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Chester Vacations

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

Hotwire can help you find your travel bliss with Chester 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 Chester

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 Chester 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 Chester well.

Top Hotel Deals

See all 142 Hotels in Chester
Holiday Inn Express Hotel & Suites Chester

Holiday Inn Express Hotel & Suites Chester

2 Bryle Place, Chester
    2.5 out of 5.0
     
     

    Situated in the business district, this hotel is 0.4 mi (0.7 km) from Castle Fun Center and 1.4 mi (2.3 km) from The Rock Sports Complex. Woodbury Common Premium ...

    Holiday Inn Express Hotel & Suites Chester$114

    Holiday Inn Express Hotel & Suites Chester$114
    The Dominion House Bed & Breakfast

    The Dominion House Bed & Breakfast

    50 Old Dominion Road, Chester
      3.5 out of 5.0
       
       

      Situated in the mountains, this bed & breakfast is close to Brotherhood Winery. Area attractions also include Museum Village and Museum Village.

      The Dominion House Bed & Breakfast$150

      The Dominion House Bed & Breakfast$150
      Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport

      Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport

      915 Union Ave, New Windsor
        2.0 out of 5.0
         
         

        Situated in New Windsor, this hotel is within 3 mi (5 km) of Orange County Choppers, National Purple Heart Hall of Honor, and New Windsor Cantonment State Historic ...

        Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport$84

        Days Inn by Wyndham Newburgh WestPoint/Stewart Intl Airport$84
        Minerals Hotel

        Minerals Hotel

        1 Stonehill Dr, Vernon
          4.0 out of 5.0
           
           

          Conveniently located near the ski slopes, this Vernon resort is within 1 mi (2 km) of Granite Peak Quad, Mountain Creek Ski Resort, and Mountain Creek Waterpark. ...

          Minerals Hotel$110

          Minerals Hotel$110
          Ramada by Wyndham Fishkill

          Ramada by Wyndham Fishkill

          542 Route 9, Fishkill
            3.0 out of 5.0
             
             

            Situated in Fishkill, this hotel is within 1 mi (2 km) of Van Wyck Homestead Museum, Fishkill Golf Course, and Blodgett Memorial Library. SplashDown Beach is ...

            Ramada by Wyndham Fishkill$99

            Ramada by Wyndham Fishkill$99
            Overlook Lodge at Bear Mountain

            Overlook Lodge at Bear Mountain

            55 Hessian Drive, Bear Mountain
              2.5 out of 5.0
               
               

              Situated in a state park, this historic hotel is 1.7 mi (2.7 km) from Bear Mountain State Park and within 6 mi (10 km) of Manitoga The Russel Wright Design Center ...

              Overlook Lodge at Bear Mountain$149

              Overlook Lodge at Bear Mountain$149
              Microtel Inn & Suites by Wyndham Middletown

              Microtel Inn & Suites by Wyndham Middletown

              19 Crystal Run Crossing, Middletown
                2.0 out of 5.0
                 
                 

                Located in the heart of Middletown, this hotel is within 3 mi (5 km) of Galleria at Crystal Run, Orange County Fair Speedway, and Orange County Fairgrounds. ...

                Microtel Inn & Suites by Wyndham Middletown$84

                Microtel Inn & Suites by Wyndham Middletown$84
                Magnuson Hotel Fishkill

                Magnuson Hotel Fishkill

                20 Schuyler Blvd, Fishkill
                  2.5 out of 5.0
                   
                   

                  Situated in Fishkill, this hotel is within 1 mi (2 km) of Van Wyck Homestead Museum, Blodgett Memorial Library, and Fishkill Golf Course. SplashDown Beach is ...

                  Magnuson Hotel Fishkill$95

                  Magnuson Hotel Fishkill$95
                  Super 8 by Wyndham Middletown

                  Super 8 by Wyndham Middletown

                  563 Route 211 E, Middletown
                    2.0 out of 5.0
                     
                     

                    Situated in Middletown, this motel is within 3 mi (5 km) of Orange County Fairgrounds, Orange County Fair Speedway, and Paramount Theatre. Soons Orchards and ...

                    Super 8 by Wyndham Middletown$73

                    Super 8 by Wyndham Middletown$73
                    Americas Best Value Inn, Central Valley

                    Americas Best Value Inn, Central Valley

                    139 Route 32, Woodbury
                      2.0 out of 5.0
                       
                       

                      Situated in a state park, this motel is 0.3 mi (0.6 km) from Woodbury Common Premium Outlets and 1.4 mi (2.2 km) from Mary H Harriman Memorial Park. Palaia Vineyards ...

                      Americas Best Value Inn, Central Valley$89

                      Americas Best Value Inn, Central Valley$89

                      Top Flight Deals

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