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Compare 395 Vacation Homes in Charlemont with updated reviews, rates, and availability.

Primely Located Dover Escape < 1 Mi to Mt Snow!
Dover Vacation Rental | 2BR | 2BA | 1,350 Sq Ft | Stairs Required

Primely Located Dover Escape < 1 Mi to Mt Snow!

9.6 out of 10, Exceptional, (15)
"Location was perfect with the Moover transfer right on the door and even walking distance to the ski mountain(8’ walk). House was clean and had everything we needed. The only thing that could be better was the communication with the apt management/ owner. We couldn’t find the pool or hot tub and got no answer after asking. We had other questions that never got answered too. But overall for it was a great New year’s holiday!"
Primely Located Dover Escape < 1 Mi to Mt Snow!
Fabulous Mountain Top Retreat - 10 minutes from mount snow!
Private kitchen

Fabulous Mountain Top Retreat - 10 minutes from mount snow!

Fabulous Mountain Top Retreat - 10 minutes from mount snow!
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

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

9.0 out of 10, Wonderful, (41)
"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!
Berkshire Village Carriage House - Super Private!!

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 AED 536
AED 821 total
includes taxes & fees
30 Dec - 31 Dec
Berkshire Village Carriage House - Super Private!!
Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating
The house was originally built in 1864 and completely updated in 2009

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
Walk to Mt. Snow! Hot tub! Sauna! Sleeps 16
Take in stunning views from our large windows while cozied by the fire

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
Beautiful 4 Bedroom Townhome Minutes from Mt Snow
Living area

Beautiful 4 Bedroom Townhome Minutes from Mt Snow

9.6 out of 10, Exceptional, (19)
"The property has a great location to so many activities, shops and places to eat. The house was a few steps from the pool which my kids loved"
Beautiful 4 Bedroom Townhome Minutes from Mt Snow
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!
Exterior

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

10.0 out of 10, Exceptional, (38)
"Great house for the family. Easy to jump on shuttle and hit the slopes. Easy to just drop your bags and enjoy the view of the mountain. Comfy couches. Big dining table to gather around. Kitchen has everything you need. Well stocked with linens and towels. Owner was communicative and helpful."
The price is AED 1,928
AED 3,200 total
includes taxes & fees
24 Jan - 25 January 2025
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!
The Jelly Mill-A River Retreat
Green River Cottage. Walk up ramp to enter patio area, lockbox on inside door.

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (43)
"It is a beautiful home with a ton of space (we only had 3 people, but it easily sleeps 6), very clean and well-kept. Our hosts provided everything we needed to make our stay perfect. I also like that the hosts were not overboard with all the rules, as with some other rentals. The hosts were beyond friendly and had excellent communication throughout the whole process. If you are looking for a lovely home with a ton of space to stay while exploring Vermont and Massachusetts, I highly recommend...
The Jelly Mill-A River Retreat
Amherst, Perfect Location, UMass, Smith, MHC!
The Valley is known for our picturesque red tobacco barns and expansive cornfields.

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!
Charlemont Retreat on Chickley River w/ EV Charger
Charlemont Vacation Rental | 4BR | 2BA | 3,000 Sq Ft | Stairs Required

Charlemont Retreat on Chickley River w/ EV Charger

9.4 out of 10, Exceptional, (20)
"We loved the property! Our family, which included 2 very young grandchildren all felt comfortable in this historic home with 2 modern bathrooms. I loved the open kitchen and family rooms, and the original wide plank floors. Plus, we were happy to find toys to entertain the 3 year old. The owners were very gracious and responsive. Visitors should just be aware that the owners' unit shares a common wall with the house. Dog barking and sounds of their kitchen preparation were evident through the...
Charlemont Retreat on Chickley River w/ EV Charger
Forest Home with Shared Pool & Hot Tub, WiFi, & Washer/Dryer - One Small Dog OK

Forest Home with Shared Pool & Hot Tub, WiFi, & Washer/Dryer - One Small Dog OK

8.4 out of 10, Very Good, (8)
"Great house in a great neighborhood for two families and our dog that wasn’t too far from Mt Snow. The clubhouse is a plus with a pool!"
Forest Home with Shared Pool & Hot Tub, WiFi, & Washer/Dryer - One Small Dog OK
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Marina

Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.

9.6 out of 10, Exceptional, (10)
"As advertised "
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!
Lush woodland setting is private, yet five minutes to Spring Street.

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

9.8 out of 10, Exceptional, (19)
"Such a gorgeous house! We loved walking the nearby trails and how close it was to Williams. Venetia was the best!"
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
Property grounds

500ft across the street to Carnitha. Gromet to main lift or take Moover to Base

10.0 out of 10, Exceptional, (32)
"We had the most enjoyable and comfortable stay at this lovely home away from home! Jen was more than welcoming and always very responsive. The house was very clean and located conveniently across the street from the mountains. Looking forward to staying here again next season! :)"
500ft across the street to Carnitha. Gromet to main lift or take Moover to Base
Outdoor Enthusiasts Paradise in Beautiful Vermont!
Main Living room - First Floor

Outdoor Enthusiasts Paradise in Beautiful Vermont!

10.0 out of 10, Exceptional, (3)
"This rental property was very clean and spacious. There is air conditioning upstairs and ceiling fans (which is hard to come by in this area). Great location. Highly recommend."
Outdoor Enthusiasts Paradise in Beautiful Vermont!
Plainfield House in a 10,000 acre state forest and private pond
Front lawn for sledding

Plainfield House in a 10,000 acre state forest and private pond

9.6 out of 10, Exceptional, (84)
"Very nice place, clean, great communication. "
Plainfield House in a 10,000 acre state forest and private pond
Modern Mount Snow Retreat with Walk to Ski Lifts & Lodge
Located across the street from the Carinthia base lodge. *Ski season only

Modern Mount Snow Retreat with Walk to Ski Lifts & Lodge

10.0 out of 10, Exceptional, (13)
"This is one of the nicest properties that I stayed at. Modern sparkling clean state of the art. Property owners were attentive when needed, definitely returning!"
Modern Mount Snow Retreat with Walk to Ski Lifts & Lodge
The dreamiest place in Southern Vermont!
Interior

The dreamiest place in Southern Vermont!

10.0 out of 10, Exceptional, (1)
"This was a great property! Only wish there was a larger fridge/ freezer and ice maker! Otherwise great! We did not get to use the fire pit as we were hardly there but it was great for what we needed."
The price is AED 1,267
AED 2,984 total
includes taxes & fees
5 Jan - 6 January 2025
The dreamiest place in Southern Vermont!
West Dover Home w/ Deck ~ 2 Mi to Mount Snow!
West Dover Vacation Rental | 4BR | 4BA | Stairs Required | 2,900 Sq Ft

West Dover Home w/ Deck ~ 2 Mi to Mount Snow!

9.8 out of 10, Exceptional, (6)
"Great experience - lots of beds! Great for 2 families"
West Dover Home w/ Deck ~ 2 Mi to Mount Snow!
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

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
View of house as seen from road near the brook

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
Exterior

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 AED 1,175
AED 1,830 total
includes taxes & fees
25 Dec - 26 Dec
Bear Creek Cabin
Vacation Village in the Berkshires
Lobby

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 AED 689
AED 792 total
includes taxes & fees
1 Jan - 2 January 2025
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.