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

Helmsley Vacations

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

Hotwire can help you find your travel bliss with Helmsley 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 Helmsley

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 Helmsley 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 Helmsley well.

Top Hotel Deals

See all 156 Hotels in Helmsley
The Black Swan Hotel

The Black Swan Hotel

Market Place, York
    4.0 out of 5.0
     
     

    Situated in a rural location, this hotel is within a 5-minute walk of Helmsley Arts Centre and Duncombe Park. Helmsley Castle and Hemsley Walled Garden are also ...

    Feversham Arms Hotel & Verbena Spa

    Feversham Arms Hotel & Verbena Spa

    High Street, York
      4.0 out of 5.0
       
       

      Situated in Helmsley, this spa hotel is within a 5-minute walk of Helmsley Castle, Duncombe Park, and Helmsley Arts Centre. Hemsley Walled Garden and Rievaulx ...

      The Royal Oak Hotel

      The Royal Oak Hotel

      15 Market Place, York
        3.0 out of 5.0
         
         

        Situated in Helmsley, this inn is steps from Helmsley Arts Centre and Duncombe Park. Helmsley Castle and Hemsley Walled Garden are also within 10 minutes.

        The Feathers Hotel

        The Feathers Hotel

        Market Place, York
          4.0 out of 5.0
           
           

          Situated in Helmsley, this inn is steps from Helmsley Arts Centre and Duncombe Park. Helmsley Castle and Hemsley Walled Garden are also within 10 minutes.

          The Carlton Lodge

          The Carlton Lodge

          Bondgate, York
             
             

            Situated in Helmsley, this guesthouse is within a 10-minute walk of Helmsley Arts Centre, Duncombe Park, and Helmsley Castle. Hemsley Walled Garden is 0.6 mi ...

            YHA Helmsley - Hostel

            YHA Helmsley - Hostel

            Carlton Lane, York
              4.0 out of 5.0
               
               

              Situated in Helmsley, this hostel is within a 10-minute walk of Helmsley Arts Centre, Helmsley Castle, and Duncombe Park. Hemsley Walled Garden is 0.6 mi (1 ...

              Mercure York Fairfield Manor Hotel

              Mercure York Fairfield Manor Hotel

              Shipton Road, York
                4.0 out of 5.0
                 
                 

                Situated on the riverwalk, this hotel is 2.4 mi (3.9 km) from Homestead Park and 3 mi (4.9 km) from York Minster. Bootham Bar and York Art Gallery are also within ...

                Mercure York Fairfield Manor Hotel$73

                Mercure York Fairfield Manor Hotel$73
                Holiday Inn Express York

                Holiday Inn Express York

                Malton Road, York
                  3.0 out of 5.0
                   
                   

                  Situated in York, this hotel is 0.5 mi (0.8 km) from York Waterworld and within 3 mi (5 km) of York Minster and Shambles. Merchant Adventurers' Hall and Jorvik ...

                  Holiday Inn Express York$56

                  Holiday Inn Express York$56
                  Aldwark Manor Golf & Spa Hotel

                  Aldwark Manor Golf & Spa Hotel

                  Aldwark, York
                    4.0 out of 5.0
                     
                     

                    Situated in the historical district, this spa hotel is within 12 mi (20 km) of Allerton Castle, Newby Hall and Gardens, and Homestead Park. York Minster and ...

                    Aldwark Manor Golf & Spa Hotel$179

                    Aldwark Manor Golf & Spa Hotel$179
                    Best Western Burn Hall Hotel

                    Best Western Burn Hall Hotel

                    Tollerton Road, York
                      3.0 out of 5.0
                       
                       

                      Situated in the historical district, this hotel is 0.8 mi (1.3 km) from Redwood Park Fishing Lakes and within 12 mi (20 km) of Beningbrough Hall and Garden and ...

                      Best Western Burn Hall Hotel$56

                      Best Western Burn Hall Hotel$56