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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 Jun

Our top choices for Pittsfield apartments

Exterior

Apartment in Stamford

Getaway Near Mass MoCA, Great Hiking, Scenic Views
10.0 out of 10, Exceptional, (29 reviews)
"We enjoyed our stay "
United States
Lydia T.
The price is €125
includes taxes & fees
3 Mar - 4 Mar
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Living area

Apartment in Adams

Penthouse Apartment on Park Street
9.6 out of 10, Exceptional, (14 reviews)
"Clean property, easy check in, and the owner was super communicative. "
United States
Amanda W.
The price is €238
includes taxes & fees
15 Mar - 16 Mar
Penthouse Apartment on Park Street
Outdoor dining

Apartment in Williamstown

Downtown | Waterfront | Walk to Shops
10.0 out of 10, Exceptional, (7 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is €243
includes taxes & fees
15 Mar - 16 Mar
Downtown | Waterfront | Walk to Shops
Outdoor dining

Apartment in Williamstown

2-Bdr Apt In Town, By the Water
9.6 out of 10, Exceptional, (12 reviews)
"Clean, close to town, very convenient. On a busy road, so just be aware of that. But overall a good place to stay. "
United States
Brian L.
The price is €238
includes taxes & fees
15 Mar - 16 Mar
2-Bdr Apt In Town, By the Water
Outdoor dining

Apartment in Williamstown

New Studio In Town, By the Water
10.0 out of 10, Exceptional, (10 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is €227
includes taxes & fees
15 Mar - 16 Mar
New Studio In Town, By the Water
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, (22 reviews)
"Great place to spend the new years holiday! Perfect location for skiing!"
United States
Alexandra D.
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Gift shop

Apartment in Hancock

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
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 €206
includes taxes & fees
3 Mar - 4 Mar
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Gift shop

Apartment in Hancock

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
10.0 out of 10, Exceptional, (5 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 €198
includes taxes & fees
4 Mar - 5 Mar
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Exterior

Apartment in Hancock

Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
10.0 out of 10, Exceptional, (2 reviews)
"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.
The price is €201
includes taxes & fees
4 Mar - 5 Mar
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Exterior

Apartment in Hancock

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
10.0 out of 10, Exceptional, (11 reviews)
"Room was perfect location for skiing. Able to see slopes and a few of the chairlifts from room. Beds were super comfortable. Parking was close by and in private area which helped avoid parking in huge resort parking lot. Owner was very responsive."
United States
Charles
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Pool

Apartment in Hancock

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
9.6 out of 10, Exceptional, (34 reviews)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is €272
includes taxes & fees
3 Mar - 4 Mar
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
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, (20 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.
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Pool

Apartment in Hancock

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
10.0 out of 10, Exceptional, (2 reviews)
"The condo was in good shape with a great location for skiing. Howard was very responsive. "
United States
John M.
The price is €199
includes taxes & fees
4 Mar - 5 Mar
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Property grounds

Apartment in Hancock

WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
8.8 out of 10, Excellent, (16 reviews)
"We enjoyed our stay. We would definitely stay here again in the future."
United States
Scott
The price is €198
includes taxes & fees
4 Mar - 5 Mar
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Outdoor dining

Apartment in Hancock

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
9.8 out of 10, Exceptional, (7 reviews)
"Great room decorations, travel with two kids they have a great time playing video games"
United States
Andres
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
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
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 €198
includes taxes & fees
4 Mar - 5 Mar
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
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
Pool

Apartment in Hancock

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
9.8 out of 10, Exceptional, (24 reviews)
"This property is spacious, clean and well- appointed. I would stay here again!"
United States
Amanda M.
The price is €198
includes taxes & fees
4 Mar - 5 Mar
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Room is attractive and clean and the staff is always welcoming. Back rooms, where we stay, are quiet and look out across a marsh to the mountain."
Nathaniel 1-night trip
Posted 1 day ago
The Yankee, Trademark Collection by Wyndham

Find out more about Pittsfield

Pittsfield Apartments information

Number of reviews
253
Accommodation
108 Apartments
Lowest Price
€125
Highest Price
€272

Frequently asked questions

What's it like to stay at an apartment in Pittsfield?
You can choose from 8 apartments in Pittsfield for your holiday. You might want to explore the local entertainment venues during your trip.
How do you know if an apartment is the best choice for your stay?
Offering a kitchen for convenient meals, an apartment often has more space than a traditional hotel room. Apartments are a good option for couples who want to live like locals, and also for families wanting the conveniences of home.
What's the top apartment for a stay in Pittsfield?
Below are some of the top apartments in the area to choose from: Chic corporate apartment in wonderful Pittsfield with AC, WiFi: Includes a Smart TV . Access to on-site laundry facilities is available on site . Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located 9.7 mi/15.6 km away in Lee . A patio and a fireplace are included . Access to on-site laundry facilities is available on site . Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Located in Great Barrington , 18.3 mi/29.4 km away. Includes free WiFi, a dining area and a Smart TV . Access to on-site laundry facilities is available on site . FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!: Located 23.9 mi/38.5 km away in Pownal . A private pool, free WiFi and a patio are included . On-site laundry facilities and an outdoor pool are on site . Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton: Located in Dalton , 5.7 mi/9.1 km from Pittsfield. Includes free WiFi, a dining area and a Smart TV . Access to on-site laundry facilities is available on site .
How many apartments should I expect to find in Pittsfield?
Expedia has 8 apartments to book in Pittsfield.
What will the weather be like in Pittsfield?
Although 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 temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm 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 make your trip smoother 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. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station.