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28 Nov - 30 Nov
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Apartments in Pittsfield

Smart TV
Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Apartment in Pittsfield

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
The price is AED 496
AED 751 total
includes taxes & fees
30 Nov - 1 Dec
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Exterior detail
Getaway Near Mass MoCA, Great Hiking, Scenic Views

Apartment in Stamford

10.0 out of 10, Exceptional, (27)
"Nice property for a quick and simple check-in. Near MassMOCA, the Clark Art Institute and much more."
United States
Mario R.
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Fridge, microwave, oven, stovetop
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

9.6 out of 10, Exceptional, (67)
"Great value, so much better than all the touristy motels in the area!"
United States
Chris G.
The price is AED 496
AED 763 total
includes taxes & fees
20 Nov - 21 Nov
Cozy Rustic Apt in 18th c Berkshire Farmhouse
1 bedroom, iron/ironing board, bed sheets
Penthouse Apartment on Park Street

Apartment in Adams

2.0 star property
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 899 total
includes taxes & fees
20 Nov - 21 Nov
Penthouse Apartment on Park Street
Fridge, microwave, oven, stovetop
New Studio In Town, By the Water

Apartment in Williamstown

10.0 out of 10, Exceptional, (10)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is AED 441
AED 945 total
includes taxes & fees
20 Nov - 21 Nov
New Studio In Town, By the Water
Exterior
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Apartment in 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 386
AED 866 total
includes taxes & fees
20 Nov - 21 Nov
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Outdoor dining
2-Bdr Apt In Town, By the Water

Apartment in Williamstown

9.6 out of 10, Exceptional, (11)
"Effortless process! We arrived and felt at home immediately. Could not have been happier with our experience."
United States
Staci A.
The price is AED 441
AED 991 total
includes taxes & fees
20 Nov - 21 Nov
2-Bdr Apt In Town, By the Water
Exterior
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Apartment in Hancock

10.0 out of 10, Exceptional, (5)
"We had a wonderful stay in our fun, pirate themed suite. Which is really what caught our attention in making our reservation. It was so thoughtfully decorated, and suited the theme, while still being a comfortable place to enjoy being in. Everything was in wonderful condition, and had all the amenities we needed. Our host, Howie, was incredibly attentive, personable, and made sure we were taken care of. I was very disorganized, and he went out of his way to get me all the information we needed...
United States
Karen
The price is AED 386
AED 866 total
includes taxes & fees
20 Nov - 21 Nov
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Outdoor dining
Downtown | Waterfront | Walk to Shops

Apartment in Williamstown

10.0 out of 10, Exceptional, (6)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is AED 477
AED 1,016 total
includes taxes & fees
20 Nov - 21 Nov
Downtown | Waterfront | Walk to Shops
Indoor pool
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Apartment in Hancock

9.8 out of 10, Exceptional, (18)
"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 386
AED 866 total
includes taxes & fees
20 Nov - 21 Nov
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Fridge, microwave, oven, stovetop
2 Bed Berkshire Getaway @ Stephentown Hotel

Apartment in Stephentown

10.0 out of 10, Exceptional, (5)
"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.
The price is AED 511
AED 974 total
includes taxes & fees
22 Nov - 23 Nov
2 Bed Berkshire Getaway @ Stephentown Hotel
Property grounds
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

Apartment in 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 386
AED 866 total
includes taxes & fees
20 Nov - 21 Nov
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Exterior
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Apartment in 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 386
AED 866 total
includes taxes & fees
20 Nov - 21 Nov
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Outdoor dining
The Allen House historic North Adams Home in the Berkshire Mountains

Apartment in North Adams

2.0 star property
The price is AED 672
AED 1,182 total
includes taxes & fees
4 Dec - 5 Dec
The Allen House historic North Adams Home in the Berkshire Mountains
Exterior
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Apartment in Hancock

9.6 out of 10, Exceptional, (30)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is AED 584
AED 1,198 total
includes taxes & fees
24 Nov - 25 Nov
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
1 bedroom, WiFi, bed sheets
Charming Apt in 18th c Berkshire Farmhouse

Apartment in Lanesborough

9.4 out of 10, Exceptional, (39)
"It’s a nice comfortable apartment with a good kitchen. We were traveling to see a concert and some art at Mass MOCA. Patrick is a friendly and welcoming host."
United States
Roy
The price is AED 496
AED 746 total
includes taxes & fees
20 Nov - 21 Nov
Charming Apt in 18th c Berkshire Farmhouse
TV, offices
The Brooks Motel: Exceptional Suite

Apartment in Hillsdale

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 AED 584
AED 740 total
includes taxes & fees
15 Dec - 16 Dec
The Brooks Motel: Exceptional Suite
Exterior
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Apartment in Hancock

9.4 out of 10, Exceptional, (16)
"Nice Place"
United States
Tom C.
The price is AED 404
AED 886 total
includes taxes & fees
20 Nov - 21 Nov
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Exterior
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Apartment in 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 404
AED 886 total
includes taxes & fees
20 Nov - 21 Nov
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Fridge, microwave, oven, stovetop
Berkshires Apartment at the Stephentown Hotel

Apartment in Stephentown

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.
The price is AED 354
AED 788 total
includes taxes & fees
23 Nov - 24 Nov
Berkshires Apartment at the Stephentown Hotel
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
"My room was amazing nice view of the mountains the staff were very friendly they have a beautiful indoor pool amazing hot tub and cute movie theater along with a game room and other activities "
Teresa 2-night trip
Posted 2 days ago
Vacation Village in the Berkshires

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: Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located in Lee, 9.7 mi/15.6 km from the heart of Pittsfield. Includes private patios and fireplaces. Access to onsite laundry facilities is available on site. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor: Located 7.6 mi/12.2 km away in Hancock. Amenities include sofa beds. A fitness center and an indoor 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 away. Includes free WiFi, separate dining areas, and Smart TVs. Access to onsite laundry facilities is available on site. Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4: Located 7.6 mi/12.2 km away in Hancock. Amenities include fireplaces. A fitness center and a hot tub 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 from Pittsfield. Includes a private pool, free WiFi, and private patios. Onsite laundry facilities and an outdoor pool are 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.