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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Pittsfield apartments

Exterior

Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (33 reviews)
"Perfect for our weekend getaway. Close to the activities we wanted in North Adams, Mass, but just across the state line in a lovely rural setting. A very nice apartment... just as described. So happy to have chosen this for our stay!"
United States
Bill
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Outdoor dining

Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (8 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is AED 551
AED 1,158 total
includes taxes & fees
20 Jul - 21 Jul
Downtown | Waterfront | Walk to Shops
Outdoor dining

2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.0 out of 10, Wonderful, (13 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
The price is AED 477
AED 1,087 total
includes taxes & fees
15 Jul - 16 Jul
2-Bdr Apt In Town, By the Water
Gift shop

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
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.
The price is AED 549
AED 1,072 total
includes taxes & fees
12 Jul - 13 Jul
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Outdoor dining

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Hancock
9.8 out of 10, Exceptional, (8 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
The price is AED 558
AED 1,054 total
includes taxes & fees
14 Jul - 15 Jul
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
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
Hancock
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 AED 558
AED 1,083 total
includes taxes & fees
14 Jul - 15 Jul
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is AED 551
AED 699 total
includes taxes & fees
13 Jul - 14 Jul
The Brooks Motel: Exceptional Suite
Dining

Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse
Lanesborough
9.4 out of 10, Exceptional, (40 reviews)
"Clean, friendly, but isolated. On premises coffee shop was a bonus."
United States
Karl K.
The price is AED 496
AED 763 total
includes taxes & fees
16 Jul - 17 Jul
Charming Apt in 18th c Berkshire Farmhouse
Property grounds

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
North Adams
The price is AED 331
AED 730 total
includes taxes & fees
15 Jul - 16 Jul
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
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
Hancock
9.6 out of 10, Exceptional, (33 reviews)
"The suite was a great. Comfortable, clean and decorated very nicely. Bed was very comfortable with nice linens and pillows. "
United States
Eileen O.
The price is AED 558
AED 1,083 total
includes taxes & fees
14 Jul - 15 Jul
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Outdoor dining

New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (15 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is AED 496
AED 1,062 total
includes taxes & fees
15 Jul - 16 Jul
New Studio In Town, By the Water
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
Hancock
9.6 out of 10, Exceptional, (17 reviews)
"Host very responsive. I gave feedback that could make stay better like more hangars and some coat hooks. Massage chair in unit was a hit with the whole family.Unit is literally the last unit in last builing of Coubtry Inn away from ski school and Express lift. Still walkable, just not in ski boots.Parking in front of unit super easy.No elevator nearby. Upstairs with luggage. "
United States
Joe C.
The price is AED 558
AED 1,083 total
includes taxes & fees
14 Jul - 15 Jul
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Living area

Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (14 reviews)
"Our stay was beautiful! The check in process was super easy and the building was easy to access. The apartment was very clean and it was a lovely stay."
United States
Margaret C.
The price is AED 533
AED 1,034 total
includes taxes & fees
3 Aug - 4 Aug
Penthouse Apartment on Park Street
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
Hancock
8.8 out of 10, Excellent, (8 reviews)
The price is AED 558
AED 1,083 total
includes taxes & fees
14 Jul - 15 Jul
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Pool

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Hancock
9.6 out of 10, Exceptional, (34 reviews)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
TV, fireplace, DVD player

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Hancock
The price is AED 823
AED 1,502 total
includes taxes & fees
14 Jul - 15 Jul
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
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
Hancock
9.0 out of 10, Wonderful, (17 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
The price is AED 558
AED 1,083 total
includes taxes & fees
14 Jul - 15 Jul
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Gift shop

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, (12 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is AED 558
AED 1,083 total
includes taxes & fees
14 Jul - 15 Jul
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very Good, (6 reviews)
"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 580
AED 736 total
includes taxes & fees
12 Jul - 13 Jul
The Brooks Motel: Exceptional Suite
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
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is AED 558
AED 1,083 total
includes taxes & fees
14 Jul - 15 Jul
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone 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 Inn

The Yankee Inn

8/10 Good
"The hotel is a few minutes from Tanglewood and the Berkshire hotspots. Super friendly staff. Very accommodating. The place is a bit dated, but that has a retro charm like places on the Cape. The grounds are lovely. The breakfast is like other hotel breakfast. Lots of options: cereal, oatmeal, eggs, sausage, hard boiled eggs, fruit, bread, pastries, etc. My only complaint was the bed, which had a mattress in desperate need of replacement. We referred to it as sleeping in the valley because it made us roll to the center. It was also really high, which was challenging in an accessible room. I called and they had a stool for me within 5 minutes so we made it work. The people were so nice so I hate adding a complaint in my review. We would have asked for a room change but were there over a holiday weekend and I was pretty sure there wouldn’t be another option. The pluses outweigh the negatives so we had a good time."
Jean 3-night trip
Posted 9 hours ago
The Yankee Inn

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?
Here are some of the more popular apartments in the area to choose from: Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield: Includes private balconies and Smart TVs. A fitness center and onsite laundry facilities are on site. Cozy 1-bedroom studio in serene Great Barrington with AC: Located 18.7 mi/30 km away in Great Barrington. Free WiFi, private balconies, and Smart TVs are included. Access to onsite laundry facilities is available on site. 2-Bdr Apt In Town, By the Water: Located 18.1 mi/29.2 km away in Williamstown. Amenities include free WiFi. Access to onsite laundry facilities is available 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 Onota Lake 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 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.

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