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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 371 Hotels in Chester
Inn Victoria

Inn Victoria

321 Main St, Chester
    4.0 out of 5.0
     
     

    Situated in Chester, this bed & breakfast is 0.3 mi (0.5 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society ...

    Fullerton Inn

    Fullerton Inn

    40 The Common, Chester
      2.5 out of 5.0
       
       

      Situated in Chester, this inn is 0.3 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont ...

      Rose Arbour Bed & Breakfast

      Rose Arbour Bed & Breakfast

      55 School Street, Chester
        2.5 out of 5.0
         
         

        Situated in the historical district, this bed & breakfast is 0.2 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical ...

        The Karass Inn

        The Karass Inn

        225 Pleasant Street, Chester
          3.0 out of 5.0
           
           

          Situated in a state park, this bed & breakfast is 0.7 mi (1.1 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society ...

          Hugging Bear Inn and Shoppe

          Hugging Bear Inn and Shoppe

          244 Main Street, Chester
            2.5 out of 5.0
             
             

            Situated in Chester, this bed & breakfast is 0.3 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society ...

            Chester House Inn

            Chester House Inn

            266 Main St, Chester
              3.0 out of 5.0
               
               

              Situated in Chester, this bed & breakfast is 0.3 mi (0.4 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society ...

              Motel in the Meadow

              Motel in the Meadow

              936 VT Route 11 West, Chester
                2.5 out of 5.0
                 
                 

                Situated in Chester, this motel is 1.7 mi (2.7 km) from Vermont Institute of Contemporary Arts and within 9 mi (15 km) of Grafton Historical Society and Vermont ...

                Pointe at Castle Hill Resort

                Pointe at Castle Hill Resort

                2940 State Route 103, Proctorsville
                  3.5 out of 5.0
                   
                   

                  Situated in a rural location, this spa hotel is within 6 mi (10 km) of Dorsey Park, Okemo Mountain Resort, and Okemo Valley Golf Club. Buttermilk Falls and Camp ...

                  Pointe at Castle Hill Resort$169

                  Pointe at Castle Hill Resort$169
                  Jackson Gore Inn

                  Jackson Gore Inn

                  111 Jackson Gore Road, Ludlow
                    3.0 out of 5.0
                     
                     

                    This Ludlow condo building is in the mountains, offering ski-in/ski-out access within 3 mi (5 km) of Okemo Valley Golf Club and Okemo Mountain Resort and close ...

                    Jackson Gore Inn$148

                    Jackson Gore Inn$148
                    Holiday Inn Express Springfield

                    Holiday Inn Express Springfield

                    818 Charlestown Rd, Springfield
                      2.5 out of 5.0
                       
                       

                      Situated in a rural location, this hotel is within a 15-minute walk of Baltimore Covered Bridge and Eureka Schoolhouse. The Fort at No.4 Open Air Museum is 1.3 ...

                      Holiday Inn Express Springfield$102

                      Holiday Inn Express Springfield$102

                      Top Flight Deals

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