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Chestertown Vacations

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

Hotwire can help you find your travel bliss with Chestertown 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 Chestertown

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 Chestertown 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 Chestertown well.

Top Hotel Deals

See all 177 Hotels in Chestertown
Friends Lake Inn

Friends Lake Inn

963 Friends Lake Rd, Chestertown
    4.0 out of 5.0
     
     

    Offering ski-in/ski-out access, this hotel in Chestertown is in the mountains, 2.5 mi (4.1 km) from Loon Lake Beach, and close to winter activities such as snow ...

    Pine Tree Motel & Cabins

    Pine Tree Motel & Cabins

    5537 State Route 8, Chestertown
      2.0 out of 5.0
       
       

      Situated near the beach, this motel is 0.6 mi (1 km) from Loon Lake Beach and within 12 mi (20 km) of Pack Demonstration Forest and Natural Stone Bridge and ...

      The Fern Lodge

      The Fern Lodge

      46 Fiddlehead Bay Rd, Chestertown
        3.5 out of 5.0
         
         

        Situated on a lake, this bed & breakfast is 4 mi (6.4 km) from Loon Lake Beach and 8.1 mi (13 km) from Pack Demonstration Forest. Natural Stone Bridge and Caves ...

        The Loft at The Remington

        The Loft at The Remington

        6369 Main Street, Chestertown
           
           
          Wingate by Wyndham Lake George

          Wingate by Wyndham Lake George

          4054 State Route 9L, Lake George
            2.5 out of 5.0
             
             

            Situated in Lake George, this hotel is within a 15-minute walk of Water Slide World and Fort William Henry. Lake George Dog Beach is 0.9 mi (1.4 km) away.

            Wingate by Wyndham Lake George$84

            Wingate by Wyndham Lake George$84
            Six Flags Great Escape Lodge & Indoor Waterpark

            Six Flags Great Escape Lodge & Indoor Waterpark

            89 Six Flags Dr, Queensbury
              3.5 out of 5.0
               
               

              Tucked into the foothills of the Adirondack Mountains, Six Flags Great Escape Lodge & Indoor Water Park is only 7 miles (11.2 km) from Lake George’s picturesque ...

              Six Flags Great Escape Lodge & Indoor Waterpark$190

              Six Flags Great Escape Lodge & Indoor Waterpark$190
              Baymont Inn & Suites Queensbury/Lake George

              Baymont Inn & Suites Queensbury/Lake George

              1 Abbey Ln, Queensbury
                2.0 out of 5.0
                 
                 

                Situated near the beach, this hotel is 0.8 mi (1.2 km) from Aviation Mall and 3.1 mi (4.9 km) from Charles R. Wood Theater. Fun Spot and Adventure Racing Family ...

                Baymont Inn & Suites Queensbury/Lake George$55

                Baymont Inn & Suites Queensbury/Lake George$55
                Country Inn & Suites by Radisson, Lake George (Queensbury), NY

                Country Inn & Suites by Radisson, Lake George (Queensbury), NY

                1130 Route 9, Queensbury
                  3.0 out of 5.0
                   
                   

                  This family-friendly Queensbury hotel is located in the entertainment district, within a 10-minute walk of Pirates Cove Adventure Golf, Adventure Racing Family ...

                  Country Inn & Suites by Radisson, Lake George (Queensbury), NY$80

                  Country Inn & Suites by Radisson, Lake George (Queensbury), NY$80
                  The Queensbury Hotel

                  The Queensbury Hotel

                  88 Ridge St, Glens Falls
                    3.0 out of 5.0
                     
                     

                    Located in the heart of Glens Falls, this hotel is within 1 mi (2 km) of Glens Falls Civic Center and Charles R. Wood Theater. World Awareness Children's Museum ...

                    The Queensbury Hotel$99

                    The Queensbury Hotel$99
                    Courtyard by Marriott Lake George

                    Courtyard by Marriott Lake George

                    365 Canada Street, Lake George
                      3.0 out of 5.0
                       
                       

                      Situated in Lake George, this hotel is within a 10-minute walk of Adirondack Winery and Shepard's Beach Park. Lake George Dog Beach and Lake George Battlefield ...

                      Courtyard by Marriott Lake George$134

                      Courtyard by Marriott Lake George$134

                      Top Flight Deals

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