Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Chepstow Vacations

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

Hotwire can help you find your travel bliss with Chepstow 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 Chepstow

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 Chepstow 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 Chepstow well.

Top Hotel Deals

See all 457 Hotels in Chepstow
St Pierre Marriott Hotel & Country Club

St Pierre Marriott Hotel & Country Club

St Pierre Park, Chepstow
    4.0 out of 5.0
     
     

    Situated in Chepstow, this spa hotel is 2.5 mi (4.1 km) from Chepstow Castle and 2.9 mi (4.6 km) from Chepstow Racecourse. Thornbury Castle and Tintern Abbey ...

    St Pierre Marriott Hotel & Country Club$125

    St Pierre Marriott Hotel & Country Club$125
    The Old Ferry Inn

    The Old Ferry Inn

    Beachley Road, Gloucestershire, Chepstow
      2.5 out of 5.0
       
       

      Situated in Beachley, this inn is close to Chepstow Castle. Area attractions also include Thornbury Castle and Chepstow Racecourse.

      Castle View

      Castle View

      16 Bridge Street, Chepstow
        3.0 out of 5.0
         
         

        Situated in Chepstow, this hotel is 0.1 mi (0.1 km) from Chepstow Castle and 1.3 mi (2.2 km) from Chepstow Racecourse. Thornbury Castle and Tintern Abbey are ...

        The First Hurdle Guest House

        The First Hurdle Guest House

        9-10 Upper Church Street, Chepstow
          3.5 out of 5.0
           
           

          Situated in Chepstow, this bed & breakfast is within 1 mi (2 km) of Chepstow Castle and Chepstow Racecourse. Tintern Abbey is 5.4 mi (8.7 km) away.

          Wye Valley Hotel

          Wye Valley Hotel

          Tintern, Monmouthshire, Chepstow
            3.0 out of 5.0
             
             

            Situated in Chepstow, this inn is close to Tintern Abbey. Area attractions also include Chepstow Racecourse and Chepstow Castle.

            The Beaufort Hotel

            The Beaufort Hotel

            Beaufort Square, Chepstow
              2.0 out of 5.0
               
               

              Located in the heart of Chepstow, this hotel is within 1 mi (2 km) of Chepstow Castle and Chepstow Racecourse. Thornbury Castle and Tintern Abbey are also within ...

              The George Hotel

              The George Hotel

              20 Moor Street, Chepstow
                3.0 out of 5.0
                 
                 

                Situated in the historical district, this inn is within 1 mi (2 km) of Chepstow Castle and Chepstow Racecourse. Thornbury Castle and Tintern Abbey are also within ...

                Mathern Palace

                Mathern Palace

                Mathern, Chepstow
                  3.0 out of 5.0
                   
                   

                  Situated in Chepstow, this guesthouse is 2.5 mi (4 km) from Chepstow Castle and 3 mi (4.8 km) from Chepstow Racecourse. Thornbury Castle and Tintern Abbey are ...

                  No. 8 Accommodation

                  No. 8 Accommodation

                  8 Lower Church Street, Chepstow
                    2.5 out of 5.0
                     
                     

                    Situated in Chepstow, this bed & breakfast is 0.2 mi (0.4 km) from Chepstow Castle and 1.4 mi (2.3 km) from Chepstow Racecourse. Thornbury Castle and Tintern ...

                    BroadRock

                    BroadRock

                    Rock Cottage, Chepstow
                      3.5 out of 5.0
                       
                       

                      Situated in Chepstow, this bed & breakfast is 1.5 mi (2.4 km) from Chepstow Castle and 2.8 mi (4.5 km) from Chepstow Racecourse. Thornbury Castle and Tintern ...

                      Top Flight Deals

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