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Vacation rentals in Charlemont

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Top-rated vacation rentals in Charlemont

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Rental unit in Shelburne Falls

4.95 out of 5 average rating, 195 reviews

Soaring 2-level loft w/ views in heart of downtown

Walk to everything from this sunny, spacious 2-level, newly renovated 3rd-floor loft in downtown Shelburne Falls, right by the Bridge of Flowers. Cathedral ceiling, giant windows with views of mountains & river. Open upstairs queen bed space. Comfy pull-out queen bed downstairs. Washer/dryer. Well-equipped kitchen w/ dishwasher. Brand-new tiled shower. Fast Internet, two smart TVs, and a 15,000 BTU air conditioner that cools the big space in minutes. 15-minute drive to Berkshire East ski resort.

Cabin in Savoy

4.98 out of 5 average rating, 210 reviews

The Camp - 20 Minutes to Berkshire East!

Enjoy the peaceful silence, private forested expanses, wildlife, and unforgettable starry night skies from this wonderful home. Only 8 minutes to the village of Charlemont and 5 to the Tannery Falls entrance of the Savoy State Forest. During your escape on the mountain rest assured that you’re only a 30 minute drive to Norths Adams, Greenfield. Highlight your visit with journeys to Berkshire East Ski Resort, Thunder Mountain Biking, Zoar Outdoor River Rafting, MASS MoCA, or the Clark Art Museum.

Guest suite in Greenfield

4.94 out of 5 average rating, 178 reviews

Pristine Oasis with Private Bath

Our studio space (250 sq ft) is separate from the main house and located on the outskirts of Greenfield MA. The location provides easy access to downtown, restaurants, shopping areas and Interstate 91. Modern decor, tiled artsy bathroom, lots of garden art, and sweeping views of Berkshire foothills make this a great choice for foliage season, summer recreation and choice winter skiing. One Queen bed. Our house is 90 miles west of Boston, 60 miles north of Hartford and a 3-hour drive to Canada.

Rental unit in Shelburne Falls

4.96 out of 5 average rating, 322 reviews

Annies’ Place by The Bridge of Flowers ~

As a guest at Annie’s Place, enjoy access to a tastefully, renovated 3 room apartment, including a fully equipped kitchen, living room, sofa with 2 recliners, a spacious bedroom, walk-in closet, full bath, TV & Internet. There is a seasonal front porch and mudroom for convenience. Meticulously maintained and located in the downtown village area. Simply park and walk to specialty shops, restaurants & the Bridge of Flowers. Shelburne Falls, designated as one of the 15 “Great Places in America.”

Rental unit in Conway

4.95 out of 5 average rating, 139 reviews

A Country Retreat-Enhanced Studio Apartment

Welcome to our lovely apartment, located in the beautiful, quiet Western MA hill-town of Conway. This is our second time as Airbnb hosts, then known as "Goat Meadow Farm". We hosted almost 150 reservations and achieved Superhost status there. We built again and downsized but included this spacious studio apartment with a bedroom alcove. Wooded and quiet yet just 3 miles from the charming tourist town of Shelburne Falls, and not far off RT91 and the cities of Amherst, Northampton and Greenfield.

Loft in Shelburne Falls

4.94 out of 5 average rating, 289 reviews

The Railroad House

The Railroad House is a cute attached converted barn in the village center with parking, private entrance, 2 floors, fridge, microwave, coffee maker, toaster, WiFI, but no television. It is located within just a minute's walk from the famous Bridge of Flowers. Other local attractions include several dining choices from a drugstore soda shop on up to 5-star dining, as well as the country's 2nd oldest bowling alley. On weekends you can often find live music. Train goes by twice/day on average.

Rental unit in Shelburne Falls

4.97 out of 5 average rating, 523 reviews

In town, newly renovated studio with private deck

Come explore our unique area and stay in a renovated, light filled studio with private entrance, secluded deck , kitchenette and bath located in the quaint New England village of Shelburne Falls.We are within easy walking distance to numerous shops, candlepin bowling, Glacial potholes, tennis/basketball courts, Bridge of Flowers, eateries/restaurants, Pothole pictures, groceries, playgrounds, hiking & swimming areas, a natural food store and art galleries.Close to Berkshire East and Zoar!

