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

Lenox Vacations

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

Hotwire can help you find your travel bliss with Lenox 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 Lenox

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 Lenox 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 Lenox well.

Top Hotel Deals

See all 147 Hotels in Lenox
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$92

    Yankee Inn$92
    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$134

      Courtyard by Marriott Lenox Berkshires$134
      Cranwell Spa and Golf Resort

      Cranwell Spa and Golf Resort

      55 Lee Road, Lenox
        3.5 out of 5.0
         
         

        Situated in Lenox, this spa resort is within 2 mi (3 km) of The Mount, Ventfort Hall Mansion and Gilded Age Museum, and Lenox Library. Shakespeare and Company ...

        Cranwell Spa and Golf Resort$149

        Cranwell Spa and Golf Resort$149
        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$118

          Hampton Inn & Suites Berkshires Lenox$118
          Howard Johnson by Wyndham Lenox

          Howard Johnson by Wyndham Lenox

          462 Pittsfield Rd, Lenox
            2.0 out of 5.0
             
             

            Situated in Lenox, this motel is within 2 mi (3 km) of Arrowhead Museum, Kennedy Park, and Bousquet Ski Area. Pleasant Valley Wilderness Sanctuary and Canoe ...

            Howard Johnson by Wyndham Lenox$51

            Howard Johnson by Wyndham Lenox$51
            Lenox Inn

            Lenox Inn

            525 Pittsfield Rd, Lenox
              2.0 out of 5.0
               
               

              Situated in Lenox, this hotel is within 3 mi (5 km) of Bousquet Ski Area, Arrowhead Museum, and Kennedy Park. Colonial Theater and Berkshire Museum are also ...

              Lenox Inn$43

              Lenox Inn$43
              Whistler's Inn Bed & Breakfast

              Whistler's Inn Bed & Breakfast

              5 Greenwood Street, Lenox
                3.5 out of 5.0
                 
                 

                Situated in the mountains, this bed & breakfast is within 1 mi (2 km) of Lenox Library, Ventfort Hall Mansion and Gilded Age Museum, and Shakespeare and Company. ...

                33 Main

                33 Main

                33 Main Street, Lenox
                  4.0 out of 5.0
                   
                   

                  Situated in the city center, this bed & breakfast is close to Lenox Library, Ventfort Hall Mansion and Gilded Age Museum, and Shakespeare and Company. Also nearby ...

                  Days Inn by Wyndham Lenox MA

                  Days Inn by Wyndham Lenox MA

                  194 Pittsfield Rd, Lenox
                    2.0 out of 5.0
                     
                     

                    Situated in Lenox, this motel is 0.4 mi (0.7 km) from Kennedy Park and within 3 mi (5 km) of Pleasant Valley Wilderness Sanctuary and Lenox Library. Arrowhead ...

                    Days Inn by Wyndham Lenox MA$59

                    Days Inn by Wyndham Lenox MA$59
                    The Ponds at Foxhollow

                    The Ponds at Foxhollow

                    3 Foxhollow Drive Route 7, Lenox
                      3.0 out of 5.0
                       
                       

                      Situated in Lenox, this condo building is within 3 mi (5 km) of The Mount, Shakespeare and Company, and Animagic Museum of Animation. Lee Library and Greenock ...

                      Top Flight Deals

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