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Compare 495 Vacation Homes in Charlemont with updated reviews, rates, and availability.

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (25)
"Easy stay, good location for us. Would stay again. "
The price is AED 474
AED 796 total
includes taxes & fees
2 Jun - 3 Jun
Lovely 2nd Floor Apartment

Contemporary Berkshire Home with Views of Taconic Golf Course

Contemporary Berkshire Home with Views of Taconic Golf Course

Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

10.0 out of 10, Exceptional, (2)
"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "
Lakeside Serenity! 4-bedroom house in charming Hinsdale next to Lake Ashmere.

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

9.6 out of 10, Exceptional, (32)
"My wife and I had a wonderful and relaxing time celebrating our anniversary. We really enjoyed sitting by the river."
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, (73)
"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

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

9.8 out of 10, Exceptional, (100)
"Great stay in Amherst again"
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

Luxury Vacation Rental in the Berkshires!

10.0 out of 10, Exceptional, (13)
"Stayed here multiple times and will come back again. Great place to stay…"
Luxury Vacation Rental in the Berkshires!

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (56)
"Perfect location and accommodation for my family. The home was as described. I would recommend it. The property owner was easy to work with. "
Lake Front Home in Heart of the Berkshires Near Jiminy Peak

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!

1840's Whaling Captain's Farm Estate, 6-10 guests

10.0 out of 10, Exceptional, (3)
"Such a beautiful home and property. We had a great time exploring during the day and spending time together at night. Sunsets over the pond are particularly lovely and the screened in porch and sitting around a fire in the chiminea outside are the perfect spots for a cocktail. We look forward to our next visit!"
1840's Whaling Captain's Farm Estate, 6-10 guests

Newly updated VT escape for all occasions w/ New Kitchen, Game Rooms, Media Room!

10.0 out of 10, Exceptional, (10)
"We loved the house, the deck and the property amenities."
The price is AED 720
AED 1,964 total
includes taxes & fees
8 Jun - 9 Jun
Newly updated VT escape for all occasions w/ New Kitchen, Game Rooms, Media Room!

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 404
AED 1,569 total
includes taxes & fees
2 Jun - 3 Jun
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Spacious 4-bedroom Pet Friendly Home Near Lakes and Hiking

10.0 out of 10, Exceptional, (1)
"We had a great experience at Erika’s place. The house was great. Spacious & cozy at the same time. Plenty of amenities to keep the kids entertained from the theater in the basement to card games, fussball, darts, backyard, and firepit,for roasting marshmallows. We hiked at Molly Stark, went to the reservoir, & skied at Mt. Snow all in under 20 min away. We had a good time, it was a perfect getaway for our spring break. "
Spacious 4-bedroom Pet Friendly Home Near Lakes and Hiking

Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

6.0 out of 10, (1)
"Inside property was great - house was very fun and spacious and clean . HOWEVER..the driveway clearly hadn’t been plowed for a long time when we got there and so once we pulled in our cars were stuck. We were trapped at the house for 3 days. The plow driver came to plow the neighbor and told us he hadn’t been paid by the owners so hadn’t been plowing for some time The owners finally arranged for a different plow to come but not being able to leave for 3 days really affected our ability to...
Home with View of Mount Snow!! Indoor-pool, spa, sauna Gym & more Sleeps 23+

Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

2.0 star property
10.0 out of 10, Exceptional, (8)
"Great place! Location was ideal, close to everything. "
Stylish new 2 bedroom property in enchanting Shelburne Falls Village.

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

10.0 out of 10, Exceptional, (19)
"Wonderful condo - clean, cozy, and very well appointed. Great location and the Moover conveniently picks up right next door. Jen and Erica are excellent hosts, very responsive and communicative. Would definitely stay here again!"
Modern Mount Snow Gnarvana - Balcony/Pet-Friendly/Walk to Lifts & Lodge

Spyglass village- Golf & Ski

10.0 out of 10, Exceptional, (3)
"Great location, close to Mount Snow, ideal for skiing. Property is newly renovated, very functional and well appointed. We really enjoyed our stay."
Spyglass village- Golf & Ski

'Luna Stella' - West Dover Home 1 Mi to Mt Snow!

9.8 out of 10, Exceptional, (64)
"Great property. Enjoyed our stay."
'Luna Stella' - West Dover Home 1 Mi to Mt Snow!

Fabulous Mountain Top Retreat - 10 minutes from mount snow!

Fabulous Mountain Top Retreat - 10 minutes from mount snow!

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (142)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
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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