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

Villas in Pittsfield

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    Check prices for these dates, December 13 – 14, 2026

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    Recommended hotels in Pittsfield

    1. Hotel On North

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

    2. Hilton Garden Inn Lenox Pittsfield

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

    3. Berkshire Mountain Lodge

    A large building with a prominent tower, surrounded by trees and a winding road.

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

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

    5. Best Western Plus Berkshire Hills Inn & Suites

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

    6. Berkshire Inn

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

    7. The Central Downtown Inn & Suites

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

    8. Holiday Inn & Suites Pittsfield-Berkshires by IHG

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

    9. FairBridge Inn Express

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

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

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

    11. Hancock Village Inn Near Jiminy Peak

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

    12. The Yankee Inn

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

    13. Hampton Inn & Suites Berkshires-Lenox

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

    14. Howard Johnson by Wyndham Lenox

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

    15. Garden Gables

    Exterior

    16. Courtyard by Marriott Lenox Berkshires

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

    17. Berkshires Untold

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

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

    A lodge with a large building and a dock by a lake, surrounded by forest.

    19. Element by Marriott Lenox Berkshires

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

    20. Quality Inn Lee - Lenox South

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

    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.

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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

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

    Element by Marriott Lenox Berkshires

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

    Hilton Garden Inn Lenox Pittsfield

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

    Inn at Silver Maple Farm

    Exterior

    Devonfield Inn B&B

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

    The Yankee Inn

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

    Prospect Berkshires

    A lakeside cabin with a reflection in the water, surrounded by autumn-colored trees.

    Shaker Mill Inn

    A red building with a sign reading "Shaker Mill Inn."

    Berkshire Mountain Lodge

    A large building with a prominent tower, surrounded by trees and a winding road.

    Brook Farm Inn

    A large, two-story house with a wrap-around porch, a covered front porch, and a small front yard.

    Hampton Inn & Suites Berkshires-Lenox

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

    Harbour House Inn

    A large, two-story house with a front porch and a well-maintained garden with various flowers and shrubs.

    Courtyard by Marriott Lenox Berkshires

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

    The Inn at Stockbridge

    Front of property

    Chambery Inn

    A two-story building with a sign reading "Chambéry Inn".

    Maple Terrace Motel

    A house with a porch, snow-covered ground, and a Christmas tree with lights.

    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.

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