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Compare 57 Condo Rentals in Pittsfield with updated reviews, rates, and availability.

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1792)
"Property needs a little upgrade."
The price is SAR 521
SAR 613 total
includes taxes & fees
24 Mar - 25 Mar
Vacation Village in the Berkshires

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 SAR 566
SAR 1,303 total
includes taxes & fees
30 Mar - 31 Mar
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

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 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

10.0 out of 10, Exceptional, (11)
"We had a great time staying at this unit. Great location on the mountain and very helpful owner. I left something in the room and Shana went out of her way to get it back to me. Thank you!"
The price is SAR 296
SAR 1,057 total
includes taxes & fees
29 Mar - 30 Mar
UNIQUE - 1BR Country Condo @ Jiminy Peak

Club Wyndham Bentley Brook Resort - 2 Bedroom

Club Wyndham Bentley Brook Resort - 2 Bedroom

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

Escape to the Heart of Jiminy Peak: Country Inn condo with full kitchen, 2 bths

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 - 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! 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! 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

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

9.4 out of 10, Exceptional, (21)
"Our stay at the Country Inn was perfect for what it was...a short weekend stay to ski for a couple days. The Inn itself is antiquated as are the rooms but the convenience of the ski-in-ski-out location was great. The room was small but adequate since we spent little time there. However, the ability to cook a couple meals there saves some bucks and was perfect. The room, and Inn, itself, could benefit from some new new furniture and decorating, but was as anticipated. Dinner on property was...
Ski-In/Ski-Out at Jiminy Peak in the Country Inn

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

Berkshires Getaway < 1 Mi Skiing & Hiking!

10.0 out of 10, Exceptional, (12)
"Location was perfect! Home is cozy and well equipped! Perfect getaway for our family with great hospitality."
Berkshires Getaway < 1 Mi Skiing & Hiking!

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

10.0 out of 10, Exceptional, (2)
"This unit was absolutely perfect for our family of 4! My husband and I do not ski, but our two boys are 10 and 11 and they LOVE to ski. I enjoyed hanging inside while they went up and down the mountain. We could see them as they went by and they would wave at us. This unit was clean and it suited our needs. Staying on property is such a game changer. The kids can come in for meals and get back out of the slopes. We would definitely stay at this unit again!"
Family-Friendly Mountain Retreat at Jiminy Peak, ski on/off, fitness, 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

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

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

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
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 Pittsfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is SAR 2,059
SAR 3,758 total
includes taxes & fees
21 Mar - 22 Mar
Hancock Village Inn at Jiminy Peak

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (56)
"Perfect location and accommodation for my family. The home was as described. I would recommend it. The property owner was easy to work with. "
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
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 Pittsfield cost?
Condos in Pittsfield range from SAR 296 to SAR 566 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 57 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.
How can I find cheap condos in Pittsfield?
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