Search The Berkshires Condo Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb

Featured Condo Rentals in The Berkshires

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2045)
"Extended stay since resort was so beautiful"
The price is AU$172
includes taxes & fees
2 Nov - 3 Nov
Vacation Village in the Berkshires
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

8.0 out of 10, Very good, (8)
"Cozy little condo, good for a group of four or five. We stayed there with my two kids 8 &10 and wife. It’s a nice place overall we had a great time. It is a short drive to the slopes, which is fine as long as you have a car but you still need to park at the inn"
The price is AU$526
includes taxes & fees
5 Nov - 6 Nov
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
UNIQUE - 1BR Country Condo @ Jiminy Peak
Interior

UNIQUE - 1BR Country Condo @ Jiminy Peak

10.0 out of 10, Exceptional, (14)
"Clean and quiet, nicely decorated! "
The price is AU$535
includes taxes & fees
10 Oct - 11 Oct
UNIQUE - 1BR Country Condo @ Jiminy Peak
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Outdoor dining

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

8.0 out of 10, Very good, (1)
"very nice and roomy! really enjoyed."
The price is AU$460
includes taxes & fees
15 Oct - 16 Oct
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Charming 1-bedroom condo in delightful Dover
Fridge, microwave, oven, stovetop

Charming 1-bedroom condo in delightful Dover

9.0 out of 10, Wonderful, (4)
"Condo was perfect for our stay. Very quiet area despite being near Mt Snow and Wilmington area. Great bakery close by for wonderful morning pastries. Updated/renovated condo. Loved our time there. Owners response to an issue we had (our personal issue) was greatly appreciated. Would stay again!!!!"
The price is AU$310
includes taxes & fees
9 Nov - 10 Nov
Charming 1-bedroom condo in delightful Dover
Charming 3-bedroom condo in serene Wilmington - Your home away from home!
Private kitchen

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"
The price is AU$996
includes taxes & fees
12 Oct - 13 Oct
Charming 3-bedroom condo in serene Wilmington - Your home away from home!
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds

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

8.6 out of 10, Excellent, (31)
"The apartment was in a great location to get to the ski lifts. "
The price is AU$438
includes taxes & fees
13 Oct - 14 Oct
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Property grounds

Cozy 3 bedroom condo 2.5 miles to Mount Snow

9.0 out of 10, Wonderful, (42)
"This is the third time I’ve stayed here and it’s very convenient and I really love what the host did for upgrades on the property. "
The price is AU$451
includes taxes & fees
15 Oct - 16 Oct
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Property grounds

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

9.4 out of 10, Exceptional, (18)
"Clean, comfortable, convenient! "
The price is AU$1,055
includes taxes & fees
13 Oct - 14 Oct
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
2BR Loft With Views | Ski-In Access
Property grounds

2BR Loft With Views | Ski-In Access

The price is AU$824
includes taxes & fees
9 Nov - 10 Nov
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top The Berkshires Hotel Reviews

Quality Inn

Quality Inn

10/10 Excellent
"Staff was very friendly. Room was ok, but the bathroom tub, floor, and walls needed more attention. Microwave and fridge in room. Perfect location for taking in shows at the beautiful Mahaiwe theatre, as well as browsing Main St shoppes and restaurants. Close driving distance to area attractions."
Petri 2-night trip
Posted 1 day ago
Quality Inn

Find out more about The Berkshires

Find out more about The Berkshires

The Berkshires Condo Rentals information

Number of reviews
Accommodation
 Condo Rentals
Lowest Price
Highest Price

Frequently asked questions

How much do condos in The Berkshires cost?
Prepare to pay from to per night for condos in The Berkshires. No matter your budget, the perfect stay is a click away on Expedia. This price was 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?
Take your pick of condos in The Berkshires. Whether you're getting away with relatives or friends, and wherever you want to go, Expedia can help you secure the ideal space.
What is there to do in The Berkshires near my condo?
Whether you're into dining, sightseeing, museums or malls, The Berkshires is one place where it's difficult to be bored! The terrific city of Williamstown has plenty of things to do and see, including Sterling and Francine Clark Art Institute, Williams College Museum of Art and Williamstown Historical Museum. If you're on your way to Pittsfield, Bousquet Ski Area, Berkshire Museum and Colonial Theatre will fill up your itinerary.

Explore a world of travel with Expedia

Explore a world of travel with Expedia