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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for The Berkshires condo rentals

Lobby
Vacation Village in the Berkshires

Condo in Williamstown

Vacation Village in the Berkshires
3.0 star property
8.8 out of 10, Excellent, (2181)
"Awesome for ski"
United States
Lazar
The price is €109
includes taxes & fees
4 Jan - 5 Jan 2026
Vacation Village in the Berkshires
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

Condo in Hancock

UNIQUE - 1BR Country Condo @ Jiminy Peak
10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
The price is €310
includes taxes & fees
22 Dec - 23 Dec
UNIQUE - 1BR Country Condo @ Jiminy Peak
Outdoor dining
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Condo in Hancock

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
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.
The price is €294
includes taxes & fees
5 Jan - 6 Jan 2026
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Condo in Hancock

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
The price is €264
includes taxes & fees
5 Jan - 6 Jan 2026
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Lobby
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Condo in Dover

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
8.8 out of 10, Excellent, (32)
"Very nice accommodations and location!"
United States
Michael M.
The price is €397
includes taxes & fees
22 Dec - 23 Dec
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Beach
Cozy 3 bedroom condo 2.5 miles to Mount Snow

Condo in West Dover

Cozy 3 bedroom condo 2.5 miles to Mount Snow
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"We were unable to stay as when we went in the condo, we found the condo damp, musty, dusty, very worn, extremely outdated and uncomfortable.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.
The price is €270
includes taxes & fees
21 Jan - 22 Jan 2026
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Living area
Charming 3-bedroom condo in serene Wilmington - Your home away from home!

Condo in Wilmington

Charming 3-bedroom condo in serene Wilmington - Your home away from home!
10.0 out of 10, Exceptional, (1)
"Beautiful condo that is spacious in a quiet spot"
United States
Linda
The price is €568
includes taxes & fees
22 Dec - 23 Dec
Charming 3-bedroom condo in serene Wilmington - Your home away from home!
Interior
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)

Condo in Dover

Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
9.4 out of 10, Exceptional, (18)
"Clean, comfortable, convenient! "
United States
Mary C.
The price is €889
includes taxes & fees
25 Dec - 26 Dec
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Terrace/patio
2BR Loft With Views | Ski-In Access

Condo in West Dover

2BR Loft With Views | Ski-In Access
The price is €987
includes taxes & fees
21 Jan - 22 Jan 2026
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
€109
Highest Price
€987

Frequently asked questions

How much do condos in The Berkshires cost?
The price range for condos in The Berkshires is €109 to €987 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 favourite. Whether you're embarking on a holiday 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 Centre, 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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