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Check prices for these dates

Next weekend
28 Mar - 30 Mar
In two weeks
4 Apr - 6 Apr
In one month
18 Apr - 20 Apr
In two months
16 May - 18 May

Compare 111 Apartments in Pittsfield with updated reviews, rates, and availability.

Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Food and drink

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.4 out of 10, Exceptional, (15)
"Great location. "
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
51 Church Street, Lenox MA - One Bedroom Unit
Fridge, microwave, oven, stovetop

51 Church Street, Lenox MA - One Bedroom Unit

10.0 out of 10, Exceptional, (26)
"Great location. Well appointed. Pictures don’t really do this place justice. "
51 Church Street, Lenox MA - One Bedroom Unit
Serene 2-bedroom apartment in North Adams.Plenty of off street parking.
Fridge, microwave, oven, stovetop

Serene 2-bedroom apartment in North Adams.Plenty of off street parking.

10.0 out of 10, Exceptional, (2)
"This apartment is roomy and fully appointed. Because of some physical issues we were unable to use the queen bed...it was too high. However, the twin beds were very comfy. The location is just right. So close to the Mohawk Trail, VT border and all the wonderful businesses that revolve around art. Our visits with family and friends were made even better because of our carefree accommodations! Thank you...SandyPeggi & Rick"
The price is AED 496
AED 866 total
includes taxes & fees
27 Mar - 28 Mar
Serene 2-bedroom apartment in North Adams.Plenty of off street parking.
Upstairs on Main with private bathroom
Property grounds

Upstairs on Main with private bathroom

9.2 out of 10, Wonderful, (32)
"We enjoyed our stay in this great place! cute little upstairs apartment with a great use of space and perfect for getting around the area. We got the benefit of a beautiful snow storm too (and the walk and parking area were shoveled when we woke up which was nice!) thanks again."
Upstairs on Main with private bathroom
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Exterior

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

10.0 out of 10, Exceptional, (23)
"The condo worked for our family of four. Really convenient to all the fun and amenities at Jiminy Peak and easy access to the condo from the parking lot made moving ski equipment really easy. The condo itself could use a refresh and a deep clean but otherwise it was adequate. "
The price is AED 382
AED 840 total
includes taxes & fees
24 Mar - 25 Mar
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
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, (5)
"Perfect location. Walking distance. Brand new apartment. "
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
Park Street Penthouse Apartment
Game room

Park Street Penthouse Apartment

9.0 out of 10, Wonderful, (2)
"Like exploring new areas. Quaint town with a few restaurants and a diner in walking distance. Huge apt - well more than needed for one night … clean and has everything you would need to stay longer including laundry and full kitchen. Little hot bc only has window AC units as it’s an old art deco building. Close driving to my resorts and things to do in zbershired"
The price is AED 606
AED 1,128 total
includes taxes & fees
24 Mar - 25 Mar
Park Street Penthouse Apartment
The Studio mini home away from home in the Berkshires
Outdoor dining

The Studio mini home away from home in the Berkshires

9.6 out of 10, Exceptional, (28)
"Zero complaints. Perfect location"
The Studio mini home away from home in the Berkshires
New Studio In Town, By the Water
Property grounds

New Studio In Town, By the Water

10.0 out of 10, Exceptional, (5)
"We spent two nights in this apartment for a weekend getaway to the mountains. This cozy little spot was the perfect size for the two of us, with just enough space so that we weren’t bumping into one another. Despite the chilly temps, the view and sound of the Green River was spectacular. Would stay again at this continently located home. "
The price is AED 441
AED 937 total
includes taxes & fees
30 Mar - 31 Mar
New Studio In Town, By the Water
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.8 out of 10, Exceptional, (25)
"Super convenient - just steps to the lift, right in the middle of resort. Can walk to lifts, the lodge ski school and restaurants. Condo has everything you need for for fun family weekend!Teen boys had lots of freedom and could come And go for night skiing on their own!Def renting from Howie again!! "
The price is AED 577
AED 1,175 total
includes taxes & fees
24 Mar - 25 Mar
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Downtown | Waterfront | Walk to Shops
Property grounds

