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Check prices for these dates

Next weekend
31 Muh. - 2 Saf.
In two weeks
7 Saf. - 9 Saf.
In one month
21 Saf. - 23 Saf.
In two months
21 Rab. I - 23 Rab. I

Compare 31 Condo Rentals in Pittsfield with updated reviews, rates, and availability.

Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1757)
"Room was right across from the pool. Beautiful view of the mountain five min drive to the base. Beautiful pool and outdoor jacuzzi. Had an amazing stay! Cant wait to go back!"
The price is SAR 703
SAR 809 total
includes taxes & fees
23 Jan - 24 Jan
Vacation Village in the Berkshires
Ski on ski off 1 Br loft condo in the village center with private gated parking
Snow and ski sports

Ski on ski off 1 Br loft condo in the village center with private gated parking

10.0 out of 10, Exceptional, (14)
"This property was unbelievable! The locetion , the amenities, the host, the beautiful and spotless residence! You will not be disappointed! Jim was extremely responsive and his home was perfect! "
Ski on ski off 1 Br loft condo in the village center with private gated parking
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Fireplace and Pullout Queen Sofa Bed in the Main Room

2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7

10.0 out of 10, Exceptional, (1)
"My friends and I planned a last minute trip to Jimmy Peak which is a great mountain for all types of skiers. The host was very communicative right away and made sure everything was ready and gave me information for not just the house but where to go into town. The house was very clean and very comfortable to stay at almost like a true “ home away from home”. The home is very cozy and brings a great vibe to the trip. Even after our stay the host made sure to stay in contact and make sure...
The price is SAR 698
SAR 1,465 total
includes taxes & fees
23 Jan - 24 Jan
2 BR Condo Mountain Views At Jiminy Peak- Sleeps 7
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
Living area

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

9.4 out of 10, Exceptional, (18)
"All you need for a ski trip"
Ski-In/Ski-Out at Jiminy Peak in the Country Inn
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)
"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 2
Snow and ski sports

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

10.0 out of 10, Exceptional, (29)
"The accommodations were great for my husband & I plus 4 young adults. The fireplace is a nice touch. The views are spectacular. Checking in was fairly easy after getting the gate remote. Would have loved if they had smart TVs to watch Netflix as I was not able to ski due to a back injury, but they did have a tv in every room. I would recommend bringing a fire-stick,gaming system, or board games of your own.We did appreciate the washer & dryer as well as the jacuzzi tub. Bring your own alcohol...
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 1
Snow and ski sports

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

10.0 out of 10, Exceptional, (36)
"This was a perfect home base for our family vacation in the Berkshires. Centrally located, clean, had everything we needed, and the pool access was a huge plus with the kids! "
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 1
Berkshires Getaway < 1 Mi Skiing & Hiking!
Charlemont Vacation Rental | 3BR | 1.5BA | 1,800 Sq Ft | 2 Steps to Enter

Berkshires Getaway < 1 Mi Skiing & Hiking!

10.0 out of 10, Exceptional, (10)
"Beautiful spot, great location right at the mountain! We had such a great time here!"
Berkshires Getaway < 1 Mi Skiing & Hiking!
UNIQUE - 1BR Country Condo @ Jiminy Peak
Room

UNIQUE - 1BR Country Condo @ Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Friendly respnsive owner. Nice suite. Was very good for my wife, my son and I. Resort is big skiing location. Was somewhat quiet in the summer though "
UNIQUE - 1BR Country Condo @ Jiminy Peak
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
Property grounds

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

10.0 out of 10, Exceptional, (11)
"My husband and I stayed here back in Oct while he attended a tattoo conference on the ski resort grounds. The place was super cute, cozy and clean. The owner replied to any question I had in a very timely manor. I would definitely recommend this place :)"
SKI-IN, SKI-OUT LOFT! IN the HEART of JIMINY PEAK VILLAGE! LIFT and MT. VIEWS!
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Exterior

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

10.0 out of 10, Exceptional, (10)
"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
Perfect for Winter Skiing!!
Exterior

Perfect for Winter Skiing!!

