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Search Charlemont Cottages

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May 14 - May 15
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May 17 - May 19
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Compare Cottages in Charlemont with updated reviews, rates, and availability.

Property grounds
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
9.2 out of 10, Wonderful, (23)
"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
Exterior
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
Property grounds
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (93)
"I had a wonderful time. The lil stone house school is restored in a loving way! It feels homie and cosy and has a lot of stories to tell. The location is great for seeing museums or just go for a hike. Rich and Cheryl are on top with everything and very nice hosts!"
Charming historic cottage on scenic road to Mt. Greylock
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Exterior
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!
Exterior
Perfect for a peaceful get away in clean fresh Vermont air!
10.0 out of 10, Exceptional, (66)
"Linda Jane’s place is absolutely wonderful! The house was sparkling clean and had everything we could need for a weekend ski getaway. Also situated on a scenic pond in a quiet neighborhood. About 30 minute drive to Mt. Snow. Only thing to note, the cabin is a bit open concept, so Linda Jane kindly provided a divider to allow for more privacy between the downstairs bedrooms. We had a great weekend with friends and would love to plan a trip back!"
Perfect for a peaceful get away in clean fresh Vermont air!
Smart TV, fireplace
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
Fridge, microwave, oven, stovetop
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.
Interior
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Interior
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
3.5 star property
Pet-friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Interior
Charlemont Retreat on Chickley River w/ EV Charger
3.5 star property
Charlemont Retreat on Chickley River w/ EV Charger
Interior
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!
Interior
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!
Interior
Jacksonville Cabin w/ Wraparound Deck & Views
3.0 star property
Jacksonville Cabin w/ Wraparound Deck & Views
Interior
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!
Interior
Cozy Treetop Hideaway Near Harriman Reservoir!
3.5 star property
Cozy Treetop Hideaway Near Harriman Reservoir!
View from property
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!
Interior
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 Home w/ Pool Access, 20 Mins to Mt Snow
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 Home w/ Pool Access, 20 Mins to Mt Snow
Interior
Spacious Wilmington Home w/ Game Room & Deck!
3.5 star property
Spacious Wilmington Home w/ Game Room & Deck!
Property grounds
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
Don't see what you're looking for?
See all available properties in Charlemont
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

Exterior
Bear Creek Cabin
10.0 out of 10, Exceptional, (12)
"We had a very pleasant stay at Bear Creek Cabin. It’s just a short ride to Berkshire East for skiing and snow tubing. The house is beautiful and has all the essentials. Bunk room was perfect for the kids, and upstairs open master bedroom had beautiful views. We’d love to come back in the summer to enjoy the creek and warm weather activities. FYI- there are limited restaurant options in the immediate area, so we stopped for groceries on the way up. The kitchen had all we needed. Thanks for a...
The price is $400
$602 total
includes taxes & fees
May 15 - May 16
Bear Creek Cabin
Exterior
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort
9.6 out of 10, Exceptional, (116)
"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
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (857)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is $145
$160 total
includes taxes & fees
May 15 - May 16
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.

Frequently asked questions

Why book your cottage in Charlemont with Expedia?
Booking a cottage in Charlemont is as simple as deciding on your travel dates and choosing an ideal place for a vacation in the outdoors. From upscale retreats to affordable properties and cottages that come with perks like a pool, Expedia has something for all styles. As for irresistible deals? We’ve got them too!
How can I find cheap cottages in Charlemont?
With Expedia’s handy filter tool, locating cheap cottages in Charlemont couldn’t be easier. To view accommodations that’ll make your bank balance smile, refine your search by amenities, star rating and budget.
What is there to do in Charlemont near my cottage?
Charlemont has enough sights to entertain you for weeks, beginning with Double Edge Theatre. Ashfield Lake, Land of Providence and Bissell Covered Bridge are other fantastic attractions. If you’re lingering longer, Charlemont Federated Church and Hawley Bog Preserve will put the finishing touches on your itinerary.