A historic stone building with a yellow roof, surrounded by a white fence and lush green grass.

Condo Rentals in Berkshire County

Compare and save

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

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

Top Cities in Berkshire County

A street lined with historic buildings, including a Morgan House restaurant.
Condo RentalsCondo Rentals

Lee

Lee

Our top choices for Berkshire County condo rentals

A heated pool

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
Exterior

2. Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires
Lenox
10.0 out of 10, Exceptional, (1 review)
"perfect location to go everywhere in the Berkshires"
United States
Edward G.
Tranquil Lakeside Escape in the Berkshires
Pool

3. 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 AEDĀ 651
AEDĀ 1,298 total
includes taxes & fees
13 Aug - 14 Aug
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Spa

4. 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!
Exterior

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, (29 reviews)
"Host was super nice and got back to me so fast. Location is great and would go back again. "
United States
Kelly C.
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Exterior

6. Peaceful 1BR Condo with Pond View

Peaceful 1BR Condo with Pond View
Lenox
8.0 out of 10, Very Good, (2 reviews)
"Beautiful grounds and views and so close to Tanglewood! We had a great time. Apartment was clean and very private. It was quiet and quaint.The only issue I should mention is the carpeting; seemed a bit dump and not very appealing."
United States
Maria C.
Peaceful 1BR Condo with Pond View
Outdoor dining

7. 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
Property grounds

8. 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, (41 reviews)
"Clean, convenient and the highlight of our winter, as always. "
United States
Leah P.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Property grounds

9. 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, (45 reviews)
"We had an excellent time slopeside at Jiminy PeakColin was very responsive; the condo was perfect for us!Look forward to returning again!Margo"
United States
Margo D.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Exterior

10. 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
Outdoor dining

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.
The price is AEDĀ 815
AEDĀ 1,506 total
includes taxes & fees
9 Sep - 10 Sep
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Coffee/tea maker, fridge, microwave, oven

12. 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, (16 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!
Exterior

13. 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
Interior

14. 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
Interior

15. 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
Interior

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
Interior

17. 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
Interior

18. 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
Property grounds

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
Exterior

20. Lots of snow! Ski, snowshoe/ heated pool - fabulous in beautiful Stockbridge

Lots of snow! Ski, snowshoe/ heated pool - fabulous in beautiful Stockbridge
West Stockbridge
Lots of snow! Ski, snowshoe/ heated pool - fabulous in beautiful Stockbridge
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 Berkshire County Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"I did not expect the faciity to be what it was, a resort. It was just awesome and everything was perfect. The only thing was, if I knew a little more about the place, I would have brought some items I wouldn't if I was in a hotel. This place has so much to offer in some catagories."
Allan 1-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

Explore a world of travel with Expedia