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Check prices for these dates

In two weeks
12 Sept - 14 Sept
In one month
26 Sept - 28 Sept
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov

Featured Cottages in Charlemont and around

Our top choices for Charlemont cottages

The Clearing - Quiet - Close To Nature
Outdoor pool

The Clearing - Quiet - Close To Nature

10.0 out of 10, Exceptional, (197)
"Amazing views, lovely cottage!"
The Clearing - Quiet - Close To Nature
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Outdoor dining

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

8.6 out of 10, Excellent, (56)
"really enjoyed our stay. Place would be much better if there was a microwave."
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Exterior

Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access

8.8 out of 10, Excellent, (3)
"Perfect cottage on the water!! Enjoyed kayaking and pedal boat with family. Beautiful greenery! Very quick respond."
Charming 3-bedroom Lakefront cottage in Woodford VT with WiFi access
Rare new Home on Lake Whitingham. Semi-priv beach
Interior

Rare new Home on Lake Whitingham. Semi-priv beach

10.0 out of 10, Exceptional, (5)
"This home is spectacular, built on a hillside overlooking a pond. Very tastefully built into the landscape. Inside was very well appointed and plenty of room for our family. Three bathrooms was a big plusCould have spent the entire day lookjng out the windows"
Rare new Home on Lake Whitingham. Semi-priv beach
Near Hiking & Skiing: Home in Wilmington!
House (3 Bedrooms) | Interior

Near Hiking & Skiing: Home in Wilmington!

3.0 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."
Near Hiking & Skiing: Home in Wilmington!
Perfect for a peaceful get away in clean fresh Vermont air!
Exterior

Perfect for a peaceful get away in clean fresh Vermont air!

10.0 out of 10, Exceptional, (74)
"Loved the place and the stay. The pictures don’t do it justice. Its was everything we hoped for and more."
Perfect for a peaceful get away in clean fresh Vermont air!
Lake life at Woodford Cottage
Smart TV, fireplace

Lake life at Woodford Cottage

9.6 out of 10, Exceptional, (15)
"Perfect getaway for a family ski trip."
Lake life at Woodford Cottage
Charming historic cottage on scenic road to Mt. Greylock
Outdoor dining

Charming historic cottage on scenic road to Mt. Greylock

10.0 out of 10, Exceptional, (114)
"We had a great stay- no complaints! Very close to Jiminy Peak, where we were skiing, and the house was very comfortable. Thank you!"
Charming historic cottage on scenic road to Mt. Greylock
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
Interior

Rustic Marlboro Cottage: 4 Mi to Lake Raponda!

3.0 star property
Rustic Marlboro Cottage: 4 Mi to Lake Raponda!
Entire cottage in Berkshire Villiage
Books, stereo

Entire cottage in Berkshire Villiage

3.0 star property
9.8 out of 10, Exceptional, (6)
"The cottage was clean and as described. The street was very quiet."
Entire cottage in Berkshire Villiage
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Interior

Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location

10.0 out of 10, Exceptional, (7)
Charming 2-Bedroom Cottage with WiFi, AC in Quiet North Berkshire Location
Charlemont Retreat on Chickley River w/ EV Charger
House (4 Bedrooms) | Interior

Charlemont Retreat on Chickley River w/ EV Charger

3.0 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
Quaint Massachusetts Home w/ Yard & Grill!
House (2 Bedrooms) | Interior

Quaint Massachusetts Home w/ Yard & Grill!

3.0 star property
Quaint Massachusetts Home w/ Yard & Grill!
Wilmington Vacation Rental Near Hiking and Skiing!
House (4 Bedrooms) | Interior

Wilmington Vacation Rental Near Hiking and Skiing!

3.0 star property
Wilmington Vacation Rental Near Hiking and Skiing!
Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!
House (1 Bedroom) | Interior

Cozy 'fiddler's Rest:' Cabin: 11 Miles to Skiing!

3.0 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!
Cozy Wilmington Home: 6 Mi to Mount Snow!
House (4 Bedrooms) | Interior

Cozy Wilmington Home: 6 Mi to Mount Snow!

3.0 star property
Cozy Wilmington Home: 6 Mi to Mount Snow!
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Exterior

Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

9.6 out of 10, Exceptional, (65)
"We enjoyed our stay in this cozy cabin on the ridge. The owners have great taste and they have thought of everything to make the stay pleasant. "
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow
Luxury Vacation Rental in the Berkshires!
House (3 Bedrooms) | Interior

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
Wilmington Retreat Near Trails, Skiing & Festivals
House (3 Bedrooms) | Interior

Wilmington Retreat Near Trails, Skiing & Festivals

3.0 star property
10.0 out of 10, Exceptional, (2)
"Great location and awesome house. Owners were easy to communicate with. "
Wilmington Retreat Near Trails, Skiing & Festivals
West Dover Vacation Rental w/ Hot Tub Near Mt Snow
House (4 Bedrooms) | Interior

West Dover Vacation Rental w/ Hot Tub Near Mt Snow

3.0 star property
West Dover Vacation Rental w/ Hot Tub Near Mt 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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Top Charlemont Hotel Reviews

Find out more about Charlemont

Find out more about Charlemont

Charlemont Cottages information

Number of reviews
Accommodation
102 Cottages
Lowest Price
Highest Price

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Why book your cottage in Charlemont with Expedia?
Expedia has some excellent cottages in Charlemont, so start planning for an unforgettable holiday on nature's doorstep. If you're sticking to a budget, select how much you want to spend and the star rating of your property. Or take advantage of our filters to search for cottages with a kitchen or a pool. We'll help you find the perfect pad whatever your style of travel or plans.
How can I find cheap cottages in Charlemont?
An excellent way to compare cheap cottages in Charlemont is with Expedia's handy filter tool. Tailor your search results by star rating, budget and amenities to secure excellent rates in just a few clicks.
What is there to do in Charlemont near my cottage?
The ultimate travel accessory is a well-planned itinerary. Hawley Bog Preserve is a terrific place to start your adventures in Charlemont.