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Recommended hotels in Pittsfield

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

1. Hotel On North

Pittsfield

Philip

CA $183 total

includes taxes & fees

Nov 29 - Nov 30

A modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Pittsfield

Ruth

CA $174 total

includes taxes & fees

Nov 15 - Nov 16

3. Berkshire Mountain Lodge

Pittsfield

Susan J

CA $153 total

includes taxes & fees

Dec 6 - Dec 7

A multi-story hotel with a prominent entrance, a parking lot, and a flagpole.

4. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

CA $187 total

includes taxes & fees

Nov 15 - Nov 16

A Best Western Plus hotel with a two-story building, a covered front entrance, and a parking lot.

5. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

James

CA $148 total

includes taxes & fees

Dec 1 - Dec 2

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

6. Berkshire Inn

Pittsfield

cheryl

CA $130 total

includes taxes & fees

Dec 9 - Dec 10

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 $153 total

includes taxes & fees

Nov 11 - Nov 12

A multi-story hotel with a prominent sign for Holiday Inn & Suites.

8. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

CA $170 total

includes taxes & fees

Dec 10 - Dec 11

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

9. FairBridge Inn Express

Pittsfield

William

CA $112 total

includes taxes & fees

Nov 10 - Nov 11

A two-story house with a balcony, a garage, and a driveway.

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

Pittsfield

Stephen L.

CA $668 total

includes taxes & fees

Nov 10 - Nov 11

A large white house with black shutters, surrounded by snow-covered trees and a fence.

11. Hancock Village Inn Near Jiminy Peak

Hancock

Price F.

CA $1,541 total

includes taxes & fees

Nov 10 - Nov 11

A hotel with a covered entrance, a registration desk, and a parking area.

12. The Yankee Inn

Lenox

Stephanie

CA $176 total

includes taxes & fees

Dec 2 - Dec 3

A hotel entrance with a covered driveway, a sign for Hampton Inn & Suites by Hilton, and a brick building with multiple windows.

13. Hampton Inn & Suites Berkshires-Lenox

Lenox

Thomas

CA $173 total

includes taxes & fees

Nov 15 - Nov 16

A multi-story motel with a central courtyard, individual rooms with balconies, and a parking lot.

14. Howard Johnson by Wyndham Lenox

Lenox

Aleksandr

CA $125 total

includes taxes & fees

Nov 10 - Nov 11

A large, multi-story hotel with a symmetrical facade, multiple balconies, and a well-lit entrance.

15. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

CA $198 total

includes taxes & fees

Nov 15 - Nov 16

A hotel room with a bed, a television, a wardrobe, and a bathroom visible through an open door.

16. Garden Gables

Lenox

Eyee

CA $309 total

includes taxes & fees

Nov 10 - Nov 11

A large, modern two-story house with a prominent gable roof, large windows, and a covered porch area.

17. Berkshires Untold

Lenox

Brian

CA $166 total

includes taxes & fees

Nov 17 - Nov 18

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

Lee

Gustavo

CA $166 total

includes taxes & fees

Dec 3 - Dec 4

A Super 8 motel with a two-story building, a parking lot, and a picnic table.

19. Quality Inn Lee - Lenox South

Lee

Bernardo Jr

CA $134 total

includes taxes & fees

Dec 2 - Dec 3

A hotel with a covered entrance, multiple floors, and a landscaped area with flowers and shrubs.

20. Element by Marriott Lenox Berkshires

Lenox

Francis

CA $213 total

includes taxes & fees

Nov 15 - Nov 16

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Learn more about Pittsfield

Nestled in the heart of the Berkshires, this cultural hub boasts the renowned Berkshire Museum and historic Colonial Theatre. Outdoor enthusiasts can hike nearby Pittsfield State Forest trails before exploring the vibrant downtown's farm-to-table restaurants and local art galleries.

See all hotels in Pittsfield

A historic building with a clock, a flag, and a street lamp.

Top reviews in Pittsfield

Hotel On North

Pittsfield

10/10 Excellent

alan

Hilton Garden Inn Lenox Pittsfield

Pittsfield

10/10 Excellent

Pete

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

10/10 Excellent

Lorraine

The Central Downtown Inn & Suites

Pittsfield

10/10 Excellent

Agnes

Berkshire Inn

Pittsfield

10/10 Excellent

Rose

An aerial view of a large estate with multiple buildings, surrounded by dense greenery and trees.

Inn at Silver Maple Farm

East Chatham

10/10 Excellent

Timothy

A large, two-story house with a well-maintained lawn and a fence.

Devonfield Inn B&B

Lee

10/10 Excellent

We stayed at the Devonfield Inn in mid-October during peak foliage season. The hotel is a wonderful historic home built in 1800 with much of its historic character preserved. Our hosts were so welcoming and made us feel at home. The room was very comfortable and breakfast was fantastic. In the morning, we got a special surprise to see a bear on the patio drinking from the fountain and robbing the bird feeder. Overall we highly recommend the Devonfield. We will definitely go back.

Lise