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Jamaica Plain Vacations

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

Hotwire can help you find your travel bliss with Jamaica Plain 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 Jamaica Plain

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 Jamaica Plain 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 Jamaica Plain well.

Top Hotel Deals

See all 1,225 Hotels in Jamaica Plain
enVision Hotel Boston Longwood, an Ascend Collection Member

enVision Hotel Boston Longwood, an Ascend Collection Member

81 S Huntington Ave, Boston
    2.5 out of 5.0
     
     

    Located in Jamaica Plain, this hotel is within 1 mi (2 km) of Brigham and Women's Hospital, Boston Museum of Fine Arts, and Dana-Farber Cancer Institute. Fenway ...

    enVision Hotel Boston Longwood, an Ascend Collection Member$199

    enVision Hotel Boston Longwood, an Ascend Collection Member$199
    Global Luxury Suites at Longwood

    Global Luxury Suites at Longwood

    35 South Huntington Avenue, Boston
      4.0 out of 5.0
       
       

      This apartment building is located in Boston (Jamaica Plain), close to Brigham and Women's Hospital, Dana-Farber Cancer Institute, and Boston Museum of Fine ...

      Beautiful bedroom in Boston

      Beautiful bedroom in Boston

      21 Wyman Street, Boston
        2.0 out of 5.0
         
         

        This residence is located in Boston (Jamaica Plain), close to Samuel Adams Brewery, Boston Museum of Fine Arts, and Fenway Park. Also nearby are Dana-Farber ...

        Global Luxury Suites at Longwood Medical Area

        Global Luxury Suites at Longwood Medical Area

        101 S. Huntington Ave, Boston
          4.0 out of 5.0
           
           

          This apartment building is located in Boston (Jamaica Plain), close to Brigham and Women's Hospital, Dana-Farber Cancer Institute, and Boston Museum of Fine ...

          206 on Washington

          206 on Washington

          3389 Washington St, Boston
            4.0 out of 5.0
             
             

            This apartment building is located in Boston (Jamaica Plain), close to Samuel Adams Brewery, Franklin Park Zoo, and Brigham and Women's Hospital. Local attractions ...

            304 on Washington

            304 on Washington

            3389 Washington St, Boston
              4.0 out of 5.0
               
               

              This apartment building is located in Boston (Jamaica Plain), close to Samuel Adams Brewery, Franklin Park Zoo, and Brigham and Women's Hospital. Local attractions ...

              201 on Washington

              201 on Washington

              3389 Washington St, Boston
                3.5 out of 5.0
                 
                 

                This apartment building is located in Boston (Jamaica Plain), close to Samuel Adams Brewery, Franklin Park Zoo, and Brigham and Women's Hospital. Local attractions ...

                Room Tank Olmsted Place

                Room Tank Olmsted Place

                161 S. Huntington Ave, Boston
                  3.5 out of 5.0
                   
                   

                  Located in Jamaica Plain, this apartment building is within 1 mi (2 km) of Brigham and Women's Hospital, Dana-Farber Cancer Institute, and Beth Israel Deaconess ...

                  306 on Washington

                  306 on Washington

                  3389 Washington St, Boston
                    3.0 out of 5.0
                     
                     

                    This apartment building is located in Boston (Jamaica Plain), close to Samuel Adams Brewery, Franklin Park Zoo, and Brigham and Women's Hospital. Local attractions ...

                    301 on Washington

                    301 on Washington

                    3389 Washington St, Boston
                      3.5 out of 5.0
                       
                       

                      This apartment building is located in Boston (Jamaica Plain), close to Samuel Adams Brewery, Franklin Park Zoo, and Brigham and Women's Hospital. Local attractions ...

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