Search Condos in The Berkshires

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

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, (1886)
"Great stay with all plenty of things to do…"
Vacation Village in the Berkshires
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Exterior

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
Property grounds

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
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 NZ$575
includes taxes & fees
3 Aug - 4 Aug
UNIQUE - 1BR Country Condo @ Jiminy Peak
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
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
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 NZ$579
includes taxes & fees
21 July - 22 July
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub
Fridge, microwave, stovetop, dishwasher

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
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, (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
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
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 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
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 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
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
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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

How much do condos in The Berkshires cost?
The price range for condos in The Berkshires is NZ$575 to NZ$579 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.
What is there to do in The Berkshires near my condo?
Whether you enjoy arts, culture, shopping or dining, The Berkshires offers the lot, and then some! The awesome city of Lenox boasts plenty of things to do and see, including Tanglewood Music Centre, Shakespeare and Company and The Mount. If you're planning an escape to Williamstown, Chapin Library of Rare Books and Manuscripts, Hopkins Observatory and Williams College Museum of Art are must-do's.