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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 924 Hotels in Chesapeake
Red Roof Inn Chesapeake Conference Center

Red Roof Inn Chesapeake Conference Center

724 Woodlake Dr, Chesapeake
    2.0 out of 5.0
     
     

    Situated in Chesapeake, this hotel is 0.3 mi (0.5 km) from Chesapeake Conference Center and within 6 mi (10 km) of Greenbrier Mall and Chesapeake City Park. ...

    Red Roof Inn Chesapeake Conference Center$57

    Red Roof Inn Chesapeake Conference Center$57
    Studios and Suites 4 Less Western Branch

    Studios and Suites 4 Less Western Branch

    3235 Western Branch Boulevard, Chesapeake
      2.5 out of 5.0
       
       

      Situated in Chesapeake, this hotel is 2.9 mi (4.7 km) from Riverfront Golf Club and within 9 mi (15 km) of Chrysler Museum of Art and Chesapeake Square Mall. ...

      Studios and Suites 4 Less Western Branch$47

      Studios and Suites 4 Less Western Branch$47
      Extended Stay America Chesapeake - Greenbrier Circle

      Extended Stay America Chesapeake - Greenbrier Circle

      809 Greenbrier Cir, Chesapeake
        2.5 out of 5.0
         
         

        Situated in Chesapeake, this hotel is 0.2 mi (0.4 km) from Chesapeake Conference Center and within 6 mi (10 km) of Greenbrier Mall and Chesapeake City Park. ...

        Extended Stay America Chesapeake - Greenbrier Circle$81

        Extended Stay America Chesapeake - Greenbrier Circle$81
        Hyatt Place Chesapeake

        Hyatt Place Chesapeake

        709 Eden Way N, Chesapeake
          3.0 out of 5.0
           
           

          Located in the heart of Chesapeake, this hotel is within 3 mi (5 km) of Greenbrier Mall, Oak Grove Lake Park, and Chesapeake City Park. Chesapeake Arboretum ...

          Hyatt Place Chesapeake$118

          Hyatt Place Chesapeake$118
          Aloft Chesapeake

          Aloft Chesapeake

          1454 Crossways Boulevard, Chesapeake
            3.0 out of 5.0
             
             

            Situated in Chesapeake, this hotel is within 3 mi (5 km) of Greenbrier Mall, Oak Grove Lake Park, and Chesapeake City Park. Chesapeake Conference Center and ...

            Aloft Chesapeake$96

            Aloft Chesapeake$96
            Delta Hotels by Marriott Chesapeake

            Delta Hotels by Marriott Chesapeake

            725 Woodlake Dr, Chesapeake
              3.5 out of 5.0
               
               

              Situated in Chesapeake, this hotel is 0.4 mi (0.7 km) from Chesapeake Conference Center and within 6 mi (10 km) of Greenbrier Mall and Chesapeake City Park. ...

              Delta Hotels by Marriott Chesapeake$97

              Delta Hotels by Marriott Chesapeake$97
              Wingate by Wyndham Chesapeake

              Wingate by Wyndham Chesapeake

              817 Greenbrier Circle, Chesapeake
                2.5 out of 5.0
                 
                 

                Situated in the business district, this hotel is 0.3 mi (0.5 km) from Chesapeake Conference Center and within 6 mi (10 km) of Greenbrier Mall and Chesapeake ...

                Wingate by Wyndham Chesapeake$93

                Wingate by Wyndham Chesapeake$93
                WoodSpring Suites Chesapeake-Norfolk South

                WoodSpring Suites Chesapeake-Norfolk South

                137 Kempsville Rd, Chesapeake
                  2.5 out of 5.0
                   
                   

                  Situated in the business district, this hotel is within 2 mi (3 km) of Chesapeake Arboretum, Chesapeake City Park, and Chesapeake Central Library. Chesapeake ...

                  Hampton Inn & Suites-Chesapeake Square Mall

                  Hampton Inn & Suites-Chesapeake Square Mall

                  4449 Peek Trail, Chesapeake
                    2.5 out of 5.0
                     
                     

                    Situated in the business district, this hotel is 0.6 mi (1 km) from Chesapeake Square Mall and within 9 mi (15 km) of Riverfront Golf Club and Frank D Lawrence ...

                    Hampton Inn & Suites-Chesapeake Square Mall$84

                    Hampton Inn & Suites-Chesapeake Square Mall$84
                    Fairfield Inn and Suites By Marriott Chesapeake

                    Fairfield Inn and Suites By Marriott Chesapeake

                    1560 Crossways Blvd, Chesapeake
                      2.5 out of 5.0
                       
                       

                      Situated in Chesapeake, this hotel is 0.8 mi (1.4 km) from Greenbrier Mall and within 3 mi (5 km) of Oak Grove Lake Park and Chesapeake City Park. Chesapeake ...

                      Fairfield Inn and Suites By Marriott Chesapeake$79

                      Fairfield Inn and Suites By Marriott Chesapeake$79

                      Top Flight Deals

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