Photo by Melanie Hill

Search Vacation Homes in Charlemont

Start date: Check-in selected.
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
12 Sep - 14 Sep
In two weeks
19 Sep - 21 Sep
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov

Vacation Homes in Charlemont

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (257)
"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "
The price is AED 551
AED 837 total
includes taxes & fees
16 Sep - 17 Sep
Berkshire Village Carriage House - Super Private!!
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Smart TV, fireplace, table tennis

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

10.0 out of 10, Exceptional, (5)
"Great location to Mt Snow and its surroundings. Easy, pleasant and accommodating communications with the host. Comfortable accommodations. "
The price is AED 426
AED 1,598 total
includes taxes & fees
3 Sep - 4 Sep
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Lovely 2nd Floor Apartment
Interior

Lovely 2nd Floor Apartment

10.0 out of 10, Exceptional, (36)
"Quiet location and comfortable stay. The space was clean and perfect for a quick overnight. Owner was on site and very responsive. "
The price is AED 426
AED 743 total
includes taxes & fees
7 Sep - 8 Sep
Lovely 2nd Floor Apartment
The White Birch near Mount Snow
Smart TV, fireplace

The White Birch near Mount Snow

The price is AED 523
AED 1,745 total
includes taxes & fees
3 Sep - 4 Sep
The White Birch near Mount Snow
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Fridge, microwave, oven, stovetop

Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat

8.6 out of 10, Excellent, (32)
"Rustic but not too rustic, great location, excellent hot tub, plenty of blankets, well-appointed kitchen. Would definitely stay again. "
The price is AED 463
AED 1,117 total
includes taxes & fees
22 Sep - 23 Sep
Cozy Vermont Lodge |Hot Tub||Stream | Private | Wifi | SatTV, Beautiful Waterfront Vermont Retreat
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

10.0 out of 10, Exceptional, (2)
"as advertised."
The price is AED 1,273
AED 2,306 total
includes taxes & fees
10 Sep - 11 Sep
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
9.0 out of 10, Wonderful, (4)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is AED 988
AED 1,822 total
includes taxes & fees
11 Sep - 12 Sep
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Dining

Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls

10.0 out of 10, Exceptional, (3)
"Friends and I were in the area for a concert at Tree House Brewing. This house wasn’t far and it is a gorgeous home. Super clean and had all amenities. Would stay here again!"
The price is AED 551
AED 1,272 total
includes taxes & fees
3 Sep - 4 Sep
Couples 2 Bedroom Retreat - Hot Tub- Air Hockey -Close to ShelburneFalls
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
Fridge, microwave, oven, stovetop

Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed

10.0 out of 10, Exceptional, (12)
"Great property, plenty of space and room for all. Location is ideal"
The price is AED 738
AED 1,855 total
includes taxes & fees
11 Sep - 12 Sep
Foliage Galore! 14mi to Mt. Snow, Arcade, King Bed
North Getaway Cottage
Exterior

North Getaway Cottage

9.6 out of 10, Exceptional, (21)
"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."
The price is AED 744
AED 1,614 total
includes taxes & fees
4 Sep - 5 Sep
North Getaway Cottage
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Smart TV, fireplace, video games, offices

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

10.0 out of 10, Exceptional, (15)
"We loved the house, the deck and the property amenities."
The price is AED 720
AED 2,073 total
includes taxes & fees
8 Sep - 9 Sep
VT escape for all occasions w/ New Kitchen, Game Rooms, Media Lounge, Chimney Hill Clubhouse Access!
Two Brooks Lodge
Panoramic House | Private kitchen

Two Brooks Lodge

3.0 star property
4.8 out of 10, (3)
"Strong dog smell, dirty shabby condition of interior surfaces. Obvious makeshift repairs, spongy floors, torn, flaking couch. Kitchen counter had multiple burn marks and some sticky substance, corner held down with duct tape. Screen door off tracks, laying against wall. Wife was stung by insect in the unit, had to go to hospital. We moved out after only 3 hours, and literally slept in the car rather than go back. Owner uncaring, rude and greedy. Slow to return security deposit. I've...
Two Brooks Lodge
Modern Mount Snow Gnarvana - Balcony, Loft, Pet-Friendly, Walk to Hiking
Interior

Modern Mount Snow Gnarvana - Balcony, Loft, Pet-Friendly, Walk to Hiking

10.0 out of 10, Exceptional, (20)
"Super nice place (very clean and modern) in a quiet area."
The price is AED 430
AED 1,486 total
includes taxes & fees
3 Sep - 4 Sep
Modern Mount Snow Gnarvana - Balcony, Loft, Pet-Friendly, Walk to Hiking
Comfortable Berkshires retreat on mtn resort, SISO
A heated pool

Comfortable Berkshires retreat on mtn resort, SISO

8.8 out of 10, Excellent, (6)
"Kind and responsive host."
The price is AED 635
AED 1,796 total
includes taxes & fees
1 Oct - 2 Oct
Comfortable Berkshires retreat on mtn resort, SISO
Hancock Village Inn at Jiminy Peak
Exterior

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Very kinda hosts, and wonderful house."
The price is AED 2,384
AED 4,315 total
includes taxes & fees
2 Oct - 3 Oct
Hancock Village Inn at Jiminy Peak
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Interior

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

The price is AED 712
AED 2,313 total
includes taxes & fees
3 Sep - 4 Sep
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
Outdoor spa tub

Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun

10.0 out of 10, Exceptional, (51)
"Great ski house in a great location!"
The price is AED 918
AED 2,523 total
includes taxes & fees
3 Sep - 4 Sep
Wilmington Family Retreat! -Hot Tub-King Beds- Air hockey-Nerf gun Fun
Farm Stay in Jasper MO
Interior

Farm Stay in Jasper MO

The price is AED 682
AED 1,331 total
includes taxes & fees
3 Sep - 4 Sep
Farm Stay in Jasper MO
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Fridge, microwave, oven, stovetop

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

10.0 out of 10, Exceptional, (6)
"Nice in all respects,"
The price is AED 1,636
AED 3,132 total
includes taxes & fees
3 Sep - 4 Sep
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Luxury ADA Unit - 101
Game room

Luxury ADA Unit - 101

The price is AED 1,084
AED 2,388 total
includes taxes & fees
3 Sep - 4 Sep
Luxury ADA Unit - 101
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.
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Room was very clean. There is a lot to do at the property, 2 pools, activities for the kids. Lots of things to do in the area "
Judy 2-night trip
Posted 5 days ago
Vacation Village in the Berkshires
The Porches Inn at Mass MoCA

The Porches Inn at Mass MoCA

10/10 Excellent
"Fantastic breakfast, perfect location, fun vibe, beautiful pool area, an environment that encourages conversation with other guests. Room was spacious but needed a nightstand on either side of the bed. "
Leigh 1-night trip
Posted 12 days ago
The Porches Inn at Mass MoCA