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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 31 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, (1786)
"It was very nice. Had a kitchen and 2 tvs!"
The price is AED 400
AED 476 total
includes taxes & fees
12 Mar - 13 Mar
Vacation Village in the Berkshires
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
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)
"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 AED 525
AED 1,256 total
includes taxes & fees
12 Mar - 13 Mar
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
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
UNIQUE - 1BR Country Condo @ Jiminy Peak
Exterior

UNIQUE - 1BR Country Condo @ Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Friendly respnsive owner. Nice suite. Was very good for my wife, my son and I. Resort is big skiing location. Was somewhat quiet in the summer though "
The price is AED 826
AED 1,692 total
includes taxes & fees
20 Mar - 21 Mar
UNIQUE - 1BR Country Condo @ Jiminy Peak
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)
"Everything was spot on. Will be back!!"
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
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)
"We love Jiminy Peak and having a week at a ski-in, ski-out unit was fantastic. We skied back for lunch and skied back out for the afternoon; skied in for a quick dinner and the boys skied back out for night skiing. Terrific location! Kitchen was clean and serviceable (no oven but two burners, sink, dishwasher, microwave, and toaster) and beds were good. Everything was easy... check in, check out, so smooth. A great time was had by all!!!!"
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
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)
"This property was clean, and in a wonderful location to the mountain and other amenities. Host was professional, kind and courtesy. This was our first experience with an Air B & B. Would rent this condo again. Thank you CP. "
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
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
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, (20)
"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
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
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, (1)
"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
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, (3)
"The Wyndham location can't be beat for access to the mountain, especially with kids (it's literally ski in/out with the kids mountain). Good communication with a very attentive owner throughout the process. He mentioned that it will be renovated this year. Good experience overall. "
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
JIMINY PEAK - 2/14-17, 3 NIGHTS - SLOPE SIDE! SKI IN/SKI OUT, 2BR DELUX UNIT
Pool

JIMINY PEAK - 2/14-17, 3 NIGHTS - SLOPE SIDE! SKI IN/SKI OUT, 2BR DELUX UNIT

JIMINY PEAK - 2/14-17, 3 NIGHTS - SLOPE SIDE! SKI IN/SKI OUT, 2BR DELUX UNIT
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)
"Always perfect!"
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)
"2-bedroom was perfect for our family of four. Great to have a kitchen, shower and tub, washer/dryer, as well as nice shampoo, conditioner, body wash, lotion, and towels for the pool. We enjoyed being so close to the mountain for skiing. JJ’s Lodge had good offerings for lunch and drinks. We also had fun at the indoor/outdoor pool and jacuzzis. Our kids have enjoyed the game room in the past but during this stay the machine to get a card loaded with money wasn’t working. They called immediately...
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
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

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, (1786)
"It was very nice. Had a kitchen and 2 tvs!"
The price is AED 400
AED 476 total
includes taxes & fees
12 Mar - 13 Mar
Vacation Village in the Berkshires
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 Ponds at Foxhollow
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is AED 547
AED 600 total
includes taxes & fees
1 Apr - 2 Apr
Jiminy Peak Mountain Resort
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 400 to AED 1,208 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 31 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.
How can I find cheap condos in The Berkshires?
The quickest way to score cheap condos in The Berkshires is with Expedia’s easy-to-use filter tool. Tailor your search results by amenities, budget and star rating to snag awesome prices in just a few clicks.