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
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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, (34 reviews)
"We were on a girls backpacking trip and this was the perfect location right off the trail to clean up, get some great rest and grab dinner. The people are so friendly in Dalton and this place had everything we needed!"
United States
Allie T.
The price is £254
includes taxes & fees
2 Nov - 3 Nov
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
A large building with a covered entrance and multiple windows, surrounded by snow-covered ground and parked cars.

2. 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
8.6 out of 10, Excellent, (18 reviews)
"Great stay! Perfect location by the pool and nicely renovated as advertised!"
United States
Matthew B.
The price is £196
includes taxes & fees
4 Oct - 5 Oct
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

3. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is £174
includes taxes & fees
4 Oct - 5 Oct
Berkshires Apartment at the Stephentown Hotel
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

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

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Hancock
9.8 out of 10, Exceptional, (22 reviews)
"Great skiing and proximity to mountain. Great for families"
United States
John F.
The price is £203
includes taxes & fees
4 Oct - 5 Oct
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
A snow-covered outdoor area with a fire pit, tables, and chairs.

5. 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 £197
includes taxes & fees
5 Oct - 6 Oct
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A rustic wooden interior with shelves stocked with various products, a 'Tree-Free' sign, and a section with bottled beverages.

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

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
Hancock
10.0 out of 10, Exceptional, (3 reviews)
"Stayed one night at one of my favorite ski spots. Will be back again!"
United States
Neil J.
The price is £203
includes taxes & fees
4 Oct - 5 Oct
Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor
A covered outdoor seating area with two chairs and a view of a grassy landscape.

7. 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 £232
includes taxes & fees
14 Oct - 15 Oct
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
A swimming pool with lounge chairs and umbrellas, surrounded by a grassy area and a mountain backdrop.

8. 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 £191
includes taxes & fees
5 Oct - 6 Oct
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Four people seated at a table with food and drinks, wearing winter sports helmets.

9. 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 £201
includes taxes & fees
6 Oct - 7 Oct
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
A Country Inn with a large, welcoming entrance and multiple parking spaces.

10. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Hancock
8.8 out of 10, Excellent, (8 reviews)
"Everything was wonderful…"
United States
Alyne K.
The price is £195
includes taxes & fees
4 Oct - 5 Oct
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

11. 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
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A living room with a sofa, armchairs, a TV, a fireplace, and a large window.

12. 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 £267
includes taxes & fees
2 Nov - 3 Nov
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.

13. 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Stephentown
8.4 out of 10, Very good, (12 reviews)
"Great location and property. thank you"
United States
Christine P.
The price is £199
includes taxes & fees
25 Oct - 26 Oct
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A sign for The Stephentown Hotel with a depiction of a red building and mountains.

14. 2 Bed Berkshire Getaway @ Stephentown Hotel

2 Bed Berkshire Getaway @ Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (7 reviews)
"This place is amazing! It is so clean and updated with lots of amenities! Lots of arcade games in the apartment thatthe whole family enjoyed! It's a quick trip to jimney peak to ski it's just down the road. Great restaurants nearby. Definitely recommend this place."
United States
elizabeth r.
The price is £210
includes taxes & fees
25 Oct - 26 Oct
2 Bed Berkshire Getaway @ Stephentown Hotel
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.

15. 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 £216
includes taxes & fees
4 Oct - 5 Oct
Penthouse Apartment on Park Street
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

16. 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 £201
includes taxes & fees
6 Oct - 7 Oct
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

17. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (19 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is £208
includes taxes & fees
25 Oct - 26 Oct
New Studio In Town, By the Water
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

18. 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 £191
includes taxes & fees
5 Oct - 6 Oct
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
"The best part of this place is the backyard. Sitting next to the river, watching the fire was real FUN! It felt like camping without the inconvenience of real camping.." ...Lina (no fee for firewood)

19. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
9.8 out of 10, Exceptional, (12 reviews)
"We had a great stay here. Clean, well-equipped, great location. Hope to come back again!"
United States
Tricia
The price is £218
includes taxes & fees
25 Oct - 26 Oct
Downtown | Waterfront | Walk to Shops
A two-story blue house with a porch, surrounded by a garden with orange flowers.

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

Getaway Near Mass MoCA, Great Hiking, Scenic Views
Stamford
10.0 out of 10, Exceptional, (35 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 £118
includes taxes & fees
4 Oct - 5 Oct
Getaway Near Mass MoCA, Great Hiking, Scenic Views
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

Hotel On North

Hotel On North

10/10 Excellent
"Delightful place with charm and warmth and character. I would love to come back."
Richard 1-night trip
Posted 8 hours ago
Hotel On North

Find out more about Pittsfield

Pittsfield Apartments information

Number of reviews
267
Accommodation
105 Apartments
Lowest Price
£118
Highest Price
£267

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 . Cozy 1-bedroom studio in serene Great Barrington with AC: Located 18.7 mi/30 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 . 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 . Cozy 1-bedroom apartment in old farm house in historic South Lee: Located 12.1 mi/19.5 km away in South Lee . Amenities include a patio . Access to on-site laundry facilities is available on site . Amazing 2-bedroom apartment sunny and quiet in Great Barrington: Located in Great Barrington , 18.3 mi/29.4 km from Pittsfield. Includes free WiFi, a dining area 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 Housatonic River and Onota Lake 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 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.