Pittsfield Villas from CA $94

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

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

Check prices for these dates

In two weeks

In two months

In three months

In four months

No exact matches found, but these alternatives could be just right

Recommended hotels in Pittsfield

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

1. Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

Prasanna

CA $139 total

includes taxes & fees

Sep 8 - Sep 9

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

2. Holiday Inn & Suites Pittsfield-Berkshires by IHG

Pittsfield

Debra

CA $182 total

includes taxes & fees

Sep 9 - Sep 10

A hotel lobby with a snow-covered entrance and a sign reading "Lobby".

3. Berkshire Mountain Lodge

Pittsfield

Robert

CA $154 total

includes taxes & fees

Oct 1 - Oct 2

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

4. Hotel On North

Pittsfield

Drew

CA $208 total

includes taxes & fees

Sep 7 - Sep 8

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

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

Pittsfield

Steve

CA $196 total

includes taxes & fees

Sep 10 - Sep 11

A motel with a parking lot, a swimming pool, and outdoor seating.

6. Berkshire Inn

Pittsfield

Ellen

CA $129 total

includes taxes & fees

Oct 7 - Oct 8

A modern hotel with a prominent entrance, multiple floors, and a clear sky.

7. Hilton Garden Inn Lenox Pittsfield

Pittsfield

James

CA $226 total

includes taxes & fees

Sep 10 - Sep 11

A covered porch with a wooden floor and white railing, overlooking a green lawn and a clear blue sky.

8. The Central Downtown Inn & Suites

Pittsfield

Rena

CA $153 total

includes taxes & fees

Sep 7 - Sep 8

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

9. FairBridge Inn Express

Pittsfield

ERICIA

CA $94 total

includes taxes & fees

Sep 7 - Sep 8

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!

Pittsfield

Ann C.

CA $767 total

includes taxes & fees

Sep 8 - Sep 9

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 $1,498 total

includes taxes & fees

Sep 9 - Sep 10

A view from a balcony with a wooden railing, a grassy landscape, and a mountain in the distance.

12. The Yankee Inn

Lenox

Karen

CA $163 total

includes taxes & fees

Sep 28 - Sep 29

13. Hampton Inn & Suites Berkshires-Lenox

Lenox

Nancy

CA $200 total

includes taxes & fees

Sep 30 - Oct 1

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

14. Howard Johnson by Wyndham Lenox

Lenox

irene

CA $121 total

includes taxes & fees

Sep 7 - Sep 8

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

15. Berkshires Untold

Lenox

David

CA $203 total

includes taxes & fees

Sep 8 - Sep 9

A covered outdoor area with stone pillars and a view of a road and green hills.

16. Courtyard by Marriott Lenox Berkshires

Lenox

Tracy

CA $301 total

includes taxes & fees

Sep 13 - Sep 14

A two-story building with a symmetrical facade, a central entrance, and a well-maintained lawn.

17. Vacation Village in the Berkshires

Williamstown

Alex

CA $162 total

includes taxes & fees

Sep 15 - Sep 16

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

James

CA $197 total

includes taxes & fees

Sep 27 - Sep 28

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

19. Quality Inn Lee - Lenox South

Lee

Christine

CA $156 total

includes taxes & fees

Sep 27 - Sep 28

A large house with a covered patio area featuring outdoor seating and a fire pit.

20. The Whitlock

Lenox

Constance

CA $222 total

includes taxes & fees

Sep 8 - Sep 9

View all properties

Find vacation rentals that suit your style

Apartments

Cabins

Save an average of 15% on thousands of hotels when you're signed in

Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

10/10 Excellent

"X"

Hotel On North

10/10 Excellent

"Beautiful boutique hotel. Our room was very large with a sitting area + TV. Bed room area equally as large, also with a TV. The bathroom was gorgeous with thoughtful touches. On the marble counter was a makeup mirror with a stool so one could sit. Parking lot was in rear of hotel, secure and easy access to the lobby. Staff couldn't have been more accessible and pleasant. Highly recommend this hotel"

Berkshire Mountain Lodge

10/10 Excellent

"We were there for a one night stay after a show at Tanglewood. Being able to check in online in advance was excellent and saved us a lot of time. There were three of us traveling (a couple and a family member) so we requested a suite. It was huge, well appointed and so clean. The cost was incredibly reasonable for the amount of space we had! The king bed in its own bedroom was super comfortable, and the pull out couch did the job. We didn’t use any of the extra amenities, but saw a few families with children. Lots of space to roam and wander, both inside and on the property. It was an easy 15 minute drive to Tanglewood, so the location worked great for us. The only negative comment would be there was no do not disturb tag for the door, so housekeeping arrived an hour before checkout and we had to send them away. We will stay again if we are in the area, highly recommended!"

Quality Inn Great Barrington

10/10 Excellent

"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."

Find out more about Pittsfield

Pittsfield Villas information

Number of reviews	10,709
Accommodation	3 Villas
Lowest Price	CA $94
Highest Price	CA $1,498

Frequently asked questions

Why book your villa in Pittsfield with Expedia?

Reserving a villa in Pittsfield is as easy as deciding on your travel dates and selecting an option that suits your style. Looking for something luxurious or low cost, or a stay that also includes a laundry and kitchen? Use Expedia's search filters to narrow your results and find your ideal pad.

How can I find cheap villas in Pittsfield?

Expedia is here to help you easily source cheap villas in Pittsfield. Use our convenient filter tool to choose star rating, amenities and budget to refine your search and find a perfect stay in a few quick keystrokes.

What is there to do near my villa in Pittsfield?

Pittsfield has enough experiences to keep you going for weeks, starting with Hancock Shaker Village. Pittsfield State Forest, Arrowhead Museum and Bousquet Ski Area are other fantastic attractions. If you're in town for longer, Barrington Stage Company and Berkshire Museum will round off your itinerary nicely.

Explore a world of travel with Expedia

Dalton Vacation Rentals

Book Villas in Pittsfield on Expedia.com

Search Pittsfield Villa Rentals from CA $94

Change your mind

Treat yourself

Be picky

Check prices for these dates

Recommended hotels in Pittsfield

1. Best Western Plus Berkshire Hills Inn & Suites

2. Holiday Inn & Suites Pittsfield-Berkshires by IHG

3. Berkshire Mountain Lodge

4. Hotel On North

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

6. Berkshire Inn

7. Hilton Garden Inn Lenox Pittsfield

8. The Central Downtown Inn & Suites

9. FairBridge Inn Express

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

11. Hancock Village Inn Near Jiminy Peak

12. The Yankee Inn

13. Hampton Inn & Suites Berkshires-Lenox

14. Howard Johnson by Wyndham Lenox

15. Berkshires Untold

16. Courtyard by Marriott Lenox Berkshires

17. Vacation Village in the Berkshires

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

19. Quality Inn Lee - Lenox South

20. The Whitlock

Find vacation rentals that suit your style

Top Pittsfield Hotel Reviews

Vacation Village in the Berkshires

Find out more about Pittsfield

Pittsfield Villas information

Frequently asked questions

Explore a world of travel with Expedia