket. A large cow print hangs on the wall, with two framed pieces nearby. A patterned rug covers the floor.

4.95 out of 5 average rating, 195 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.

4.88 out of 5 average rating, 357 reviews

A cozy bedroom is filled with natural light from two windows, dressed with blue curtains. A spacious bed with striped bedding is centered in the room. A white dresser and a television are positioned along the walls, creating a relaxing atmosphere.

Flat in Stamford

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!

4.98 out of 5 average rating, 540 reviews

A well-lit kitchen and dining area features a wooden dining table surrounded by six chairs. Light hardwood flooring complements the gray cabinetry. A potted plant sits on the table, and modern appliances are visible in the background, including a refrigerator and stove.

Flat in Wilmington

**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!!!

4.88 out of 5 average rating, 160 reviews

A rustic wooden cabin exterior is shown, featuring a balcony on the upper level. Two garage doors are visible below, with a small seating area made of metal in the foreground. Lush green grass surrounds the cabin, framed by trees.

Flat in Arlington

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.

4.98 out of 5 average rating, 331 reviews

The exterior of a two-story house is visible, featuring a sloped roof and white siding. Lush green bushes frame the front yard, where a small decorative archway and white picket fence add charm. Surrounding trees provide a natural backdrop for the property.

Flat in Manchester

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.

Two wooden chairs are positioned on a grassy area, facing a gently sloping hill. A modern white farmhouse is visible alongside a deck with stairs. In the background, trees frame the serene landscape, and mountains are faintly visible under a cloudy sky.

4.92 out of 5 average rating, 202 reviews

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.