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Chesterfield Vacations

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

Hotwire can help you find your travel bliss with Chesterfield 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 Chesterfield

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 Chesterfield 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 Chesterfield well.

Top Hotel Deals

See all 547 Hotels in Chesterfield
Casa Hotel

Casa Hotel

Lockoford Lane, Chesterfield
    4.0 out of 5.0
     
     

    Situated in Chesterfield, this hotel is 1.2 mi (2 km) from Chesterfield Market and within 9 mi (15 km) of Beauchief Abbey and Bolsover Castle. Renishaw Hall ...

    Casa Hotel$116

    Casa Hotel$116
    The Sandpiper Hotel

    The Sandpiper Hotel

    Sheffield Road, Chesterfield
      3.0 out of 5.0
       
       

      Situated in Chesterfield, this hotel is close to Chesterfield Market. Area attractions also include Beauchief Abbey and Dore and Totley Golf Club.

      ibis Chesterfield Centre – Market Town

      ibis Chesterfield Centre – Market Town

      Lordsmill Street, Chesterfield
        3.0 out of 5.0
         
         

        Situated in Chesterfield, this hotel is 0.4 mi (0.7 km) from Chesterfield Market and within 9 mi (15 km) of Bolsover Castle and Hardwick Hall. Renishaw Hall ...

        ibis Chesterfield Centre – Market Town$45

        ibis Chesterfield Centre – Market Town$45
        ibis Chesterfield North - Barlborough

        ibis Chesterfield North - Barlborough

        3 Tallys End, Chesterfield
          3.0 out of 5.0
           
           

          Situated in Barlborough, this hotel is 2.7 mi (4.3 km) from Renishaw Hall and within 6 mi (10 km) of Bolsover Castle and Rother Valley Country Park. Beauchief ...

          Ringwood Hall Hotel & Spa

          Ringwood Hall Hotel & Spa

          Chesterfield Road, Chesterfield
            4.0 out of 5.0
             
             

            Situated in the suburbs, this spa hotel is 2.9 mi (4.7 km) from Chesterfield Market and within 6 mi (10 km) of Bolsover Castle and Renishaw Hall. University ...

            Ringwood Hall Hotel & Spa$97

            Ringwood Hall Hotel & Spa$97
            Hotel Van Dyk

            Hotel Van Dyk

            Worksop Road, Chesterfield
              4.0 out of 5.0
               
               

              Situated in Chesterfield, this hotel is within 9 mi (15 km) of Renishaw Hall, Rother Valley Country Park, and Worksop Golf Club. Tropical Butterfly House, Wildlife ...

              Peak Edge Hotel

              Peak Edge Hotel

              Darley Road Stone Edge, Chesterfield
                4.0 out of 5.0
                 
                 

                Situated in Chesterfield, this hotel is within 9 mi (15 km) of Chesterfield Market, Heights of Abraham, and Chatsworth House. Birchall Golf and Leisure and Lea ...

                Twin Oaks Hotel

                Twin Oaks Hotel

                Church Lane, Chesterfield
                  3.0 out of 5.0
                   
                   

                  Situated in Chesterfield, this hotel is within 9 mi (15 km) of Bolsover Castle, Hardwick Hall, and Chesterfield Market. East Midlands Designer Outlet and Renishaw ...

                  The Old Poets Corner

                  The Old Poets Corner

                  1 Butts Road, Chesterfield
                    3.5 out of 5.0
                     
                     

                    Situated in the historical district, this inn is in the same area as Lea Gardens, Heights of Abraham, and Gulliver's Kingdom. Area attractions also include Wingfield ...

                    The Old Rectory Guest House

                    The Old Rectory Guest House

                    8 Church Street, Staveley, Chesterfield
                      2.5 out of 5.0
                       
                       

                      Situated in Chesterfield, this guesthouse is in the same region as Renishaw Hall, Bolsover Castle, and Hardwick Hall. Regional attractions also include Ponds ...

                      Top Flight Deals

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