A historic building with a tall tower, surrounded by lush green trees and a well-maintained lawn.

Condo Rentals in Berkshire County

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Top Cities in Berkshire County

A town hall with a central dome and columns, surrounded by trees and people.
Condo RentalsCondo Rentals

Lenox

Lenox

Our top choices for Berkshire County condo rentals

A hot tub area with a wooden gazebo structure, surrounded by a fence, and a view of a lush green landscape.

1. Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Hancock
8.8 out of 10, Excellent, (10 reviews)
"We love Bentley at Jiminy Peak ww have been coming here for 10 years always a great experience "
United States
Aggie S.
Club Wyndham Bentley Brook Resort - 2 Bedroom
A ski resort with a large crowd, a building with a sign, and a clear sky.

2. SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Hancock
10.0 out of 10, Exceptional, (48 reviews)
"Very basic and fairly well kept ski condo. Clean, large bathrooms, bedrooms that can accommodate 9 people, and then a sleeper sofa as well. Convenient in the summer to Williamstown and Mt. Greylock and other attractions. Fun attractions on site as well."
United States
Jeffrey G.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
A large, multi-story residential building with a pond in the foreground.

3. Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires
Lenox
8.8 out of 10, Excellent, (3 reviews)
"perfect location to go everywhere in the Berkshires"
United States
Edward G.
Tranquil Lakeside Escape in the Berkshires
A large, multi-story residential building with a pond in the foreground.

4. Peaceful 1BR Condo with Pond View

Peaceful 1BR Condo with Pond View
Lenox
8.6 out of 10, Excellent, (4 reviews)
"Clean and well managed. Needs update of bathroom and stove."
United States
Jackie H.
Peaceful 1BR Condo with Pond View
A snow-covered Christmas tree in a courtyard with residential buildings in the background.

5. Ski-In/Ski-Out at Jiminy Peak in the Country Inn

Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Hancock
9.2 out of 10, Wonderful, (31 reviews)
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
A large, multi-story building with a snow-covered roof and a prominent entrance.

6. Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5

Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Hancock
9.8 out of 10, Exceptional, (7 reviews)
"It was exactly as described, perfect for a family stay with easy ski on and off. I was pleasantly surprised with all the amenities of the property. Would stay again!"
United States
Christine O.
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
A kitchen with dark cabinets, a stainless steel refrigerator, and a countertop. There is a wooden staircase leading to another level.

7. SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Hancock
10.0 out of 10, Exceptional, (18 reviews)
"Perfect spot to relax!"
United States
Tisha C.
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
A spa room with a hot tub, wooden benches, a window, and wall-mounted lights.

8. Year-round fun! Condo at Jiminy Peak Resort. Treat yourself!

Year-round fun! Condo at Jiminy Peak Resort. Treat yourself!
Hancock
8.8 out of 10, Excellent, (3 reviews)
"Great location, clean and convenient."
United States
Jennifer K.
Year-round fun! Condo at Jiminy Peak Resort. Treat yourself!
A snowy outdoor area with people, a building, and a hill in the background.

9. SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Hancock
9.8 out of 10, Exceptional, (44 reviews)
"Great location and fabulous host, very helpful and kind."
United States
Richard H.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

10. 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.6 out of 10, Exceptional, (7 reviews)
"Excellent communication with our host and property exactly as described. Easy check in/check out."
United States
Jillian G.
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Four people seated at a table with food and drinks, wearing winter sports helmets.

11. 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.
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
An outdoor deck with a grill, a table, chairs, and an umbrella.

12. 3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Hancock
9.6 out of 10, Exceptional, (17 reviews)
"This condo was just as advertised, and a perfect spot about a mile from Jiminy Peak. Marc was a gracious host but we didn't really need him for much. Condo was clean and had all the amenities needed. Great spot."
United States
AWPtvK0AAACqAQICAHhRqf5uyCh4rhrpAEcd0Lr3O2ECPWffSl2fK29sG1pXlAEXDIyjS9Lfhgf6r1JBey7kAAAAcDBuBgkqhkiG9w0BBwagYTBfAgEAMFoGCSqGSIb3DQEHATAeBglghkgBZQMEAS4wEQQMGHdM80ZH+MkhH73tAgEQgC1FqVTBMbjIddZfQHBgz+GSyzUulTm74hN1W/5sKmcJO7ihg8R8E6963C2HrSDaKM10iydobw2AMCr5VzI9/VL/MFE+THKEeGaPrn5YDAw A.
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
A rustic interior with a stone fireplace, a plaid sofa, and a wooden ceiling.

13. The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Hancock
10.0 out of 10, Exceptional, (5 reviews)
"Staff and services were outstanding. Great family gathering."
United States
Gerard D.
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
A Country Inn with a covered entrance, stone facade, and a white fence.

14. Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths

Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"The clean room was very comfortable and we enjoyed the mountain view"
United States
Susan C.
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
A rustic interior with a stone fireplace, a plaid sofa, and a wooden ceiling.

15. The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Hancock
8.8 out of 10, Excellent, (5 reviews)
"Staying at the Wyndham made is so easy for us while we were there skiing. The property is right on the slopes and offers a lot of amenities."
United States
Andrew B.
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
A rustic interior with a stone fireplace, a plaid sofa, and a wooden ceiling.

16. The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Hancock
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
A rustic interior with a stone fireplace, a plaid sofa, and a wooden ceiling.

17. The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Hancock
10.0 out of 10, Exceptional, (14 reviews)
"Great location, all the amenities were available to us. Right on the base of the mountain. Thx for the stay! "
United States
lauren t.
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
A spacious living area with a stone fireplace, comfortable seating, and a view of the kitchen.

18. UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak
Hancock
9.8 out of 10, Exceptional, (18 reviews)
"lovely place to stay"
United States
Nancy P.
UNIQUE - 1BR Country Condo @ Jiminy Peak
A snow-covered landscape with a prominent building in the background, a street lamp in the foreground, and a forested hill.

19. Ski Jiminy Peak Mt @Bentley Brook 2025: X-Mas Wk Fri 12/26 -Mon 12/29 3 nites

Ski Jiminy Peak Mt @Bentley Brook 2025: X-Mas Wk Fri 12/26 -Mon 12/29 3 nites
Hancock
Ski Jiminy Peak Mt @Bentley Brook 2025: X-Mas Wk Fri 12/26 -Mon 12/29 3 nites
A rustic interior with a stone fireplace, a plaid sofa, and a wooden ceiling.

20. The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Hancock
8.8 out of 10, Excellent, (3 reviews)
"This was a great one bedroom Andy was very responsive !"
United States
Susan F.
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
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

Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires

10/10 Excellent
"Everything was great!"
Nika 1-night trip
Posted less than an hour ago
Courtyard by Marriott Lenox Berkshires