Photo by Melanie Hill

Holiday Rentals in Charlemont

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Charlemont

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (127)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Bear Creek Cabin

9.8 out of 10, Exceptional, (22)
"It was beautiful to wake up the first morning to see freshly fallen snow! Easy to get to, lots for the kids to do, wonderful place to share with my family for Thanksgiving! Only thing that I would change is having wood in the wood holder by the stove so that we didn’t have to carry it in. Would recommend to others. "
The price is €585
includes taxes & fees
29 Dec - 30 Dec
Bear Creek Cabin

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is €207
includes taxes & fees
1 Jan - 2 Jan 2025
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (921)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is €197
includes taxes & fees
1 Jan - 2 Jan 2025
Jiminy Peak Mountain Resort

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (232)
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike. "
The price is €220
includes taxes & fees
30 Dec - 31 Dec
Berkshire Village Carriage House - Super Private!!

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.8 out of 10, Excellent, (43)
"Cabin was perfect for our long weekend. Master bed mattress needs an update, but otherwise everything was fantastic."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

8.8 out of 10, Excellent, (42)
"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

Cozy apartment located in quiet Williamsburg

9.4 out of 10, Exceptional, (47)
"Convenient location, comfortable."
The price is €249
includes taxes & fees
4 Jan - 5 Jan 2025
Cozy apartment located in quiet Williamsburg

Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

10.0 out of 10, Exceptional, (40)
"We enjoyed our stay at the tiny home!"
Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

8.6 out of 10, Excellent, (21)
"Good Condo in a great location"
The price is €339
includes taxes & fees
9 Jan - 10 Jan 2025
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Walk to Mount Snow, Cozy, Clean and Comfortable!

9.6 out of 10, Exceptional, (30)
"Cozy 1 bdrm very close to the slopes. The host are vey cooperative abd get back to you quickly."
Walk to Mount Snow, Cozy, Clean and Comfortable!

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

9.8 out of 10, Exceptional, (41)
"This property is stunning. It fit our group of 14 perfectly. There are so many unique details and beautiful furniture. The kitchen was well-stocked for pots/pans/utensils/cleaning supplies which I always appreciate - makes group meals so much easier to manage. Quiet area, would be great all year round depending on what activities you like. Hot tub was a major highlight!"
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Berkshire Lake access

10.0 out of 10, Exceptional, (49)
"The house worked was exceptionally clean and worked great for us. The landowner was exceptionally helpful in providing suggestions. We loved visiting the Norman Rockwell Museum and walking around Lenox. Thanks for everything!"
Berkshire Lake access

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

9.8 out of 10, Exceptional, (96)
"Easy check in, very clean and well stocked with everything needed. I was visiting my daughter at UMass who had to have knee surgery. There was lots of space for her to get around. It was also close to the University which was important for us as well."
The price is €204
includes taxes & fees
8 Jan - 9 Jan 2025
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

The Brown House. Indoor pool - Spa - Sauna - Gameroom

8.0 out of 10, Very good, (23)
"It was our yearly Guys weekend, everyone had a Great time. The house with every bedroom having a full bath was fantastic you couldn’t ask for more We spent many hours in the indoor pool and the 2 jacuzzi’s we will definitely stay there again"
The Brown House. Indoor pool - Spa - Sauna - Gameroom

Jacksonville Cabin w/ Wraparound Deck & Views

9.6 out of 10, Exceptional, (27)
"We enjoyed our stay. Everything was clean. The only thing I would suggest is checking the stairs to the basement. "
Jacksonville Cabin w/ Wraparound Deck & Views

Chic Pittsfield Home With A View!

9.0 out of 10, Wonderful, (9)
"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "
Chic Pittsfield Home With A View!

Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

10.0 out of 10, Exceptional, (21)
"The property is exactly as described! We loved the proximity to the mountain. The house is adorable and perfectly suited for our family. The host was VERY responsive and had great customer service during our stay. We can not wait to come back again!"
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (14)
"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. "
Amherst, Perfect Location, UMass, Smith, MHC!

Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym

8.8 out of 10, Excellent, (3)
"My stay with a friend at this location was extremely pleasant overall; the home was well furnished, stocked, and the surroundings of rural Vermont were beyond gorgeous. The interior was very well cleaned when I arrived, though my friend and I very quickly noticed that there was a distinct septic-like odor in the house's central hallway area and the home's exterior (walking up to the entryway, etc). This smell persisted throughout the duration of the stay, but was most noticeable on days where...
Classic Vermont cabin with forest views, woodstove, pools, hot tub & gym
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Charlemont
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Charlemont you may be interested in

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (127)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Bear Creek Cabin

9.8 out of 10, Exceptional, (22)
"It was beautiful to wake up the first morning to see freshly fallen snow! Easy to get to, lots for the kids to do, wonderful place to share with my family for Thanksgiving! Only thing that I would change is having wood in the wood holder by the stove so that we didn’t have to carry it in. Would recommend to others. "
The price is €585
includes taxes & fees
29 Dec - 30 Dec
Bear Creek Cabin

Hotel UMass

2.5 star property
8.8 out of 10, Excellent, (925)
"Ver clean, big room. Pillows were not comfortable. Nice breakfast. Cute lobby"
The price is €156
includes taxes & fees
7 Jan - 8 Jan 2025
Hotel UMass
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Are there holiday rentals in Charlemont?

Yes, there are holiday rentals in Charlemont close to Thunderbolt Mountain Coaster, or you can select a more secluded option if you're looking for a relaxing stay. Charlemont is known for its ski areas and parks. Make sure you have time to check out the monuments while you're in the area.

What are some of the best holiday rentals that Charlemont has to offer?

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort: This highly rated holiday home rental in Charlemont is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Charlemont?

Expedia has 7 holiday rentals for your stay in Charlemont.

What’s there to see and do in Charlemont?

Mohawk Trail State Forest and Deerfield River are a couple of lovely local spots to get outside and enjoy nature. While here, Berkshire East Ski Resort and Zoar Outdoor/Deerfield Valley Canopy Tours are other places worth a visit.

What’s a holiday rental in Charlemont like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Charlemont. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for a small group gathering.