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

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Check prices for these dates

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov
In one month
4 Dec - 6 Dec
In two months
1 Jan - 3 Jan
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, (978 reviews)
"Very nice hotel"
United States
Philip
The price is AED 426
AED 476 total
includes taxes & fees
29 Nov - 30 Nov
Hotel On North
Exterior

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,255 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is AED 304
AED 421 total
includes taxes & fees
8 Nov - 9 Nov
Berkshire Mountain Lodge
A hotel patio with outdoor seating and a fire pit.

3. Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (716 reviews)
"Great place to stay. Great staff and convenient location. Nice restaurant as well."
United States
James
The price is AED 436
AED 487 total
includes taxes & fees
15 Nov - 16 Nov
Hilton Garden Inn Lenox Pittsfield
An indoor swimming pool with clear water, tiled floors, and a blue wall.

4. 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, (255 reviews)
"The room was clean and well kept, breakfast was amazing!"
United States
Ruth
The price is AED 378
AED 423 total
includes taxes & fees
2 Dec - 3 Dec
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
A hotel room with a large bed, a flat-screen TV, a fireplace, a desk with a chair, and a nightstand with lamps.

5. 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, (1,001 reviews)
"Room was spacious and clean"
United States
James
The price is AED 343
AED 384 total
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Berkshire Hills Inn & Suites
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, (941 reviews)
"It was an ok place to stay for 2 nights"
United States
cheryl
The price is AED 304
AED 340 total
includes taxes & fees
28 Nov - 29 Nov
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, (434 reviews)
"Consistently, a clean, quiet, convenient location and comfortable stay."
United States
Debra
The price is AED 364
AED 406 total
includes taxes & fees
5 Nov - 6 Nov
The Central Downtown Inn & Suites
A large indoor swimming pool with multiple levels of balconies, surrounded by tables and chairs.

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, (1,001 reviews)
"enjoyed our stay"
United States
Mark
The price is AED 378
AED 423 total
includes taxes & fees
4 Dec - 5 Dec
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, (934 reviews)
"Friendly staff"
United States
William
The price is AED 261
AED 292 total
includes taxes & fees
5 Nov - 6 Nov
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
8.6 out of 10, Excellent, (11 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 AED 988
AED 1,728 total
includes taxes & fees
5 Nov - 6 Nov
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 AED 2,310
AED 4,007 total
includes taxes & fees
17 Nov - 18 Nov
Hancock Village Inn Near Jiminy Peak
Two Adirondack chairs facing a river with a forested hill in the background.

12. The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,011 reviews)
"The location was good for our trip."
United States
Basil
The price is AED 376
AED 420 total
includes taxes & fees
20 Nov - 21 Nov
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, (1,001 reviews)
"Breakfast was great"
United States
Thomas
The price is AED 403
AED 450 total
includes taxes & fees
10 Nov - 11 Nov
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, (934 reviews)
"Really enjoyed our one night stay in this hotel"
United States
Aleksandr
The price is AED 290
AED 324 total
includes taxes & fees
5 Nov - 6 Nov
Howard Johnson by Wyndham 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, (684 reviews)
"Great stay!"
United States
Vandhana
The price is AED 461
AED 515 total
includes taxes & fees
8 Nov - 9 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, (1,065 reviews)
"Very nice place beautiful view"
United States
Brian
The price is AED 448
AED 501 total
includes taxes & fees
29 Nov - 30 Nov
Berkshires Untold
Dining

17. Garden Gables

Garden Gables
4.0 star property
Lenox
10.0 out of 10, Exceptional, (2 reviews)
"Lovely place!"
United States
Eyee
The price is AED 474
AED 797 total
includes taxes & fees
1 Dec - 2 Dec
Garden Gables
A lodge with a large building and a dock by a lake, surrounded by forest.

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

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,005 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 AED 401
AED 448 total
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".

19. Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.6 out of 10, Excellent, (1,002 reviews)
"Perfect for a travel stop-over."
United States
James
The price is AED 311
AED 348 total
includes taxes & fees
2 Dec - 3 Dec
Quality Inn Lee - Lenox South
A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

20. Element by Marriott Lenox Berkshires

Element by Marriott Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (51 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 AED 496
AED 554 total
includes taxes & fees
10 Nov - 11 Nov
Element by Marriott Lenox 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.
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Top Pittsfield Hotel Reviews

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Very nice place beautiful view"
Brian 1-night trip
Posted 5 hours ago
Berkshires Untold

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: In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants - Ski resort right by Jiminy Peak Mountain Resort. 7.6 mi (12.3 km) from Pittsfield. Has ski-in/ski-out access, a fitness center, and a garden. 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. Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out - Ski resort, 5-minute walk from Jiminy Peak Mountain Resort. 7.7 mi (12.4 km) from Pittsfield. Access to ski-in/ski-out access, a fitness center, and an indoor pool.
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 Colonial Theater or Barrington Stage Company. A few other attractions you may want to see are Bousquet Ski Area and Housatonic River.
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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