
Holiday houses in Charlemont
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Charlemont
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Charlemont holiday rentals
Other great holiday rentals in Charlemont
Top Guest favourite

Home in Charlemont
5 out of 5 average rating, 28 reviewsAbove the Oaks - Modern Luxury near Berkshire East
ChristinaRating, 5 stars2 weeks ago
We stayed at this beautiful Airbnb for my daughter’s wedding, and it was truly perfect in every way! From the moment we arrived, we felt at home. The space was immaculate, incredibly spacious, and the location was perfect and private. The hosts truly thought of everything. Every little detail was in place, making our stay seamless and stress-free. From extra towels to thoughtful touches around the home, you can tell they really care about their guests’ experience. We are so grateful to have found this gem—Thank you for helping make our daughter’s big day even more memorable!
Guest favourite

Home in Charlemont
4.95 out of 5 average rating, 58 reviewsTall Pines Rental
GeorgiaRating, 5 stars4 weeks ago
Hands down one of the best Airbnbs in the western MA area. We’ve rented the space 4 times now, and will continue to do so. The host is welcoming and responsive, and the house has everything you could need. They also help to accommodate your dog/pet which is a huge plus!
Top Guest favourite

Guest suite in Colrain
5 out of 5 average rating, 22 reviewsCozy elegant suite between Deerfield/NMH/Shelburne
MarianneRating, 5 stars1 month ago
Roxanne’s home is absolutely beautiful and peaceful. We were in the area for college graduation and as a result, our only regret is that we did not have more free time to spend at this tucked away oasis… we would love to visit again! We highly recommend Roxanne’s home for anyone looking to enjoy quiet, some local trails, and to take in nature. The suite is beautifully decorated and so inviting. I wanted to sit outside with a book and enjoy the surroundings. Roxanne baked us hot bread that was beyond delicious and made us feel like we were on vacation and being cared for. I hope we go back one day. I have a friend in mind who is a huge hiker and I will be recommending this stay as a beautiful place for some R & R…. Thanks for everything!!
Guest favourite

Cabin in Guilford
4.96 out of 5 average rating, 73 reviewsGuilford Grove Cottage
JulieRating, 5 stars4 days ago
Joel's place was impeccably clean and free of clutter. The shower pressure was excellent. The kitchen had everything you need ro cook, and it was a treat to have milk, eggs, english muffins and coffee available for breakfast as well as tea which you can enjoy sitting out on the porch. It is a short drive to Brattleboro and the surrounding area is exquisitely beautiful.
Guest favourite

Apartment in Conway
4.96 out of 5 average rating, 25 reviewsSpacious, Sunny* Woodland Retreat
MollyRating, 5 stars1 week ago
We had a fantastic stay at Erica's with our 2 month old. Erica provided a crib, and it was safe for infant sleeping. We enjoyed sitting on the porch, and ended up cooking a full dinner for local friends one night. The kitchen had all the basics that we needed. It was a short trip so we didn't have much time to explore the property, but it looked beautiful and we enjoyed hearing the frogs at night and birds during the day. The apartment is HUGE, and we found it very comfortable. It'll be our go-to for future visits in the area!
Guest favourite

Home in Ashfield
4.98 out of 5 average rating, 57 reviewsAn 18th century farmhouse
NateRating, 5 stars1 week ago
What a beautiful, idyllic getaway Susan offers for her guests. A kind welcoming soul who provides a stay that brings you back in history – we had the most lovely time!
Superhost

Cabin in Florida
5 out of 5 average rating, 4 reviewsLux Berkshires Mtn Cabin: Near MassMOCA & Williams
JordanRating, 5 stars2 days ago
We loved staying at Tito's cabin. The land is beautiful and the space is well taken care of. It's a cozy, restful cabin that's off the beaten path and has everything you need for a weekend away.
Guest favourite

Home in Charlemont
4.97 out of 5 average rating, 65 reviewsSpring brings music festivals & mountain biking.
KyraRating, 5 stars1 week ago
My children and sister and I had a lovely few days at the Parsonage. Charming and comfortable house with plenty of updates— especially the bathrooms and kitchen. We cooked every night and had interesting day trips. Highly recommend the Clark Museum in Williamstown. We spent a good deal of time on the porch, with our bird apps, identifying all the wonderful bird songs. Bring some bug repellent for June.
Quick stats about holiday rentals in Charlemont
Total rentals
30 properties
Nightly prices starting at
$83 NZD before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Stratton Mountain
- Six Flags New England
- Monadnock State Park
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Bash Bish Falls State Park
- Stratton Mountain Resort
- Magic Mountain Ski Resort
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Brimfield State Forest
- Norman Rockwell Museum
- The Shattuck Golf Club
- Beartown State Forest
- Bright Nights at Forest Park
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Naumkeag
- Hildene, The Lincoln Family Home
- Brignole Vineyards