A historic stone building with a yellow roof, surrounded by a white fence and lush green grass.

Vacation Rentals in Berkshire County

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Top Cities in Berkshire County

Our top choices for Berkshire County vacation rentals

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,157 reviews)
"Absolutely wonderful room with many amenities with short drive to Tanglewood and restaurant options."
United States
Jay
$109 nightly
The price is $121
Oct 1 - Oct 2
Total with taxes and fees
Berkshire Mountain Lodge

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,678 reviews)
"Love this place for a weekend getaway."
United States
Jacob
$122 nightly
The price is $136
Sep 28 - Sep 29
Total with taxes and fees
Vacation Village in the Berkshires

3. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (178 reviews)
"Great little place."
United States
Kim
$113 nightly
The price is $127
Oct 1 - Oct 2
Total with taxes and fees
Micosta Leisure Inn

4. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
$499 nightly
The price is $554
Oct 5 - Oct 6
Total with taxes and fees
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

5. Two Brooks Lodge

Two Brooks Lodge
3.0 star property
Bennington
4.8 out of 10, (3 reviews)
"Stayed at this property everything was as stated but then property manager made me pay cleaning fee and deposit through cash app , Then later Said I didn’t pay for property when I clearly did had receipts then after confronted by Expedia , He lies say I left the house a mess and that displaced half the water out of the hot tub that I didn’t use at all and didn’t do the dishes which I did , not to mentions I paid a cleaning fee either way . So this unprofessional listing gets keep the deposit...
United States
Hunter
$374 nightly
The price is $396
Sep 28 - Sep 29
Total with taxes and fees
Two Brooks Lodge

6. Charming Wilmington Cabin, 8 Mi. to Mt Snow!

Charming Wilmington Cabin, 8 Mi. to Mt Snow!
3.0 star property
Wilmington
10.0 out of 10, Exceptional, (1 review)
"The house was everything we wanted and more. Loaded with space, kitchen supplies, comfort, a grill, gorgeous stone fireplace. The location on. sleepy back road in the woods was beautiful and quiet. The only complaint is that they make you take your trash with you when you go. There was a pass for the local dump which helped offset the inconvenience. Otherwise, A+"
United States
Mark
$366 nightly
The price is $403
Oct 5 - Oct 6
Total with taxes and fees
Charming Wilmington Cabin, 8 Mi. to Mt Snow!

7. Spacious Vermont Farmhouse 3 Mi to Mount Snow

Spacious Vermont Farmhouse 3 Mi to Mount Snow
3.0 star property
West Dover
$710 nightly
The price is $781
Sep 28 - Sep 29
Total with taxes and fees
Spacious Vermont Farmhouse 3 Mi to Mount Snow
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

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 $121 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.  


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