Browse the Best Pittsfield Resorts from CA $100

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

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Recommended hotels in Pittsfield

A bedroom with a large bed, two armchairs, a wooden dresser, a mirror, and a piano in the background.

1. Hotel On North

Pittsfield

Devon

CA $180 total

includes taxes & fees

Nov 8 - Nov 9

A hotel patio with outdoor seating and a fire pit.

2. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

CA $186 total

includes taxes & fees

Nov 15 - Nov 16

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

3. Berkshire Mountain Lodge

Pittsfield

ulla

CA $165 total

includes taxes & fees

Nov 10 - Nov 11

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

Pittsfield

James

CA $153 total

includes taxes & fees

Nov 15 - Nov 16

An indoor swimming pool with clear water, tiled floors, and a blue wall.

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

Pittsfield

Ginger

CA $155 total

includes taxes & fees

Nov 22 - Nov 23

A hotel room with a large bed, two bedside lamps, a chair, and a window with curtains.

6. Berkshire Inn

Pittsfield

cheryl

CA $126 total

includes taxes & fees

Nov 23 - Nov 24

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

Pittsfield

Debra

CA $155 total

includes taxes & fees

Oct 25 - Oct 26

A hotel room with a large bed, a separate sitting area, a bathtub, and a large mirror.

8. FairBridge Inn Express

Pittsfield

Richard

CA $100 total

includes taxes & fees

Oct 27 - Oct 28

A wooden deck with a table and chairs, surrounded by a white railing.

9. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Pittsfield

Stephen L.

CA $696 total

includes taxes & fees

Oct 26 - Oct 27

A wooden deck with outdoor furniture, including chairs and a table, surrounded by a lush garden and trees.

10. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

CA $1,609 total

includes taxes & fees

Oct 27 - Oct 28

A spacious hotel lobby with multiple seating areas, large windows, and a television.

11. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

CA $172 total

includes taxes & fees

Oct 30 - Oct 31

Two Adirondack chairs facing a river with a forested hill in the background.

12. The Yankee Inn

Lenox

Basil

CA $149 total

includes taxes & fees

Nov 1 - Nov 2

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

Lenox

Aleksandr

CA $124 total

includes taxes & fees

Oct 25 - Oct 26

A modern outdoor patio with seating, a fire pit, and a building with large windows and stone pillars.

14. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

CA $197 total

includes taxes & fees

Nov 1 - Nov 2

A spacious hotel lobby with high ceilings, large windows, and a central seating area with a chandelier.

15. Berkshires Untold

Lenox

Madhavi R

CA $204 total

includes taxes & fees

Nov 1 - Nov 2

16. Quality Inn Lee - Lenox South

Lee

Lucinda

CA $145 total

includes taxes & fees

Nov 15 - Nov 16

A lakeside setting with Adirondack chairs and a covered seating area, surrounded by trees and hills in the background.

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

Lee

Gustavo

CA $172 total

includes taxes & fees

Nov 15 - Nov 16

A modern kitchen with a central island, bar seating, and a dining area with chairs and a table.

18. Element by Marriott Lenox Berkshires

Lenox

Francis

CA $211 total

includes taxes & fees

Nov 8 - Nov 9

A snow-covered outdoor area with a patio, seating, and a covered dining area.

19. The Cornell Inn, Lenox & The Berkshires

Lenox

judith

CA $247 total

includes taxes & fees

Oct 27 - Oct 28

20. Garden Gables

Lenox

CA $306 total

includes taxes & fees

Oct 28 - Oct 29

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Top Pittsfield Hotel Reviews

The Red Lion Inn

8/10 Good

"Absolutely great location! An older property- the lobby and hallways seemed dark and aging (yes it’s historic). Our room was surprisingly cheerful! I’d stay here again!!"

