Cottages in Helmsley and Houses - Holiday Lettings - Holiday Rentals Helmsley

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780 Holiday homes

    14

    Holiday home in Helmsley

    North Yorkshire / Helmsley

    2 4 7 nights min

    • 2 bedrooms
    • sleeps 4
    • 7 nights min
    • Child friendly
    • Pet friendly

    from £44 / night

    £304 - £631 / week

    Enquire View

    from £44 / night

    (3) Excellent 

      10

      Holiday cottage in Helmsley

      North Yorkshire / Helmsley

      3 5 3 nights min

      • 3 bedrooms
      • sleeps 5
      • 3 nights min
      • Child friendly

      from £126 / night

      £882 / week

      Book View

      from £126 / night

      (16) Excellent 

      Certificate of Excellence

        16

        Caravan/mobile home rental in Helmsley

        North Yorkshire / Helmsley

        3 6 2 nights min

        • 3 bedrooms
        • sleeps 6
        • 2 nights min
        • Nearest beach 50 km
        • Child friendly
        • Private garden

        Certificate of Excellence

        from £73 / night

        £436 - £596 / week

        Book View

        Responds fast!
        avg. 37 minutes

        from £73 / night

        (6) Very Good 

          22

          Holiday barn in Helmsley

          North Yorkshire / Helmsley

          2 6 min stay varies

          • 2 bedrooms
          • sleeps 6
          • min stay varies
          • Child friendly
          • Pet friendly

          from £102 / night

          £436 - £916 / week

          Book View

          Responds fast!
          avg. 2 hours 35 minutes

          from £102 / night

          (2) Excellent 

            15

            Holiday yurt in Nawton

            Helmsley / Nawton

            2 4 3 nights min

            • 2 bedrooms
            • sleeps 4
            • 3 nights min
            • Child friendly
            • Pet friendly

            from £138 / night

            £642 / week

            Book View

            from £138 / night

            (6) Excellent 

              18

              Holiday cottage in Helmsley

              North Yorkshire / Helmsley

              1 2 3 nights min

              • 1 bedroom
              • sleeps 2
              • 3 nights min
              • Private garden

              from £136 / night

              £544 - £749 / week

              Book View

              from £136 / night

              (1) Excellent 

                16

                Holiday home rental

                North Yorkshire / Helmsley

                4 6 7 nights min

                • 4 bedrooms
                • sleeps 6
                • 7 nights min
                • Child friendly
                • Private garden

                from £114 / night

                £796 / week

                Book View

                from £114 / night

                  20

                  Helmsley holiday home rental

                  3 6 7 nights min

                  • 3 bedrooms
                  • sleeps 6
                  • 7 nights min
                  • Child friendly

                  from £133 / night

                  £928 - £1,465 / week

                  Book View

                  from £133 / night

                    11

                    Hawnby holiday home rental

                    Helmsley / Hawnby

                    2 4 3 nights min

                    • 2 bedrooms
                    • sleeps 4
                    • 3 nights min
                    • Child friendly
                    • Pet friendly
                    • Private garden

                    from £104 / night

                    £310 - £1,017 / week

                    Enquire View

                    from £104 / night

                      16

                      Hawnby holiday home rental

                      Helmsley / Hawnby

                      2 4 3 nights min

                      • 2 bedrooms
                      • sleeps 4
                      • 3 nights min
                      • Child friendly
                      • Pet friendly

                      from £104 / night

                      £348 - £991 / week

                      Enquire View

                      from £104 / night

                      (4) Excellent 

                        9

                        Holiday home rental

                        North Yorkshire / Helmsley

                        1 2 3 nights min

                        • 1 bedroom
                        • sleeps 2
                        • 3 nights min
                        • Child friendly

                        from £67 / night

                        £285 - £688 / week

                        Enquire View

                        from £67 / night

                        (26) Excellent 

                          22

                          Holiday home in Helmsley

                          North Yorkshire / Helmsley

                          4 10 3 nights min

                          • 4 bedrooms
                          • sleeps 10
                          • 3 nights min
                          • Child friendly