Downtown | Waterfront | Walk to Shops

10.0 out of 10, Exceptional, (2)
"My two friends and I stayed for the night after visiting Mass MoCa. The apartment was lovely, clean and conveniently located. The kitchen was lovely; we enjoyed the layout and the counter space. My friend and I grabbed a nice dinner across the street. It’s a great stay! "
The price is AED 477
AED 1,008 total
includes taxes & fees
30 Mar - 31 Mar
Downtown | Waterfront | Walk to Shops
Gateway to the Berkshires - Renovated downtown apartment
Exterior

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (7)
"Thanks, Emmy, for a great visit. The apartment was exactly what we hoped for, clean and convenient to downtown and to all things in the Berkshires. We explored and relaxed and thoroughly enjoyed our getaway over a beautiful October weekend. I'd recommend the apartment to anyone who wants that in-town setting and wishes to explore all that the area has to offer. Great host, thank you!"
Gateway to the Berkshires - Renovated downtown apartment
Heart of Lenox!! - renovated downtown apartment
Flat-screen TV

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (68)
"The place was beautiful and comfortable. Everything was new and clean. Loved the location. Thanks again."
Heart of Lenox!! - renovated downtown apartment
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Exterior

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

9.8 out of 10, Exceptional, (18)
"Planned on a Thursday. Arrived late Friday, skied Sat, home early Sun. All fell into place quickly and without much "research". Turned out to be an amazing trip."
The price is AED 382
AED 840 total
includes taxes & fees
24 Mar - 25 Mar
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Property grounds

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

10.0 out of 10, Exceptional, (3)
"Condo in great location for skiing and really in good shape. Nicely decorated. Kids loved the moose toy. Kitchen had everything we needed. Perfect winter break for us. "
The price is AED 382
AED 840 total
includes taxes & fees
24 Mar - 25 Mar
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Tiny House 2.5 hrs NYC and Boston Waterfront WIFI
Fridge, microwave, stovetop, coffee/tea maker

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
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Exterior

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 "
The price is AED 382
AED 840 total
includes taxes & fees
24 Mar - 25 Mar
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Golf

1500 sqft private entrance with beautiful views of the Berkshire Mountains

10.0 out of 10, Exceptional, (41)
"My husband and I stayed at this clean, spacious, and well-equipped apartment adjacent to the hosts' home for three nights to visit nearby attractions in Lenox, Pittsfield, Great Barrington, and Stockbridge. It was a wonderful property and the hosts couldn't have been nicer. We especially loved the gift basket prepared with some of their favorite area treats. Communication about the check-in/check-out process was simple. FYI for future travelers: there are no bathroom toiletries provided so...
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Exterior

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

9.0 out of 10, Wonderful, (2)
"Great stay with a great view of the slopes. The owner was in touch with us the whole time. He was great."
The price is AED 382
AED 840 total
includes taxes & fees
24 Mar - 25 Mar
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Vacation Rental Home in the Berkshires!
Outdoor dining

Vacation Rental Home in the Berkshires!

3.0 star property
Vacation Rental Home 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.
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Other property types in Pittsfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (139)
"We have stayed at this property twice before and have been very pleased with the amount of bedrooms and sleeping available. The property is always very clean and is equipped with everything you need for cooking and dining.the property is a half way point for family members in several directions. "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Berkshire Retreat: Grand Home W/Hot Tub & Large Yard, 5 mins from Jiminy Peak
Miscellaneous

Berkshire Retreat: Grand Home W/Hot Tub & Large Yard, 5 mins from Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
The price is AED 2,016
AED 3,680 total
includes taxes & fees
28 Mar - 29 Mar
Berkshire Retreat: Grand Home W/Hot Tub & Large Yard, 5 mins from Jiminy Peak
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Exterior

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

10.0 out of 10, Exceptional, (56)
"Perfect location and accommodation for my family. The home was as described. I would recommend it. The property owner was easy to work with. "
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
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 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: Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Situated in Great Barrington, 18.3 mi/29.4 km from the heart of Pittsfield. Includes free WiFi, separate dining areas, and Smart TVs. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located 9.7 mi/15.6 km away in Lee. Private patios and fireplaces are included. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor: Located in Hancock, 7.6 mi/12.2 km away. Includes sofa beds. A fitness center and an indoor pool are on site. Park Street Penthouse Apartment: 13.8 mi/22.3 km away in Adams. Amenities include sofa beds. The Studio mini home away from home in the Berkshires: It’s located in Lee, 9.7 mi/15.5 km from Pittsfield. Includes private patios.
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.