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In two weeks
17 Oct - 19 Oct
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec
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23 Jan - 25 Jan

Condo Rentals in Pittsfield

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (2028)
"Really nice place at a reasonable price"
The price is AED 364
AED 447 total
includes taxes & fees
20 Oct - 21 Oct
Vacation Village in the Berkshires
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Pool

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

8.0 out of 10, Very Good, (8)
"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 518
AED 1,255 total
includes taxes & fees
2 Oct - 3 Oct
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
Outdoor dining

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

8.0 out of 10, Very Good, (1)
"very nice and roomy! really enjoyed."
The price is AED 500
AED 1,104 total
includes taxes & fees
30 Sep - 1 Oct
2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous
UNIQUE - 1BR Country Condo @ Jiminy Peak
Interior

UNIQUE - 1BR Country Condo @ Jiminy Peak

10.0 out of 10, Exceptional, (13)
"Clean and quiet, nicely decorated! "
The price is AED 474
AED 1,280 total
includes taxes & fees
6 Oct - 7 Oct
UNIQUE - 1BR Country Condo @ Jiminy Peak
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Exterior

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

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. "
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, (40)
"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
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
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
Tranquil Lakeside Escape in the Berkshires
Property grounds

Tranquil Lakeside Escape in the Berkshires

10.0 out of 10, Exceptional, (1)
"perfect location to go everywhere in the Berkshires"
Tranquil Lakeside Escape in the Berkshires
Peaceful 1BR Condo with Pond View
Property grounds

Peaceful 1BR Condo with Pond View

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."
Peaceful 1BR Condo with Pond View
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
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, (34)
"Hot tub was nice. We took a chair lift to the top of the mountain. The view was spectacular. The condo was very comfortable and clean. The only thing that can use some improvement is the water pressure in the shower and definitely a new shower head. The one in the bunk room bathroom really needs an upgrade. Otherwise we had a delightful stay."
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
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 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, (13)
"We'll be back!"
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Exterior

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

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!"
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
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
Club Wyndham Bentley Brook Resort - 2 Bedroom
Exterior

Club Wyndham Bentley Brook Resort - 2 Bedroom

6.0 out of 10, (2)
"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
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.
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Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Clean room and friendly staff. No issues at all. Will definitely stay again."
Yang 2-night trip
Posted 5 hours ago
Vacation Village in the Berkshires

Frequently asked questions

How much do condos in Pittsfield cost?
Condos in Pittsfield range from AED 447 to AED 1,280 per night. These properties offer extra space for the whole family at a price that doesn't break the bank. 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 Pittsfield?
Pittsfield has 67 condos. To help you locate a place that's perfect, use our filters to search for the amenities or perks you need.
Why book your condo in Pittsfield with Expedia?
Vacays should be hassle-free, so if you're in search of condos at a competitive rate, Expedia has your back. Keep the budget in check and pick something small and affordable, or book a 5-star condo and spoil your favorite people. Our search filters make it simple to find a stay in Pittsfield that checks your boxes.