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Lanesborough Vacations

Pack those stellar shades. We have Lanesborough 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 Lanesborough – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Lanesborough 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 Lanesborough

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 Lanesborough 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 Lanesborough well.

Top Hotel Deals

See all 133 Hotels in Lanesborough
The Weathervane Motel

The Weathervane Motel

475 South Main St. Route 7, Lanesborough
    2.0 out of 5.0
     
     

    Situated in Lanesborough, this motel is within 6 mi (10 km) of Berkshire Athenaeum, Mount Greylock State Reservation Visitor Center, and Berkshire Museum. Crane ...

    The Weathervane Motel$44

    The Weathervane Motel$44
    Vacation Village in the Berkshires

    Vacation Village in the Berkshires

    276 Brodie Mountain Rd, Hancock
      3.0 out of 5.0
       
       

      Situated in Hancock, this condo building is 5.8 mi (9.3 km) from Mount Greylock State Reservation Visitor Center and within 12 mi (20 km) of Waubeeka Golf Links ...

      Vacation Village in the Berkshires$105

      Vacation Village in the Berkshires$105
      Jiminy Peak Mountain Resort

      Jiminy Peak Mountain Resort

      37 Corey Rd, Hancock
        3.0 out of 5.0
         
         

        Located in the mountains, this Hancock condo resort offering ski-in/ski-out access is 6.1 mi (9.8 km) from Mount Greylock State Reservation Visitor Center and ...

        Jiminy Peak Mountain Resort$115

        Jiminy Peak Mountain Resort$115
        Yankee Inn

        Yankee Inn

        461 Pittsfield Rd, Lenox
          2.5 out of 5.0
           
           

          Located in the heart of Lenox, this hotel is 0.5 mi (0.9 km) from Kennedy Park and within 3 mi (5 km) of Pleasant Valley Wilderness Sanctuary and Arrowhead Museum. ...

          Yankee Inn$72

          Yankee Inn$72
          Courtyard by Marriott Lenox Berkshires

          Courtyard by Marriott Lenox Berkshires

          70 Pittsfield Rd, Lenox
            3.0 out of 5.0
             
             

            Situated in Lenox, this hotel is within 2 mi (3 km) of Kennedy Park, Lenox Library, and Pleasant Valley Wilderness Sanctuary. Ventfort Hall Mansion and Gilded ...

            Courtyard by Marriott Lenox Berkshires$114

            Courtyard by Marriott Lenox Berkshires$114
            Hampton Inn & Suites Berkshires Lenox

            Hampton Inn & Suites Berkshires Lenox

            445 Pittsfield Rd, Lenox
              2.5 out of 5.0
               
               

              Situated in a rural location, this hotel is within 2 mi (3 km) of Arrowhead Museum, Kennedy Park, and Bousquet Ski Area. Pleasant Valley Wilderness Sanctuary ...

              Hampton Inn & Suites Berkshires Lenox$101

              Hampton Inn & Suites Berkshires Lenox$101
              Best Western Plus Berkshire Hills Inn & Suites

              Best Western Plus Berkshire Hills Inn & Suites

              1350 W Housatonic St, Pittsfield
                2.5 out of 5.0
                 
                 

                Located in the heart of Pittsfield, this hotel is 1.7 mi (2.8 km) from Hancock Shaker Village and 2.9 mi (4.7 km) from Bousquet Ski Area. Colonial Theater and ...

                Best Western Plus Berkshire Hills Inn & Suites$87

                Best Western Plus Berkshire Hills Inn & Suites$87
                The Red Lion Inn

                The Red Lion Inn

                30 Main Street, Stockbridge
                  3.5 out of 5.0
                   
                   

                  This family-friendly Stockbridge hotel is located in the historical district, within a 15-minute walk of Mission House, Berkshire Theatre Festival, and Naumkeag. ...

                  The Red Lion Inn$139

                  The Red Lion Inn$139
                  Crowne Plaza Pittsfield-Berkshires

                  Crowne Plaza Pittsfield-Berkshires

                  1 West St, Pittsfield
                    3.5 out of 5.0
                     
                     

                    Located in the heart of Pittsfield, this hotel is within a 5-minute walk of Berkshire Museum, Colonial Theater, and Berkshire Athenaeum. Canoe Meadows Wildlife ...

                    Crowne Plaza Pittsfield-Berkshires$85

                    Crowne Plaza Pittsfield-Berkshires$85
                    Holiday Inn Berkshires

                    Holiday Inn Berkshires

                    40 Main St, North Adams
                      3.0 out of 5.0
                       
                       

                      Located in the heart of North Adams, this hotel is within a 10-minute walk of Mass MoCA, North Adams Public Library, and Western Gateway Heritage State Park. ...

                      Holiday Inn Berkshires$111

                      Holiday Inn Berkshires$111

                      Top Flight Deals

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