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Compare Pittsfield Resorts

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Featured Resorts in Pittsfield

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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.

Resort Hotels

Resort hotels in Pittsfield
Find your next great getaway when you book at a resort hotel in Pittsfield. Resorts are great for families or couples, or even solo travelers looking for a piece of paradise. Sure, you can leave your hotel and explore Pittsfield at your leisure…but with everything these sorts of hotels offer, you may never want to. From food and shopping to entertainment and organized tours, a resort hotel in Pittsfield is a great way to score an amazing vacation—and Orbitz can help you get there.

Resort hotels for everyone in Pittsfield
If you’re traveling with the kids, you know how hard it is to keep them entertained. Let them have some fun on their own: some resorts have clubs for the kiddos, including kid-friendly pools and adventure camps where they can explore, do some crafts and even take part in learning activities. (Don’t worry, no one will tell them this vacation is actually educational.) Of course, there’s plenty for adults to do at Pittsfield resorts as well. Take a yoga class, book a few treatments at the spa, or do a little shopping. Go ahead, charge it to the room. You’re on vacation!

Ready to wow your special someone? Plan a romantic getaway complete with luxury accommodations. Surprise your partner with a couples massage, followed by a candlelit dinner at the 5-star on-site hotel. Some of these luxury hotels even have adults-only pools with swim-up bars so you can float about with a couple of cocktails, watching the sunset and enjoying your time together.

Hotel Options in Pittsfield

    Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

    Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

    One West Street, Pittsfield, MA
    The price is $98 per night from Apr 21 to Apr 22
    4/5Very Good! (10 reviews)
    Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
    Hotel On North

    Hotel On North

    297 North Street, Pittsfield, MA
    The price is $130 per night from Apr 25 to Apr 26
    4.6/5Wonderful! (7 reviews)
    Hotel On North
    Best Western Plus Berkshire Hills Inn & Suites

    Best Western Plus Berkshire Hills Inn & Suites

    1350 W Housatonic St, Pittsfield, MA
    The price is $96 per night from Apr 23 to Apr 24
    4.1/5Very Good! (49 reviews)
    Best Western Plus Berkshire Hills Inn & Suites