A historic building with classical architecture, a traffic light, and a yellow taxi.

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Pittsfield apartments

A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

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

Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Dalton
9.8 out of 10, Exceptional, (31 reviews)
"This was a wonderful place to stay. We especially loved the easy access to the toys so the kids could start playing while we unloaded the car. It was perfect and just what we needed."
United States
Megan A.
The price is HK$1,023
HK$2,562 total
includes taxes & fees
31 Aug - 1 Sept
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

2. 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, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
United States
Ann
The price is HK$755
HK$1,754 total
includes taxes & fees
31 Aug - 1 Sept
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A snow-covered outdoor area with a fire pit, tables, and chairs.

3. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor

Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
United States
Maura D.
The price is HK$931
HK$1,986 total
includes taxes & fees
31 Aug - 1 Sept
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

4. Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (4 reviews)
"Quiet location"
United States
Alicia S.
The price is HK$981
HK$2,041 total
includes taxes & fees
1 Sept - 2 Sept
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

5. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center

Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Lenox
The price is HK$1,764
HK$2,496 total
includes taxes & fees
31 Aug - 1 Sept
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

6. 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, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
United States
patricia f.
The price is HK$875
HK$1,914 total
includes taxes & fees
1 Sept - 2 Sept
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

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

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Hancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
United States
Kristina L.
The price is HK$776
HK$1,786 total
includes taxes & fees
1 Sept - 2 Sept
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

8. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Hancock
9.4 out of 10, Exceptional, (6 reviews)
"Convenience to slopes and restaurants really great….,had a nice stay"
United States
Thomas S.
The price is HK$804
HK$1,818 total
includes taxes & fees
31 Aug - 1 Sept
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

9. 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
9.4 out of 10, Exceptional, (18 reviews)
"Nice Place"
United States
Tom C.
The price is HK$819
HK$1,843 total
includes taxes & fees
1 Sept - 2 Sept
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

10. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (2 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
United States
bob i.
The price is HK$882
HK$1,292 total
includes taxes & fees
7 Sept - 8 Sept
Cozy 1-bedroom studio in serene Great Barrington with AC
A living room with a sofa, armchair, coffee table, and a TV on a stand.

11. 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 HK$967
HK$2,026 total
includes taxes & fees
1 Sept - 2 Sept
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
A spacious living room with a wooden floor, a sofa, a coffee table, and a lamp. There is a dining area in the background with a table and chairs.

12. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (15 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 HK$1,137
HK$2,198 total
includes taxes & fees
31 Aug - 1 Sept
Penthouse Apartment on Park Street
A wicker sofa with a floral cushion, a wicker table with magazines, and a standing fan in a room with large windows and wooden floors.

13. 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
8.0 out of 10, Very good, (2 reviews)
"Excellent accommodations. Outside patio with grill was very nice. Private parking is a plus. Would definitely rent this apartment again."
United States
Ruthie K.
The price is HK$741
HK$1,589 total
includes taxes & fees
31 Aug - 1 Sept
Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

14. 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, (35 reviews)
"Great and clean property! Very easy to access and good parking too."
United States
Todd A.
The price is HK$1,270
HK$2,618 total
includes taxes & fees
31 Aug - 1 Sept
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
A living room with a sofa, armchairs, a TV, a fireplace, and a large window.

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

Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Hancock
8.0 out of 10, Very good, (1 review)
"I chose this place at the very last minute. It was all that I expected and wanted and more: two bedrooms with three beds, a comfortable living space, two full bathrooms, kitchen with all the basic necessities, TV in each bedroom and in the living room, a dining table and chairs, an outside porch with table, a big open space, and grill, easy parking and access, quiet, .and access to two pools. The place was well tended: clean, with towels and extras blankets ready. Howard, the owner, checked on...
United States
Cecilia S.
The price is HK$1,108
HK$2,411 total
includes taxes & fees
31 Aug - 1 Sept
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
A two-story blue house with a porch, surrounded by a garden with orange flowers.

16. Getaway Near Mass MoCA, Great Hiking, Scenic Views

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (34 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
The price is HK$600
HK$1,199 total
includes taxes & fees
1 Sept - 2 Sept
Getaway Near Mass MoCA, Great Hiking, Scenic Views

17. 2-Bdr Apt In Town, By the Water

2-Bdr Apt In Town, By the Water
Williamstown
9.2 out of 10, Wonderful, (17 reviews)
"Great place with easy access to town and even better access to a nice spot to hangout by the creek. I will definitely stay here again."
United States
Thomas
The price is HK$1,058
HK$2,364 total
includes taxes & fees
10 Sept - 11 Sept
2-Bdr Apt In Town, By the Water
Four people seated at a table with food and drinks, wearing winter sports helmets.

18. 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, (9 reviews)
"A great, comfy suite! We had a great stay! "
United States
Wendy D.
The price is HK$826
HK$1,850 total
includes taxes & fees
31 Aug - 1 Sept
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

19. 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 HK$903
HK$1,946 total
includes taxes & fees
31 Aug - 1 Sept
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

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

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Hancock
9.8 out of 10, Exceptional, (6 reviews)
"Great location on mountain and great communication by unit owner."
United States
Marc F.
The price is HK$755
HK$1,754 total
includes taxes & fees
31 Aug - 1 Sept
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 & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"Look good for being under constructikn"
Debra 1-night trip
Posted 1 hour ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Find out more about Pittsfield

Pittsfield Apartments information

Number of reviews
10,019
Accommodation
108 Apartments
Lowest Price
HK$544
Highest Price
HK$1,777

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?
Below are some of the top apartments in the area to choose from: Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield: Includes a balcony and a Smart TV . A fitness centre and on-site laundry facilities are on site . FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!: Located 23.9 mi/38.5 km away in Pownal . A private pool, free WiFi and a patio are included . On-site laundry facilities and an outdoor pool are on site . Getaway Near Mass MoCA, Great Hiking, Scenic Views: Located in Stamford , 23 mi/37 km away. Includes free WiFi . Access to on-site laundry facilities is available on site . Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake: Located 17.6 mi/28.4 km away in Great Barrington . Free WiFi, a balcony and a Smart TV are included . Access to on-site laundry facilities is available on site . Cozy 1-bedroom studio in serene Great Barrington with AC: Located in Great Barrington , 18.7 mi/30 km from Pittsfield. Includes free WiFi, a balcony and a Smart TV . 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 Pontoosuc Lake and Housatonic River 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.

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