Vacation Rentals in Berkshire County
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Our top choices for Berkshire County vacation rentals
8.8 out of 10, Excellent, (2184)
"Awesome for ski"
Lazar
The price is ￥16,234
￥19,847 total
includes taxes & fees
Jan 4 - Jan 5, 2026
8.2 out of 10, Very Good, (987)
"nice and clean, good customer service, but the room is smell. "
Huang
The price is ￥33,511
￥37,431 total
includes taxes & fees
Jan 4 - Jan 5, 2026
10.0 out of 10, Exceptional, (4)
"Place was super clean. Beds were comfortable. Location was great."
Tristan e.
The price is ￥31,970
￥57,082 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Guesthouse Cabin vacation rentals in Berkshire County
Guesthouse Cabin vacation rentals in Berkshire CountySheffield
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. "
deborah d.
The price is ￥61,363
￥105,343 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Hupi House: A Peaceful, Wooded, Lakeside Sanctuary
Hupi House: A Peaceful, Wooded, Lakeside SanctuaryMonterey
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."
Kim H.
The price is ￥132,407
￥276,832 total
includes taxes & fees
Jan 18 - Jan 19, 2026
10.0 out of 10, Exceptional, (7)
"Perfect place for a relaxing getaway! We loved everything! "
Cammie
The price is ￥31,619
￥35,318 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness roomGreat Barrington
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!"
Roberta
The price is ￥88,391
￥207,390 total
includes taxes & fees
Jan 4 - Jan 5, 2026
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
judy r.
The price is ￥18,112
￥38,196 total
includes taxes & fees
Jan 2 - Jan 3, 2026
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.
Find vacation rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Berkshire County Hotel Reviews
The Yankee, Trademark Collection by Wyndham
10/10 Excellent
Find out more about Berkshire County
Vacation Apartments in Berkshire County
Search for Vacation rentals in Berkshire County on Expedia! You can easily find your home rentals, villas, Vacation apartments in Berkshire County using one of the methods below:
- View our selection of featured Vacation rentals in Berkshire County
- Use the map to find apartments and other Vacation homes in the Berkshire County neighbourhood you prefer
- Enter your travel dates to view the best deals on Vacation rentals in Berkshire County while they last
Look no further and take a look at our great range of rental properties in Berkshire County!