Charlemont Vacation Rentals from CA $143: Short-Term Rentals for 2026

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Our top choices for Charlemont vacation rentals

A spacious living area with a stone fireplace, wooden flooring, and a cozy seating area.

1. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

Charlemont

Georgia P.

CA $1,888 total

includes taxes & fees

Nov 3 - Nov 4

A log cabin with a balcony, surrounded by trees.

2. Bear Creek Cabin

Charlemont

Hillary S.

CA $862 total

includes taxes & fees

Oct 18 - Oct 19

A two-story house with a front porch, a staircase leading to the entrance, and a well-maintained garden.

3. 2 Twin beds on 1st floor with En-suite bathroom.

Shelburne Falls

CA $267 total

includes taxes & fees

Nov 4 - Nov 5

A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

4. Private bed with En-suite bathroom Marigold Room

Shelburne Falls

CA $301 total

includes taxes & fees

Nov 8 - Nov 9

A two-story blue house with a porch, surrounded by a garden with orange flowers.

5. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Stamford

Bill

CA $232 total

includes taxes & fees

Oct 12 - Oct 13

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

6. Vacation Village in the Berkshires

Williamstown

Denton

CA $143 total

includes taxes & fees

Nov 1 - Nov 2

A blue house with a porch, a wooden bench, and a door.

7. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

Greenfield

Andrew R.

CA $351 total

includes taxes & fees

Nov 4 - Nov 5

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

8. Berkshire Mountain Lodge

Pittsfield

marilyn

CA $177 total

includes taxes & fees

Nov 2 - Nov 3

A hallway with wooden flooring, white walls, and a bed in the background.

9. Cozy private 2 bed apartment in Shelburne Falls

Shelburne Falls

maureen

CA $610 total

includes taxes & fees

Oct 12 - Oct 13

A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

10. Lovely 2nd Floor Apartment

Greenfield

Jane P.

CA $328 total

includes taxes & fees

Nov 3 - Nov 4

11. Rose room Victorian home queen bed private bath

Shelburne Falls

CA $285 total

includes taxes & fees

Oct 28 - Oct 29

A living room with a beige sofa, a patterned rug, and a wooden floor.

12. Spacious & Cozy Ground Floor 2/3 Bed private suite

Shelburne Falls

Russ D.

CA $530 total

includes taxes & fees

Nov 4 - Nov 5

13. Balcony Room in Victorian Home private bath

Shelburne Falls

CA $296 total

includes taxes & fees

Oct 28 - Oct 29

A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

14. Penthouse Apartment on Park Street

Adams

Margaret C.

CA $400 total

includes taxes & fees

Oct 18 - Oct 19

"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

15. Downtown | Waterfront | Walk to Shops

Williamstown

Tricia

CA $396 total

includes taxes & fees

Nov 4 - Nov 5

16. New Studio In Town, By the Water

Williamstown

Lydia J.

CA $383 total

includes taxes & fees

Nov 3 - Nov 4

A house with a staircase leading to a porch, surrounded by snow and string lights.

17. Light-filled treetop apartment close to downtown Greenfield and Highland Park

Greenfield

Tom

CA $409 total

includes taxes & fees

Oct 14 - Oct 15

A wooden interior with a kitchen, bar area, and dining space.

18. The Studio with a View. Bring your dog, too!

Brattleboro

James M.

CA $384 total

includes taxes & fees

Oct 25 - Oct 26

An aerial view of a house surrounded by a forest with autumn foliage.

19. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

Whitingham

Jonathan

CA $801 total

includes taxes & fees

Nov 2 - Nov 3

"Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping." ...Lina -- "the fire pit and creek are like a private oasis in the backyard." ... Nachama -- ( no firewood fees )

20. 2-Bdr Apt In Town, By the Water

Williamstown

Thomas

CA $431 total

includes taxes & fees

Oct 19 - Oct 20

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Top Charlemont Hotel Reviews

Hotel On North

10/10 Excellent

"This is a great hotel. Large rooms, great amenities and a steak house restaurant that is superb. We like it so much we are staying an extra night."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"This hotel was clean and in a good location. The staff was friendly and helpful. I loved their nice pool and jacuzzi and enjoyed it. Breakfast was OK. Rooms are clean and big enough to make your money worth for it. One more important thing for us was its free and big parking lot."

Latchis Hotel

8/10 Good

"We enjoyed our stay at the historic Latchis Hotel. You really get the feeling of stepping back in time. The staff were very helpful and provided recommendations on places to eat besides just checking us in. The room was fine and the working record player with records was a nice touch. Parking is about a half block away behind the hotel. Make sure you see the historic Latchis Theater’s main room. It is really amazing and will definitely take you back in time."

Hideaway Inn Mt. Snow

8/10 Good

"The room was VERY small, but it was clean and the bed was comfortable. There is not an attendant or any staff onsite. I had a bit of trouble getting the pet registration taken care of since I booked through a 3rd party. We asked for a 1st floor room since there's not an elevator. When we received our check-in information, we were given a room on the 2nd floor. If we only had to carry backpacks, it might have been fine. However, we had large cases, so it was difficult to drag them up the stairs. Also, if you are an above average size person, know that these rooms are small spaces. The bathroom is barely big enough to turn around in and the shower is tiny."

Find out more about Charlemont

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Charlemont. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

Frequently asked questions

Are there vacation rentals in Charlemont?

Yes, there are vacation rentals in Charlemont close to Thunderbolt Mountain Coaster, or you can choose a secluded option if you're looking for extra privacy while you relax. Charlemont is known for its ski areas and parks. Make sure you have time to check out the monuments while you're in the area.

What's the top vacation rental that Charlemont has to offer?

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort: This Charlemont vacation home rental is located in the mountains and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Charlemont?

Expedia has 14 vacation rentals for your stay in Charlemont.

What’s there to see and do in Charlemont?

Deerfield River and Swift River are a couple of lovely local spots to get outside and enjoy nature. While here, Thunderbolt Mountain Coaster and Berkshire East Ski Resort are other places worth a visit.

What’s a vacation rental in Charlemont like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Charlemont. Vacation rentals feature amenities like laundry facilities and kitchens so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can offer a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family trip or a small group gathering.

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Check prices for these dates

Our top choices for Charlemont vacation rentals

1. Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike MTB Rafting

2. Bear Creek Cabin

3. 2 Twin beds on 1st floor with En-suite bathroom.

4. Private bed with En-suite bathroom Marigold Room

5. Getaway Near Mass MoCA, Great Hiking, Scenic Views

6. Vacation Village in the Berkshires

7. Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

8. Berkshire Mountain Lodge

9. Cozy private 2 bed apartment in Shelburne Falls

10. Lovely 2nd Floor Apartment

11. Rose room Victorian home queen bed private bath

12. Spacious & Cozy Ground Floor 2/3 Bed private suite

13. Balcony Room in Victorian Home private bath

14. Penthouse Apartment on Park Street

15. Downtown | Waterfront | Walk to Shops

16. New Studio In Town, By the Water

17. Light-filled treetop apartment close to downtown Greenfield and Highland Park

18. The Studio with a View. Bring your dog, too!

19. Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11

20. 2-Bdr Apt In Town, By the Water

Find vacation rentals that suit your style

Top Charlemont Hotel Reviews

Hotel On North

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

The Yankee Inn

Hotel UMass

Latchis Hotel

Hideaway Inn Mt. Snow

Vacation Village in the Berkshires

Grand Summit Resort, A Vail Resorts Property

Hotel Downstreet, an Ascend Collection Hotel

Find out more about Charlemont

Frequently asked questions

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