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Charlestown Vacations

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

Hotwire can help you find your travel bliss with Charlestown 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 Charlestown

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 Charlestown 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 Charlestown well.

Top Hotel Deals

See all 20 Properties in Charlestown
Tamarind Beach Hotel & Yacht Club

Tamarind Beach Hotel & Yacht Club

Grand Bay 1, Canouan Island
    4.0 out of 5.0
     
     

    Overlooking the Caribbean Sea, this Canouan Island hotel is situated directly on a white sand beach, less than a mile from Trump International Golf Club.

    Tamarind Beach Hotel & Yacht Club$280

    Tamarind Beach Hotel & Yacht Club$280
    Pink Sands Club Canouan

    Pink Sands Club Canouan

    Carenage Bay, Canouan Island
      5.0 out of 5.0
       
       

      Nestled on the beach, this Canouan Island hotel is within 3 mi (5 km) of Canouan Golf Club, Mysore Bay Beach, and Mahault Beach. South Glossy Bay Beach and Mount ...

      Villa 17 - Four Bedroom Villa

      Villa 17 - Four Bedroom Villa

      Grand Bay Street, Canouan Island
        4.0 out of 5.0
         
         

        Situated by the ocean, this villa is 0.7 mi (1.2 km) from Canouan Golf Club and within 3 mi (5 km) of Mount Royal and Mysore Bay Beach. Mahault Beach and South ...

        Anchorage Yacht Club Hotel

        Anchorage Yacht Club Hotel

        Clifton, Union Island
          3.0 out of 5.0
           
           

          Located in Union Island, this beachfront hotel is next to a golf course and within a 15-minute walk of Captain Hugh Mulzac Square and Belmont Bay. Chatham Bay ...

          Anchorage Yacht Club Hotel$90

          Anchorage Yacht Club Hotel$90
          Palm Island Resort All Inclusive

          Palm Island Resort All Inclusive

          Palm Island, Palm Island
            4.0 out of 5.0
             
             

            By the ocean, nestled on a private white sand beach, this resort is in Palm Island, within easy reach of area attractions such as Captain Hugh Mulzac Square ...

            The Islander's Inn

            The Islander's Inn

            Zion, near Clifton, Union Island
              3.0 out of 5.0
               
               

              Nestled on the beach, this Union Island inn is within a 15-minute walk of Belmont Bay and Captain Hugh Mulzac Square. Chatham Bay Beach is 2.4 mi (3.9 km) ...

              The Clifton Hotel

              The Clifton Hotel

              Clifton, Union Island
                2.5 out of 5.0
                 
                 

                Located in the heart of Union Island, this hotel is within a 15-minute walk of Captain Hugh Mulzac Square and Belmont Bay. Chatham Bay Beach is 2.9 mi (4.7 km) ...

                Sunwings Union Island

                Sunwings Union Island

                Clifton, Union Island
                  3.0 out of 5.0
                   
                   

                  Located in the heart of Union Island, this apartment building is within 1 mi (2 km) of Captain Hugh Mulzac Square and Belmont Bay. Chatham Bay Beach is 2.6 mi ...

                  Sunwings Union Island$36

                  Sunwings Union Island$36
                  Kings Landing Hotel

                  Kings Landing Hotel

                  Clifton, Union Island
                    3.0 out of 5.0
                     
                     

                    Nestled on the beach, this Union Island hotel is within 1 mi (2 km) of Captain Hugh Mulzac Square and Belmont Bay. Chatham Bay Beach is 2.8 mi (4.6 km) ...

                    Kings Landing Hotel$95

                    Kings Landing Hotel$95
                    FireFly Hotel Mustique

                    FireFly Hotel Mustique

                    Firefly, Mustique Island
                      4.0 out of 5.0
                       
                       

                      Situated near the beach, this hotel is 1.3 mi (2 km) from Macaroni Beach.

                      Top Flight Deals

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