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Chestnut Street Vacations

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

Hotwire can help you find your travel bliss with Chestnut Street 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 Chestnut Street

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 Chestnut Street 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 Chestnut Street well.

Chestnut Street Flight + Hotel packages

Top Hotel Deals

See all 665 Hotels in Chestnut Street
Hotel Zephyr

Hotel Zephyr

250 Beach Street, San Francisco
    3.5 out of 5.0
     
     

    This family-friendly San Francisco hotel is located on the waterfront, within a 5-minute walk of Wax Museum at Fisherman's Wharf, Pier 39, and Ripley's Believe ...

    Hotel Zephyr$186

    Hotel Zephyr$186
    Serrano Hotel

    Serrano Hotel

    405 Taylor St, San Francisco
      4.0 out of 5.0
       
       

      The Serrano Hotel is steps away from Union Square, perfectly positioned in the Theater District of San Francisco, 2 blocks from the Powell Street cable car.

      Serrano Hotel$119

      Serrano Hotel$119
      Hotel Focus SFO

      Hotel Focus SFO

      111 Mitchell Ave, South San Francisco
        3.0 out of 5.0
         
         

        Hotel Focus SFO is 3 miles (4.8 km) from San Francisco International Airport and a 15-minute walk from So. California Caltrain Station. It's a half-hour drive ...

        Hotel Focus SFO$107

        Hotel Focus SFO$107
        The Park Central San Francisco

        The Park Central San Francisco

        50 3rd St, San Francisco
          4.0 out of 5.0
           
           

          Located in the heart of the South of Market district (SoMa), The Park Central San Francisco is across from Yerba Buena Gardens and close to the San Francisco ...

          Hotel Union Square

          Hotel Union Square

          114 Powell St, San Francisco
            3.5 out of 5.0
             
             

            Situated on the cable car line in the downtown shopping district, the boutique hotel is 2 blocks from Union Square and 4 blocks from the Moscone Center and San ...

            Hotel Union Square$108

            Hotel Union Square$108
            Handlery Union Square Hotel

            Handlery Union Square Hotel

            351 Geary St, San Francisco
              3.5 out of 5.0
               
               

              A half-block from cable cars, this hotel is 2 blocks from Westfield San Francisco Shopping Centre; the Moscone Center and the San Francisco Museum of Modern ...

              Handlery Union Square Hotel$149

              Handlery Union Square Hotel$149
              Fairmont San Francisco

              Fairmont San Francisco

              950 Mason Street Atop Nob Hill, San Francisco
                5.0 out of 5.0
                 
                 

                Fairmont San Francisco is located atop swanky Nob Hill, the only spot in the city where every cable car line intersects. Guests can hop a ride past the Cable ...

                Fairmont San Francisco$199

                Fairmont San Francisco$199
                Hotel Whitcomb

                Hotel Whitcomb

                1231 Market St, San Francisco
                  3.5 out of 5.0
                   
                   

                  Located in the San Francisco theater district with a BART and MUNI station at its entrance, this downtown hotel is 6 blocks from Union Square and within a mile ...

                  Hotel Whitcomb$119

                  Hotel Whitcomb$119
                  Hyatt Regency San Francisco

                  Hyatt Regency San Francisco

                  5 Embarcadero Center, San Francisco
                    4.0 out of 5.0
                     
                     

                    The 17-story Hyatt Regency is located on the Embarcadero waterfront, across from the Ferry Building Marketplace, close to the Embarcadero Center, Union Square, ...

                    Hyatt Regency San Francisco$199

                    Hyatt Regency San Francisco$199
                    Hilton San Francisco Union Square

                    Hilton San Francisco Union Square

                    333 O'Farrell St., San Francisco
                      4.0 out of 5.0
                       
                       

                      Iconic, AAA 4-Diamond hotel a few steps from Union Square, Cable Car station, theatre district, BART, Chinatown, SFMOMA, and Moscone Center. Upgraded rooms offer ...

                      Hilton San Francisco Union Square$161

                      Hilton San Francisco Union Square$161

                      Top Flight Deals

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