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Search Cottages in Charlemont

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Compare 76 Cottages in Charlemont with updated reviews, rates, and availability.

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.0 out of 10, Wonderful, (24)
"Awesome cabin, fireplace was amazing. Spacious open and a great place to spend time and relax"
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Summer
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (94)
"I adored my stay at The Stone School. Rich and Cheryl were terrific hosts who had great suggestions for food and things to do. And the whole experience was easy to navigate. Excellent marks for cleanliness, comfort, ease of parking, quiet & solitude, quaintness, local pleasures. I found it perfect for myself and it would also be ideal for a couple (or perhaps a couple with one or two young children.) The bathroom is on the first floor with a modern sink and vanity; everything looks brand...
Charming historic cottage on scenic road to Mt. Greylock
Green River Cottage
Cozy Cottage Along Idyllic Green River
10.0 out of 10, Exceptional, (33)
"Charming house with everything we needed!"
Cozy Cottage Along Idyllic Green River
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Book now for a magical & peaceful fall stay before its too late!
Great Place to get away and have clean fresh air surround you!
9.8 out of 10, Exceptional, (120)
"The house has a beautiful view of the lake and is very clean. It is beautifully decorated, and has all the supplies that are needed for comfortable stay. The owner is very thoughtful and the house is nicely organized. We appreciated the Christmas decorations during our holiday stay, extra towels prepared for the dog and the dog treats. The house is nicely stocked with family games, and there is beautiful trail in walking distance: up the hill to vast trail, and path through the forest to Little...
Great Place to get away and have clean fresh air surround you!
Newly sided entire house and garage
Perfect for a peaceful get away in clean fresh Vermont air!
10.0 out of 10, Exceptional, (67)
"We travel to Vermont frequently. This was the best rental we have had. The property is sparkling clean and very cozy. The location is beautiful, and the host is very responsive, taking great pride in her property. I wish I could add more stars to my recommendation. My husband and I will definitely return."
Perfect for a peaceful get away in clean fresh Vermont air!
Livingroom - Woodburning stove and sleeper double size pull out couch.
Lake life at Woodford Cottage
9.6 out of 10, Exceptional, (11)
"Stayed Fri - Mon over Columbus Day weekend - overall the cabin itself was very nice. Clean, cozy and all the amenities listed. Some things to note: -There’s no dishwasher so bring paper plates and bowls to make life easier! -There’s a washer dryer combo in the kitchen but only the dryer is available for use -The front door is tricky with the lock but you’ll quickly get the hang of it -The shower is also tricky at first but you’ll also get the hang of that! -Not really any closet or drawer space...
Lake life at Woodford Cottage
Interior
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (20)
"the property was very well maintain, the host put alot of very personal and special touches inside the house.i have stayed in alot of houses over the years, but this one the host made you feel right at home."
Cozy Berkshire cottage with fireplace.
Property grounds
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Property grounds
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
3.5 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Living area
Charlemont Retreat on Chickley River w/ EV Charger
3.5 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property! Check-in was effortless, and communication was excellent. The property had the southern charm my family and I desired, with ample space. The kids and our dog Rider had a ball. All the amenities you could think of, just in case you may have forgotten something. The quiet and serene nature of the property was beautiful, and I am so happy we chose to stay here. It is a historic house with nice modern updates and a country appeal. Thank you for making our weekend pleasant...
Charlemont Retreat on Chickley River w/ EV Charger
Exterior
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
3.5 star property
10.0 out of 10, Exceptional, (1)
"We had a truly wonderful stay. The cottage and property are beautiful, peaceful and very special. Great views! Our host thought of everything, it's very comfortable and lovely. Best place to stay in Southern Vermont! Don't miss the Tiny Bread Box on Saturdays; it's just up the road. We'll defiantly be back for another visit."
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
Property grounds
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.5 star property
10.0 out of 10, Exceptional, (1)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
Charming Wilmington Cabin, 8 Mi. to Mt Snow!
Property grounds
Jacksonville Cabin w/ Wraparound Deck & Views
3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Living area
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
3.0 star property
10.0 out of 10, Exceptional, (1)
"The host was so kind and helpful. I will definitely cime abck here. "
Bennington Home w/ Deck ~ 5 Mi to Bald Mountain!
Exterior
Cozy Treetop Hideaway Near Harriman Reservoir!
3.5 star property
Cozy Treetop Hideaway Near Harriman Reservoir!
Hinsdale Vacation Rental | 3BR | 2BA | 1,340 Sq Ft | Stairs Required
Picturesque Cottage with Sunroom on Ashmere Lake!
9.6 out of 10, Exceptional, (17)
"It was perfect for me and my close friends. We enjoyed the lake each day and all remarked that the beds were very comfortable. Wish we could have stayed longer."
Picturesque Cottage with Sunroom on Ashmere Lake!
Exterior
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
3.5 star property
10.0 out of 10, Exceptional, (1)
Wilmington Home on 18 Acres ~ 9 Mi to Skiing!
Interior
Wilmington Getaway w/ Pool Access: Near Hiking!
3.5 star property
10.0 out of 10, Exceptional, (1)
"Owner Brent was helpful and quick to respond to questions. The house is near Mount Snow great for skiing! Very nice place to stay, we will definitely stay again when booking for next year."
Wilmington Getaway w/ Pool Access: Near Hiking!
Exterior
Spacious Wilmington Home w/ Game Room & Deck!
3.5 star property
Spacious Wilmington Home w/ Game Room & Deck!
Private dock with 2 Adirondack chairs.
Berkshires - Charming Lakefront Cottage
10.0 out of 10, Exceptional, (1)
"We stayed for a week at Stacy and Bob's place. Communication was excellent ahead of time. The house was incredibly clean upon arrival and everything was just as listed. They even went above and beyond with a wonderful welcome basket. They even had a small first aid/medicine kit, "just in case." We truly enjoyed their place."
Berkshires - Charming Lakefront Cottage
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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.

Other property types in Charlemont

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, (117)
"Another great stay at Hawley. House never disappoints. Weather even cooperated. Thanks Again Lark! Lew"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
Exterior
Bear Creek Cabin
10.0 out of 10, Exceptional, (14)
"Had such a wonderful stay in the beautiful Berkshires at this unique cabin property! Everything was clean and well-maintained. Very rustic and charming. We had a lot of fun by the fire and walking down to the river in the backyard. So many things to do in this area! Hiking, rafting, and dining in the nearby towns! Would definitely return!"
The price is SAR 1,500
SAR 2,266 total
includes taxes & fees
29 Jum. I - 30 Jum. I
Bear Creek Cabin
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (858)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is SAR 596
SAR 654 total
includes taxes & fees
29 Jum. I - 30 Jum. I
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.

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