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Brookline Vacations

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

Hotwire can help you find your travel bliss with Brookline 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 Brookline

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 Brookline 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 Brookline well.

Brookline Flight + Hotel packages

Top Hotel Deals

See all 1,230 Hotels in Brookline
Holiday Inn Boston-Brookline

Holiday Inn Boston-Brookline

1200 Beacon St, Brookline
    3.0 out of 5.0
     
     

    Situated in the suburbs, this historic hotel is within 1 mi (2 km) of Coolidge Corner Theatre, John Fitzgerald Kennedy National Historic Site, and Beth Israel ...

    Holiday Inn Boston-Brookline$93

    Holiday Inn Boston-Brookline$93
    Coolidge Corner Guest House

    Coolidge Corner Guest House

    17-19 Littell Road, Brookline
      2.5 out of 5.0
       
       

      Situated in the suburbs, this bed & breakfast is within 1 mi (2 km) of Coolidge Corner Theatre, Boston University, and Beth Israel Deaconess Medical Center. ...

      Coolidge Corner Guest House$119

      Coolidge Corner Guest House$119
      Courtyard by Marriott Boston Brookline

      Courtyard by Marriott Boston Brookline

      40 Webster St, Brookline
        3.0 out of 5.0
         
         

        Situated in Brookline, this hotel is within 1 mi (2 km) of Coolidge Corner Theatre, Boston University, and Beth Israel Deaconess Medical Center. Fenway Park ...

        Courtyard by Marriott Boston Brookline$185

        Courtyard by Marriott Boston Brookline$185
        Homewood Suites by Hilton Boston Brookline-Longwood Medical

        Homewood Suites by Hilton Boston Brookline-Longwood Medical

        111 Boylston Street, Brookline
          3.0 out of 5.0
           
           

          Situated in a shopping district, this hotel is within 1 mi (2 km) of Brigham and Women's Hospital, Dana-Farber Cancer Institute, and Beth Israel Deaconess Medical ...

          Homewood Suites by Hilton Boston Brookline-Longwood Medical$184

          Homewood Suites by Hilton Boston Brookline-Longwood Medical$184
          Beacon Inn 1087

          Beacon Inn 1087

          1087 Beacon St, Brookline
            2.5 out of 5.0
             
             

            Located in Longwood, this bed & breakfast is within a 15-minute walk of Boston University and Beth Israel Deaconess Medical Center. Fenway Park and Dana-Farber ...

            The Bertram Inn

            The Bertram Inn

            92 Sewall Ave, Brookline
              3.5 out of 5.0
               
               

              Situated in Brookline, this bed & breakfast is within a 15-minute walk of Coolidge Corner Theatre, Beth Israel Deaconess Medical Center, and Dana-Farber Cancer ...

              The Samuel Sewall Inn

              The Samuel Sewall Inn

              143 Saint Paul St, Brookline
                3.5 out of 5.0
                 
                 

                Situated in Brookline, this bed & breakfast is within a 15-minute walk of Coolidge Corner Theatre and Beth Israel Deaconess Medical Center. Boston University ...

                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. ...

                  One Bedroom Apartment Near Fenway Park by Namastay

                  One Bedroom Apartment Near Fenway Park by Namastay

                  1440 Beacon St #408, Brookline
                    3.5 out of 5.0
                     
                     

                    Situated in Brookline, this apartment building is close to Coolidge Corner Theatre, Boston University, and Fenway Park. Also nearby are Boston Museum of Fine ...

                    Beautiful 1BR in Brookline by Sonder

                    Beautiful 1BR in Brookline by Sonder

                    Beacon Street, Brookline
                      4.0 out of 5.0
                       
                       

                      Top Flight Deals

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