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Compare 89 Apartments in Pittsfield with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Living area

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.6 out of 10, Exceptional, (8)
"Super cute, cozy and excellent location. Loved our stay. Will be back!"
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
Living area

Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!

2.0 star property
10.0 out of 10, Exceptional, (1)
"Was a great spot to enjoy Jiminy Peak!"
Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!
Cozy Rustic Apt in 18th c Berkshire Farmhouse

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (60)
"Beautiful property with flower farm, pick your own berries and vegetable farm stand. Rustic log cabin feel with all amenities needed with kitchen."
The price is AED 533
AED 797 total
includes taxes & fees
3 Jan - 4 January 2025
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Lovely two bedroom river-view rental unit
Property grounds

Lovely two bedroom river-view rental unit

9.2 out of 10, Wonderful, (19)
"Typical New England older home. 2nd floor unit. Comfy beds, well-stocked kitchen (that did remind me a bit of my first place out of college). This is definitely not The Ritz, but the linens were soft and the place worked for us."
The price is AED 551
AED 1,173 total
includes taxes & fees
2 Jan - 3 January 2025
Lovely two bedroom river-view rental unit
The Penthouse, Downtown Lenox by Evergreen Home
Gorgeous open concept living room

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (6)
"Amazing space and location!"
The Penthouse, Downtown Lenox by Evergreen Home
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Exterior

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (59)
"Cute and comfy place, great location. We walked to dinner twice and enjoyed how convenient this place was to all of the Berkshires. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Charming Apt in 18th c Berkshire Farmhouse

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (31)
"The space was cozy and clean and the owners were very easy to communicate with and knowledgeable about the area. The bathroom has very fun lights. "
The price is AED 533
AED 797 total
includes taxes & fees
7 Jan - 8 January 2025
Charming Apt in 18th c Berkshire Farmhouse
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
Interior

New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.

10.0 out of 10, Exceptional, (6)
"Comfortable and spacious, in a lovely setting. "
New listing! Dublinshire Farm #3: Stunning grand apt in lovely country barn.
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
Kitchen comes fully stocked with all essentials. Gas stove, double side fridge, dishwasher, Keurig machine, etc.

5 Bed / 3 bath Apt Near Jiminy Peak Berkshires

10.0 out of 10, Exceptional, (1)
"We stayed here because we had Tanglewood tickets which turned out to be a great stay… It was a beautiful drive getting there and close enough to Tanglewood. Our host gave wonderful advice on where to eat and places to go. Thanks so much for sharing your place with us. Would absolutely consider going back "
5 Bed / 3 bath Apt Near Jiminy Peak Berkshires
Upstairs on Main
Exterior

Upstairs on Main

9.2 out of 10, Wonderful, (31)
"Check in was easy, beds are comfortable. I’m a big and tall guy, so only qualm I had was the small toilet, and low shower head. Aside from those, great stay!"
Upstairs on Main
Main Street Delight 1bedroom
Living area

Main Street Delight 1bedroom

10.0 out of 10, Exceptional, (18)
"The location was fantastic for our stay in the Berkshires. Walkable to many restaurants & shops. It was very well decorated & cozy. Very convenient being above a coffee shop, however not ideal if you enjoy sleeping in. We could hear the consistent squeaking of the coffee shop door as soon as it opened in the morning (~7:00 am) from the bedroom. However, good motivation to get up and enjoy the beautiful Berkshires!"
Main Street Delight 1bedroom
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Beautiful State of Art Kitchen Awaits in this spacious 900 Sq FT Suite

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.8 out of 10, Exceptional, (20)
"We had a lovely time at this large and welcoming condo. It was easy to find, had all the amenities we needed and was just the perfect place for an off-season get away. Would easily re-book at any time during the year. "
The price is AED 826
AED 1,482 total
includes taxes & fees
6 Jan - 7 January 2025
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Heart of Lenox!! - renovated downtown apartment
Private kitchen

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (64)
"The bathroom was less than tidy and when I recall it was like that last time. Bathroom rug is dirty or just dirty looking. I advise property Meg to buy several Along with a Terry bath mat so you can cover it when using. No little extras like soap/shampoo are offered. I had My own. Overall the apartment is very cute would stay again. "
Heart of Lenox!! - renovated downtown apartment
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Super comfortable Mountain Decor

