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

Holiday Homes in Charlemont

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Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Charlemont holiday homes

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

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (7 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
United States
Jason F.
The price is €589
includes taxes & fees
16 Sept - 17 Sept
5BR Berkshire Home Mins To The Mountain
A two-story house with a front porch, a staircase leading to the entrance, and a large tree in the foreground.

2. Private bed with En-suite bathroom Marigold Room

Private bed with En-suite bathroom Marigold Room
Shelburne Falls
The price is €191
includes taxes & fees
16 Sept - 17 Sept
Private bed with En-suite bathroom Marigold Room
A hallway with wooden flooring, white walls, and a bed in the background.

3. Cozy private 2 bed apartment in Shelburne Falls

Cozy private 2 bed apartment in Shelburne Falls
Shelburne Falls
"I really enjoyed the kitchen setup and how everything I needed was there. The beds were very comfortable and having a light nearby for reading was a plus. The walk to downtown was nice. We explored Shelburne Falls out days and it did have something for everyone. I would stay here again."
United States
maureen
The price is €321
includes taxes & fees
16 Sept - 17 Sept
Cozy private 2 bed apartment in Shelburne Falls
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

4. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (65 reviews)
"Beautiful decor, cozy furnishings, comfy comfy beds, all the amenities we needed and more, such a perfect apartment. Great communication with the host. Lots of yummy restaurant options in the area. We loved staying here!"
United States
Christa B.
The price is €177
includes taxes & fees
20 Sept - 21 Sept
Lovely 2nd Floor Apartment
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

5. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (55 reviews)
"This is the second time we have stayed at this property. It is very spacious, cozy, and clean. The beds are very comfortable. It had everything we needed "
United States
Staci M.
The price is €572
includes taxes & fees
16 Sept - 17 Sept
Spacious 5BR w/ Hot Tub & Games
An aerial view of a house surrounded by a forest with autumn foliage.

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

Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
Whitingham
10.0 out of 10, Exceptional, (15 reviews)
"Great 2 family group vacation spot. Very clean and right in between great ski mountains"
United States
Jonathan
The price is €466
includes taxes & fees
28 Sept - 29 Sept
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

7. The Greylock Cabin

The Greylock Cabin
Florida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
United States
Margaret M.
The price is €409
includes taxes & fees
7 Oct - 8 Oct
The Greylock Cabin
A kitchen with white cabinets, a wooden dining table, and pendant lights.

8. A roomy remodeled retreat close to MassMoCA

A roomy remodeled retreat close to MassMoCA
North Adams
10.0 out of 10, Exceptional, (59 reviews)
"Lovely home with everything we needed. The beds were very comfortable!"
United States
Jennifer O.
The price is €409
includes taxes & fees
16 Sept - 17 Sept
A roomy remodeled retreat close to MassMoCA
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

9. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (8 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
United States
Jess M.
The price is €160
includes taxes & fees
27 Sept - 28 Sept
Cozy Home in Pownal VT
A red barn with a black door and a heart-shaped cutout, surrounded by lush greenery and trees.

10. Charming, updated 3 bedroom farmhouse farm stay.

Charming, updated 3 bedroom farmhouse farm stay.
Williamsburg
10.0 out of 10, Exceptional, (41 reviews)
"Great hosts! Very nice and helpful. "
United States
Anonymous traveller
Charming, updated 3 bedroom farmhouse farm stay.
A two-story house with a red roof, a front porch with a railing, and a gravel driveway.

11. The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont

The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
Woodford
The price is €363
includes taxes & fees
16 Sept - 17 Sept
The Ravens Nest - your next retreat tucked into the woods of Woodford, Vermont
A cozy interior with a wooden ceiling, a large window, and a table with chairs.

12. VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!

VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Wilmington
10.0 out of 10, Exceptional, (19 reviews)
"Great place!"
United States
Jack & Heather G.
The price is €496
includes taxes & fees
16 Sept - 17 Sept
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

13. Stunning Glass House nestled in the Vermont wilderness!

Stunning Glass House nestled in the Vermont wilderness!
Guilford
9.4 out of 10, Exceptional, (3 reviews)
"The glass part of the house is stunning! We wanted to spend all of our time there, and wished that we could enjoy the view from the kitchen and bedroom too. We opted to sleep on the fold-out bed in the glass room instead of in the below-ground bedroom. It was a nice experience!"
United States
Chris O.
The price is €476
includes taxes & fees
24 Sept - 25 Sept
Stunning Glass House nestled in the Vermont wilderness!
A room with a wooden bed, a mirror, and a window.

14. MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is €571
includes taxes & fees
16 Sept - 17 Sept
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A wicker basket with a plant on a table, a green bottle, and a cushion on a chair.

15. Walk to Williams * Steam Sauna * Ritz-Carlton Bed

Walk to Williams * Steam Sauna * Ritz-Carlton Bed
Williamstown
10.0 out of 10, Exceptional, (2 reviews)
"Easy breezy, short walk to walk into town/Williams Campus. Down to Earth, yet sophisticated vibe, great art scene. "
United States
Michelle B.
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

16. Walk To Town, Hottub, Firepit, Games, Mt Snow

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (63 reviews)
"A fantastic spot for a cozy, small town vibe. Highly recommend"
United States
Nicholas G.
The price is €677
includes taxes & fees
16 Sept - 17 Sept
Walk To Town, Hottub, Firepit, Games, Mt Snow
A wooden staircase leading to a cabin with a balcony, surrounded by trees.

17. New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly

New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
Wilmington
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful house and a terrific central location for all things outdoors."
United States
Alex B.
The price is €600
includes taxes & fees
18 Sept - 19 Sept
New England Lake View Chalet near Downtown Wilmington & Mt Snow l Pet Friendly
A spacious indoor area with multiple wooden tables and green chairs, large windows offering a view of a snowy mountain, and a stone fireplace with a fire.

18. Modern Mount Snow Gnarvana - Steps to Carinthia

Modern Mount Snow Gnarvana - Steps to Carinthia
Dover
10.0 out of 10, Exceptional, (26 reviews)
"Perfect for our getaway, convenient for getting to the slopes and a beautiful area to visit"
United States
Lynn B.
The price is €380
includes taxes & fees
16 Sept - 17 Sept
Modern Mount Snow Gnarvana - Steps to Carinthia

19. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
United States
Maura L.
The price is €470
includes taxes & fees
21 Sept - 22 Sept
Comfortable Berkshires retreat on mtn resort, SISO
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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"We were here for a good night’s rest on a cross country roadtrip. This place had very good Expedia reviews and I agree. Very clean, decent breakfast, plenty of hot water, a toilet that flushed properly. Did not use amenities. Sleep, shower, quiet time to read some, eat and on down the highway. Would gladly stay here again the next time thru the Berkshires."
Al 1-night trip
Posted 8 hours ago
The Yankee Inn

Find out more about Charlemont

Charlemont Holiday Homes information

Number of reviews
317
Accommodation
445 Holiday Homes
Lowest Price
€160
Highest Price
€677