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Top Cities in Berkshire County

Our top choices for Berkshire County condo rentals

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,343 reviews)
"great stay. "
United States
John
$108 nightly
The price is $120
May 6 - May 7
Total with taxes and fees
Vacation Village in the Berkshires

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Hancock
8.8 out of 10, Excellent, (9 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

Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Hancock
10.0 out of 10, Exceptional, (8 reviews)
"Very clean, fantastic location. "
United States
Kevin O.
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

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.
$303 nightly
The price is $338
May 4 - May 5
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

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)
"Unit was clean and tidy, fully stocked with bathroom and kitchen items. Main bedroom bed was comfortable and the shower was nice and hot. Overall, we enjoyed our short stay."
United States
S W.
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5

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, (39 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

Clean+Comfy1BRw/Views! OpenLR/D/K! GasFP, HPool,HTub, WorkRemote+Play AllYear!🤗

Clean+Comfy1BRw/Views! OpenLR/D/K! GasFP, HPool,HTub, WorkRemote+Play AllYear!🤗
Hancock
10.0 out of 10, Exceptional, (1 review)
"Absolutely amazing host. There was initial issues with the stay and she stayed up to date and got everything squared away to keep a family vacation on track. 10/10 recommend host!"
United States
Shawn D.
Clean+Comfy1BRw/Views! OpenLR/D/K! GasFP, HPool,HTub, WorkRemote+Play AllYear!🤗

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, (3 reviews)
"we had an amazing time. The room is great and the location is perfect. If you’re skiing love having our own parking section love the proximity to the mountain. Love the size and space of the room. Everything is really well taken care of. Also host with extremely responsive to any requests of things that we still needed and we’re super helpful Everything a great VRBO rental should be. thank you so much for a wonderful stay. "
United States
Paul Y.
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths

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, (43 reviews)
"Colin was very helpful and made sure we had everything we needed for a great stay "
United States
Maureen W.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

🌞Views! 2mi2Ski+Dtw! Great 1BR OpenLR/DR/Kit! FP,HPool,Htub,Gym,PetsOk,EVchg🌞!

🌞Views! 2mi2Ski+Dtw! Great 1BR OpenLR/DR/Kit! FP,HPool,Htub,Gym,PetsOk,EVchg🌞!
Pittsfield
🌞Views! 2mi2Ski+Dtw! Great 1BR OpenLR/DR/Kit! FP,HPool,Htub,Gym,PetsOk,EVchg🌞!

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

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)
"Perfect place for our annual ski-cation. Great accommodations minutes from Jiminy Peak. Equipped with everything you need for a great vacation!"
United States
Nancy S.
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Hancock
9.4 out of 10, Exceptional, (3 reviews)
"Good stay. Convenient to ski slopes. Thankful for Pet Friendly."
United States
Jim H.
$269 nightly
The price is $300
May 4 - May 5
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

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)
"We had a great experience with this rental. Nice location for skiing on and off the mountain and close to the heart of the ski facility. "
United States
Nicole S.
Ski-In/Ski-Out at Jiminy Peak in the Country Inn

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

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!

🌞Views! 2m2Ski! 1BR King Condo! OpenLR/DR/K! FP HPool,Jacuzzi, Gym+KidsStuff🌞!

🌞Views! 2m2Ski! 1BR King Condo! OpenLR/DR/K! FP HPool,Jacuzzi, Gym+KidsStuff🌞!
Hancock
4.0 out of 10, (1 review)
"The host called the morning of our reservation saying the property was no longer available because of a pipe bursting. They were able to secure us another property at double the cost. I made the mistake of not contacting Vrbo to handle this. We did have a place to stay during February break, but a half hour away and not what we had rented. "
United States
Monique L.
🌞Views! 2m2Ski! 1BR King Condo! OpenLR/DR/K! FP HPool,Jacuzzi, Gym+KidsStuff🌞!

Charming 3-bedroom condo with WiFi in Williamstown, MA

Charming 3-bedroom condo with WiFi in Williamstown, MA
Williamstown
Charming 3-bedroom condo with WiFi in Williamstown, MA

Large Mountainside Condo with Private Trail to Grouse Run

Large Mountainside Condo with Private Trail to Grouse Run
Hancock
10.0 out of 10, Exceptional, (1 review)
"Everything was wonderful. The host was available for anything we needed. The house was extremely clean, it had everything. A great place to stay! Would highly recommend it. "
United States
Beth B.
Large Mountainside Condo with Private Trail to Grouse Run

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
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

Find out more about Berkshire County

Berkshire County Condo Rentals information

Number of reviews
2,516
Accommodation
46 Condo Rentals
Lowest Price
$123
Highest Price
$338

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