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Check prices for these dates

In two weeks
30 Jan - 1 Feb
In two months
13 Mar - 15 Mar
In three months
10 Apr - 12 Apr
In four months
8 May - 10 May

Our top choices for Pittsfield apartments

Smart TV

Apartment in Pittsfield

Chic corporate apartment in wonderful Pittsfield with AC, WiFi
2.0 star property
2.0 out of 10, (1 review)
"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
15 Jan - 16 Jan
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Living area

Apartment in Adams

Penthouse Apartment on Park Street
2.0 star property
9.6 out of 10, Exceptional, (14 reviews)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is AED 533
AED 1,030 total
includes taxes & fees
27 Jan - 28 Jan
Penthouse Apartment on Park Street
Exterior

Apartment in North Adams

The Allen House historic North Adams Home in the Berkshire Mountains
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"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 716
AED 1,239 total
includes taxes & fees
13 Feb - 14 Feb
The Allen House historic North Adams Home in the Berkshire Mountains
Private kitchen

Apartment in Lee

Updated and inviting home in Lenoxdale
2.0 star property
The price is AED 555
AED 1,379 total
includes taxes & fees
28 Jan - 29 Jan
Updated and inviting home in Lenoxdale
WiFi, bed sheets

Apartment in Lanesborough

Cozy Rustic Apt in 18th c Berkshire Farmhouse
9.6 out of 10, Exceptional, (67 reviews)
"What a quaint and comfy place!"
United States
Lori A.
The price is AED 496
AED 763 total
includes taxes & fees
15 Jan - 16 Jan
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Dining

Apartment in Lanesborough

Charming Apt in 18th c Berkshire Farmhouse
9.4 out of 10, Exceptional, (40 reviews)
"Patrick was super nice and his farmers market/ cafe is great. Got to cut my own flowers from his field for free! I would definitely stay there again if in the area."
United States
Patricia A.
The price is AED 496
AED 763 total
includes taxes & fees
15 Jan - 16 Jan
Charming Apt in 18th c Berkshire Farmhouse
Dining

Apartment in Lanesborough

Bright Boho Apt in 18th c Berkshire Farmhouse
9.0 out of 10, Wonderful, (22 reviews)
"I loved staying here the weekend with my friends, the owner Patrick was so accommodating and helpful!"
United States
Mckenna d.
The price is AED 533
AED 808 total
includes taxes & fees
19 Jan - 20 Jan
Bright Boho Apt in 18th c Berkshire Farmhouse
Exterior

Apartment in Hancock

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
10.0 out of 10, Exceptional, (8 reviews)
"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
19 Jan - 20 Jan
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Pool

Apartment in Hancock

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"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.
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Indoor pool

Apartment in Hancock

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
9.8 out of 10, Exceptional, (20 reviews)
"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
19 Jan - 20 Jan
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Indoor pool, a heated pool

Apartment in Hancock

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
9.4 out of 10, Exceptional, (6 reviews)
"Great location. Very nice vacation. Would def go again. "
United States
Elizabeth M.
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Indoor pool

Apartment in Hancock

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
9.6 out of 10, Exceptional, (19 reviews)
"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
19 Jan - 20 Jan
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Gift shop

Apartment in Hancock

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
10.0 out of 10, Exceptional, (3 reviews)
"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
19 Jan - 20 Jan
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Pool

Apartment in Hancock

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
9.8 out of 10, Exceptional, (31 reviews)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is AED 775
AED 1,444 total
includes taxes & fees
15 Jan - 16 Jan
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Property grounds

Apartment in Hancock

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
10.0 out of 10, Exceptional, (5 reviews)
"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
20 Jan - 21 Jan
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Exterior

Apartment in Hancock

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
8.8 out of 10, Excellent, (8 reviews)
"Everything was wonderful…"
United States
Alyne K.
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Property grounds

Apartment in Hancock

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
9.2 out of 10, Wonderful, (12 reviews)
"We enjoyed our stay. We would definitely stay here again in the future."
United States
Scott
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Exterior

Apartment in Hancock

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
10.0 out of 10, Exceptional, (1 review)
"The one-bedroom aparment is spacious, very clean, nice and funtional furniture and a perfectly well equipped kitchen area. Our 2 grandchildren had a fun time. And the apartament is footsteps from the ski lifts - a real treat! I highly recommend it!Ps. And the owner is always at hand, very helpful, and concerned that all is perfect for the guest's stay."
United States
Antonio S.
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Pool

Apartment in Hancock

Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
9.6 out of 10, Exceptional, (30 reviews)
"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
19 Jan - 20 Jan
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Pool

Apartment in Hancock

Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
9.4 out of 10, Exceptional, (16 reviews)
"Nice Place"
United States
Tom C.
The price is AED 503
AED 1,013 total
includes taxes & fees
15 Jan - 16 Jan
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Clean & warm room, nice desk & chair area. Very nice breakfast spread. At the front desk, Shelly was very helpful & cheerful! We'd like to stay there again. "
Leslieann 1-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

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 Guido's Marketplace.
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.