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

Lexington Vacations

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

Hotwire can help you find your travel bliss with Lexington 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 Lexington

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 Lexington 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 Lexington well.

Top Hotel Deals

See all 148 Hotels in Lexington
Morning Glory B&B Woodstock NY

Morning Glory B&B Woodstock NY

141 Tinker Street, Woodstock
    3.0 out of 5.0
     
     

    Situated in a state park, this bed & breakfast is 0.3 mi (0.5 km) from Woodstock Public Library and 3.1 mi (5 km) from Overlook Mountain Trailhead. Karma Triyana ...

    Winwood Inn & Condominiums

    Winwood Inn & Condominiums

    5220 NY-23, Windham
      3.0 out of 5.0
       
       

      Conveniently located near the ski slopes, this Windham resort is in the mountains, within 2 mi (3 km) of Windham Country Club and Windham Mountain Resort, and ...

      Black Bear Lodge

      Black Bear Lodge

      11985 RT23A, Prattsville
        2.5 out of 5.0
         
         

        Situated in Prattsville, this motel is 10.9 mi (17.6 km) from Hunter Mountain and 11.8 mi (19 km) from Windham Mountain Resort. Windham Vineyards and Winery ...

        Bavarian Manor Country Inn

        Bavarian Manor Country Inn

        866 Mountain Avenue, Purling
          2.5 out of 5.0
           
           

          Situated on a lake, this bed & breakfast is within 12 mi (20 km) of Bailiwick Ranch and Discovery Zoo, Thunderhart Golf Course, and Thomas Cole National Historic ...

          The Queen of the Catskills B&B

          The Queen of the Catskills B&B

          157 W Main St, Stamford
            3.0 out of 5.0
             
             

            Situated in Stamford, this bed & breakfast is 1.6 mi (2.6 km) from Stamford Golf Club and within 25 mi (40 km) of Hanford Mills Museum and Windham Vineyards ...

            Meadowood Inn

            Meadowood Inn

            50 Hornbeck St , Margaretville
              3.0 out of 5.0
               
               

              Situated in Arkville, this bed & breakfast is close to Union Grove Distillery and Delaware & Ulster Railroad. Area attractions also include Canada Falls and ...

              The Wheelhouse Inn

              The Wheelhouse Inn

              282 Main st, Pine Hill
                 
                 

                Situated in a state park, this hotel is close to Belleayre Beach at Pine Hill Lake and Belleayre Mountain. Regional attractions also include Delaware & Ulster ...

                Margaretville Motel

                Margaretville Motel

                42480 State Highway Rte. 28, Margaretville
                  2.5 out of 5.0
                   
                   

                  Situated in Margaretville, this motel is 5.7 mi (9.2 km) from Canada Falls and 9.2 mi (14.9 km) from Belleayre Mountain. Plattekill Mountain and Giant Ledge ...

                  Catskill Seasons Inn

                  Catskill Seasons Inn

                  178 Route 42, Shandaken
                    2.5 out of 5.0
                     
                     

                    Situated in Shandaken, this hotel is in the same area as Belleayre Beach at Pine Hill Lake and Belleayre Mountain. Regional attractions also include Giant Ledge ...

                    Antique Rose Inn Windham

                    Antique Rose Inn Windham

                    326 State Route 296, Windham
                      3.0 out of 5.0
                       
                       

                      Situated in Windham, this bed & breakfast is 1.1 mi (1.8 km) from Windham Country Club and 2.4 mi (3.9 km) from Windham Mountain Resort. Mountain Top Arboretum ...

                      Top Flight Deals

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