Berkshires Untold

10/10 Excellent

"The lobby was absolutely beautiful, aesthetically and structurally! From all the greenery from the plants to the high ceilings, cute seating areas, and nice bar. The outdoor furniture was a plus, especially with the fire pits and the surrounded by the nice view of the berkshires. After an evening out, we came back and played a board game in the lobby and even did a little painting of our own while enjoying some good cocktails…you can definitely create a vibe. The room was clean, and overall it was a great stay if you’re just looking to relax, unwind, and get away for a bit!"

Berkshire Mountain Lodge

10/10 Excellent

"We've stayed at Berkshire Mountain Lodge in October a number of times now, and we really enjoy the property. The rooms are well-appointed, very clean, and quite comfortable. We appreciate the free washers and dryers as well as the many other amenities, and you cannot beat the location. There's a supermarket down the driveway and across the street and an excellent specialty grocer--Guido's Market--just down the road. We highly recommend this property. The District Restaurant in Pittsfield is excellent. We've also seen several great plays at Barrington Theatre Company. The area is loaded with historical and cultural activities. We like the proximity to Lenox and the Edith Wharton mansion as well as The Clark art museum in Williamstown, both of which have lovely grounds/gardens typically exhibiting sculptures. There are also abundant outdoor activities and opportunities for hiking and lovely scenic drives. This was a good year for fall color, and the red maples were glorious! It's a short ride to Vermont where we checked out Mt. Equinox for the first time. Highly recommend the drive to the top on a sunny, clear day."

Best Western Plus Berkshire Hills Inn & Suites

8/10 Good

"We had a good stay the staff when I arrived was super nice and personable and we really like the amenities. I really like the water that was filtered in the front and the breakfast was very good choices. Our room was very clean and the TV selection was great."

Find out more about Pittsfield

Pittsfield Resorts information

Number of reviews	13,256
Accommodation	12 Resorts
Lowest Price	CA $100
Highest Price	CA $1,609

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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Recommended hotels in Pittsfield

1. Hotel On North

2. Hilton Garden Inn Lenox Pittsfield

3. Berkshire Mountain Lodge

4. Best Western Plus Berkshire Hills Inn & Suites

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

6. Berkshire Inn

7. The Central Downtown Inn & Suites

8. FairBridge Inn Express

9. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

10. Hancock Village Inn Near Jiminy Peak

11. Hampton Inn & Suites Berkshires-Lenox

12. The Yankee Inn

13. Howard Johnson by Wyndham Lenox

14. Courtyard by Marriott Lenox Berkshires

15. Berkshires Untold

16. Quality Inn Lee - Lenox South

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

18. Element by Marriott Lenox Berkshires

19. The Cornell Inn, Lenox & The Berkshires

20. Garden Gables

Top Pittsfield Hotel Reviews

The Red Lion Inn

Berkshires Untold

Berkshire Mountain Lodge

The Yankee Inn

The Williams Inn

Best Western Plus Berkshire Hills Inn & Suites

Hotel On North

Berkshire Inn

The Central Downtown Inn & Suites

Find out more about Pittsfield

Pittsfield Resorts information

Frequently asked questions

Explore a world of travel with Expedia

Search Resort Hotels in Pittsfield from CA $100

Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Pittsfield

1. Hotel On North

2. Hilton Garden Inn Lenox Pittsfield

3. Berkshire Mountain Lodge

4. Best Western Plus Berkshire Hills Inn & Suites

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

6. Berkshire Inn

7. The Central Downtown Inn & Suites

8. FairBridge Inn Express

9. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

10. Hancock Village Inn Near Jiminy Peak

11. Hampton Inn & Suites Berkshires-Lenox

12. The Yankee Inn

13. Howard Johnson by Wyndham Lenox

14. Courtyard by Marriott Lenox Berkshires

15. Berkshires Untold

16. Quality Inn Lee - Lenox South

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

18. Element by Marriott Lenox Berkshires

19. The Cornell Inn, Lenox & The Berkshires

20. Garden Gables

Top Pittsfield Hotel Reviews

The Red Lion Inn

Find out more about Pittsfield

Pittsfield Resorts information

Frequently asked questions

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