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

Search Pittsfield Condo Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

A multi-story hotel with a classic facade, large windows, and a prominent entrance.

1. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (959 reviews)
"This was an excellent hotel. Super convenient right in the middle of town, clean, huge rooms, historic, and comfortable, I would love to stay here again I would recommend it to anyone!"
United States
Devon
The price is €133
includes taxes & fees
1 Nov - 2 Nov
Hotel On North
An indoor swimming pool with clear water, tiled floors, and a blue wall.

2. Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (244 reviews)
"Very nice rooms, staff friendly."
United States
Ginger
The price is €98
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

3. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,222 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
The price is €105
includes taxes & fees
22 Nov - 23 Nov
Berkshire Mountain Lodge
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

4. Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.4 out of 10, Very good, (1,007 reviews)
"Room was spacious and clean"
United States
James
The price is €97
includes taxes & fees
18 Nov - 19 Nov
Best Western Plus Berkshire Hills Inn & Suites
A hotel patio with outdoor seating and a fire pit.

5. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (715 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is €127
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Lenox Pittsfield
A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

6. Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (938 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
The price is €86
includes taxes & fees
28 Oct - 29 Oct
Berkshire Inn
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

7. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (427 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is €98
includes taxes & fees
26 Oct - 27 Oct
The Central Downtown Inn & Suites
A modern hotel room with a sofa, a TV, a kitchen area with bar stools, and a patterned floor.

8. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
7.8 out of 10, Good, (1,000 reviews)
"enjoyed our stay"
United States
Mark
Holiday Inn & Suites Pittsfield-Berkshires by IHG
A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

9. FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (925 reviews)
"This motel was well-cared for and a good value compared to anywhere close boy on our early-October Saturday night in the busy Berkshires!"
United States
Richard
The price is €71
includes taxes & fees
25 Oct - 26 Oct
FairBridge Inn Express
A wooden deck with a table and chairs, surrounded by a white railing.

10. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.4 out of 10, Very good, (10 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is €446
includes taxes & fees
25 Oct - 26 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

11. Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (22 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is €1,030
includes taxes & fees
27 Oct - 28 Oct
Hancock Village Inn Near Jiminy Peak
A hotel room with a four-poster bed, two armchairs, a small table with a book, and a decorative canopy.

12. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,012 reviews)
"The location was good for our trip."
United States
Basil
The price is €105
includes taxes & fees
1 Nov - 2 Nov
The Yankee Inn
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

13. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (929 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
The price is €79
includes taxes & fees
28 Oct - 29 Oct
Howard Johnson by Wyndham Lenox
A spacious hotel lobby with multiple seating areas, large windows, and a television.

14. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,002 reviews)
"Breakfast was great"
United States
Thomas
The price is €109
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Berkshires-Lenox
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

15. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (679 reviews)
"Great stay!"
United States
Vandhana
The price is €125
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Lenox Berkshires
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

16. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,046 reviews)
"A very good place to stay"
United States
Madhavi R
The price is €129
includes taxes & fees
1 Nov - 2 Nov
Berkshires Untold
A lodge with a large building and a dock by a lake, surrounded by forest.

17. The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,006 reviews)
"Amazing place, clean, staff is awesome , amazing location , amazing views! Free breakfast, free coffee bar , free gym and the best it’s pet friendly !"
United States
Gustavo
The price is €114
includes taxes & fees
15 Nov - 16 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

18. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,004 reviews)
"Had a comfortable stay."
United States
Lucinda
The price is €92
includes taxes & fees
12 Nov - 13 Nov
Quality Inn Lee - Lenox South
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

19. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (47 reviews)
"Clean, spacious room Accommodating staff especially Shawn and Jennifer at the front desk. Very nice pool and gym Definitely coming back"
United States
Francis
The price is €134
includes taxes & fees
8 Nov - 9 Nov
Element by Marriott Lenox Berkshires
A snow-covered outdoor area with a patio, seating, and a covered dining area.

20. The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,000 reviews)
"Lovely room, comfortable bed and a nice breakfast."
United Kingdom
judith
The price is €157
includes taxes & fees
28 Oct - 29 Oct
The Cornell Inn, Lenox & The Berkshires
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

The Williams Inn

The Williams Inn

10/10 Excellent
"A very nice Inn in the center of William Town. Love the staff. Spacious room and great complimentary coffee and tea bar in each floor."
Yolanda 1-night trip
Posted 3 hours ago
The Williams Inn

Find out more about Pittsfield

Pittsfield Condo Rentals information

Number of reviews
6,981
Accommodation
26 Condo Rentals
Lowest Price
€71
Highest Price
€1,030

Frequently asked questions

How much do condos in Pittsfield cost?
Condos in Pittsfield range from €71 to €1,030 per night. These properties offer extra space for the whole family at a price that doesn't break the bank. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Pittsfield?
Pittsfield has 26 condos. To help you locate a place that's perfect, use our filters to search for the amenities or perks you need.
Are there any family-friendly condos in Pittsfield?
If you're planning a visit to Pittsfield and searching for a family-friendly condo, consider Holiday Village In The Berkshires. This 3-star option has a terrace and a swimming pool. Pittsfield has no shortage of family-friendly attractions to visit when the kids are getting restless. Jiminy Peak Mountain Resort and Bousquet Ski Area promise a fun day out for all ages.
Why book your condo in Pittsfield with Expedia?
Vacays should be hassle-free, so if you're in search of condos at a competitive rate, Expedia has your back. Keep the budget in check and pick something small and affordable, or book a 5-star condo and spoil your favourite people. Our search filters make it simple to find a stay in Pittsfield that checks your boxes.
How can I find cheap condos in Pittsfield?
Expedia can help you easily locate cheap condos in Pittsfield. To book your ideal stay in just a few keystrokes, try out our handy filter tool to refine your search results by star rating, budget and amenities.
What is there to do in Pittsfield near my condo?
You'll find loads of awesome things to do in Pittsfield. You won't want to miss leading attractions like Hancock Shaker Village, Pittsfield State Forest and Arrowhead Museum. Bousquet Ski Area, Barrington Stage Company and Berkshire Museum are other must-do's.