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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for The Berkshires condo rentals

Pool

1. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.8 out of 10, Exceptional, (6 reviews)
"Good stay. Convenient to ski slopes. Thankful for Pet Friendly."
United States
Jim H.
The price is AED 731
AED 1,378 total
includes taxes & fees
15 Sep - 16 Sep
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Outdoor dining

2. 2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Hancock
7.6 out of 10, Good, (13 reviews)
"Great location, right on the mountain's property "
United States
J S.
The price is AED 738
AED 1,407 total
includes taxes & fees
15 Sep - 16 Sep
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Beach

3. Cozy 3 bedroom condo 2.5 miles to Mount Snow

Cozy 3 bedroom condo 2.5 miles to Mount Snow
West Dover
9.2 out of 10, Wonderful, (52 reviews)
"Fire place was awesome! Great place to stay! Had everything in the kitchen we needed. All the beds were comfy! "
United States
Susan S.
The price is AED 311
AED 1,065 total
includes taxes & fees
30 Aug - 31 Aug
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Lobby

4. 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
8.6 out of 10, Excellent, (37 reviews)
"Location was fantastic! Great ski-in, ski-out location! Unit itself was very dated but location made up for it."
United States
Evan C.
The price is AED 386
AED 1,325 total
includes taxes & fees
18 Aug - 19 Aug
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Interior

5. 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, (23 reviews)
"Great location, comfortable and spacious living room and bedrooms. "
United States
Emma C.
The price is AED 926
AED 2,366 total
includes taxes & fees
18 Aug - 19 Aug
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Exterior

6. Expansive 2BR | Sleeps 10 | Ski-In

Expansive 2BR | Sleeps 10 | Ski-In
West Dover
The price is AED 1,572
AED 1,970 total
includes taxes & fees
18 Aug - 19 Aug
Expansive 2BR | Sleeps 10 | Ski-In
Terrace/patio

7. 2BR Loft With Views | Ski-In Access

2BR Loft With Views | Ski-In Access
West Dover
The price is AED 1,697
AED 2,124 total
includes taxes & fees
18 Aug - 19 Aug
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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

8/10 Good
"The location just off busy route 20 was a minus, especially since it is difficult to make a left hand turn out of the property with the heavy traffic. The hotel itself was clean, modern and comfortable. All staff were friendly and helpful. The breakfast was generous and well prepared/presented. We enjoyed the pool, hot tub and the exercise room."
Sharon G. 1-night trip
Posted 2 hours ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Frequently asked questions

How much do condos in The Berkshires cost?
The price range for condos in The Berkshires is AED 380 to AED 1,032 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 32 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.

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