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Chesapeake Vacations

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

Hotwire can help you find your travel bliss with Chesapeake 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 Chesapeake

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 Chesapeake 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 Chesapeake well.

Top Hotel Deals

See all 31 Properties in Chesapeake
Travelers Motel

Travelers Motel

56 Township Rd 1039, Chesapeake
    2.5 out of 5.0
     
     

    Situated in Chesapeake, this motel is 1.7 mi (2.7 km) from Big Sandy Superstore Arena and 2 mi (3.2 km) from Keith Albee Theatre. Pullman Square and Marshall ...

    Travelers Motel$47

    Travelers Motel$47
    Red Roof Inn Huntington

    Red Roof Inn Huntington

    5190 Us Route 60 E, Huntington
      2.0 out of 5.0
       
       

      Situated in Huntington, this hotel is within 6 mi (10 km) of Village of Barboursville Park, Joan C Edwards Stadium, and Huntington Mall. Keith Albee Theatre ...

      Red Roof Inn Huntington$55

      Red Roof Inn Huntington$55
      BEST WESTERN Huntington Mall Inn

      BEST WESTERN Huntington Mall Inn

      3441 US Route 60 E, Barboursville
        2.5 out of 5.0
         
         

        This family-friendly Barboursville hotel is located in a shopping district, 0.8 mi (1.3 km) from Huntington Mall, and within 9 mi (15 km) of Village of Barboursville ...

        BEST WESTERN Huntington Mall Inn$65

        BEST WESTERN Huntington Mall Inn$65
        Days Inn by Wyndham Ashland

        Days Inn by Wyndham Ashland

        12700 Route 180, Ashland
          2.0 out of 5.0
           
           

          Situated in Ashland, this hotel is 1.4 mi (2.2 km) from KYOVA Tri-State Mall and within 6 mi (10 km) of Sandy Creek Golf Course and Armco Park. Diamond Links ...

          Days Inn by Wyndham Ashland$60

          Days Inn by Wyndham Ashland$60
          Knights Inn Ashland

          Knights Inn Ashland

          7216 Sr 60, Ashland
            1.5 out of 5.0
             
             

            Situated in Ashland, this motel is 1.1 mi (1.8 km) from Armco Park and 1.9 mi (3 km) from KYOVA Tri-State Mall. Sandy Creek Golf Course and Sundowner Golf Course ...

            Knights Inn Ashland$51

            Knights Inn Ashland$51
            Hampton Inn Huntington/Barboursville

            Hampton Inn Huntington/Barboursville

            1 Cracker Barrel Dr, Barboursville
              2.5 out of 5.0
               
               

              Situated in Barboursville, this hotel is 0.7 mi (1.2 km) from Huntington Mall and within 9 mi (15 km) of Village of Barboursville Park and Esquire Country Club. ...

              Hampton Inn Huntington/Barboursville$129

              Hampton Inn Huntington/Barboursville$129
              Super 8 by Wyndham Huntington WV

              Super 8 by Wyndham Huntington WV

              3090 16th Street Road, Huntington
                2.0 out of 5.0
                 
                 

                Situated in the mountains, this motel is 2.3 mi (3.6 km) from Ritter Park and 2.7 mi (4.4 km) from Marshall University. Keith Albee Theatre and Huntington Museum ...

                Super 8 by Wyndham Huntington WV$75

                Super 8 by Wyndham Huntington WV$75
                Ramada Limited Huntington

                Ramada Limited Huntington

                3094 16th Street Road, Huntington
                  2.0 out of 5.0
                   
                   

                  Situated in Huntington, this hotel is 2.2 mi (3.6 km) from Ritter Park and 2.7 mi (4.4 km) from Marshall University. Keith Albee Theatre and Huntington Museum ...

                  Ramada Limited Huntington$93

                  Ramada Limited Huntington$93
                  Days Inn by Wyndham Huntington

                  Days Inn by Wyndham Huntington

                  5196 Us Route 60 I 64 Exit 15, Huntington
                    2.0 out of 5.0
                     
                     

                    Situated in Huntington, this hotel is within 6 mi (10 km) of Village of Barboursville Park, Joan C Edwards Stadium, and Huntington Mall. Keith Albee Theatre ...

                    Days Inn by Wyndham Huntington$54

                    Days Inn by Wyndham Huntington$54
                    Holiday Inn & Suites Huntington - Barboursville

                    Holiday Inn & Suites Huntington - Barboursville

                    3551 Route 60 E, Barboursville
                      3.0 out of 5.0
                       
                       

                      Situated in Barboursville, this hotel is 0.5 mi (0.8 km) from Huntington Mall and within 9 mi (15 km) of Village of Barboursville Park and Esquire Country Club. ...

                      Holiday Inn & Suites Huntington - Barboursville$101

                      Holiday Inn & Suites Huntington - Barboursville$101

                      Top Flight Deals

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