Search and Rent Berkshire County Condos

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Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
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Mar 27 - Mar 29

Top Cities in Berkshire County

Williamstown featuring cafe lifestyle
Condo RentalsCondo Rentals

Williamstown

Williamstown

Condo Rentals in Berkshire County

Lobby
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3.0 star property
Williamstown
8.8 out of 10, Excellent, (2163)
"Great stay and beautiful scenery close to Jiminy’s Peak Ski slopes. They have a heated pool for winter weather and extra outdoor for the summer plus other family oriented amenities"
United States
Karla
$111 nightly
The price is $124
Dec 7 - Dec 8
Total with taxes and fees
Vacation Village in the Berkshires
Living area
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool

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

Hancock
10.0 out of 10, Exceptional, (3)
"Good base for Berkshires, responsive host, good rates, secure."
United States
Robert
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, pool
Fridge, microwave, oven, stovetop
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!

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

Hancock
10.0 out of 10, Exceptional, (14)
"We'll be back!"
United States
Jeanne D.
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Pool
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

Hancock
8.0 out of 10, Very Good, (8)
"Perfect spot for Mountain Adventures, property was well equipped with comfortable necessities. It was very clean and spacious for six people, 3 adults and 3 young boys. We would definitely stay again. "
United States
PK N.
$301 nightly
The price is $336
Dec 8 - Dec 9
Total with taxes and fees
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Property grounds
Tranquil Lakeside Escape in the Berkshires

Tranquil Lakeside Escape in the Berkshires

Lenox
10.0 out of 10, Exceptional, (1)
"perfect location to go everywhere in the Berkshires"
United States
Edward G.
Tranquil Lakeside Escape in the Berkshires
Fridge, microwave, oven, stovetop
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2

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

Hancock
10.0 out of 10, Exceptional, (36)
"Great location and fabulous host, very helpful and kind."
United States
Richard H.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
Property grounds
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1

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

Hancock
10.0 out of 10, Exceptional, (41)
"We loved our stay at this condo! It was immaculate, comfortable, and convenient to all of the local spots we wanted to visit. Our host, Colin, was very responsive. We would definitely stay here again. It would likely be fabulous in the fall too!"
United States
Kathy C.
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
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

Hancock
10.0 out of 10, Exceptional, (1)
"The clean room was very comfortable and we enjoyed the mountain view"
United States
Susan C.
Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths
Interior
UNIQUE - 1BR Country Condo @ Jiminy Peak

UNIQUE - 1BR Country Condo @ Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (14)
"Clean, comfortable place with nice amenities. "
United States
Mike H.
$504 nightly
The price is $563
Dec 8 - Dec 9
Total with taxes and fees
UNIQUE - 1BR Country Condo @ Jiminy Peak
Pool
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Hancock
9.0 out of 10, Wonderful, (2)
"very nice and roomy! really enjoyed."
United States
Shack M.
$270 nightly
The price is $302
Dec 8 - Dec 9
Total with taxes and fees
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Exterior
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Hancock
9.6 out of 10, Exceptional, (17)
"Perfect place for our annual ski-cation. Great accommodations minutes from Jiminy Peak. Equipped with everything you need for a great vacation!"
United States
Nancy S.
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Property grounds
Peaceful 1BR Condo with Pond View

Peaceful 1BR Condo with Pond View

Lenox
8.0 out of 10, Very Good, (2)
"Beautiful grounds and views and so close to Tanglewood! We had a great time. Apartment was clean and very private. It was quiet and quaint.The only issue I should mention is the carpeting; seemed a bit dump and not very appealing."
United States
Maria C.
Peaceful 1BR Condo with Pond View
Exterior
Ski-In/Ski-Out at Jiminy Peak in the Country Inn

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

Hancock
9.0 out of 10, Wonderful, (27)
"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. "
United States
Nicole S.
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Outdoor dining
Charming 3-bedroom condo with WiFi in Williamstown, MA

Charming 3-bedroom condo with WiFi in Williamstown, MA

Williamstown
Charming 3-bedroom condo with WiFi in Williamstown, MA
Exterior
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5

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

Hancock
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!"
United States
Christine O.
Ski In & Ski Out - Deluxe 1 Bedroom Condo Sleeps 5
Fridge, microwave, stovetop, dishwasher
Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025

Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025

Pittsfield
8.0 out of 10, Very Good, (1)
"Convenient location. Noisy guests in room above ours. "
United States
Anne C.
Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 11/26-11/29/2025
Interior
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook

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

Hancock
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! "
United States
lauren t.
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

Hancock
10.0 out of 10, Exceptional, (5)
"Staff and services were outstanding. Great family gathering."
United States
Gerard D.
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Living area
Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.

Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.

Lee
Summer in the Berkshires: Cozy country condo in charming Stockbridge MA.
Lobby
2-bedroom Condo at Vacation Village in the Berkshires Available 11/21-11/28/25

2-bedroom Condo at Vacation Village in the Berkshires Available 11/21-11/28/25

3.0 star property
hancock
2-bedroom Condo at Vacation Village in the Berkshires Available 11/21-11/28/25
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 Berkshire County Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"I am a cross country traveling nurse. The Berkshire Mountain Lodge was perfect for my needs. A fully functioning well appointed kitchen. Spacious living quarters with excellent views. The best water pressure on a shower that I have ever known. Fantastic after a long day of work or out hiking the many nature trails here. And the bed was so perfectly firm and cozy that I drifted effortlessly to sleep. The grounds, the amenities and the coordinated activities to bring you together in community made me feel included. Definitely a place I will continue to return to for many years."
salena 9-night trip
Posted 16 hours ago
Berkshire Mountain Lodge

Find out more about Berkshire County

Berkshire County Condo Rentals information

Number of reviews
2,321
Accommodation
62 Condo Rentals
Lowest Price
$124
Highest Price
$563

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