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Compare 487 Vacation Homes in Charlemont with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (245)
"What a great spot to stay for the few days we were there Can’t wait to come back! "
The price is AED 551
AED 841 total
includes taxes & fees
10 May - 11 May
Berkshire Village Carriage House - Super Private!!

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (50)
"Great location, communicative and welcoming hosts, and great amenities. We loved grilling and using the firepit. The surrounding area is great to walk around in. Easy drive from here to Mt Snow."
The Jelly Mill-A River Retreat

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is AED 2,016
AED 3,810 total
includes taxes & fees
12 May - 13 May
Hancock Village Inn at Jiminy Peak

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

9.8 out of 10, Exceptional, (98)
"We were attending a horse show locally. We stayed a few nights and everything about this day was easy from start to finish."
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

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

10.0 out of 10, Exceptional, (73)
"Very spacious and comfortable. Biggest selling point was its proximity to family in the area."
1810 Brook Side Mill/House / EV Level 2 Charging on Site

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

10.0 out of 10, Exceptional, (6)
"We had an absolute amazing stay at Todd‘s place. Communication was extremely responsive. This was a last-minute trip with the family during the holiday and we had an absolute blast. The kids had so much fun in the bunk bedroom. The house is extremely spacious and absolutely beautiful. To be able to ski to the backyard was such a luxury. This was a special house with an unreal location. We will be coming back in February. Thank you so much for the memories."
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

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"Unit is a little outdated but nice.Not truly a ski in - out since you have to walk on the road about 200 yards to get to the Sachem trail.Condo does need ice cube trays since the ice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

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (11)
"The property is very large. Lots of sleeping area. Many activities within the rental to keep everyone off all ages busy, kept finding new things in nooks and crannies. Lots of property got our dog to run. "
GAMERS HAVEN, River Wine Inn!

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"Lovely ski weekend! Best memory: hot tubbing at sunset after skiing with snow falling all around! "
Mountain Blossom Retreat by Evergreen Home

Wilmington Vacation Rental Near Hiking and Skiing!

9.4 out of 10, Exceptional, (19)
"Perfect weekend house close to mt snow"
Wilmington Vacation Rental Near Hiking and Skiing!

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

7.8 out of 10, Good, (68)
"Several items, microwave and dishwasher, were not working. House was somewhat clean. Great location, but very dated and in need of a upgrade."
Mountain-view home near the slopes with at-home entertainment - dog-friendly

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

8.4 out of 10, Very Good, (27)
"Awesome Cabin, private and peaceful location."
Bright three-level home with water views, jetted tub, firepit, and pool table

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (14)
"House was great, very comfortable, location was perfect for our needs. All of us had an excellent stay."
Amherst, Perfect Location, UMass, Smith, MHC!

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

10.0 out of 10, Exceptional, (217)
"The owner was available through call/text, although we didn’t need anything. Beautiful house with even more beautiful views. The game room was a big hit. Hot tub and sauna were great as well. This house has everything! We will definitely be back!"
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

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

9.6 out of 10, Exceptional, (5)
"We usually don’t book places that don’t have several reviews, but since we knew the area, we decided to “take a chance”. We are very glad we did! We stayed 5 nights and were very happy. The heat pumps were great since the temperature dipped below 0. The accommodations were very comfortable and we had everything we needed to make our stay enjoyable. "
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

Dancing Horse Lodge

9.6 out of 10, Exceptional, (41)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

10.0 out of 10, Exceptional, (4)
"great Place, quiet, clean and very comfortable."
The price is AED 474
AED 1,656 total
includes taxes & fees
11 May - 12 May
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Modern Mount Snow Gnarvana - Balcony/Pet-Friendly/Walk to Lifts & Lodge

10.0 out of 10, Exceptional, (19)
"Great location directly across from Mount Snow great place, clean, all amenities, definitely will return "
The price is AED 569
AED 1,656 total
includes taxes & fees
11 May - 12 May
Modern Mount Snow Gnarvana - Balcony/Pet-Friendly/Walk to Lifts & Lodge

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (21)
"Easy stay, good location for us. Would stay again. "
The price is AED 474
AED 808 total
includes taxes & fees
18 May - 19 May
Lovely 2nd Floor Apartment

2.5mi from the lake! Fire pit, arcade, yard games!

10.0 out of 10, Exceptional, (12)
"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. "
The price is AED 786
AED 1,917 total
includes taxes & fees
2 Jun - 3 Jun
2.5mi from the lake! Fire pit, arcade, yard games!
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, (30)
"Loved it, will definitely book again!"
The price is AED 1,469
AED 2,150 total
includes taxes & fees
9 May - 10 May
Bear Creek Cabin

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

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1804)
"The property was clean and the staff very accommodated."
The price is AED 372
AED 455 total
includes taxes & fees
11 May - 12 May
Vacation Village in the Berkshires
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.