Vacation Rentals in Berkshire County

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Our top choices for Berkshire County vacation rentals

3.0 star property
8.8 out of 10, Excellent, (2184)
"Awesome for ski"
United States
Lazar
The price is ¥16,213
¥19,821 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Vacation Village in the Berkshires

Condo resort in Hancock

Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (987)
"nice and clean, good customer service, but the room is smell. "
United States
Huang
The price is ¥33,468
¥37,383 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Jiminy Peak Mountain Resort

Vacation Home in Florida

Florida Mountain Log Cabin
2.0 star property
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
United States
Tristan e.
The price is ¥31,970
¥57,082 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Florida Mountain Log Cabin
10.0 out of 10, Exceptional, (9)
"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "
United States
deborah d.
The price is ¥61,284
¥105,208 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Guesthouse Cabin vacation rentals in Berkshire County
10.0 out of 10, Exceptional, (1)
"Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."
United States
Kim H.
The price is ¥132,407
¥276,832 total
includes taxes & fees
Jan 18 - Jan 19, 2026
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary

Camping in Williamstown

Huttopia Berkshires
1.0 star property
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
United States
Cammie
The price is ¥31,578
¥35,273 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Huttopia Berkshires
10.0 out of 10, Exceptional, (3)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ¥88,278
¥198,415 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
2.0 star property
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is ¥18,112
¥38,196 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Penthouse Apartment on Park Street
9.0 out of 10, Wonderful, (22)
"I loved staying here the weekend with my friends, the owner Patrick was so accommodating and helpful!"
United States
Mckenna d.
The price is ¥22,640
¥33,985 total
includes taxes & fees
Dec 28 - Dec 29
Bright Boho Apt in 18th c Berkshire Farmhouse
The price is ¥32,789
¥53,891 total
includes taxes & fees
Jan 12 - Jan 13, 2026
3-bedroom house in beautiful Berkshires, close to amenities!
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ¥22,765
¥58,391 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is ¥23,578
¥40,097 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Home in Great Barrington
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is ¥25,014
¥61,253 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Vacation Home in Florida

The Greylock Cabin
10.0 out of 10, Exceptional, (5)
"Wonderful view, peaceful quiet area, cosy cabin."
United States
Anonymous traveler
The price is ¥36,888
¥62,236 total
includes taxes & fees
Jan 19 - Jan 20, 2026
The Greylock Cabin
10.0 out of 10, Exceptional, (5)
"It was great experience and we loved the ammenities."
United States
Carrie C.
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Vacation Home in Hancock

Hancock Village Inn Near Jiminy Peak
10.0 out of 10, Exceptional, (16)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is ¥93,528
¥163,888 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hancock Village Inn Near Jiminy Peak
9.8 out of 10, Exceptional, (35)
"Great cottage - well appointed and very clean. No air conditioning so a bit warm when it’s hot out, but all in all a great stay"
United States
Lindsey E.
The price is ¥31,618
¥73,339 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
10.0 out of 10, Exceptional, (7)
"This was a very lovely home to stay in for our family, everything you need is in the house (basic things minus food of course) We would definitely book this house again when we visit the Berkshires again."
United States
Jason W.
Catamount, Zip Line, Private Setting, Book Now!
The price is ¥34,663
¥59,299 total
includes taxes & fees
Jan 12 - Jan 13, 2026
The Allen House historic North Adams Home in the Berkshire Mountains
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 Berkshire County Hotel Reviews

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Vacation Apartments in Berkshire County

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