A wooden covered bridge with a 'DANGER KEEP OFF DAM' sign, surrounded by lush greenery.

Charlemont Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Charlemont vacation rentals

A cozy living room with a fireplace, a large TV, a Christmas tree, and a leather sofa.

1. 5BR Berkshire Home Mins To The Mountain

Charlemont

Jason F.

￥156,282 total

includes taxes & fees

Nov 21 - Nov 22

A log cabin with a balcony, surrounded by trees.

2. Bear Creek Cabin

Charlemont

Hillary S.

￥90,367 total

includes taxes & fees

Nov 15 - Nov 16

A wooden deck with a railing, a house with windows, and a forested area with a stream.

3. The Cottage on Mill Brook is walking distance to Berkshire East and the River.

Charlemont

￥97,075 total

includes taxes & fees

Nov 13 - Nov 14

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

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

Charlemont

Georgia P.

￥190,410 total

includes taxes & fees

Nov 16 - Nov 17

5. Vacation Village in the Berkshires

Williamstown

Carol

￥15,913 total

includes taxes & fees

Nov 12 - Nov 13

A spacious kitchen with wooden flooring, a central island with stools, a dining table, and pendant lighting.

6. Spacious 5BR w/ Hot Tub & Games

Colrain

Griffin S.

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

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

Shelburne Falls

Russ D.

￥54,716 total

includes taxes & fees

Nov 30 - Dec 1

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

8. Shelburne Falls on Main

Shelburne Falls

maureen

￥61,997 total

includes taxes & fees

Nov 12 - Nov 13

A cozy living room with a large flat-screen TV, a wooden cabinet, a round coffee table, and a potted plant.

9. Lovely 2nd Floor Apartment

Greenfield

heather

￥37,594 total

includes taxes & fees

Nov 19 - Nov 20

A modern kitchen with large windows, a built-in dishwasher, and a refrigerator.

10. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Whitingham

Nicole H.

￥118,625 total

includes taxes & fees

Nov 12 - Nov 13

A log cabin with a balcony, surrounded by snow-covered trees and a wind turbine in the background.

11. Greylock Cabin

Florida

Margaret M.

￥71,310 total

includes taxes & fees

Dec 8 - Dec 9

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

12. 2 Twin beds on 1st floor with En-suite bathroom.

Shelburne Falls

￥27,123 total

includes taxes & fees

Nov 16 - Nov 17

13. Berkshire Mountain Lodge

Pittsfield

Susan J

￥17,077 total

includes taxes & fees

Dec 6 - Dec 7

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

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

Greenfield

Tom

￥43,065 total

includes taxes & fees

Nov 18 - Nov 19

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

15. Private room with En-suite bathroom Marigold Room

Shelburne Falls

￥31,240 total

includes taxes & fees

Nov 12 - Nov 13

A bedroom with a bed, a window with patterned curtains, and a wall-mounted lamp.

16. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

Whitingham

Jacqueline M.

￥76,452 total

includes taxes & fees

Nov 12 - Nov 13

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.

17. Penthouse Apartment on Park Street

Adams

Lisa M.

￥42,182 total

includes taxes & fees

Nov 13 - Nov 14

A cozy living room with a fireplace, leather sofas, and a television mounted on the wall.

18. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Whitingham

Ben B.

￥96,804 total

includes taxes & fees

Nov 12 - Nov 13

A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

19. Charming, updated 3 bedroom farmhouse farm stay.

Williamsburg

Nancy M.

￥62,739 total

includes taxes & fees

Dec 6 - Dec 7

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

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

Greenfield

JAMES S.

￥36,040 total

includes taxes & fees

Nov 18 - Nov 19

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Find vacation rentals that suit your style

Top Charlemont Hotel Reviews

A two-story house with a porch, a balcony, and a chimney.

Blooming Inn

Shelburne Falls

10/10 Excellent

Philip M

A hotel room with a bed, a sofa, a TV, and a desk with a lamp.

Hotel Downstreet, an Ascend Collection Hotel

North Adams

10/10 Excellent

Ann

A two-story house with a large porch and multiple windows, surrounded by autumn foliage.

