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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 54 Condo Rentals in The Berkshires with updated reviews, rates, and availability.

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1801)
"Great property"
The price is AED 434
AED 516 total
includes taxes & fees
6 May - 7 May
Vacation Village in the Berkshires
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Beach

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

10.0 out of 10, Exceptional, (37)
"Family trip with kids. Condo is great. Excellent location with great views of the mountain. Everything you need is within walking distance. Beds are comfortable and owner supplied plenty of towels and linens. We will definitely be back next year. "
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

7.2 out of 10, Good, (5)
"My friends and I planned a last minute trip to Jimmy Peak which is a great mountain for all types of skiers. The host was very communicative right away and made sure everything was ready and gave me information for not just the house but where to go into town. The house was very clean and very comfortable to stay at almost like a true “ home away from home”. The home is very cozy and brings a great vibe to the trip. Even after our stay the host made sure to stay in contact and make sure...
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
UNIQUE - 1BR Country Condo @ Jiminy Peak
Exterior

UNIQUE - 1BR Country Condo @ Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Clean and quiet, nicely decorated! "
The price is AED 327
AED 1,104 total
includes taxes & fees
30 Apr - 1 May
UNIQUE - 1BR Country Condo @ Jiminy Peak
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
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, (30)
"Had an amazing stay here! Place was exactly like the photos. Fireplace was perfect! Great places to hike around the area. Host was great with fast communication. "
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
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
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
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
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Exterior

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

9.4 out of 10, Exceptional, (22)
"All you need for a ski trip"
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Snow and ski sports

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

10.0 out of 10, Exceptional, (12)
"My husband and I stayed here back in Oct while he attended a tattoo conference on the ski resort grounds. The place was super cute, cozy and clean. The owner replied to any question I had in a very timely manor. I would definitely recommend this place :)"
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
Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
Exterior

Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds

9.6 out of 10, Exceptional, (18)
"We all had a great visit. Property fantastic. "
Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
Ski on ski off 1 Br loft condo in the village center with private gated parking
Fridge, microwave, oven, stovetop

Ski on ski off 1 Br loft condo in the village center with private gated parking

10.0 out of 10, Exceptional, (16)
"Clean and & comfortable, the location cannot be beat for a ski trip to Jiminy Peak! Jim (owner) was very communicative and great to work with!"
Ski on ski off 1 Br loft condo in the village center with private gated parking
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, (2)
"Condo is very clean and has a well stocked kitchen, and the property has lots of nice amenities. Perfect location that’s essentially ski in ski out. Loved our stay and can’t wait to come back. "
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Perfect for Winter Skiing!!
Fridge, microwave, oven, stovetop

Perfect for Winter Skiing!!

Perfect for Winter Skiing!!
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Interior

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

8.8 out of 10, Excellent, (5)
"Clean, up to date and spacious! Great location for beginner skiiers, also easy to access the rest of the mountain."
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Interior

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

10.0 out of 10, Exceptional, (13)
"Great location, all the amenities were available to us. Right on the base of the mountain. Thx for the stay! "
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Interior

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

10.0 out of 10, Exceptional, (5)
"The room and location were great! The owner was extremely helpful and responsive. We had a great time!"
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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Other property types in The Berkshires

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1801)
"Great property"
The price is AED 434
AED 516 total
includes taxes & fees
6 May - 7 May
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (928)
"Staff was exceptionally helpful and friendly."
The price is AED 493
AED 550 total
includes taxes & fees
30 Apr - 1 May
Jiminy Peak Mountain Resort
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is AED 824
AED 920 total
includes taxes & fees
9 May - 10 May
The Ponds at Foxhollow
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.

Frequently asked questions

How much do condos in The Berkshires cost?
The price range for condos in The Berkshires is AED 434 to AED 434 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 54 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.