Best Apartments in Pittsfield, MA for Your Vacation from $155

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

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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

Dalton

Megan A.

$293 nightly

Aug 31 - Sep 1

Total with taxes and fees

2. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Hancock

Jen B.

$208 nightly

Aug 25 - Aug 26

Total with taxes and fees

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

Hancock

Alicia S.

$220 nightly

Aug 25 - Aug 26

Total with taxes and fees

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

Hancock

patricia f.

$208 nightly

Aug 25 - Aug 26

Total with taxes and fees

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

Hancock

John F.

$208 nightly

Aug 25 - Aug 26

Total with taxes and fees

6. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

Hancock

Thomas S.

$220 nightly

Aug 25 - Aug 26

Total with taxes and fees

7. Berkshires Apartment at the Stephentown Hotel

Stephentown

Nicole O.

$257 nightly

Aug 25 - Aug 26

Total with taxes and fees

8. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

Hancock

Tom C.

$208 nightly

Aug 25 - Aug 26

Total with taxes and fees

9. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

Hancock

Matthew B.

$208 nightly

Aug 25 - Aug 26

Total with taxes and fees

10. 2-Bdr Apt In Town, By the Water

Williamstown

Dan R.

$262 nightly

Sep 10 - Sep 11

Total with taxes and fees

11. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

Hancock

Eileen O.

$208 nightly

Aug 25 - Aug 26

Total with taxes and fees

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

Hancock

Kristina L.

$231 nightly

Aug 31 - Sep 1

Total with taxes and fees

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

Hancock

"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...

Cecilia S.

$313 nightly

Aug 31 - Sep 1

Total with taxes and fees

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

Hancock

Marc F.

$208 nightly

Aug 25 - Aug 26

Total with taxes and fees

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

Stamford

Bill

$150 nightly

Aug 25 - Aug 26

Total with taxes and fees

16. Downtown | Waterfront | Walk to Shops

Williamstown

Michael P.

$257 nightly

Aug 26 - Aug 27

Total with taxes and fees

17. Penthouse Apartment on Park Street

Adams

Margaret C.

$251 nightly

Aug 26 - Aug 27

Total with taxes and fees

18. New Studio In Town, By the Water

Williamstown

Lydia J.

$257 nightly

Aug 26 - Aug 27

Total with taxes and fees

19. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Hancock

Alyne K.

$220 nightly

Aug 26 - Aug 27

Total with taxes and fees

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

Great Barrington

bob i.

$139 nightly

Aug 31 - Sep 1

Total with taxes and fees

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Top Pittsfield Hotel Reviews

Hotel On North

8/10 Good

"It’s a good place to stay. The rooms are but dark and could you add more lamps to the room?"

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good

"It's an old property and it looks it with outdated interior and exterior, stains on really worn carpet, one light out in the room (we lived without it), tiny bathroom and towels so worn out they felt like sandpaper. However, the bed was exactly what I like: mattress was firm enough, bed linens were bright white, pillows were plump enough, and I slept decently. The blinds were truly light-blocking and they closed well. The reason we stayed here was to sleep overnight before heading home the next day, so that objective was achieved. Breakfast included bacon and buffet was stocked. Other breakfast guests were pleasant. Desk staff members did what they were supposed to do. There was a mini fridge, which I wanted so we could have cold drinks for the day we departed. As I recall from reserving two months ago, the rate was a good deal. Would not stay longer than one night, but for a single night, this was a problem-free experience."

A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything

10/10 Excellent

"Our host was very gracious and thoughtful offering amenities that were exceptional. The space by the lake was a wonderful retreat with only the sounds of birds, an occasional chipmunk and a soft breeze.Great house!! And not too far from Tanglewood"

Find out more about Pittsfield

Pittsfield Apartments information

Number of reviews	237
Accommodation	102 Apartments
Lowest Price	$155
Highest Price	$350

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.

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Pittsfield Vacation Rentals

Apartments in Pittsfield for Rent

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Our top choices for Pittsfield apartments

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

2. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

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

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

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

6. 1st FL Mtn View Woodland Suite on Jiminy Sleeps 4 Ski On/Off, Fully Redone Count

7. Berkshires Apartment at the Stephentown Hotel

8. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn

9. WOW-New Ski OnOff Suite By Pool Sleeps 4 Jiminy Pk - Fully Redone Gorgeous Inn

10. 2-Bdr Apt In Town, By the Water

11. Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base

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

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

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

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

16. Downtown | Waterfront | Walk to Shops

17. Penthouse Apartment on Park Street

18. New Studio In Town, By the Water

19. 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

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

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

Hotel On North

Find out more about Pittsfield

Pittsfield Apartments information

Frequently asked questions

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