Photo by Melanie Hill

Search Vacation Homes in Charlemont

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 469 Vacation Homes in Charlemont with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (240)
"This beautiful carriage house is ingeniously designed with no wasted space. Surrounded by nature, it is totally private, yet it is two minutes from shops and restaurants. The window seats are sublime and the heated floors offered relief after afternoons spent hiking in the cold. "
The price is SAR 563
SAR 859 total
includes taxes & fees
1 Apr - 2 Apr
Berkshire Village Carriage House - Super Private!!

The Jelly Mill-A River Retreat

10.0 out of 10, Exceptional, (46)
"Stayed for sugar season. Spring thaw makes river road a bit sketch but place and hosts were great! Will b back. "
The Jelly Mill-A River Retreat

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is SAR 2,059
SAR 3,882 total
includes taxes & fees
4 Apr - 5 Apr
Hancock Village Inn at Jiminy Peak

kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

9.8 out of 10, Exceptional, (97)
"Great stay in Amherst again"
The price is SAR 544
SAR 775 total
includes taxes & fees
1 Apr - 2 Apr
kimball upstairs: Private Elegant 2 Bedroom Close To Everything In The Valley

1810 Brook Side Mill/House / EV Level 2 Charging on Site

10.0 out of 10, Exceptional, (71)
"Highly recommend this charming, historic place.  Well appointed. Has everything you need for your stay.  Cozy…yet plenty of space for everyone.  Looks like it was just renovated.  Took my daughter and two granddaughters for a ski weekend.  Wouldn’t hesitate to come back here.  "
1810 Brook Side Mill/House / EV Level 2 Charging on Site

Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

10.0 out of 10, Exceptional, (6)
"Great house, great location, Great communication with Todd. Will be back for sure!!!! Thanks for everything Todd. "
Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit.

Cozy retreat near slopes

5.0 out of 10, (8)
"Unit is a little outdated but nice.Not truly a ski in - out since you have to walk on the road about 200 yards to get to the Sachem trail.Condo does need ice cube trays since the ice maker is not working.Also the down stairs bath room heater does not work and would be nice since this is where the bath tub is located"
Cozy retreat near slopes

GAMERS HAVEN, River Wine Inn!

2.0 star property
10.0 out of 10, Exceptional, (8)
"We had such a great time staying here with endless games and activities! We would gladly stay here again and recommend to anyone!"
GAMERS HAVEN, River Wine Inn!

Mountain Blossom Retreat by Evergreen Home

10.0 out of 10, Exceptional, (5)
"Had a great long weekend getaway in Lanesboro. The property manager was super communicative, which was helpful. Would highly recommend!"
Mountain Blossom Retreat by Evergreen Home

Wilmington Vacation Rental Near Hiking and Skiing!

9.2 out of 10, Wonderful, (19)
"We loved the feel of this rustic yet modern cabin. It had everything we needed and was the perfect getaway for us for a few nights of skiing at mount snow. The stairs and pathway to get down to the place are not ideal for older individuals with limited mobility as it can get slippery and we found the driveway very icy but that comes with the reality of living in New England. I just thought I would put this in here for those who are in their later years and have to consider their mobility. We are...
Wilmington Vacation Rental Near Hiking and Skiing!

Mountain-view home near the slopes with at-home entertainment - dog-friendly

7.8 out of 10, Good, (66)
"Parents, kids and dog had a terrific time. Perfect distance to Mount Snow. Will definitely return! "
Mountain-view home near the slopes with at-home entertainment - dog-friendly

Bright three-level home with water views, jetted tub, firepit, and pool table

8.4 out of 10, Very Good, (27)
"Had a fantastic weekend at this cabin. Beautifully maintained, sparking clean and beautiful cabin. Everything was exactly as pictured and is even better in person. Would stay here again x100"
Bright three-level home with water views, jetted tub, firepit, and pool table

Amherst, Perfect Location, UMass, Smith, MHC!

10.0 out of 10, Exceptional, (14)
"The house was perfect for us as we moved our daughter into UMASS. Close to the college, restaurants and shopping. Very clean house and had everything we needed. "
Amherst, Perfect Location, UMass, Smith, MHC!

Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

10.0 out of 10, Exceptional, (215)
"We had a great long weekend with the family in this warm and comfortable house overlooking a beautiful lake. The place was spotless and well-appointed. The best mark of a good host is someone who goes above and beyond to make your visit"
Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews

6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

10.0 out of 10, Exceptional, (4)
"We had a great weekend stay here with our dog. He loved the backyard and felt right at home. Everything was clean and great location."
6 Mi to Skiing: Pet-Friendly Home in Pittsfield!

Dancing Horse Lodge

9.4 out of 10, Exceptional, (40)
"Cozy home with a cabin like feel. Plenty of room and warmth. The 3 bedrooms accommodated our group perfectly! Easy check in instructions"
Dancing Horse Lodge

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

10.0 out of 10, Exceptional, (4)
"Great location to Mt Snow and its surroundings. Easy, pleasant and accommodating communications with the host. Comfortable accommodations. "
The price is SAR 559
SAR 1,806 total
includes taxes & fees
1 Apr - 2 Apr
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Modern Mount Snow Gnarvana - Balcony/Pet-Friendly/Walk to Lifts & Lodge

10.0 out of 10, Exceptional, (19)
"Jen and Erica thought of everything a guest might need. It was a welcoming, clean and cozy house with a 3 minute drive to Snow Mountain. "
The price is SAR 746
SAR 1,924 total
includes taxes & fees
1 Apr - 2 Apr
Modern Mount Snow Gnarvana - Balcony/Pet-Friendly/Walk to Lifts & Lodge

Lovely 2nd Floor Apartment

9.8 out of 10, Exceptional, (19)
"Clean, comfortable and quiet. All necessities for kitchen provided. "
The price is SAR 484
SAR 809 total
includes taxes & fees
1 Apr - 2 Apr
Lovely 2nd Floor Apartment

14mi to Mt. Snow! Arcade, Private Suite, King Bed!

9.8 out of 10, Exceptional, (10)
"This place is immaculate and the host is responsive. We stayed here to ski in Mount snow which is about 25 minutes drive. We arrived later in the evening and the place was warm and cozy. "
The price is SAR 671
SAR 1,794 total
includes taxes & fees
8 Apr - 9 Apr
14mi to Mt. Snow! Arcade, Private Suite, King Bed!
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.
Don't see what you're looking for?
See all available properties in Charlemont
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Charlemont

Bear Creek Cabin

9.8 out of 10, Exceptional, (27)
"Perfect place to stay while skiing Berkshire East! Clean, spacious, and beautiful surroundings!"
The price is SAR 1,500
SAR 2,246 total
includes taxes & fees
1 Apr - 2 Apr
Bear Creek Cabin

Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

9.6 out of 10, Exceptional, (127)
"A cozy spot to watch the snow come down!"
Country Home with Babbling Brook and Pond View- Minutes to Berkshire East Resort

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"The location to jimney peak was great."
The price is SAR 484
SAR 572 total
includes taxes & fees
1 Apr - 2 Apr
Vacation Village in the Berkshires
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.