Shelburne Springs Hotel

Shelburne Falls

10/10 Excellent

Brian

A garden with a swing set, a blue chair, and a flower bed.

Maple Terrace Motel

Williamstown

10/10 Excellent

Eric

Two people relaxing by a poolside with drinks, a building in the background, and a clear sky.

The Porches Inn at Mass MoCA

North Adams

10/10 Excellent

Stacey

A blue wooden deck with white picket railings, surrounded by a well-maintained lawn and colorful autumn foliage.

Williamstown Motel

Williamstown

10/10 Excellent

Grantley

An indoor swimming pool with clear water, surrounded by windows with a view of trees.

Hampton Inn & Suites Greenfield

Greenfield

10/10 Excellent

Carol

A modern building with a brick facade and large windows, surrounded by lush greenery and flowers.

The Inn At Crumpin Fox

Bernardston

10/10 Excellent

I've traveled quite frequently the past several years and I can say in all honesty that this is without doubt one of the nicest places I have stayed. I was there for 2 nights and could not have asked for nicer accomodations. The room was spacious, the bed very comfortable and the bathroom spotless. The manager was very gracious, he even lent me his umbrella when it rained the day I had planned to do genealogy research in a local cemetery.

Anonymous traveler

A patio area with wooden chairs and tables, surrounded by dense greenery and trees.

Willows Motel Williamstown

Williamstown

10/10 Excellent

Sandra

An outdoor deck with a wooden table and wicker chairs, surrounded by a wooden railing and string lights.

The Wilmington Inn

Wilmington

10/10 Excellent

Sophia

A room with two single beds, a desk, and a radiator.

Colonel Williams Inn

Brattleboro

10/10 Excellent

Beautiful Vermont Inn with exceptional breakfast: changes everyday - we had frittata, fresh fruit, steel cut oats fried with maple syrup and pecans and always muffins or other baked goods. Our hosts were friendly, accommodating and know the area well. We had room 3- spacious and comfortable. When it snows there is a 5 mile snowshoe,cross country trail on the property for guests only. We were there to attend a show at the Vermont Jazz Center in Brattleboro-about 20 min away. Also hiked...

Ann

A large, white colonial-style house with a porch, surrounded by lush greenery and trees.

The White House Inn

Wilmington

10/10 Excellent

Rya

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

Hotel On North

Pittsfield

10/10 Excellent

The Hotel on North is a thoughtful and beautiful transformation of 2 old contiguous buildings, a store and factory, into a hip and fun hotel. The spaces are extremely large and open from the common spaces to the guest rooms, including the bathrooms. The aesthetic is colorful and friendly rather than the cookie cutter faux luxury I usually find in expensive hotels. The quirky design features such as vintage furniture and painted floors are a great juxtaposition to the perfect bed linens and...

Steve

Find out more about Charlemont

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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.

Charlemont Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Charlemont vacation rentals

1. 5BR Berkshire Home Mins To The Mountain

2. Bear Creek Cabin

3. The Cottage on Mill Brook is walking distance to Berkshire East and the River.

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

5. Vacation Village in the Berkshires

6. Spacious 5BR w/ Hot Tub & Games

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

8. Shelburne Falls on Main

9. Lovely 2nd Floor Apartment

10. Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

11. Greylock Cabin

12. 2 Twin beds on 1st floor with En-suite bathroom.

13. Berkshire Mountain Lodge

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

15. Private room with En-suite bathroom Marigold Room

16. Mt Snow Ski Escape • Fire Pit • Arcade • Sleeps 11

17. Penthouse Apartment on Park Street

18. Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

19. Charming, updated 3 bedroom farmhouse farm stay.

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

Find vacation rentals that suit your style

Top Charlemont Hotel Reviews

Blooming Inn

10/10 Excellent

Find out more about Charlemont

Frequently Asked Questions

Are there vacation rentals in Charlemont?

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

How many vacation rentals are there in Charlemont?

What’s there to see and do in Charlemont?

What’s a vacation rental in Charlemont like?