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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 114 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

9.6 out of 10, Exceptional, (21)
"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, (27)
"Clean, comfortable and great location."
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 862 total
includes taxes & fees
7 May - 8 May
Serene 2-bedroom apartment in North Adams.Plenty of off street parking.
Park Street Penthouse Apartment
Game room

Park Street Penthouse Apartment

9.0 out of 10, Wonderful, (2)
"We stayed in this beautiful penthouse for an overnight get away- we both walked in and were just in love. The high ceilings and tons of windows made it so open feeling. Stunning place!"
The price is AED 606
AED 1,128 total
includes taxes & fees
5 May - 6 May
Park Street Penthouse Apartment
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)
"Very clean and nicely decorated apartment in center of town. Great location. Really enjoyed our vacation."
Brand-New 3-bedroom apartment with WiFi, AC in downtown Stockbridge
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
Charming Apt in 18th c Berkshire Farmhouse
Miscellaneous

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (31)
"The property was perfect for us !! Lots of room and the beds are very comfortable. "
The price is AED 496
AED 758 total
includes taxes & fees
4 May - 5 May
Charming Apt in 18th c Berkshire Farmhouse
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
Exterior

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

9.6 out of 10, Exceptional, (26)
"My family had a great ski weekend at Howard’s place. Everything was as described and the location could not be beat! Howard was an excellent host - super communicative and very prompt in responding to the few questions we had. We would absolutely stay here again. "
The price is AED 577
AED 1,190 total
includes taxes & fees
8 May - 9 May
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, (3)
"Beautiful property and wonderful hosts. Terrific location."
The price is AED 569
AED 1,129 total
includes taxes & fees
17 May - 18 May
Downtown | Waterfront | Walk to Shops
Upstairs on Main with private bathroom
Property grounds

Upstairs on Main with private bathroom

9.2 out of 10, Wonderful, (32)
"The place is as described. Excellent location."
Upstairs on Main with private bathroom
2-Bdr Apt In Town, By the Water
Outdoor dining

2-Bdr Apt In Town, By the Water

9.6 out of 10, Exceptional, (4)
"The apartment was clean, bright and quiet. Comfortable beds, and well equipped kitchen. About 3 minute walk to shops on spring street and a nice spot out back by the Green river. Perfect spot for a visit to Williamstown! "
The price is AED 441
AED 991 total
includes taxes & fees
7 May - 8 May
2-Bdr Apt In Town, By the Water
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
Living area

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

2.0 star property
The price is AED 551
AED 800 total
includes taxes & fees
31 May - 1 Jun
Chic corporate apartment in wonderful Pittsfield with AC, WiFi
A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite.
Fridge, microwave, oven, stovetop

A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite.

10.0 out of 10, Exceptional, (23)
"We had a wonderful stay in this historic house and were overwhelmed with the kindness and generosity of our hosts. If we are ever in the area again, we will book again!"
A Haven of Rest in Stately Historic Home Cozy 2nd floor Suite.
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)
"Great place to spend the new years holiday! Perfect location for skiing!"
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 857 total
includes taxes & fees
8 May - 9 May
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
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 "
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)
"Perfect get away, convenient to everything."
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)
"Loved our short stay! Very clean, well maintained, and super cozy. Communication was very prompt and pleasant. Would definitely stay again! "
The price is AED 382
AED 857 total
includes taxes & fees
8 May - 9 May
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Vacation Rental Home in the Berkshires!
Interior

Vacation Rental Home in the Berkshires!

3.0 star property
Vacation Rental Home in the Berkshires!
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio

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

9.4 out of 10, Exceptional, (61)
"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
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

Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is AED 2,016
AED 3,810 total
includes taxes & fees
5 May - 6 May
Hancock Village Inn at Jiminy Peak
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, (140)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Dancing Horse Lodge
Fridge, microwave, oven, stovetop

Dancing Horse Lodge

9.6 out of 10, Exceptional, (41)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge
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: Chic corporate apartment in wonderful Pittsfield with AC, WiFi: Situated in Pittsfield, 0.4 mi/0.7 km from the heart of Pittsfield. Charming Apartment In Berkshire Victorian Home: Located 0.4 mi/0.7 km away in Pittsfield. Private balconies and sofa beds are included. Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located in Lee, 9.7 mi/15.6 km away. Includes private patios and fireplaces. Access to onsite laundry facilities is available on site. Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Located 18.3 mi/29.4 km away in Great Barrington. Free WiFi, separate dining areas, and Smart TVs are included. Access to onsite laundry facilities is available on site. 51 Church Street, Lenox MA - One Bedroom Unit: It’s situated in Lenox, 6.4 mi/10.3 km from Pittsfield.
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 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.