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Cleveland Circle Vacations

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

Hotwire can help you find your travel bliss with Cleveland Circle 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 Cleveland Circle

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 Cleveland Circle 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 Cleveland Circle well.

Cleveland Circle Flight + Hotel packages

Top Hotel Deals

See all 1,232 Properties in Cleveland Circle
Hotel Boston

Hotel Boston

40 Mt. Hood Rd , Boston
    3.0 out of 5.0
     
     

    Located in Cleveland Circle, this hotel is 1 mi (1.6 km) from Great Scott and within 3 mi (5 km) of Boston College and Boston University. Fenway Park and Harvard ...

    Hotel Boston$132

    Hotel Boston$132
    AC Hotel Boston Cleveland Circle

    AC Hotel Boston Cleveland Circle

    395 Chestnut Hill Ave, Boston
      3.5 out of 5.0
       
       

      Located in Cleveland Circle, this hotel is within 3 mi (5 km) of Boston College, Boston University, and Fenway Park. Beth Israel Deaconess Medical Center and ...

      AC Hotel Boston Cleveland Circle$149

      AC Hotel Boston Cleveland Circle$149
      Beacon Inn 1750

      Beacon Inn 1750

      1750 Beacon Street, Brookline
        3.0 out of 5.0
         
         

        Located in Cleveland Circle, this bed & breakfast is 1.1 mi (1.7 km) from Coolidge Corner Theatre and within 3 mi (5 km) of Boston College and Boston University. ...

        Beacon Inn 1750$99

        Beacon Inn 1750$99
        Artsy 3BR in Brighton by Sonder

        Artsy 3BR in Brighton by Sonder

        South Street, Boston
          3.5 out of 5.0
           
           

          Located in Cleveland Circle, this condo building is within 3 mi (5 km) of Boston College, Boston University, and Beth Israel Deaconess Medical Center. Dana-Farber ...

          Bright 1BR in Brighton by Sonder

          Bright 1BR in Brighton by Sonder

          , Boston
            4.0 out of 5.0
             
             

            Located in Cleveland Circle, this apartment building is within 3 mi (5 km) of Boston College, Boston University, and Fenway Park. Beth Israel Deaconess Medical ...

            Modern 2BR in Brighton by Sonder

            Modern 2BR in Brighton by Sonder

            Commonwealth Ave, Boston
              3.5 out of 5.0
               
               

              Located in Cleveland Circle, this condo building is within 3 mi (5 km) of Boston College, Boston University, and Fenway Park. Beth Israel Deaconess Medical Center ...

              Playful 3BR in Brighton by Sonder

              Playful 3BR in Brighton by Sonder

              South Street, Boston
                3.5 out of 5.0
                 
                 

                Located in Cleveland Circle, this apartment building is within 3 mi (5 km) of Boston College, Boston University, and Beth Israel Deaconess Medical Center. Dana-Farber ...

                Charming 2BR in Brighton by Sonder

                Charming 2BR in Brighton by Sonder

                , Boston
                  3.5 out of 5.0
                   
                   

                  Located in Cleveland Circle, this apartment building is within 3 mi (5 km) of Boston College, Boston University, and Fenway Park. Beth Israel Deaconess Medical ...

                  Chic 1BR in Brighton by Sonder

                  Chic 1BR in Brighton by Sonder

                  Chestnut Hill Avenue, Boston
                    3.5 out of 5.0
                     
                     

                    Located in Cleveland Circle, this apartment building is within 3 mi (5 km) of Boston College, Boston University, and Fenway Park. Dana-Farber Cancer Institute ...

                    Smart 2BR in Brighton by Sonder

                    Smart 2BR in Brighton by Sonder

                    Commonwealth Avenue and Chestnut Hill av, Boston
                      3.5 out of 5.0
                       
                       

                      Located in Cleveland Circle, this apartment building is within 3 mi (5 km) of Boston College, Boston University, and Fenway Park. Beth Israel Deaconess Medical ...

                      Top Flight Deals

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