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

10.0 out of 10, Exceptional, (22)
"We loved our stay. The rental was as described. Jiminy Peak is great and everything is within walking distance. We had a great time !!!"
The price is AED 577
AED 1,078 total
includes taxes & fees
6 Jan - 7 January 2025
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI

Tiny House 2.5 hrs NYC and Boston Waterfront WIFI

9.6 out of 10, Exceptional, (23)
"We were treated with such kindness and understanding of our situation. We would gladly recommend Alisha to anyone wanting to stay at their property. In fact, we are going back in May. "
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
Vacation Rental Home in the Berkshires!
Living area

Vacation Rental Home in the Berkshires!

3.0 star property
Vacation Rental Home in the Berkshires!
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Fully Redone Suite with master King Bed

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

10.0 out of 10, Exceptional, (2)
"Stayed one night at one of my favorite ski spots. Will be back again!"
The price is AED 577
AED 1,078 total
includes taxes & fees
6 Jan - 7 January 2025
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Renovated Downtown 1bedroom
Living area

Renovated Downtown 1bedroom

10.0 out of 10, Exceptional, (21)
"Location, location, location. Great use of space in this nicely decorated, conveniently located apt. Steps away from restaurants and shopping. 7 minutes from Kripalu. Great communication from owner. Looking forward to next stay."
Renovated Downtown 1bedroom
Baldwin Hill Retreat Guest House
Living area

Baldwin Hill Retreat Guest House

2.0 star property
10.0 out of 10, Exceptional, (1)
"The property and neighborhood were gorgeous! Walkable roads with low speed limits and a nearby park were major bonuses. Plenty of food options nearby, and downtown Great Barrington is only a short drive away. The house was super clean, gorgeously furnished, and very cozy. The beds and linens were very good quality and I had an incredibly restful stay. I will certainly be renting this spot for my next trip to the area! "
Baldwin Hill Retreat Guest House
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
Living area

Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great location! The apartment was brand new. Well decorated and clean. "
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
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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Other property types in Pittsfield

Chic Pittsfield Home With A View!

Chic Pittsfield Home With A View!

9.0 out of 10, Wonderful, (9)
"This property was just as shown in the listing and met our needs very well. It was well appointed and had many inviting areas to gather and relax in. The kitchen was well equipped and easy to use. Some very nice touches with closets and bathroom storage areas that made staying there user friendly. "
Chic Pittsfield Home With A View!
Hancock Village Inn at Jiminy Peak
The Hancock Village Inn

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (8)
"We loved this large, well-kept home. The house has tons of room, so even though we had a large group, everyone found space and we never felt crowded. The kitchen/dining area is a great space for gathering and sharing a meal. And, the younger members of our group loved the hot tub and large yard for playing in. The owner was extremely easy to communicate with. We hope to be back!"
The price is AED 2,380
AED 4,073 total
includes taxes & fees
2 Jan - 3 January 2025
Hancock Village Inn at Jiminy Peak
Vacation Village in the Berkshires
Lobby

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1750)
"Nice and quiet family get a way"
The price is AED 689
AED 792 total
includes taxes & fees
7 Jan - 8 January 2025
Vacation Village in the Berkshires
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.

Frequently asked questions

What's it like to stay at an apartment in Pittsfield?
You’ll find 7 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: Charming Apartment In Berkshire Victorian Home: Includes private balconies and sofa beds. Cozy Rustic Apt in 18th c Berkshire Farmhouse: Located 6.2 mi/10 km away in Lanesborough. Fireplaces and sofa beds are included. Lovely two bedroom river-view rental unit: It’s situated in Williamstown, 19.3 mi/31.1 km away. Includes sofa beds. 1st Floor Mountain View Suite Ski On/Off At Jiminy- 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. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: It’s located in Lee, 9.7 mi/15.6 km from Pittsfield. Includes private patios and fireplaces.
How many apartments are there in Pittsfield?
Expedia has 7 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 Pittsfield State Forest and Housatonic River 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.