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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.

Chester Flight + Hotel packages

Top Hotel Deals

See all 155 Hotels in Chester
Clarion Hotel & Aqua Lagoon Waterpark

Clarion Hotel & Aqua Lagoon Waterpark

1080 Riverdale St, West Springfield
    2.5 out of 5.0
     
     

    This family-friendly hotel is located in the city center, within 3 mi (5 km) of Josiah Day House and Holyoke Mall. Springfield Armory and Naismith Memorial Basketball ...

    Clarion Hotel & Aqua Lagoon Waterpark$99

    Clarion Hotel & Aqua Lagoon Waterpark$99
    La Quinta Inn & Suites Springfield

    La Quinta Inn & Suites Springfield

    100 Congress Street, Springfield
      3.0 out of 5.0
       
       

      Located in the heart of Springfield, this hotel is within 1 mi (2 km) of Quadrangle and Springfield Armory. Naismith Memorial Basketball Hall of Fame is 1.4 ...

      La Quinta Inn & Suites Springfield$98

      La Quinta Inn & Suites Springfield$98
      Hilton Garden Inn Lenox Pittsfield

      Hilton Garden Inn Lenox Pittsfield

      1032 South Street, Pittsfield
        3.0 out of 5.0
         
         

        Situated in Pittsfield, this hotel is 1.2 mi (1.9 km) from Bousquet Ski Area and within 3 mi (5 km) of Arrowhead Museum and Kennedy Park. Colonial Theater and ...

        Hilton Garden Inn Lenox Pittsfield$110

        Hilton Garden Inn Lenox Pittsfield$110
        The Red Lion Inn

        The Red Lion Inn

        30 Main Street, Stockbridge
          3.5 out of 5.0
           
           

          This family-friendly Stockbridge hotel is located in the historical district, within a 15-minute walk of Mission House, Berkshire Theatre Festival, and Naumkeag. ...

          The Red Lion Inn$140

          The Red Lion Inn$140
          Econo Lodge

          Econo Lodge

          329 Russell St, Hadley
            2.0 out of 5.0
             
             

            Situated in the business district, this hotel is within 3 mi (5 km) of Hadley Farm Museum, University of Massachusetts-Amherst, and Amherst College. Emily Dickinson ...

            Econo Lodge$84

            Econo Lodge$84
            D. Hotel & Suites

            D. Hotel & Suites

            1 Country Club Rd, Holyoke
              3.0 out of 5.0
               
               

              Located in the suburbs, this family-friendly hotel is 4.3 mi (7 km) from Smith College and 11.8 mi (19.1 km) from University of Massachusetts-Amherst. MassMutual ...

              D. Hotel & Suites$116

              D. Hotel & Suites$116
              Quality Inn West Springfield

              Quality Inn West Springfield

              1150 Riverdale St, West Springfield
                2.5 out of 5.0
                 
                 

                Located in the heart of West Springfield, this hotel is 2.4 mi (3.9 km) from Holyoke Mall and 2.5 mi (3.9 km) from Josiah Day House. Springfield Armory and Naismith ...

                Quality Inn West Springfield$104

                Quality Inn West Springfield$104
                Crowne Plaza Pittsfield-Berkshires

                Crowne Plaza Pittsfield-Berkshires

                1 West St, Pittsfield
                  3.5 out of 5.0
                   
                   

                  Located in the heart of Pittsfield, this hotel is within a 5-minute walk of Berkshire Museum, Colonial Theater, and Berkshire Athenaeum. Canoe Meadows Wildlife ...

                  Crowne Plaza Pittsfield-Berkshires$96

                  Crowne Plaza Pittsfield-Berkshires$96
                  Yankee Inn

                  Yankee Inn

                  461 Pittsfield Rd, Lenox
                    2.5 out of 5.0
                     
                     

                    Located in the heart of Lenox, this hotel is 0.5 mi (0.9 km) from Kennedy Park and within 3 mi (5 km) of Pleasant Valley Wilderness Sanctuary and Arrowhead Museum. ...

                    Yankee Inn$92

                    Yankee Inn$92
                    Hampton Inn Hadley/Amherst area

                    Hampton Inn Hadley/Amherst area

                    24 Bay Rd, Hadley
                      2.5 out of 5.0
                       
                       

                      Situated near the airport, this hotel is 1.2 mi (1.9 km) from Hadley Farm Museum and within 3 mi (5 km) of Calvin Theater and Academy of Music Theater. Smith ...

                      Hampton Inn Hadley/Amherst area$114

                      Hampton Inn Hadley/Amherst area$114

                      Top Flight Deals

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