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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Pittsfield apartments

Pool

1. 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.
Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor
Gift shop

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, (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 CA $147
CA $326 total
includes taxes & fees
Aug 19 - Aug 20
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Coffee/tea maker, fridge, microwave, oven

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, (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 CA $181
CA $446 total
includes taxes & fees
Aug 31 - Sep 1
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Indoor pool

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 CA $134
CA $307 total
includes taxes & fees
Aug 19 - Aug 20
Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn
Gift shop

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 CA $165
CA $345 total
includes taxes & fees
Aug 20 - Aug 21
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Exterior

6. 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 CA $154
CA $333 total
includes taxes & fees
Aug 19 - Aug 20
1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor
Pool

7. 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 CA $141
CA $317 total
includes taxes & fees
Aug 19 - Aug 20
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Beach

8. Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel
Stephentown
10.0 out of 10, Exceptional, (4 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 CA $194
CA $377 total
includes taxes & fees
Aug 19 - Aug 20
Berkshires Apartment at the Stephentown Hotel
TV, DVD player, books

9. 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 CA $147
CA $326 total
includes taxes & fees
Aug 19 - Aug 20
WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn
Pool

10. 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 CA $226
CA $460 total
includes taxes & fees
Aug 19 - Aug 20
Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous
TV, fireplace, DVD player

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 CA $244
CA $481 total
includes taxes & fees
Aug 19 - Aug 20
Gorgeous 2BR 2BA Condo At Jiminy Peak w Mtn Views
Indoor pool, a heated pool

12. 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 CA $142
CA $319 total
includes taxes & fees
Aug 19 - Aug 20
1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count
Living area

13. Penthouse Apartment on Park Street

Penthouse Apartment on Park Street
Adams
9.6 out of 10, Exceptional, (14 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 CA $201
CA $387 total
includes taxes & fees
Aug 20 - Aug 21
Penthouse Apartment on Park Street
Coffee/tea maker, fridge, microwave, oven

14. 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 CA $144
CA $215 total
includes taxes & fees
Aug 31 - Sep 1
Cozy 1-bedroom studio in serene Great Barrington with AC
Outdoor dining

15. New Studio In Town, By the Water

New Studio In Town, By the Water
Williamstown
10.0 out of 10, Exceptional, (18 reviews)
"Great location, we really enjoyed our stay! "
United States
Lydia J.
The price is CA $166
CA $371 total
includes taxes & fees
Aug 19 - Aug 20
New Studio In Town, By the Water
Exterior

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 CA $100
CA $205 total
includes taxes & fees
Aug 19 - Aug 20
Getaway Near Mass MoCA, Great Hiking, Scenic Views
Outdoor dining

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

2-Bdr Apt In Town, By the Water
Williamstown
9.2 out of 10, Wonderful, (16 reviews)
"Location was very good-close to campus. Host was responsive. Accommodations were just right"
United States
Dan R.
The price is CA $173
CA $398 total
includes taxes & fees
Aug 19 - Aug 20
2-Bdr Apt In Town, By the Water
Beach

18. 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 CA $214
CA $410 total
includes taxes & fees
Aug 23 - Aug 24
2 Bed Berkshire Apt minutes to Jiminy Peak Ski
Outdoor dining

19. Downtown | Waterfront | Walk to Shops

Downtown | Waterfront | Walk to Shops
Williamstown
10.0 out of 10, Exceptional, (9 reviews)
"Perfect setup for anyone visiting Williamstown."
United States
Michael P.
The price is CA $187
CA $407 total
includes taxes & fees
Aug 31 - Sep 1
Downtown | Waterfront | Walk to Shops
TV, fireplace, DVD player, offices

20. Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
Hancock
9.6 out of 10, Exceptional, (4 reviews)
"Excellent instructions by the owner for the check in process, which was easy. The room was beautiful and very clean, and exactly as advertised. We would absolutely recommend and stay again!!"
United States
Chad J.
The price is CA $215
CA $428 total
includes taxes & fees
Sep 15 - Sep 16
Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4
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

The Williams Inn

The Williams Inn

10/10 Excellent
"Our stay at The Williams Inn was amazing. The rooms were clean and beautiful, the staff was helpful and friendly, and our overall experience was superb. Would recommend 100%!"
Devorah 1-night trip
Posted 1 hour ago
The Williams Inn

Find out more about Pittsfield

Pittsfield Apartments information

Number of reviews
218
Accommodation
107 Apartments
Lowest Price
CA $205
Highest Price
CA $481

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. Downtown | Waterfront | Walk to Shops: Located in Williamstown, 18.1 mi/29.2 km from Pittsfield. Includes free WiFi, private balconies, and sofa beds. A fitness center and onsite laundry facilities are 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 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.

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