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Compare 410 Vacation Homes in Charlemont with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (239)
"Property was very nice Kirchen could use some additons -starting with a ladle "
The price is AED 551
AED 833 total
includes taxes & fees
10 Mar - 11 Mar
Berkshire Village Carriage House - Super Private!!

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"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...
The price is AED 2,196
AED 3,898 total
includes taxes & fees
11 Mar - 12 Mar
Hancock Village Inn at Jiminy Peak

Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!

9.6 out of 10, Exceptional, (29)
"We had a wonderful stay here in Pownal!! We came for a writing retreat, looking for a cozy property with space to think, work, catch up, and relax. Talk about inspiring surroundings!! The property is cozy and well kept, with a spacious kitchen and plenty of little luxuries! Warm floors in the bathroom and a hot tub, fireplace… it’s a perfect spot. The property manager was communicative and friendly. Highly recommended! "
Vintage BARN Apartment-POOL-HotTub-FirePit-Hiking-Museums-Theater-Pets welcome!

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 AED 533
AED 759 total
includes taxes & fees
10 Mar - 11 Mar
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (6)
"Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Comfortable Berkshires retreat on mtn resort, SISO

The price is AED 591
AED 1,768 total
includes taxes & fees
2 Apr - 3 Apr
Comfortable Berkshires retreat on mtn resort, SISO

Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

9.6 out of 10, Exceptional, (32)
"The house was nicer than we expected we had a wonderful time and will recommend to friends."
Beautiful 3BR river view, huge glass wall Log House -2200 sq/ft

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (71)
"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.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site

Relaxing Retreat in the Heart of Dover

Relaxing Retreat in the Heart of Dover

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

10.0 out of 10, Exceptional, (47)
"Condo was spacious and supplied with everything we needed for a great stay! We cooked 2 out of 3 nights so we appreciated that the kitchen was stocked with any spice you would need to prepare meals, not just the usual salt & pepper only. The location was perfect for our ski trip to Mount Snow and the market was also close by so once we were settled in there was very little driving to do. The living room furniture was comfy, and the dining area was huge and both had gorgeous views of the...
The price is AED 386
AED 1,295 total
includes taxes & fees
24 Mar - 25 Mar
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Bright three-level home with water views, jetted tub, firepit, and pool table

8.4 out of 10, Very Good, (26)
"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"
Bright three-level home with water views, jetted tub, firepit, and pool table

Cozy retreat near slopes

5.0 out of 10, (8)
"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"
Cozy retreat near slopes

Wilmington Vacation Rental Near Hiking and Skiing!

9.2 out of 10, Wonderful, (19)
"Perfect stay for the boys to get together and ski. "
Wilmington Vacation Rental Near Hiking and Skiing!

Dog-friendly home w/ WiFi, private washer/dryer, and wood & electric fireplaces

8.4 out of 10, Very Good, (9)
"The house was great for our family vacation- ages four to eighty four. Well stocked kitchen, comfortable beds, 2 living spaces with TVs. The grill and dining deck aren’t immediately accessible from the kitchen as is off the upstairs rec room, but would work fine if planned ahead. Located in a quiet area in a natural lot but close to restaurants and within an hour of several attractions"
Dog-friendly home w/ WiFi, private washer/dryer, and wood & electric fireplaces

19th c. Barn in the Berkshires

9.6 out of 10, Exceptional, (85)
"We planned to stay at this property in order to ski at Jiminy peak, and it was perfect, not a long drive at all. The barn stays very warm with the individual heaters as well as the wood stove in the middle of the main room. The kitchen was equipped with everything you need, they even had coffee and sugar! .. Communication with the hosts was seamless. We lost power due to a winter storm, the entire area did, and that wood stove worked its magic. The property owners made sure we were alright...
19th c. Barn in the Berkshires

Mountain-view home near the slopes with at-home entertainment - dog-friendly

7.8 out of 10, Good, (66)
"Parents, kids and dog had a terrific time. Perfect distance to Mount Snow. Will definitely return! "
Mountain-view home near the slopes with at-home entertainment - dog-friendly

6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

10.0 out of 10, Exceptional, (4)
"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."
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

Dog-friendly cabin with pools, hot tub, tennis & pickleball - near Mt. Snow

8.8 out of 10, Excellent, (3)
"We had an awesome stay! Clean house"
Dog-friendly cabin with pools, hot tub, tennis & pickleball - near Mt. Snow

Massachusetts Vacation Rental w/ Deck & Grill

9.2 out of 10, Wonderful, (14)
"There’s a backup generator if you lose power!! Great log cabin feel and plenty of space. "
Massachusetts Vacation Rental w/ Deck & Grill

Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!

9.8 out of 10, Exceptional, (20)
"The home was modern, clean and efficient space for the 6 of us. The interior is actually a bit brighter than the pictures would suggest. Kitchen was well stocked. The loft had a TV room, plenty of DVDs and games, and an extra Twin Bed. Beds in general were comfortable and the sheets and comforters were modern.We were there during a heavy snowstorm and Venetia and her family were prompt and very responsive with our questions. They went over and beyond in helping us with one of our cars that...
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!
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.
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Other property types in Charlemont

Bear Creek Cabin

9.8 out of 10, Exceptional, (27)
"Loved it, will definitely book again!"
The price is AED 1,469
AED 2,199 total
includes taxes & fees
10 Mar - 11 Mar
Bear Creek Cabin

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1786)
"It was very nice. Had a kitchen and 2 tvs!"
The price is AED 400
AED 476 total
includes taxes & fees
13 Mar - 14 Mar
Vacation Village in the Berkshires

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 547
AED 600 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort
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.