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

Search Vacation Homes in Charlemont

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Charlemont vacation homes

A spacious kitchen with wooden cabinets, a stainless steel refrigerator, and a central island.

1. 5BR Berkshire Home Mins To The Mountain

5BR Berkshire Home Mins To The Mountain
Charlemont
10.0 out of 10, Exceptional, (8 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 AED 1,193
AED 2,666 total
includes taxes & fees
18 Oct - 19 Oct
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 AED 441
AED 788 total
includes taxes & fees
19 Oct - 20 Oct
Private bed with En-suite bathroom Marigold Room
A round wooden table with a woven placemat, a wicker basket, and a small potted plant.

3. Lovely 2nd Floor Apartment

Lovely 2nd Floor Apartment
Greenfield
10.0 out of 10, Exceptional, (70 reviews)
"It was absolutely amazing Beautiful apartment Clean cozy Beautiful back yard I will definitely stay here again if I am back in this area It’s a 10 out of 10 Thank you David"
United States
Jane P.
The price is AED 459
AED 784 total
includes taxes & fees
18 Oct - 19 Oct
Lovely 2nd Floor Apartment
A hallway with wooden flooring, white walls, and a bed in the background.

4. 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 AED 771
AED 1,571 total
includes taxes & fees
19 Oct - 20 Oct
Cozy private 2 bed apartment in Shelburne Falls
A wooden cabin with a balcony, surrounded by trees and a gravel driveway.

5. Greylock Cabin

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 AED 955
AED 1,596 total
includes taxes & fees
12 Nov - 13 Nov
Greylock Cabin
A kitchen with open shelves, a coffee maker, a blender, and a trash bin.

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 AED 738
AED 1,876 total
includes taxes & fees
2 Nov - 3 Nov
Vermont Summer Getaway • Fire Pit, Yard Games, Near Lake • Sleeps 11
A modern kitchen with wooden countertops, a central island with stools, hanging pendant lights, and a chalkboard menu.

7. Spacious 5BR w/ Hot Tub & Games

Spacious 5BR w/ Hot Tub & Games
Colrain
10.0 out of 10, Exceptional, (56 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.
Spacious 5BR w/ Hot Tub & Games
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, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
United States
Diane
The price is AED 841
AED 1,764 total
includes taxes & fees
26 Oct - 27 Oct
A roomy remodeled retreat close to MassMoCA
A modern interior with large windows, a wooden ceiling, and a cozy seating area.

9. 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 AED 758
AED 1,865 total
includes taxes & fees
8 Nov - 9 Nov
Stunning Glass House nestled in the Vermont wilderness!
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, (43 reviews)
"Wonderful place to stay with our two teens. We visited family in Amherst, looked at colleges and had a great time touring historic sites. Definitely recommend!"
United States
Nancy M.
The price is AED 992
AED 1,619 total
includes taxes & fees
18 Oct - 19 Oct
Charming, updated 3 bedroom farmhouse farm stay.
A wooden kitchen with a central island, bar stools, and a dining table with chairs.

11. Cozy Home in Pownal VT

Cozy Home in Pownal VT
Pownal
10.0 out of 10, Exceptional, (10 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 AED 426
AED 753 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Home in Pownal VT
A two-story house with a porch, surrounded by trees and snow.

12. Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat

Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
Bennington
8.6 out of 10, Excellent, (36 reviews)
"The location was quite and peaceful. We enjoyed our stay and were suprised how great the wifi was for the location."
United States
Malika R.
The price is AED 602
AED 1,339 total
includes taxes & fees
20 Oct - 21 Oct
Cozy Vermont Lodge Hot Tub Stream Private SatTV, Beautiful Waterfront VT Retreat
A bedroom with a bed, bedside tables, a window, and a radiator.

13. 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
10.0 out of 10, Exceptional, (1 review)
"Enjoyed our stay! Very clean and comfortable."
United States
Dana W.
The price is AED 579
AED 1,591 total
includes taxes & fees
19 Oct - 20 Oct
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.

14. 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, (21 reviews)
"Beautiful home and property with quick access to a clubhouse with a gym, indoor and outdoor pools, and hot tub. Great for our family trip (including two kids) and lots of games/entertainment for the kids. The house had everything we needed (including kitchenware needed for cooking and preparing food)."
United States
Natalie
The price is AED 720
AED 2,102 total
includes taxes & fees
19 Oct - 20 Oct
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
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.
The price is AED 1,116
AED 2,273 total
includes taxes & fees
18 Oct - 19 Oct
Walk to Williams * Steam Sauna * Ritz-Carlton Bed
A compact kitchen with a red bench, a microwave, a sink, and a window with a view of a snowy landscape.

16. Cozy Vermont Tiny Home Get Away

Cozy Vermont Tiny Home Get Away
Brattleboro
The price is AED 264
AED 382 total
includes taxes & fees
31 Oct - 1 Nov
Cozy Vermont Tiny Home Get Away
A bedroom with a wooden headboard, a bed with patterned bedding, and a framed picture on the wall.

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

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington
The price is AED 769
AED 2,389 total
includes taxes & fees
20 Oct - 21 Oct
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
A bedroom with a large bed, a window with blinds, a bookshelf, and a wall-mounted ship's wheel.

18. The Eagles Wing at The CHM - Private Apartment

The Eagles Wing at The CHM - Private Apartment
Dover
9.6 out of 10, Exceptional, (5 reviews)
"I loved the super comfy bed and fully stocked coffee cart!"
United States
Ava M.
The price is AED 459
AED 602 total
includes taxes & fees
19 Oct - 20 Oct
The Eagles Wing at The CHM - Private Apartment
A spacious living room with a fireplace, leather furniture, wooden beams, and a cityscape painting.

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

Walk To Town, Hottub, Firepit, Games, Mt Snow
Wilmington
10.0 out of 10, Exceptional, (65 reviews)
"Beautiful house, amazing location, helpful and responsive hosts."
United States
Jeremy P.
The price is AED 1,131
AED 2,835 total
includes taxes & fees
19 Oct - 20 Oct
Walk To Town, Hottub, Firepit, Games, Mt Snow
Pool

20. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
United States
Amit
The price is AED 591
AED 1,988 total
includes taxes & fees
18 Oct - 19 Oct
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Charlemont Hotel Reviews

Jiminy Peak Mountain Resort

Jiminy Peak Mountain Resort

8/10 Good
"Everything was great here except our keys did not work so I had to go back to front desk for new keys on check in. Then on our 2nd morning we went to breakfast and came back to keys not working again. Front desk was helpful and reprogrammed them right away so not a huge deal. The hotel also has pretty thin walls so noise travels. Luckily our neighbors for the weekend were mostly quiet. I wish we knew John Harvards was closed till Thanksgiving but the other pub was great with an excellent beer selection on tap, great service & live entertainment every night. I wish there was free breakfast but thats not a big deal. I would recommend this place especially if you like to ski. We will consider this location for future Berkshire trips as its a fairly good central county location. Just keep in mind most shopping and restaurants are about 15-20+ minutes away."
Christopher 3-night trip
Posted 3 hours ago
Jiminy Peak Mountain Resort