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Chesterland Vacations

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

Hotwire can help you find your travel bliss with Chesterland 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 Chesterland

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 Chesterland 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 Chesterland well.

Top Hotel Deals

See all 148 Hotels in Chesterland
Radisson Hotel Cleveland Gateway

Radisson Hotel Cleveland Gateway

651 Huron Rd E, Cleveland
    3.0 out of 5.0
     
     

    This Cleveland hotel is across the street from Quicken Loans Arena, one block from Progressive Field, four blocks from Tower City Center, and a half-mile from ...

    Radisson Hotel Cleveland Gateway$67

    Radisson Hotel Cleveland Gateway$67
    Hyatt Regency Cleveland At The Arcade

    Hyatt Regency Cleveland At The Arcade

    420 Superior Ave E, Cleveland
      4.0 out of 5.0
       
       

      Located in Cleveland's Entertainment District, adjacent to East 4th Street and within walking distance of the Horseshoe Casino, the Theater District, the Rock ...

      The Westin Cleveland Downtown

      The Westin Cleveland Downtown

      777 Saint Clair Ave Ne, Cleveland
        4.0 out of 5.0
         
         

        Located in Downtown Cleveland, this hotel is within a 10-minute walk of Cleveland Convention Center and Rock and Roll Hall of Fame. Great Lakes Science Center ...

        The Westin Cleveland Downtown$129

        The Westin Cleveland Downtown$129
        Hilton Garden Inn Cleveland Downtown

        Hilton Garden Inn Cleveland Downtown

        1100 Carnegie Ave, Cleveland
          3.0 out of 5.0
           
           

          This downtown Cleveland hotel is adjacent to Progressive Field and within 3 blocks of CSU Wolstein Center and Quicken Loans Arena. PlayhouseSquare Centre and ...

          Hilton Garden Inn Cleveland Downtown$110

          Hilton Garden Inn Cleveland Downtown$110
          Red Roof Inn Cleveland - Independence

          Red Roof Inn Cleveland - Independence

          6020 Quarry Ln, Independence
            2.0 out of 5.0
             
             

            Situated in Independence, this hotel is within 9 mi (15 km) of Christmas Story House, Cleveland Metroparks Zoo, and Progressive Field. Quicken Loans Arena and ...

            Red Roof Inn Cleveland - Independence$63

            Red Roof Inn Cleveland - Independence$63
            Hampton Inn Cleveland Downtown

            Hampton Inn Cleveland Downtown

            1460 E 9th St, Cleveland
              3.0 out of 5.0
               
               

              Hampton Inn Cleveland Downtown is a 10-minute walk from the Rock and Roll Hall of Fame and the streets of the Playhouse Square Theater District. The hip Historic ...

              Hampton Inn Cleveland Downtown$115

              Hampton Inn Cleveland Downtown$115
              The Tudor Arms Cleveland - a DoubleTree by Hilton

              The Tudor Arms Cleveland - a DoubleTree by Hilton

              10660 Carnegie Ave, Cleveland
                3.5 out of 5.0
                 
                 

                Located in University Circle, this historic hotel is within a 15-minute walk of Children's Museum of Cleveland and Cleveland Museum of Art. Severance Hall and ...

                The Tudor Arms Cleveland - a DoubleTree by Hilton$108

                The Tudor Arms Cleveland - a DoubleTree by Hilton$108
                The Glidden House

                The Glidden House

                1901 Ford Dr, Cleveland
                  3.5 out of 5.0
                   
                   

                  The historic Glidden House is located in the center of Cleveland's cultural district and adjacent to the Cleveland Botanical Garden. Case Western Reserve University ...

                  The Glidden House$149

                  The Glidden House$149
                  Kimpton Schofield Hotel

                  Kimpton Schofield Hotel

                  2000 East Ninth Street, Cleveland
                    4.5 out of 5.0
                     
                     

                    Located in Downtown Cleveland, this luxury hotel is within a 10-minute walk of Cleveland Arcade, Cathedral of St. John the Evangelist, and Allen Theatre. PlayhouseSquare ...

                    Kimpton Schofield Hotel$104

                    Kimpton Schofield Hotel$104
                    SkyLight Inn Cleveland - Willoughby

                    SkyLight Inn Cleveland - Willoughby

                    34600 Maplegrove Rd, Willoughby
                      2.5 out of 5.0
                       
                       

                      Situated in Willoughby, this motel is within 16 mi (25 km) of Alpine Valley, Cleveland Museum of Natural History, and Cleveland Institute of Art. Cleveland Museum ...

                      SkyLight Inn Cleveland - Willoughby$46

                      SkyLight Inn Cleveland - Willoughby$46

                      Top Flight Deals

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