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Featured Condo Rentals in The Berkshires and around

Vacation Village in the Berkshires
Relax in a stylish living area with a large carpet, comfortable sofas, and a wooden coffee table.

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1901)
"Great stay with all plenty of things to do…"
The price is €92
includes taxes & fees
25 Aug - 26 Aug
Vacation Village in the Berkshires
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Warm winter scenes set the tone in this charming neighborhood.

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

9.6 out of 10, Exceptional, (24)
"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
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Guests can enjoy skiing and mountain views from the central lodge.

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

10.0 out of 10, Exceptional, (37)
"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
Relax in a spacious spa room with a large hot tub and comfortable seating area.

UNIQUE - 1BR Country Condo @ Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Clean and quiet, nicely decorated! "
UNIQUE - 1BR Country Condo @ Jiminy Peak
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
Country Inn's charming entrance features a covered porch and white columns, flanked by a picket fence.

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
Peaceful 1BR Condo with Pond View
Steps lead down to the tranquil lake's edge, surrounded by trees and shrubs.

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
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Relax by the pool surrounded by lush surroundings and enjoy the view.

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 €307
includes taxes & fees
28 Jul - 29 Jul
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub
Spa

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

1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Enjoy cooking in this well-equipped kitchen with a dishwasher, coffee maker, and ample storage.

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

10.0 out of 10, Exceptional, (31)
"Everything was spot on. Will be back!!"
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Relax in a cozy seating area with a large window offering a view of the outdoors, a flat-screen TV, and a comfortable sofa.

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
Club Wyndham Bentley Brook Resort - 2 Bedroom
Situated in a beautifully landscaped area, this gazebo offers a serene escape with a symmetrical roof and vertical slats.

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 LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Kitchen features stainless steel appliances, a small island with stools, and a large window with an outdoor view.

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
Situated in a serene garden, this gazebo offers a peaceful retreat.

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Stunning traditional architecture with a central entrance and evergreen tree.

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 on ski off 1 Br loft condo in the village center with private gated parking
Enjoy cooking in this well-equipped kitchen with stainless steel appliances, white cabinetry, and a granite countertop.

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
Perfect for Winter Skiing!!
Kitchen features a microwave, oven, refrigerator, coffee maker, toaster, sink, and countertop with a fruit basket.

Perfect for Winter Skiing!!

Perfect for Winter Skiing!!
Club Wyndham Bentley Brook Resort - 2 Bedroom
Situated in a landscaped area, this gazebo offers a serene escape with a pathway leading to it.

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Club Wyndham Bentley Brook Resort - 2 Bedroom
Escape to a serene oasis with a gazebo-style structure surrounded by a beautifully landscaped lawn and a pathway.

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Club Wyndham Bentley Brook Resort - 2 Bedroom
Situated in a landscaped area, this gazebo offers a serene ambiance.

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom
Club Wyndham Bentley Brook Resort - 2 Bedroom
Stroll through the serene landscaped area to this charming gazebo, situated near a building with a staircase.

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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Top The Berkshires Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"We came up for our aon's bagpipe competition and it was the perfect spot."
Anthony 1-night trip
Posted 17 hours ago
Vacation Village in the Berkshires

Frequently asked questions

How much do condos in The Berkshires cost?
The price range for condos in The Berkshires is €92 to €307 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 63 condos in The Berkshires and then select your favourite. Whether you're embarking on a holiday 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.