Home in Charlemont

4.92 out of 5 average rating, 106 reviews

Skiing, Rafting, Biking Paradise

Experience the charm of a beautifully renovated 1901 Odd Fellows Hall! Nestled in Charlemont, MA, this historic gem boasts stunning views of Berkshire East Ski & Mountain Bike Park, a serene field, and the Deerfield River from the back deck. Surrounded by state forests, it’s perfect for hiking, biking, and fishing. Enjoy modern comforts with high-speed internet, air conditioning, a sleek kitchen, and two well-appointed bathrooms. Your perfect blend of history and adventure awaits!

Guest suite in Charlemont

4.9 out of 5 average rating, 198 reviews

Unique People & Pet-Welcoming Haven

Your own gracious living space with very well equipped kitchen, private deck, entrance, garden, country roads for dog walks, forests, meadows, mountain streams, stone walls, tranquility. The cottage is attached to the main house but is a "separate" entity and again has its own private entrance as mentioned above. No smoking in the cottage please but on the deck just fine. There is an air purifier that runs 24/7. Wi-Fi signal is strong and reliable. MA Taxpayer ID: 10352662

Rental unit in Plainfield

4.97 out of 5 average rating, 259 reviews

Sunny, light filled loft in 1873 Colonial

Relax in our bright, very spacious, and quiet loft, on six open acres. Lounge on the stone terrace, under the stars, by a cozy fire, near the garden. 35 min to Northampton, 35 min to MassMoca, 10 min to Berk. East. Pellet stove, Fiber Optic Wi-Fi, streaming options, and cell coverage. Fully outfitted kitchen with home made granola, and assorted beverages. Two hybrid bikes available for use. There are 3, 5-ft long skylights, and a cathedral ceiling= much natural light!

Cottage in Monroe

4.9 out of 5 average rating, 110 reviews

Pumpkin Pine Cottage: your next adventure awaits!

Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

Rental unit in Greenfield

4.96 out of 5 average rating, 360 reviews

Mohawk Trail View/ private apt. no cleaning Fee

Small, cozy private Apt is located in West Greenfield in a quiet, save neighborhood. Guests have own private driveway and entrance. There are 2 TV’s, one in living room & bedroom. High speed internet. Queen size bed & desk. Apt. Is 2 min's to Rt. 2, Mohawk Trail, Rt. 91, Supermarket, Restaurants & GCC. Less than 5 min's to Greenfield Center. <10 minutes to Deerfield Academy, Bement, Stonleigh. Berkshire East Resort Ski Area 24 minutes

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Popular amenities for Charlemont vacation rentals

Free parking on premises

Air conditioning

Stay near Charlemont's top sights

Berkshire East Mountain Resort107 locals recommend

Zoar Outdoor Adventure Resort78 locals recommend

Crab Apple Whitewater Inc37 locals recommend

Thunder Mountain Bike Park4 locals recommend

Mohawk Trail State Forest15 locals recommend

Floodwater Brewing Company13 locals recommend

Other great vacation rentals in Charlemont

Cabin in Cummington

4.98 out of 5 average rating, 196 reviews

Just Be Cabin

Home in Colrain

4.93 out of 5 average rating, 167 reviews

Secluded Farmhouse Retreat - stunning views

Guest suite in Wilmington

4.92 out of 5 average rating, 752 reviews

Architectural GuestSuite

Rental unit in Vernon

4.96 out of 5 average rating, 153 reviews

Farm land view.

Guest suite in Guilford

4.97 out of 5 average rating, 126 reviews

Private, Quiet Studio With Mountain Views

Chalet in Charlemont

4.99 out of 5 average rating, 81 reviews

The Lodge on Warner Hill

Cottage in Shaftsbury

4.98 out of 5 average rating, 642 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

Rental unit in North Adams

4.97 out of 5 average rating, 491 reviews

Steps to MoCA, near SKI: 2bd + SAUNA!

Quick stats about vacation rentals in Charlemont

Total rentals
30 properties
Nightly prices starting at
$50 before taxes and fees
Total number of reviews
1.5K reviews
Family-friendly rentals
20 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

Frequently Asked Questions

Do house rentals in Charlemont have free parking?
Absolutely! We offer over 10 house rentals with free parking in Charlemont. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Charlemont have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Charlemont. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Charlemont have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Charlemont. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Charlemont have wifi?
Absolutely! We offer over 10 house rentals with wifi in Charlemont. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Charlemont?
Experience the best of Charlemont with our house rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Charlemont?
Yes! Work meets play with ease at over 10 vacation rentals in Charlemont featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Charlemont?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with a kitchen, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Charlemont?
Charlemont has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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