Photo by Melanie Hill

Search Vacation Homes in Charlemont

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check prices for these dates

Next weekend

28 Rab. I - 30 Rab. I

In two weeks

4 Rab. II - 6 Rab. II

In one month

18 Rab. II - 20 Rab. II

In two months

16 Jum. I - 18 Jum. I

Compare 469 Vacation Homes in Charlemont with updated reviews, rates, and availability.

"Property was very nice Kirchen could use some additons -starting with a ladle "

SAR 859 total

includes taxes & fees

23 Mar - 24 Mar

"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...

SAR 3,758 total

includes taxes & fees

28 Mar - 29 Mar

"The pictures were absolutely spot on! The space was incredibly quiet and cozy, with a warm and inviting atmosphere—even in zero-degree weather. The hot tub was fantastic, and the heated bathroom floors were a luxurious touch. The WiFi worked flawlessly throughout the property. The chef’s kitchen was spacious and well-equipped, making it perfect for cooking. Plus, the rental is conveniently close to town, and the breathtaking mountain views made the stay even more special. Highly recommend!"

"Great stay in Amherst again"

SAR 775 total

includes taxes & fees

26 Mar - 27 Mar

"Unit is a little outdated but nice.Not truly a ski in - out since you have to walk on the road about 200 yards to get to the Sachem trail.Condo does need ice cube trays since the ice maker is not working.Also the down stairs bath room heater does not work and would be nice since this is where the bath tub is located"

"Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. "

"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"

"Highly recommend this charming, historic place. Well appointed. Has everything you need for your stay. Cozy…yet plenty of space for everyone. Looks like it was just renovated. Took my daughter and two granddaughters for a ski weekend. Wouldn’t hesitate to come back here. "

"Had a great long weekend getaway in Lanesboro. The property manager was super communicative, which was helpful. Would highly recommend!"

"I came with my husband and 2 kids (7 and 10 yrs old). We loved this condo. It was so close to the mountain (maybe a 5 minute drive) and great restaurants. Richard was so responsive and send a lot of helpful information in advance of our stay. The condo has a beautiful view of the mountain and is perfect for families. Games, books, and was so cozy to hang out at after a day at the mountain. We can't wait to come back. "

SAR 1,322 total

includes taxes & fees

24 Mar - 25 Mar

SAR 1,818 total

includes taxes & fees

2 Apr - 3 Apr

"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "

"We really enjoyed ourselves in Marcella's home, to the point where we did not want to leave the house to go skiing/snowboarding. Upon arrival you are greeted with a cute little bridge to cross over and you see a beautiful red house and barn. The home was very comfortable, with enough bedrooms and space for us our group to be in the kitchen or playing in the pool area, basketball court, ping pong table or 3 different sitting areas and hot tub. The kitchen has everything that you need from...

"We had a great weekend stay here with our dog. He loved the backyard and felt right at home. Everything was clean and great location."

"The house was nicer than we expected we had a wonderful time and will recommend to friends."

4 bedrooms, desk, iron/ironing board, WiFi

"Great spot for a ski weekend at Berkshire East. "

"Great location to Mt Snow and its surroundings. Easy, pleasant and accommodating communications with the host. Comfortable accommodations. "

SAR 1,712 total

includes taxes & fees

24 Mar - 25 Mar

"Jen and Erica thought of everything a guest might need. It was a welcoming, clean and cozy house with a 3 minute drive to Snow Mountain. "

SAR 2,882 total

includes taxes & fees

24 Mar - 25 Mar

"This place is immaculate and the host is responsive. We stayed here to ski in Mount snow which is about 25 minutes drive. We arrived later in the evening and the place was warm and cozy. "

SAR 1,794 total

includes taxes & fees

8 Apr - 9 Apr