House vacation rentals in Charlemont

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Top-rated house rentals in Charlemont

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Top guest favorite
A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.
Home in Guilford
4.94 out of 5 average rating, 122 reviews

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

Guest favorite
An open concept living space features four arched windows that allow ample natural light. Wooden floors complement the revealed post and beam construction. A wooden dining table is centrally placed, with a cozy seating area in a corner, creating a relaxed environment.
Home in Putney
4.89 out of 5 average rating, 263 reviews

Spacious Loft with View

Located off a quiet dirt road, this rental features a great view of Putney Mountain, a private Hot Tub(exclusive to just the loft), miles of trails right from your doorstep, & a private rock quarry with swimming spot! Nestled amongst 100+ acres of conserved forest, with many VT destinations just minutes away, we are at the top of a hill overlooking the Putney Mountain ridge line.Just a 7 minute drive to downtown Putney and 20 minutes to Brattleboro.Landmark College (6min) & Putney School (12min)

Guest favorite
A bright living area features a yellow couch and two accent chairs, inviting relaxation. A patterned area rug centers the space, while natural light filters through large windows. A staircase is visible in the background, along with decorative plants and artwork adorning the walls.
Home in Pittsfield
4.95 out of 5 average rating, 207 reviews

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

Top guest favorite
The exterior of a charming house features a gabled roof and a welcoming front porch with a wooden rocking chair. Lush green grass surrounds the home, and neatly trimmed shrubs are visible, complemented by tall trees in the background against a partly cloudy sky.
Home in Bennington
4.99 out of 5 average rating, 350 reviews

Southern Vermont Home

Beautiful home that offers privacy on over one acre of land. It is only a short drive to the conveniences of downtown shopping, restaurants, Bennington College, and much more. This house is 35 minutes from Manchester's famous outlets, 20 minutes from Williamstown, MA, and 45 minutes from Albany, NY. Bromley and Mount Snow ski areas are 40 minutes. The home has wonderful finishes and you will feel right at home upon arrival. Please come explore Vermont from our country escape!

Guest favorite
A light blue two-story house is positioned along a road, featuring a covered front porch with white railings and red doors. Lush greenery frames the property, while distant mountains create a scenic backdrop.
Home in Charlemont
4.98 out of 5 average rating, 101 reviews

Red Door River House

1 min from Berkshire East Ski Mt and Thunder Mt and the Crazy Horse Bar, Across Street from Zoar Outdoor. Walk to cold river cafe and liquor store, Close to crabapple whitewater rafting. On River for Tubing, kayaking, canoeing right to and from the house. Close to Shelburne fall’s& Bridge Of Flowers outdoor rec: skiing, fishing, rafting, kayaking, zip lining and mountain biking, hiking, 5 bed + sofa bed. 4 bedrooms ,2 kings, two queens and one room- full bed. 1 full bath.1/2 bath.

Top guest favorite
A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.
Home in Bennington
5 out of 5 average rating, 110 reviews

The Vermont Farmhouse|Hiking+Dog Trails+Village

Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

Guest favorite
Home in Colrain
4.94 out of 5 average rating, 210 reviews

Colrain Winter Adventure HotTub AirHockey Firepit

Escape to Millhouse 254, a historic 5-bedroom home blending modern luxury with classic charm. Perfect for large groups & families, it comfortably sleeps 10 and features a hot tub, game room, and an accessible main-floor suite. Located just 5 minutes from the shops and restaurants of Shelburne Falls, it's your ideal retreat for exploring the outdoors or simply relaxing in style. Enjoy a fully equipped kitchen, private yard, and year-round fun in this thoughtfully updated home.

Top guest favorite
Home in North Adams
4.98 out of 5 average rating, 510 reviews

Steps to MoCA private house + SAUNA! Near SKI

Near Ski & Museums! Welcome to the Gardener’s Cottage at Chase Hill—the historic estate of the owners of the factory that became MASS MoCA. More than just houses, Chase Hill is an experience: gardens, fire pits, sauna, massages, occasional music rehearsals. Just a 5-minute walk to MASS MoCA, 10 mins by car to Williams & Clark. YOUR STAY SPONSORS PRO BONO RESIDENCE FOR REFUGEE & iMMIGRANT MUSICIANS. Nearest ⛷️ SKI resorts: Jiminy Peak, Berkshire East Mountain and many others!

Guest favorite
A charming Victorian home is showcased at dusk, with bright windows illuminating the exterior. The wraparound porch features decorative railings and flower planters, complementing the elegant architectural details. The two-story structure is framed by a darkening sky, enhancing its inviting presence in the neighborhood.
Home in Adams
4.9 out of 5 average rating, 143 reviews

Beautiful Victorian. The heart of the Berkshires.

The whole group will enjoy easy access to everything from this centrally located place. The house has been completely renovated. The side patio has plenty of room for a large group with a brand new Weber grill and propane fire pit. Enjoy morning coffee on the front porch. Just steps from the Ashuwillicook Rail Trail. Greylock Glen is less than a half mile away with hiking trails. Mass MoCA is 5 miles away. This Victorian beauty is cozy, warm, and inviting.

Top guest favorite
The kitchen features modern appliances, including a stainless steel refrigerator and a sleek oven range. An orange barn-style door adds a pop of color, contrasting with the navy cabinetry. Cooking utensils are organized in a vibrant holder, and a soft area rug is placed on the floor.
Home in North Adams
4.99 out of 5 average rating, 177 reviews

North Adams Getaway-walk to MASS MoCA

BRAND NEW! Ready for guests to enjoy all the Berkshires has to offer! Whether you are visiting for work or pleasure, with family or friends this is a perfect place for you. Located in downtown North Adams you are surrounded by breath taking mountains and foliage, nestled between award winning museums, access to great food, and a short drive to ski resorts, breweries, Tanglewood, the highest peak in MA, and more. A true outdoorsman paradise. BOOK NOW!

Superhost
A rustic red barn stands among lush greenery, featuring large glass doors inviting natural light inside. The path leading to the barn is lined with gravel, and a stack of wood is neatly arranged beside the structure.
Home in Cheshire
4.86 out of 5 average rating, 223 reviews

Ski at 19th c. Barn in The Berkshires

<b> Mason Hill Farm </b> is a celebration of everything we love about the Berkshires. Mountain views, a rushing swimmable brook, an historic restored barn and outbuildings surrounded by lush forest and grazing sheep. Follow us @ <b> mason_hill_farm </b> For weddings & events, please contact us for information on our sister property: Hinterland Hall!

Top guest favorite
The exterior of the house is framed by lush greenery and trees. A gentle path leads to the front entrance, which is sheltered by a small porch. The metal roof and pastel siding complement the natural surroundings, creating a cozy and inviting facade.
Home in Putney
4.95 out of 5 average rating, 361 reviews

Cozy Train Depot in Putney Vermont

Charming and cozy 1 bedroom house in Putney, Vermont. A former train depot, this home is just a few minutes walk to the Connecticut River with boat launch for enjoying fishing, swimming, canoeing and kayaking. Or curl up in the window seat and enjoy the fire!

Popular amenities for Charlemont house rentals

Quick stats about house rentals in Charlemont

  • Total vacation rentals

    Explore 20 vacation rentals in Charlemont

  • Nightly prices starting at

    Charlemont vacation rentals start at ﺩ.ﺇ184 per night before taxes and fees

  • Verified guest reviews

    Over 420 verified reviews to help you choose

  • Family-friendly vacation rentals

    10 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Charlemont vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Charlemont rentals

  • 4.9 Average rating

    Charlemont stays are highly rated by guests—averaging 4.9 out of 5!