Search Resorts in Pittsfield

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months
No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,000 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is AED 404
AED 451 total
includes taxes & fees
11 May - 12 May
Best Western Plus Berkshire Hills Inn & Suites

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (924 reviews)
"Spacious, clean, and the pool was warm and perfect for family swimming "
United States
Danielle
The price is AED 322
AED 442 total
includes taxes & fees
24 May - 25 May
Berkshire Mountain Lodge

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (92 reviews)
"Room was clean, bed was comfortable, pool was nice, breakfast and coffee were good!"
United States
Haley
The price is AED 481
AED 537 total
includes taxes & fees
13 May - 14 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (854 reviews)
"Clean comfortable room. Very nice staff. Close to everything in downtown Pittsfield. This is the only place I stay when I’m in Pittsfield. Very peaceful. Excellent place to relax. "
United States
Jennifer
The price is AED 282
AED 315 total
includes taxes & fees
25 May - 26 May
Berkshire Inn

Hotel On North

Hotel On North
3.5 star property
Pittsfield
9.6 out of 10, Exceptional, (846 reviews)
"Awesome boutique rooms! "
United States
Denise
The price is AED 547
AED 611 total
includes taxes & fees
10 May - 11 May
Hotel On North

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (675 reviews)
" Nice staff - beautiful hotel!"
United States
MARY
The price is AED 496
AED 555 total
includes taxes & fees
14 May - 15 May
Hilton Garden Inn Lenox Pittsfield

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
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is AED 988
AED 1,810 total
includes taxes & fees
7 May - 8 May
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,001 reviews)
"The room was comfortable, and clean. The staff was very courteous and helpful. Breakfast was adequate. Check in and check out went smoothly."
United States
Sharon
The price is AED 433
AED 484 total
includes taxes & fees
17 May - 18 May
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Central Downtown Inn & Suites

The Central Downtown Inn & Suites
4.0 star property
Pittsfield
8.6 out of 10, Excellent, (363 reviews)
"Easy access to parking, nearby everything and room was very clean. Definitely will come back here to stay again! "
United States
Aisha
The price is AED 389
AED 435 total
includes taxes & fees
31 May - 1 Jun
The Central Downtown Inn & Suites

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (818 reviews)
"This the worst hotel we’ve ever stayed in. Shower walls were so dirty, dirt on the walls, curtains, etc…I’ve learned from this experience to not go as cheap. "
United States
Lynne
The price is AED 260
AED 290 total
includes taxes & fees
20 May - 21 May
FairBridge Inn Express

Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak
Hancock
10.0 out of 10, Exceptional, (19 reviews)
"Amazing Inn. Cozy and everything we needed. "
United States
Price F.
The price is AED 2,310
AED 4,220 total
includes taxes & fees
19 May - 20 May
Hancock Village Inn Near Jiminy Peak

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,003 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is AED 364
AED 406 total
includes taxes & fees
7 May - 8 May
The Yankee Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (449 reviews)
"Everything was great— the cleanliness, the plentiful breakfast, the character and coziness, and the proximity to Amici across the street (free dessert with your room key)."
United States
Patrick
The price is AED 400
AED 438 total
includes taxes & fees
10 May - 11 May
Shaker Mill Inn

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (931 reviews)
"Great stay!"
United States
Aditya
The price is AED 331
AED 369 total
includes taxes & fees
28 May - 29 May
Berkshires Untold

Maple Terrace Motel

Maple Terrace Motel
2.5 star property
Williamstown
9.6 out of 10, Exceptional, (601 reviews)
"Very clean and comfortable room and grounds, pleasant and helpful hosts, relaxing setting. Highly recommended."
United States
David J.
The price is AED 400
AED 447 total
includes taxes & fees
13 May - 14 May
Maple Terrace Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (849 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is AED 251
AED 281 total
includes taxes & fees
11 May - 12 May
Monument Mountain Motel

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (577 reviews)
"Clean"
United States
Brian
The price is AED 275
AED 308 total
includes taxes & fees
7 May - 8 May
Travelodge by Wyndham Great Barrington Berkshires

The Revival House

The Revival House
3.0 star property
Adams
9.2 out of 10, Wonderful, (29 reviews)
"Great place. Large rooms amazing common areas super fun w friends. "
United States
James
The price is AED 634
AED 708 total
includes taxes & fees
7 May - 8 May
The Revival House

Rodeway Inn

Rodeway Inn
2.0 star property
Adams
7.4 out of 10, Good, (241 reviews)
"Found dead flies in the beds and the sheets were stained. I would not expect much from an inexpensive room but I do expect it to be clean."
United States
Heidi
The price is AED 261
AED 292 total
includes taxes & fees
12 May - 13 May
Rodeway Inn

Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,347 reviews)
"great stay. "
United States
John
The price is AED 317
AED 394 total
includes taxes & fees
10 May - 11 May
Vacation Village in 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Pittsfield Hotel Reviews

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?
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more! - Features a fitness center, an indoor pool, and an outdoor pool. Mountain Lodge Apt! - Has a fitness center.
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.

Explore a world of travel with Expedia