Apartments in Pittsfield

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Apartments in Pittsfield

Charming Apt in 18th c Berkshire Farmhouse
1 bedroom, WiFi, bed sheets

Charming Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (34)
"The property was perfect for us !! Lots of room and the beds are very comfortable. "
The price is NZ$351
includes taxes & fees
17 Aug - 18 Aug
Charming Apt in 18th c Berkshire Farmhouse
Park Street Penthouse Apartment
Game room

Park Street Penthouse Apartment

9.4 out of 10, Exceptional, (9)
"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 NZ$451
includes taxes & fees
20 Aug - 21 Aug
Park Street Penthouse Apartment
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
Smart TV, fireplace, DVD player, music library

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

9.4 out of 10, Exceptional, (82)
"Nice place, just what we were looking for to stay the weekend. "
FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!
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, (63)
"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
Downtown Gateway to the Berkshires. Walk to Everything.
Exterior detail

Downtown Gateway to the Berkshires. Walk to Everything.

2.0 star property
8.0 out of 10, Very good, (1)
"This cute and cozy apartment was in an excellent location. We were the first guest to stay here and we had a few concerns: the chairs in the kitchen were broken as was a door frame. The command hooks fell off the several times. There was no place to hang clothes and shelves which held the dishes were dirty and dusty as well as appliances. Some coffee and Kleenex would have a nice. The place has the potential to be amazing with a little more attention to details. We have stayed in many, many...
Downtown Gateway to the Berkshires. Walk to Everything.
Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge
Living area

Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge

9.0 out of 10, Wonderful, (2)
"The apartment is in downtown Stockbridge. We were there to aid our son and his fiancee who are traversing the Appalachia Trail. The location was perfect for us. The apartment is complete new and immaculate. It was very comfortable for the four of us. The only reason that the overall review is four not five stars is that the dryer wasn't working and the kitchen had absolutely now supplies or an ice tray. The dryer not working could have been a disaster for us as we needed to clean our son's...
Brand NEW Charming 2-bedroom apartment with WiFi, AC on Main Street Stockbridge
2-Bdr Apt In Town, By the Water
Outdoor dining

2-Bdr Apt In Town, By the Water

9.8 out of 10, Exceptional, (6)
"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 NZ$506
includes taxes & fees
25 Aug - 26 Aug
2-Bdr Apt In Town, By the Water
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Fridge, microwave, oven, stovetop

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton

2.0 star property
9.8 out of 10, Exceptional, (9)
"Clean and well stock"
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Gateway to the Berkshires - Renovated downtown apartment
Exterior

Gateway to the Berkshires - Renovated downtown apartment

10.0 out of 10, Exceptional, (8)
"Emmy is a great hostess. The apartment is nicely appointed and in a great location to restaurants and shops and attractions in the Berkshires. "
Gateway to the Berkshires - Renovated downtown apartment
The Brooks Motel: Exceptional Suite
TV, offices

The Brooks Motel: Exceptional Suite

7.0 out of 10, Good, (4)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
The price is NZ$339
includes taxes & fees
17 Aug - 18 Aug
The Brooks Motel: Exceptional Suite
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Exterior

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

9.8 out of 10, Exceptional, (7)
"This property was awesome for our family! Quick walk to the Mountain and all the shops!!! Great family spot!!"
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Fridge, microwave, oven, stovetop

Amazing 2-bedroom apartment sunny and quiet in Great Barrington

9.6 out of 10, Exceptional, (27)
"Perfect place for what we needed. Loved the location."
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
Bright Boho Apt in 18th c Berkshire Farmhouse
Property grounds

Bright Boho Apt in 18th c Berkshire Farmhouse

9.0 out of 10, Wonderful, (22)
"Really enjoyed our stay"
The price is NZ$372
includes taxes & fees
17 Aug - 18 Aug
Bright Boho Apt in 18th c Berkshire Farmhouse
Vacation Rental Home in the Berkshires!
Outdoor dining

Vacation Rental Home in the Berkshires!

9.8 out of 10, Exceptional, (17)
"Lovely cottage with beautiful views"
Vacation Rental Home in the Berkshires!
Heart of Lenox!! - renovated downtown apartment
Exterior

Heart of Lenox!! - renovated downtown apartment

10.0 out of 10, Exceptional, (71)
"Beautiful property in a perfect location for a girls ski weekend getaway! "
Heart of Lenox!! - renovated downtown apartment
Cozy Rustic Apt in 18th c Berkshire Farmhouse
Fridge, microwave, oven, stovetop

Cozy Rustic Apt in 18th c Berkshire Farmhouse

9.6 out of 10, Exceptional, (62)
"Great value, so much better than all the touristy motels in the area!"
The price is NZ$351
includes taxes & fees
17 Aug - 18 Aug
Cozy Rustic Apt in 18th c Berkshire Farmhouse
The Penthouse, Downtown Lenox by Evergreen Home
Fridge, microwave, oven, stovetop

The Penthouse, Downtown Lenox by Evergreen Home

10.0 out of 10, Exceptional, (8)
"Amazing space and location!"
The Penthouse, Downtown Lenox by Evergreen Home
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Exterior

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

10.0 out of 10, Exceptional, (8)
"Great location. Howie is very communicative. Wish we could have stayed longer. "
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Available February 17-21 2025. Sleep 8 - 2-bed apt on Jiminy Peak. Ski in/out!
Interior

Available February 17-21 2025. Sleep 8 - 2-bed apt on Jiminy Peak. Ski in/out!

Available February 17-21 2025. Sleep 8 - 2-bed apt on Jiminy Peak. Ski in/out!
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! "
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
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

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"Pleasant stay"
Lisa 3-night trip
Posted 17 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Frequently asked questions

What's it like to stay at an apartment in Pittsfield?
You can choose from 8 apartments in Pittsfield for your holiday. You might want to explore the local entertainment venues during your trip.
How do you know if an apartment is the best choice for your stay?
Offering a kitchen for convenient meals, an apartment often has more space than a traditional hotel room. Apartments are a good option for couples who want to live like locals, and also for families wanting the conveniences of home.
What's the top apartment for a stay in Pittsfield?
Listed below are some of the favourite apartments in the area to choose from: Charming Apartment In Berkshire Victorian Home: Includes a balcony and a sofa bed . FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!: Located in Pownal , 23.9 mi/38.5 km away. Includes a private pool, free WiFi and a patio . On-site laundry facilities and an outdoor pool are on site . Elegant 19th Century New England Newly Renovated 1BR Vacation Rental: Located 9.7 mi/15.6 km away in Lee . A patio and a fireplace are included . Access to on-site laundry facilities is available on site . Charming Apt in 18th c Berkshire Farmhouse: Located in Lanesborough , 6.2 mi/10 km from Pittsfield. Includes a fireplace . Access to on-site laundry facilities is available on site .
How many apartments should I expect to find in Pittsfield?
Expedia has 8 apartments to book in Pittsfield.
What will the weather be like in Pittsfield?
Although 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 temperature of 19°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Pittsfield are January, March, February and November, with each month seeing an average of 18 cm 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 make your trip smoother 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. Otherwise, you can search for flights to Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. To see more of the surrounding area, ride one of the trains from Pittsfield Intermodal Transportation Center or Pittsfield Station.