Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Pittsfield Vacations

Pack those stellar shades. We have Pittsfield vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Pittsfield – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Pittsfield vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Pittsfield

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Pittsfield vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Pittsfield well.

Top Hotel Deals

See all 435 Hotels in Pittsfield
Clear River Inn

Clear River Inn

2640 Route 100, Pittsfield
    3.0 out of 5.0
     
     

    Situated in Pittsfield, this inn is within 9 mi (15 km) of Green Mountain National Golf Course, Gifford Woods State Park, and Pico Mountain at Killington Ski ...

    Casa Bella Inn & Restaurant

    Casa Bella Inn & Restaurant

    3911 Route 100 North, Pittsfield
      3.0 out of 5.0
       
       

      Situated in the mountains, this inn is in the same area as White River Golf Club, Green Mountain National Golf Course, and Lefferts Pond. Regional attractions ...

      Hawk Landing by RedAwning

      Hawk Landing by RedAwning

      132 Hawk Ln, Pittsfield
        3.5 out of 5.0
         
         

        Situated in Pittsfield, this vacation home is in the same area as White River Golf Club, Green Mountain National Golf Course, and Lefferts Pond. Regional attractions ...

        Wintergreen

        Wintergreen

        2358 Route 100 North, Pittsfield
          3.0 out of 5.0
           
           

          Situated in Pittsfield, this condo building is within 9 mi (15 km) of Green Mountain National Golf Course, Gifford Woods State Park, and Pico Mountain at Killington ...

          Sweet Life

          Sweet Life

          64 Dove Drive, Pittsfield
            3.5 out of 5.0
             
             

            Situated in Pittsfield, this vacation home is within 9 mi (15 km) of Green Mountain National Golf Course, Gifford Woods State Park, and White River Golf Club. ...

            Lookout by RedAwning

            Lookout by RedAwning

            39 Lookout Rd, Pittsfield
              3.0 out of 5.0
               
               

              Situated in Pittsfield, this vacation home is 5.9 mi (9.5 km) from Green Mountain National Golf Course and within 12 mi (20 km) of Killington Resort and Gifford ...

              Blue Diamond by RedAwning

              Blue Diamond by RedAwning

              565 Tweed River Dr, Pittsfield
                3.5 out of 5.0
                 
                 

                Situated in Pittsfield, this vacation home is within 9 mi (15 km) of Green Mountain National Golf Course, Gifford Woods State Park, and White River Golf Club. ...

                Pittsfield Chalet

                Pittsfield Chalet

                241 Townsend Brook Road, Pittsfield
                  3.0 out of 5.0
                   
                   
                  Killington Mountain Lodge, BW Signature Collection

                  Killington Mountain Lodge, BW Signature Collection

                  2617 Killington Rd, Killington
                    3.5 out of 5.0
                     
                     

                    Conveniently near skiing facilities, this Killington hotel is located in the mountains, within 3 mi (5 km) of Killington Golf Course and Killington Resort, and ...

                    Killington Mountain Lodge, BW Signature Collection$89

                    Killington Mountain Lodge, BW Signature Collection$89
                    Hillside Inn at Killington

                    Hillside Inn at Killington

                    375 Killington Rd, Killington
                      2.0 out of 5.0
                       
                       

                      Conveniently near skiing facilities, this Killington motel is located in the mountains, within 3 mi (5 km) of Gifford Woods State Park and Pico Mountain at Killington ...

                      Hillside Inn at Killington$65

                      Hillside Inn at Killington$65

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.