Pittsfield Houseboats from CA $100

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Find vacation rentals that suit your style

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

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

1. Hotel On North

Pittsfield

Rosemarie

CA $182 total

includes taxes & fees

Nov 17 - Nov 18

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

2. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

CA $187 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 modern hotel with a large entrance, multiple floors, and a well-lit facade.

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

Pittsfield

Ruth

CA $173 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 $147 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 $136 total

includes taxes & fees

Nov 15 - Nov 16

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 17 - Nov 18

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

8. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Mark

CA $155 total

includes taxes & fees

Dec 11 - Dec 12

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 15 - Nov 16

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 $667 total

includes taxes & fees

Nov 15 - Nov 16

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 $1,466 total

includes taxes & fees

Dec 1 - Dec 2

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

12. The Yankee Inn

Lenox

Stephanie

CA $175 total

includes taxes & fees

Dec 12 - Dec 13

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 17 - Nov 18

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 15 - Nov 16

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

15. Garden Gables

Lenox

Eyee

CA $299 total

includes taxes & fees

Nov 17 - Nov 18

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

16. Courtyard by Marriott Lenox Berkshires

Lenox

Vandhana

CA $198 total

includes taxes & fees

Nov 15 - Nov 16

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

17. Berkshires Untold

Lenox

Juan

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 $169 total

includes taxes & fees

Dec 6 - Dec 7

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

19. Element by Marriott Lenox Berkshires

Lenox

Francis

CA $213 total

includes taxes & fees

Nov 29 - Nov 30

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

20. Quality Inn Lee - Lenox South

Lee

Bernardo Jr

CA $136 total

includes taxes & fees

Dec 6 - Dec 7

View all properties

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

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