Perfect for Winter Skiing!!
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Exterior

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

8.0 out of 10, Very Good, (1)
"Andrew was great and very communicative about some issues the property was having due to a burst pipe leak. He was super responsive."
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
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
IN/OUT SKIING CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES
Property grounds

IN/OUT SKIING CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES

10.0 out of 10, Exceptional, (3)
"Our family all met at Jiminy Peak and stayed in this wonderful condo. It was as exactly as advertised, a true ski in & ski out at the base of the mountain. Check in was easy and we were very happy with this beautiful, clean and convenient condo. We had someone sleeping on the pull out couch, finding the sheets was very easy and he said it was comfortable!!! We had a great weekend and plan to stay here again next year!!!"
IN/OUT SKIING CONDO , POOL, MOVIE THEATER/ KIDS ACTIVITIES
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Exterior

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
Exterior

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

8.8 out of 10, Excellent, (5)
"Clean, up to date and spacious! Great location for beginner skiiers, also easy to access the rest of the mountain."
The Berkshire's Jiminy Mountain's Club Wyndham Bentley Brook
Club Wyndham Bentley Brook Resort - 2 Bedroom
Bentley_20Brook_20CW_20EX_20019_S.jpg

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 Jiminy Peak Xmas Wk: Fri-Mon 12/27-30 for 3 Nites; @Wyndham Bentley Brook
Exterior

Ski Jiminy Peak Xmas Wk: Fri-Mon 12/27-30 for 3 Nites; @Wyndham Bentley Brook

10.0 out of 10, Exceptional, (1)
"The space worked perfectly for us and we love the mountain for the convenience and character."
Ski Jiminy Peak Xmas Wk: Fri-Mon 12/27-30 for 3 Nites; @Wyndham Bentley Brook
Jiminy Peak 2 Bedroom 2 Bath Deluxe Condo. Wyndham Bentley Brook
Snow and ski sports

Jiminy Peak 2 Bedroom 2 Bath Deluxe Condo. Wyndham Bentley Brook

2.0 star property
Jiminy Peak 2 Bedroom 2 Bath Deluxe Condo. 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

Chic Pittsfield Home With A View!

Chic Pittsfield Home With A View!

8.6 out of 10, Excellent, (10)
"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "
Chic Pittsfield Home With A View!
Hancock Village Inn at Jiminy Peak
Hancock Village Inn in Winter

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (9)
"Annual mother/son ski and food fest!Lots of fun with family and friends. Plenty of space for everyone.. Kitchen wascwell"
The price is SAR 2,243
SAR 3,936 total
includes taxes & fees
28 Jan - 29 Jan
Hancock Village Inn at Jiminy Peak
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1757)
"Room was right across from the pool. Beautiful view of the mountain five min drive to the base. Beautiful pool and outdoor jacuzzi. Had an amazing stay! Cant wait to go back!"
The price is SAR 703
SAR 809 total
includes taxes & fees
23 Jan - 24 Jan
Vacation Village in the Berkshires
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 698 to SAR 703 per night. These stays provide lots of room 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?
Pick from 31 condos in Pittsfield. No matter if you’re vacationing with the kids or getting away with some friends, Expedia will help you find the ideal base for your squad.
Why book your condo in Pittsfield with Expedia?
Vacationing should be stress-free, so if you’re in search of condos at a competitive rate, Expedia can help. Save cash and opt for something small and affordable, or book a 5-star condo and pamper your loved ones. Our search filters make it a breeze to secure a stay in Pittsfield that matches your needs.
How can I find cheap condos in Pittsfield?
Expedia can help you easily locate cheap condos in Pittsfield. To find a fantastic stay in just a few clicks, simply use our convenient filter tool to tailor your search results by star rating, amenities and budget.