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Check prices for these dates

In two weeks
11 Sep - 13 Sep
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

Coffee/tea maker, fridge, microwave, oven

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 AED 479
AED 1,200 total
includes taxes & fees
31 Aug - 1 Sep
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Pool

2. 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 AED 452
AED 948 total
includes taxes & fees
31 Aug - 1 Sep
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Property grounds

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 AED 430
AED 919 total
includes taxes & fees
1 Sep - 2 Sep
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Gift shop

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, (5 reviews)
"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"
United States
Jen B.
The price is AED 430
AED 919 total
includes taxes & fees
27 Aug - 28 Aug
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Interior

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 AED 866
AED 1,222 total
includes taxes & fees
15 Sep - 16 Sep
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Gift shop

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

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.
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
Indoor pool, a heated pool

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 AED 430
AED 919 total
includes taxes & fees
27 Aug - 28 Aug
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Gift shop

9. 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 AED 430
AED 919 total
includes taxes & fees
1 Sep - 2 Sep
Disney Magic Suite at Jiminy - Ski On Off Sleeps 4- A Must See Mountain Retreat
TV, DVD player, books

10. 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.
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Coffee/tea maker, fridge, microwave, oven

11. 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 AED 413
AED 605 total
includes taxes & fees
2 Sep - 3 Sep
Cozy 1-bedroom studio in serene Great Barrington with AC
Living area

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 AED 533
AED 1,034 total
includes taxes & fees
27 Aug - 28 Aug
Penthouse Apartment on Park Street
Pool

13. 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 AED 734
AED 1,402 total
includes taxes & fees
27 Aug - 28 Aug
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
TV, fireplace, DVD player

14. 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.
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Outdoor dining

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 AED 408
AED 890 total
includes taxes & fees
1 Sep - 2 Sep
Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4
Outdoor dining

16. 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 AED 477
AED 1,083 total
includes taxes & fees
10 Sep - 11 Sep
2-Bdr Apt In Town, By the Water
Indoor pool

17. 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 AED 430
AED 919 total
includes taxes & fees
27 Aug - 28 Aug
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
A heated pool

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
Pool

19. 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 AED 452
AED 948 total
includes taxes & fees
31 Aug - 1 Sep
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Pool

20. 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 AED 408
AED 890 total
includes taxes & fees
1 Sep - 2 Sep
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
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
"Remo, specious"
Evan 1-night trip
Posted less than an 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. 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 private patios are included. Onsite 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 onsite 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, private balconies, and Smart TVs are included. Access to onsite 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, private balconies, 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 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 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.