Vacation Rentals in Berkshire County

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Top Cities in Berkshire County

Our top choices for Berkshire County vacation rentals

3.0 star property
8.8 out of 10, Excellent, (2187)
"Awesome for ski"
United States
Lazar
$126 nightly
The price is $141
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
$212 nightly
The price is $237
Jan 5 - Jan 6, 2026
Total with taxes and fees
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.
$339 nightly
The price is $365
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
$604 nightly
The price is $675
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
$1,587 nightly
The price is $1,773
Jan 18 - Jan 19, 2026
Total with taxes and fees
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
$180 nightly
The price is $201
Jan 7 - Jan 8, 2026
Total with taxes and fees
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
$1,193 nightly
The price is $1,332
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
$219 nightly
The price is $245
Jan 2 - Jan 3, 2026
Total with taxes and fees
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.
$199 nightly
The price is $219
Dec 29 - Dec 30
Total with taxes and fees
Bright Boho Apt in 18th c Berkshire Farmhouse
$279 nightly
The price is $312
Jan 20 - Jan 21, 2026
Total with taxes and fees
3-bedroom house in beautiful Berkshires, close to amenities!
$271 nightly
The price is $303
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
$335 nightly
The price is $374
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
$224 nightly
The price is $250
Jan 26 - Jan 27, 2026
Total with taxes and fees
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.
$351 nightly
The price is $392
Jan 4 - Jan 5, 2026
Total with taxes and fees
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
$369 nightly
The price is $399
Jan 19 - Jan 20, 2026
Total with taxes and fees
The Greylock Cabin
10.0 out of 10, Exceptional, (5)
"It was great experience and we loved the ammenities."
United States
Carrie C.
$271 nightly
The price is $303
Jan 4 - Jan 5, 2026
Total with taxes and fees
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.
$971 nightly
The price is $1,050
Jan 6 - Jan 7, 2026
Total with taxes and fees
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.
$420 nightly
The price is $469
Jan 5 - Jan 6, 2026
Total with taxes and fees
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.
$1,200 nightly
The price is $1,372
Jan 19 - Jan 20, 2026
Total with taxes and fees
Catamount, Zip Line, Private Setting, Book Now!
$337 nightly
The price is $376
Jan 12 - Jan 13, 2026
Total with taxes and fees
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Berkshire County Hotel Reviews

Find out more about Berkshire County

Discover your perfect Berkshire County vacation rental with Expedia

How many vacation rentals are available in Berkshire County?


Expedia has plenty of vacation rentals to choose from in and around  Berkshire County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Berkshire County?


The selection of Berkshire County vacation rentals we have selected for you start as low as $141 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Berkshire County?


Vacation rentals in Berkshire County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Berkshire County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Berkshire County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Berkshire County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Berkshire County?


Find vacation rentals in Berkshire County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Berkshire County.  


What amenities are available in a vacation rental in Berkshire County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Berkshire County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Berkshire County?   


Everytime is a great time to head to Berkshire County! Staying in a Berkshire County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Berkshire County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Berkshire County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Berkshire County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Berkshire County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.