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Search and Rent The Berkshires Condos

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Our top choices for The Berkshires condo rentals

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Vacation Village in the Berkshires

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2181)
"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
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
$317 nightly
The price is $354
Dec 22 - Dec 23
Total with taxes and fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
Pool
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock
8.0 out of 10, Very Good, (8)
"Perfect spot for Mountain Adventures, property was well equipped with comfortable necessities. It was very clean and spacious for six people, 3 adults and 3 young boys. We would definitely stay again. "
United States
PK N.
$301 nightly
The price is $336
Jan 5 - Jan 6, 2026
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
$270 nightly
The price is $302
Jan 5 - Jan 6, 2026
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Property grounds
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Dover
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
$403 nightly
The price is $456
Dec 22 - Dec 23
Total with taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.0 out of 10, Wonderful, (45)
"We were unable to stay as when we went in the condo, we found the condo damp, musty, dusty, very worn, extremely outdated and uncomfortable. We left and found different accommodations for the weekend at Chateau 239 which I highly recommend. "
United States
Diana W.
$272 nightly
The price is $307
Jan 14 - Jan 15, 2026
Total with taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Private kitchen
Charming 3-bedroom condo in serene Wilmington - Your home away from home!

Charming 3-bedroom condo in serene Wilmington - Your home away from home!

Charming 3-bedroom condo in serene Wilmington - Your home away from home!
Wilmington
10.0 out of 10, Exceptional, (1)
"Beautiful condo that is spacious in a quiet spot"
United States
Linda
$575 nightly
The price is $650
Dec 22 - Dec 23
Total with taxes and fees
Charming 3-bedroom condo in serene Wilmington - Your home away from home!
Property grounds
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)

Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)

Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Dover
9.4 out of 10, Exceptional, (18)
"Clean, comfortable, convenient! "
United States
Mary C.
$900 nightly
The price is $1,017
Dec 25 - Dec 26
Total with taxes and fees
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Property grounds
2BR Loft With Views | Ski-In Access

2BR Loft With Views | Ski-In Access

2BR Loft With Views | Ski-In Access
West Dover
$1,028 nightly
The price is $1,134
Dec 22 - Dec 23
Total with taxes and fees
2BR Loft With Views | Ski-In Access
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 The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"My stay was great with no problems. "
scott 2-night trip
Posted 2 days ago
Vacation Village in the Berkshires

Find out more about The Berkshires

The Berkshires Condo Rentals information

Number of reviews
2,289
Accommodation
45 Condo Rentals
Lowest Price
$141
Highest Price
$1,134

Frequently asked questions

How much do condos in The Berkshires cost?
The price range for condos in The Berkshires is $141 to $1,134 per night. No matter your budget, you'll find someplace that suits your needs — as well as your entire squad! These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in The Berkshires?
Explore our 45 condos in The Berkshires and then select your favorite. Whether you're embarking on a vacation with all the fam or kicking it with friends, your perfect stay is just clicks away.
Why book your condo in The Berkshires with Expedia?
Reserving a condo in The Berkshires is as easy as entering your travel dates and choosing a place that has what you need. On the lookout for something low cost or luxurious, or a stay that also offers a kitchenette? Use Expedia's search filters to narrow your results even further and find the perfect pad.
How can I find cheap condos in The Berkshires?
The quickest way to score cheap condos in The Berkshires is with Expedia's easy-to-use filter tool. Tailor your search results by amenities, budget and star rating to snag awesome prices in just a few clicks.
What is there to do in The Berkshires near my condo?
Whether you enjoy arts, culture, shopping or dining, The Berkshires offers the lot, and then some! The awesome city of Lenox boasts plenty of things to do and see, including Tanglewood Music Center, Shakespeare and Company and The Mount. If you're planning an escape to Williamstown, Chapin Library of Rare Books and Manuscripts, Hopkins Observatory and Williams College Museum of Art are must-do's.

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