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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Pittsfield apartments

A snow-covered outdoor area with a fire pit, tables, and chairs.

1. 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 SAR 450
SAR 951 total
includes taxes & fees
14 Oct - 15 Oct
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
A modern living room with a grey sofa, a bed with grey bedding, and a wooden wall with a mounted TV.

2. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
United States
Nicole O.
The price is SAR 330
SAR 857 total
includes taxes & fees
12 Oct - 13 Oct
Berkshires Apartment at the Stephentown Hotel
A modern kitchen with white cabinetry, a stainless steel dishwasher, and a window with a view.

3. 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 SAR 545
SAR 1,284 total
includes taxes & fees
2 Nov - 3 Nov
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.

4. 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 SAR 450
SAR 951 total
includes taxes & fees
14 Oct - 15 Oct
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

5. 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 SAR 423
SAR 917 total
includes taxes & fees
14 Oct - 15 Oct
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
A covered outdoor seating area with two chairs and a view of a grassy landscape.

6. 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 SAR 845
SAR 1,196 total
includes taxes & fees
13 Oct - 14 Oct
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

7. 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 SAR 463
SAR 970 total
includes taxes & fees
13 Oct - 14 Oct
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
A rustic wooden interior with various stalls selling items like books, snacks, and wine.

8. Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat

Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
Hancock
9.8 out of 10, Exceptional, (21 reviews)
"Great location! "
United States
shannon m.
The price is SAR 450
SAR 951 total
includes taxes & fees
14 Oct - 15 Oct
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
A swimming pool with lounge chairs and a hot tub, surrounded by buildings and greenery.

9. 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 SAR 426
SAR 920 total
includes taxes & fees
14 Oct - 15 Oct
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
A bedroom with a large bed, a nightstand, an air conditioning unit, and a view through the window.

10. 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 SAR 434
SAR 1,027 total
includes taxes & fees
12 Oct - 13 Oct
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
A wooden deck with outdoor furniture, a glass door leading to a view of a grassy area with trees.

11. 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 SAR 629
SAR 1,273 total
includes taxes & fees
14 Oct - 15 Oct
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
A sign for The Stephentown Hotel with a depiction of a red building and mountains.

12. 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 SAR 496
SAR 1,125 total
includes taxes & fees
12 Oct - 13 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.

13. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.8 out of 10, Exceptional, (16 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 SAR 545
SAR 1,057 total
includes taxes & fees
18 Oct - 19 Oct
Penthouse Apartment on Park Street
A modern kitchen with a central island, stainless steel appliances, and a ceiling fan.

14. Urban Peak Escape, Lenox, MA

Urban Peak Escape, Lenox, MA
Lenox
8.0 out of 10, Very good, (1 review)
"Very nice. A few suggestions:- A higher end coffee maker would go a long way, or a latte machine. - Needs a toaster- Instructions on how to work the shower. We could only get the primary shower to work- A table and chairs (for eating a meal) would be good. Otherwise very comfortable and clean, and great location! "
United States
Nancy H.
The price is SAR 1,585
SAR 2,861 total
includes taxes & fees
13 Oct - 14 Oct
Urban Peak Escape, Lenox, MA
Four people seated at a table with food and drinks, wearing winter sports helmets.

15. 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 SAR 426
SAR 920 total
includes taxes & fees
14 Oct - 15 Oct
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
A Country Inn with a large, welcoming entrance and multiple parking spaces.

16. 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 SAR 423
SAR 917 total
includes taxes & fees
14 Oct - 15 Oct
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
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.

17. 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 SAR 602
SAR 1,079 total
includes taxes & fees
14 Oct - 15 Oct
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.

18. 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.
Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby
Four people seated at a table with food and drinks, wearing winter sports helmets.

19. Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- Home Away From Home

Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- Home Away From Home
Hancock
10.0 out of 10, Exceptional, (2 reviews)
"Great stay. Thank you for being a great host. "
United States
Rony N.
The price is SAR 463
SAR 970 total
includes taxes & fees
13 Oct - 14 Oct
Ski On/Off Winter Mountain Suite Jiminy Peak-- Sleeps4- Home Away From Home
"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)

20. 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 SAR 469
SAR 1,039 total
includes taxes & fees
3 Nov - 4 Nov
New Studio In Town, By the Water
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

10/10 Excellent
"Beautiful location!"
Pofen 1-night trip
Posted 1 hour ago
Vacation Village in the Berkshires

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?
Here are some of the more popular apartments in the area to choose from: Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield: Includes private balconies and Smart TVs. A fitness center and onsite 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, private balconies, and Smart TVs are included. Access to onsite 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 private patios. Onsite 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 private patios. Access to onsite 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, separate dining areas, and Smart TVs. Access to onsite laundry facilities is available on site.
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 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 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.