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Chatham Vacations

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

Hotwire can help you find your travel bliss with Chatham 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 Chatham

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 Chatham 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 Chatham well.

Chatham Flight + Hotel packages

Top Hotel Deals

See all 679 Hotels in Chatham
Chatham Bars Inn

Chatham Bars Inn

297 Shore Rd, Chatham
    4.0 out of 5.0
     
     

    This Chatham hotel is a short walk to the beach, within a mile of Veterans Field and the Chatham Lighthouse. Red River Beach is 6.6 miles from this luxurious ...

    Chatham Bars Inn$299

    Chatham Bars Inn$299
    Chatham Highlander Motel

    Chatham Highlander Motel

    946 Main Street (Rte 28), Chatham
      2.0 out of 5.0
       
       

      Situated in the historical district, this motel is within a 10-minute walk of Monomoy Theatre, Chatham Drama Guild, and Veterans Field. Chatham Railroad Museum ...

      The Chatham Motel

      The Chatham Motel

      1487 Main Street, Chatham
        2.0 out of 5.0
         
         

        Situated near the beach, this motel is within 2 mi (3 km) of Hardings Beach, Monomoy Theatre, and Chatham Drama Guild. Veterans Field and Chatham Railroad Museum ...

        Surfside Inn Chatham

        Surfside Inn Chatham

        25 Holway St, Chatham
          2.5 out of 5.0
           
           

          Situated near the beach, this bed & breakfast is within a 10-minute walk of Chatham Lighthouse Beach and Chatham Lighthouse. Chatham Seaside Links and Chatham ...

          Captain's House Inn

          Captain's House Inn

          369 Old Harbor Road, Chatham
            4.0 out of 5.0
             
             

            Situated near the beach, this bed & breakfast is within a 15-minute walk of Chatham Fish Pier, Chatham Railroad Museum, and Veterans Field. Chatham Drama Guild ...

            Pleasant Bay Village Resort

            Pleasant Bay Village Resort

            1191 Orleans Road, Chatham
              3.0 out of 5.0
               
               

              Situated in Chatham, this hotel is within a 15-minute walk of Caleb Nickerson House and Chatham Marconi Complex. Fox Hill and Chatham Drama Guild are also within ...

              Pleasant Bay Village Resort$167

              Pleasant Bay Village Resort$167
              Chatham Wayside Inn

              Chatham Wayside Inn

              512 Main St, Chatham
                3.5 out of 5.0
                 
                 

                Situated near the beach, this inn is within a 10-minute walk of Chatham Windmill and Monomoy Theatre. Chatham Seaside Links and Chatham Railroad Museum are also ...

                The Hawthorne

                The Hawthorne

                196 Shore Rd, Chatham
                  2.0 out of 5.0
                   
                   

                  Nestled on the beach, this Chatham hotel is within a 15-minute walk of Chatham Seaside Links, Chatham Fish Pier, and Chatham Windmill. Chatham Lighthouse Beach ...

                  Chatham Gables Inn

                  Chatham Gables Inn

                  364 Old Harbor Rd, Chatham
                    4.0 out of 5.0
                     
                     

                    Situated near the beach, this bed & breakfast is within a 15-minute walk of Chatham Fish Pier, Chatham Railroad Museum, and Veterans Field. Chatham Drama Guild ...

                    Carriage House Inn

                    Carriage House Inn

                    407 Old Harbor Rd, Chatham
                      4.0 out of 5.0
                       
                       

                      Situated near the beach, this bed & breakfast is within a 15-minute walk of Chatham Fish Pier, Chatham Railroad Museum, and Chatham Seaside Links. Veterans Field ...

                      Top Flight Deals

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