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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, (1942)
"Very relaxing, clean and convenient for a family vacation. Pool area and grills are well kept and also convenient "
The price is AU$203
includes taxes & fees
27 Aug - 28 Aug
Vacation Village in the Berkshires
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Property grounds

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

10.0 out of 10, Exceptional, (39)
"3rd time staying here. The host is great, the place is clean, and the location couldn't be better!"
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
UNIQUE - 1BR Country Condo @ Jiminy Peak
Interior

UNIQUE - 1BR Country Condo @ Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Clean and quiet, nicely decorated! "
The price is AU$412
includes taxes & fees
24 Aug - 25 Aug
UNIQUE - 1BR Country Condo @ Jiminy Peak
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (12)
"We'll be back!"
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

7.8 out of 10, Good, (6)
"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$541
includes taxes & fees
13 Aug - 14 Aug
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Tranquil Lakeside Escape in the Berkshires
Property grounds

Tranquil Lakeside Escape in the Berkshires

10.0 out of 10, Exceptional, (1)
"perfect location to go everywhere in the Berkshires"
Tranquil Lakeside Escape in the Berkshires
Peaceful 1BR Condo with Pond View
Property grounds

Peaceful 1BR Condo with Pond View

8.0 out of 10, Very good, (1)
"The location was very close to Tanglewood and The Mount, but the front drive off the main road was really dark, no street lights, so we missed our turn a few times but did eventually find the place. The community was pretty and tranquil, we did not hear any noise at all. The WiFi was a little wonky but no big deal because we were able to get cell service. "
Peaceful 1BR Condo with Pond View
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Exterior

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

9.2 out of 10, Wonderful, (26)
"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. "
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Living area

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

10.0 out of 10, Exceptional, (3)
"Good base for Berkshires, responsive host, good rates, secure."
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub
Spa

1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub

10.0 out of 10, Exceptional, (1)
"You'll love this house, it feels just like home but more relaxing and enjoyable! We used the community heated pool and hot tub several times during our stay. The house is just as pictures, but better. Everything you could need is supplied n the rental, all you need is food and clothes. We slept great at this house, better than any other vacation, no one got up early. The kitchen and grill were great to cook with. Staying at this house was very enjoyable!"
1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Exterior

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

10.0 out of 10, Exceptional, (6)
"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!"
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Outdoor dining

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

The price is AU$469
includes taxes & fees
13 Aug - 14 Aug
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (32)
"Everything was spot on. Will be back!!"
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
Exterior

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
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

10.0 out of 10, Exceptional, (1)
"Great spot for family ski trip. Location was great. Condo and amenities were great. Overall super happy and would stay again. "
Club Wyndham Bentley Brook Resort - 2 Bedroom
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Perfect for Winter Skiing!!
Fridge, microwave, oven, stovetop

Perfect for Winter Skiing!!

Perfect for Winter Skiing!!
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
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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Frequently asked questions

How much do condos in The Berkshires cost?
Prepare to pay from AU$203 to AU$541 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 62 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.