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31 Oct - 2 Nov
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Featured Apartments in Pittsfield and around

Smart TV
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
2.0 star property
2.0 out of 10, (1)
"THIS. PLACE. IS. A. DUMP. Do NOT STAY HERE under any circumstances."
United States
Michael
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Games room
Park Street Penthouse Apartment
Park Street Penthouse Apartment
9.6 out of 10, Exceptional, (12)
"Adams is a beautiful town and looks and feels like the appalachian trail! "
United States
judy r.
The price is €172
includes taxes & fees
27 Oct - 28 Oct
Park Street Penthouse Apartment
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
10.0 out of 10, Exceptional, (8)
"Great location. Howie is very communicative. Wish we could have stayed longer. "
United States
Una D.
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Outdoor dining
Downtown | Waterfront | Walk to Shops
Downtown | Waterfront | Walk to Shops
10.0 out of 10, Exceptional, (6)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is €242
includes taxes & fees
23 Oct - 24 Oct
Downtown | Waterfront | Walk to Shops
Outdoor dining
2-Bdr Apt In Town, By the Water
2-Bdr Apt In Town, By the Water
9.4 out of 10, Exceptional, (9)
"Lovely property, in good shape. Close to many Williamstown attractions."
United States
Scott M.
The price is €237
includes taxes & fees
30 Oct - 31 Oct
2-Bdr Apt In Town, By the Water
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
9.8 out of 10, Exceptional, (18)
"We had a great time with our 2 kids during our stay at the Disney Magic Suite. The kids loved all of the Disney decor and surprise touches (and their stuffed animals thank you!). Location was amazing, walk to the lifts, and the ski school was one of the best we've been to. Thanks for a great stay, we'll be back!"
United States
Debbie H.
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Indoor pool
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
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 €205
includes taxes & fees
21 Oct - 22 Oct
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Exterior
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
9.8 out of 10, Exceptional, (19)
"The condo was clean and well located for easy access to the mountain. We were there for tri-state races and having easy acass to the mountain was exactly what we needed for a fun weekend. We would stay here again."
United States
Eric C.
The price is €205
includes taxes & fees
21 Oct - 22 Oct
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel
Berkshires Apartment at the Stephentown Hotel
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
Berkshires Apartment at the Stephentown Hotel
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
10.0 out of 10, Exceptional, (4)
"It was great experience and we loved the ammenities."
United States
Carrie C.
The price is €205
includes taxes & fees
21 Oct - 22 Oct
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Fridge, microwave, oven, stovetop
New Studio In Town, By the Water
New Studio In Town, By the Water
10.0 out of 10, Exceptional, (8)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is €227
includes taxes & fees
21 Oct - 22 Oct
New Studio In Town, By the Water
Fridge, microwave, oven, stovetop
2 Bed Berkshire Getaway @ Stephentown Hotel
2 Bed Berkshire Getaway @ Stephentown Hotel
10.0 out of 10, Exceptional, (4)
"This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place."
United States
elizabeth r.
2 Bed Berkshire Getaway @ Stephentown Hotel
Fridge, microwave, oven, stovetop
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
8.4 out of 10, Very good, (12)
"The apartment is cozy, clean, and perfect for visiting Jiminy Peak."
United States
William G.
The price is €237
includes taxes & fees
26 Oct - 27 Oct
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Exterior
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
9.6 out of 10, Exceptional, (30)
"We really enjoyed our stay it was a very nice place for a family."
United States
Shmaya G.
The price is €288
includes taxes & fees
21 Oct - 22 Oct
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
TV, offices
The Brooks Motel: Exceptional Suite
The Brooks Motel: Exceptional Suite
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is €176
includes taxes & fees
21 Oct - 22 Oct
The Brooks Motel: Exceptional Suite
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
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 €205
includes taxes & fees
21 Oct - 22 Oct
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Exterior
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
9.4 out of 10, Exceptional, (16)
"We absolutely enjoyed this pleasant apartment. Its within the walking distance from the ski lifts which was perfect for all of us including 5 year old kid. "
United States
Janja
The price is €210
includes taxes & fees
21 Oct - 22 Oct
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Pool
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
10.0 out of 10, Exceptional, (2)
"The Game Night Theme Room was booked as a surprise for my 7 year old. Upon seeing the on theme welcome mat and decals on the door he was so excited. Thoughtful touches like the Minecraft Pig made this a camp visiting day weekend that he will never forget. Jiminy Peak is a great spot and we love the walkable restaurant Bluebird Cafe for dinner and the Country Store for a quick breakfast grab. Howie was communicative and described everything perfectly."
United States
Erica G.
The price is €210
includes taxes & fees
21 Oct - 22 Oct
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Exterior
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
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 €205
includes taxes & fees
21 Oct - 22 Oct
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Exterior
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
9.6 out of 10, Exceptional, (30)
"Perfect 1 bedroom, ski in ski off , updated unit with great amenities! Owner super responsive and accommodating. Will definitely be back "
United States
Doris B.
The price is €205
includes taxes & fees
21 Oct - 22 Oct
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Front desk was friendly and helpful. Plenty of parking near our specific unit. Our room was clean, spacious, and very comfortable. The pool and hot tub area were clean and had plenty of towels to use. This was our first time here and we will definitely come back. "
Theresa 1-night trip
Posted 2 days ago
Vacation Village in the Berkshires

Find out more about Pittsfield

Pittsfield Apartments information

Number of reviews
140
Accommodation
117 Apartments
Lowest Price
€172
Highest Price
€288

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?
Listed below are some of the more popular apartments in the area to choose from: Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton: Located in Dalton , 5.7 mi/9.1 km from the heart of Pittsfield. 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 . The Studio mini home away from home in the Berkshires: It's situated in Lee , 9.7 mi/15.5 km away. Includes a patio . 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 . Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4: Located in Hancock , 7.6 mi/12.2 km from Pittsfield. Includes a fireplace . A fitness centre and 1 hot tub are 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 Barrington Stage Company and Bousquet Ski Area.
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.

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