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Check prices for these dates

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16 Jan - 18 Jan
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23 Jan - 25 Jan
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6 Feb - 8 Feb
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6 Mar - 8 Mar

Our top choices for Pittsfield apartments

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Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Chic corporate apartment in wonderful Pittsfield with AC, WiFi
2.0 star property
Pittsfield
2.0 out of 10, (1)
"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."
United States
Michael
The price is AED 496
AED 751 total
includes taxes & fees
8 Jan - 9 Jan
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Exterior
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (28)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
The price is AED 248
AED 525 total
includes taxes & fees
8 Jan - 9 Jan
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Living area
Penthouse Apartment on Park Street

Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
2.0 star property
Adams
9.6 out of 10, Exceptional, (13)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is AED 426
AED 894 total
includes taxes & fees
8 Jan - 9 Jan
Penthouse Apartment on Park Street
Exterior
The Allen House historic North Adams Home in the Berkshire Mountains

The Allen House historic North Adams Home in the Berkshire Mountains

The Allen House historic North Adams Home in the Berkshire Mountains
2.0 star property
North Adams
10.0 out of 10, Exceptional, (1)
"The Allen House was a wonderful stay for my family and we cannot wait to go back! The view was incredible; the host was very approachable for questions; and there were lots of nice touches like ample dishes and silverware.Very spacious, clean and cared for location. "
United States
Annemarie M.
The price is AED 643
AED 1,169 total
includes taxes & fees
9 Jan - 10 Jan
The Allen House historic North Adams Home in the Berkshire Mountains
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Hancock
10.0 out of 10, Exceptional, (8)
"We had a wonderful 3 day weekend! Perfect location for families."
United States
Eric B.
The price is AED 503
AED 1,013 total
includes taxes & fees
8 Jan - 9 Jan
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Pool
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
2.0 star property
Hancock
10.0 out of 10, Exceptional, (1)
"The host communicated everything and ensured we had all the necessary information for our arrival. The room was super clean and everything was new. Really enjoyed our stay and had plenty of room and closets for storage. Would definitely stay again and truly a premiere host!! Angelica "
United States
Jeffrey R.
The price is AED 503
AED 1,013 total
includes taxes & fees
8 Jan - 9 Jan
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Indoor pool
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (20)
"Great place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
The price is AED 503
AED 1,013 total
includes taxes & fees
8 Jan - 9 Jan
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Property grounds
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (5)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is AED 503
AED 1,013 total
includes taxes & fees
8 Jan - 9 Jan
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Indoor pool
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Hancock
9.6 out of 10, Exceptional, (19)
"We enjoyed our stay in this adorable Disney Themed condo. The attention to detail in the theming was fantastic and the condo was perfect for our February Vacation ski trip."
United States
Allison V.
The price is AED 503
AED 1,013 total
includes taxes & fees
8 Jan - 9 Jan
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Gift shop
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Hancock
10.0 out of 10, Exceptional, (3)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is AED 503
AED 1,013 total
includes taxes & fees
8 Jan - 9 Jan
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Pool
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.8 out of 10, Exceptional, (31)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is AED 775
AED 1,440 total
includes taxes & fees
8 Jan - 9 Jan
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Indoor pool, a heated pool
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6)
"Great location. Very nice vacation. Would def go again. "
United States
Elizabeth M.
The price is AED 503
AED 1,013 total
includes taxes & fees
8 Jan - 9 Jan
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Pool
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock
9.4 out of 10, Exceptional, (16)
"Nice Place"
United States
Tom C.
The price is AED 503
AED 1,013 total
includes taxes & fees
8 Jan - 9 Jan
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Exterior
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock
8.8 out of 10, Excellent, (8)
"Everything was wonderful…"
United States
Alyne K.
The price is AED 503
AED 1,013 total
includes taxes & fees
8 Jan - 9 Jan
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Property grounds
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Hancock
9.2 out of 10, Wonderful, (12)
"We enjoyed our stay. We would definitely stay here again in the future."
United States
Scott
The price is AED 503
AED 1,013 total
includes taxes & fees
8 Jan - 9 Jan
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Pool
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Hancock
9.6 out of 10, Exceptional, (30)
"Was in town for my HS reunion and loved my stay! Great location and amenities and the condo itself is super cute."
United States
Maura S.
The price is AED 503
AED 1,013 total
includes taxes & fees
8 Jan - 9 Jan
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Pool
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
10.0 out of 10, Exceptional, (23)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is AED 503
AED 1,013 total
includes taxes & fees
8 Jan - 9 Jan
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Very good "
Fernando 5-night trip
Posted 2 days ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Frequently asked questions

What's it like to stay at an apartment in Pittsfield?
You'll find 8 apartments to choose from in Pittsfield for your vacation. You might want to check out the local entertainment venues during your trip.
How do you know if an apartment is a good option for your stay?
An apartment features a kitchen for convenient meals, and is often more spacious than a traditional hotel room. Apartments are a good option for solo travelers who want to live like locals, and also for families wanting the conveniences of home.
What's the best apartment for my stay in Pittsfield?
Listed below are some of the top apartments in the area to choose from: Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Located in Great Barrington, 18.3 mi/29.4 km from the heart of Pittsfield. Includes free WiFi, separate dining areas, and Smart TVs. Access to onsite laundry facilities is available on site. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn: Located 7.7 mi/12.3 km away in Hancock. Amenities include sofa beds. A fitness center and onsite laundry facilities are on site. FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!: Located in Pownal, 23.9 mi/38.5 km away. Includes a private pool, free WiFi, and private patios. Onsite laundry facilities and an outdoor pool are on site. Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous: Located 7.7 mi/12.4 km away in Hancock. Fireplaces and sofa beds are included. A fitness center and onsite laundry facilities are on site. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located in Lee, 9.7 mi/15.6 km from Pittsfield. Includes private patios and fireplaces. Access to onsite laundry facilities is available on site.
How many apartments are there in Pittsfield?
Expedia has 8 apartments to book in Pittsfield.
What will the weather be like in Pittsfield?
Though weather is just one factor, it can really affect your travel plans, especially if you're planning an extended stay in Pittsfield. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Pittsfield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What are the must-see places to visit in Pittsfield?
Pittsfield is known for its entertainment venues. Cultural attractions include Berkshire Museum and Colonial Theater, whereas Housatonic River and Canoe Meadows Wildlife Sanctuary are a couple of picturesque spots to enjoy the outdoors. Other places in town to visit include Bousquet Ski Area and Hancock Shaker Village.
What's the best way to get to and around Pittsfield?
Knowing a bit about the transportation options can you save you a headache when you get to your destination. Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the heart of the city. You can also search for flights into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. To venture out into the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station.