
Holiday rentals in Charlemont
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Top-rated holiday rentals in Charlemont
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Charlemont
Top guest favourite

Home in Charlemont
5 out of 5 average rating, 27 reviewsAbove the Oaks - Modern Luxury near Berkshire East
ChristinaRating, 5 stars1 week 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

Cabin in Guilford
4.96 out of 5 average rating, 69 reviewsGuilford Grove Cottage
BobRating, 5 stars2 weeks ago
Joel's place is exactly as described in the listing. The cabin more than met our needs. It was very clean, the bed was so comfortable, the shower had good pressure and enough hot water for the two of us, and the location is peaceful and quiet. We hope to return in the future.
Guest favourite

Flat in Conway
4.96 out of 5 average rating, 25 reviewsSpacious, Sunny* Woodland Retreat
MollyRating, 5 stars1 day 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

Cabin in Cambridge
4.97 out of 5 average rating, 31 reviewsPond View Cabin. Off-Grid, Rustic & Dog Friendly.
EmilyRating, 5 stars1 week ago
Highly recommend Brian’s off grid cabin! His directions were very helpful and made navigating the generator, camp shower, and other on-site details super easy to understand and execute. His property is beautiful and peaceful. We’re already looking at our calendars for another time to visit. Our dog, Stumpy, very much enjoyed the outdoor access and pond. He didn’t want to leave!
Superhost

Cabin in Florida
5 out of 5 average rating, 3 reviewsLux Berkshires Mtn Cabin: Near MassMOCA & Williams
AdrianRating, 5 stars2 weeks ago
Me and my girlfriend had a wonderful weekend out in western Mass. Tito was an amazing host with a stylish cabin away from the noise. Close to North Adams and hiking trails, would definitely stay here again!
Top guest favourite

Flat in Shelburne Falls
5 out of 5 average rating, 11 reviewsCharming Family Retreat: Steps from Downtown
GabrielleRating, 5 stars1 week ago
My friends and I stayed at Jen's place for our high school reunion. The pictures did not do it justice. Not only was her place spacious, clean, and homey but it was less than a 5 minute walk to the Main Street. Jen's recommendations for coffee and food were great and the home was equipped with everything we needed, and even some things we didn't think about like books and board games. The bedrooms were all spacious and there were plenty areas for a group movie night or some quiet alone time. When we first arrived, my friends and I did not know how to lock the door. However, as soon as we reached out to Jen she responded and with patience and grace walked us through the process. My friends and I will be returning every time we visit the area ! Thank you for a great stay.
Top guest favourite

Flat in Conway
4.99 out of 5 average rating, 95 reviewsHouse Above the Hollow
AnnaRating, 5 stars2 weeks ago
Meg’s place was truly amazing. The apartment itself was very well maintained, well-appointed, and Meg went out of her way to ask what kind of milk/creamer we liked with our coffee so that she had stocked in our fridge upon arrival. The property is stunning- from Meg’s flower beds to her gardens, to the open fields, to the bird feeds attracting the most beautiful birds, this property is truly serene and a place where we felt relaxed. Our visit was filled with hiking, biking, and exploring nearby towns (Northampton, Amherst, Hadley, etc.). Meg herself is an incredibly talented artist and has beautiful pottery she crafts in her studio located under the apartment. She was kind enough to show us the studio and sell us a couple of her beautiful vases which we know we’ll always think of our wonderful trip whenever we see them. Thanks for everything, Meg!
Guest favourite

Home in Charlemont
4.97 out of 5 average rating, 65 reviewsSpring brings music festivals & mountain biking.
KyraRating, 5 stars3 days 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
₹4,286 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
- Jiminy Peak Mountain Resort
- Albany Center Gallery
- Bash Bish Falls State Park
- Stratton Mountain Resort
- Taconic State Park
- Catamount Mountain Ski Resort
- Magic Mountain Ski Resort
- Mount Snow Ski Resort
- Mount Greylock Ski Club
- Berkshire East Mountain Resort
- Brimfield State Forest
- Norman Rockwell Museum
- Bright Nights at Forest Park
- Dorset Field Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Naumkeag
- Hildene, The Lincoln Family Home
- The Shattuck Golf Club
- Brignole Vineyards