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

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Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

1. 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, (1,009 reviews)
"It was clean and amenities were above average."
United States
Prasanna
The price is CA $124
CA $139 total
includes taxes & fees
Sep 9 - Sep 10
Best Western Plus Berkshire Hills Inn & Suites

2. 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, (1,001 reviews)
"Look good for being under constructikn"
United States
Debra
The price is CA $163
CA $182 total
includes taxes & fees
Sep 9 - Sep 10
Holiday Inn & Suites Pittsfield-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, (1,129 reviews)
"Clean & comfortable stay"
United States
Robert
The price is CA $110
CA $154 total
includes taxes & fees
Oct 1 - Oct 2
Berkshire Mountain Lodge
A building entrance with a large planter with purple flowers and a small tree.

4. Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (908 reviews)
"Very nice and reasonably priced hotel for the region."
United States
Drew
The price is CA $186
CA $208 total
includes taxes & fees
Sep 7 - Sep 8
Hotel On North
An indoor swimming pool with clear water, tiled floors, and a blue wall.

5. 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, (194 reviews)
"Clean & easy to stay there"
United States
Steve
The price is CA $176
CA $196 total
includes taxes & fees
Sep 10 - Sep 11
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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, (917 reviews)
"Quiet location set back from road, comfortable beds and nice shower. Located right on Rt. 20 and near downtown."
United States
Ellen
The price is CA $115
CA $129 total
includes taxes & fees
Oct 7 - Oct 8
Berkshire Inn
A restaurant with a large Buddha statue in the center, multiple dining tables with chairs, and a carpeted floor.

7. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (705 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is CA $202
CA $226 total
includes taxes & fees
Sep 10 - Sep 11
Hilton Garden Inn Lenox Pittsfield
A building with a registration sign above the entrance, a white porch railing, and flower baskets on the railing.

8. The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.4 out of 10, Very good, (407 reviews)
"Large, clean, comfortable suite."
United States
Rena
The price is CA $137
CA $153 total
includes taxes & fees
Sep 7 - Sep 8
The Central Downtown Inn & Suites
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, (893 reviews)
"It was very nice and everyone was extremely helpful"
United States
ERICIA
The price is CA $84
CA $94 total
includes taxes & fees
Sep 7 - Sep 8
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 clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is CA $435
CA $767 total
includes taxes & fees
Sep 8 - Sep 9
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 CA $798
CA $1,498 total
includes taxes & fees
Sep 9 - Sep 10
Hancock Village Inn Near Jiminy Peak
A modern bathroom with a freestanding bathtub, a fireplace, and two framed posters on the wall.

12. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,012 reviews)
"Very nice and convenient hotel."
United States
Karen
The price is CA $146
CA $163 total
includes taxes & fees
Sep 28 - Sep 29
The Yankee Inn
A spacious hotel lobby with multiple seating areas, large windows, and a television.

13. Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox
2.5 star property
Lenox
9.0 out of 10, Wonderful, (1,002 reviews)
"Great comfortable beds Good breakfast"
United States
Nancy
The price is CA $167
CA $186 total
includes taxes & fees
Sep 13 - Sep 14
Hampton Inn & Suites Berkshires-Lenox
A hotel room with a large bed, bedside lamps, a desk with a computer, a microwave, and framed pictures on the wall.

14. Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (908 reviews)
"Stay again"
United States
irene
The price is CA $108
CA $121 total
includes taxes & fees
Sep 7 - Sep 8
Howard Johnson by Wyndham Lenox
A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

15. Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,018 reviews)
"Standard roadside motel converted into a boutique hotel with great food and services. Will stay again if in the area."
United States
David
The price is CA $182
CA $203 total
includes taxes & fees
Sep 8 - Sep 9
Berkshires Untold
A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

16. Courtyard by Marriott Lenox Berkshires

Courtyard by Marriott Lenox Berkshires
3.0 star property
Lenox
9.2 out of 10, Wonderful, (653 reviews)
"Nice hotel."
United States
Tracy
The price is CA $269
CA $301 total
includes taxes & fees
Sep 13 - Sep 14
Courtyard by Marriott Lenox Berkshires
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

17. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,611 reviews)
"All the amenities offered are an excellent plus. Good rates for rooms. Good place to stay at, lots to do even around the area"
United States
Alex
The price is CA $132
CA $162 total
includes taxes & fees
Sep 15 - Sep 16
Vacation Village in the Berkshires
A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,004 reviews)
"enjoyable stay"
United States
James
The price is CA $176
CA $197 total
includes taxes & fees
Sep 27 - Sep 28
The Black Swan Lee - Lenox, an Ascend Collection Hotel
A reception area with a fireplace, seating, and a doormat with the logo "Quality".

19. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,012 reviews)
"Very nice stay"
United States
Christine
The price is CA $140
CA $156 total
includes taxes & fees
Sep 27 - Sep 28
Quality Inn Lee - Lenox South
A large house with a covered patio area featuring outdoor seating and a fire pit.

20. The Whitlock

The Whitlock
2.0 star property
Lenox
8.4 out of 10, Very good, (367 reviews)
"Lovely room, nice amenities."
United States
Constance
The price is CA $199
CA $222 total
includes taxes & fees
Sep 8 - Sep 9
The Whitlock
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

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

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

8/10 Good
"Clean room and breakfast was great. Very good location to Tanglewood."
Irene and Norberto 1-night trip
Posted less than an hour ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews
11,968
Accommodation
12 Resorts
Lowest Price
CA $94
Highest Price
CA $301

Frequently asked questions

What can I expect from a resort vacation in Pittsfield?
You deserve a getaway, and a resort is just the place to pamper yourself with the amenities and services you need for a relaxing time in Pittsfield. One of the comfortable resort hotels in the surrounding area could be just what you're looking for, whether you're hoping for an amazing pool, a state-of-the-art fitness center, or fun activities to try.
What's the best resort for my stay in Pittsfield?
Our highest-rated resorts near Pittsfield: COZY CABIN IN BERKSHIRES RESORT. - Ski resort right by Jiminy Peak Mountain Resort. 7.7 mi (12.4 km) from Pittsfield. Enjoy the ski-in/ski-out access, fitness center, and beach sun loungers. In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort steps from Jiminy Peak Mountain Resort. 7.6 mi (12.3 km) from Pittsfield. Amenities include ski-in/ski-out access, a fitness center, and a garden.
What can I do in Pittsfield?
Travelers enjoy the cultural offerings in Pittsfield, and have good things to say about its entertainment choices and theaters. Check out the interesting exhibits at Berkshire Museum and Hancock Shaker Village, or catch the latest production at Barrington Stage Company or Colonial Theater. A few other attractions you may want to see are Bousquet Ski Area and Pontoosuc Lake.
What's the seasonal weather like 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's the best way to get to and around Pittsfield?
Fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is located 2.5 mi (4 km) from the city center. Otherwise, look for flights into Hudson, NY (HCC-Columbia County), which is 25.7 mi (41.4 km) away. To explore the surrounding area, hop aboard a train at Pittsfield Intermodal Transportation Center or Pittsfield Station.

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