                          from £166 / night

                          £555 - £2,317 / week

                          Enquire View

                          from £166 / night

                            11

                            Home accommodation in Helmsley

                            North Yorkshire / Helmsley

                            2 4 3 nights min

                            • 2 bedrooms
                            • sleeps 4
                            • 3 nights min
                            • Child friendly

                            from £142 / night

                            £465 - £1,389 / week

                            Enquire View

                            from £142 / night

                            (3) Very Good 

                              11

                              Home rental in Nawton

                              Helmsley / Nawton

                              2 4 3 nights min

                              • 2 bedrooms
                              • sleeps 4
                              • 3 nights min
                              • Child friendly

                              from £97 / night

                              £291 - £842 / week

                              Enquire View

                              from £97 / night

                              (4) Very Good 

                                12

                                Holiday home in Helmsley

                                North Yorkshire / Helmsley

                                2 4 3 nights min

                                • 2 bedrooms
                                • sleeps 4
                                • 3 nights min
                                • Child friendly

                                from £72 / night

                                £267 - £878 / week

                                Enquire View

                                from £72 / night

                                (5) Very Good 

                                  8

                                  Holiday home in Nawton

                                  Helmsley / Nawton

                                  1 2 3 nights min

                                  • 1 bedroom
                                  • sleeps 2
                                  • 3 nights min
                                  • Child friendly

                                  from £66 / night

                                  £244 - £532 / week

                                  Enquire View

                                  from £66 / night

                                    11

                                    Holiday cottage in Hawnby

                                    Helmsley / Hawnby

                                    1 2 3 nights min

                                    • 1 bedroom
                                    • sleeps 2
                                    • 3 nights min
                                    • Pet friendly

                                    from £68 / night

                                    £225 - £597 / week

                                    Enquire View

                                    from £68 / night

                                    (1) Excellent 

                                      11

                                      Holiday home rental

                                      North Yorkshire / Helmsley

                                      2 3 3 nights min

                                      • 2 bedrooms
                                      • sleeps 3
                                      • 3 nights min
                                      • Child friendly

                                      from £92 / night

                                      £293 - £847 / week

                                      Enquire View

                                      from £92 / night

                                      (4) Excellent 

                                        11

                                        Holiday home in Helmsley

                                        North Yorkshire / Helmsley

                                        2 4 3 nights min

                                        • 2 bedrooms
                                        • sleeps 4
                                        • 3 nights min
                                        • Child friendly

                                        from £87 / night

                                        £300 - £939 / week

                                        Enquire View

                                        from £87 / night

                                          13

                                          Holiday home in Helmsley

                                          North Yorkshire / Helmsley

                                          4 8 3 nights min

                                          • 4 bedrooms
                                          • sleeps 8
                                          • 3 nights min
                                          • Child friendly
                                          • Private garden

                                          from £148 / night

                                          £467 - £1,712 / week

                                          Enquire View

                                          from £148 / night

                                          (1) Excellent 

                                            6

                                            Hawnby holiday home rental

                                            Helmsley / Hawnby

                                            1 2 3 nights min

                                            • 1 bedroom
                                            • sleeps 2
                                            • 3 nights min
                                            • Child friendly
                                            • Pet friendly
                                            • Private garden

                                            from £84 / night

                                            £251 - £715 / week

                                            Enquire View

                                            from £84 / night

                                              14

                                              Holiday cottage in Helmsley

                                              North Yorkshire / Helmsley

                                              2 4 3 nights min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 3 nights min
                                              • Child friendly
                                              • Pet friendly

                                              from £110 / night

                                              £328 - £1,088 / week

                                              Enquire View

                                              from £110 / night

                                                17

                                                Holiday home rental

                                                North Yorkshire / Helmsley

                                                4 8 3 nights min

                                                • 4 bedrooms
                                                • sleeps 8
                                                • 3 nights min
                                                • Child friendly

                                                from £153 / night

                                                £518 - £1,645 / week

                                                Enquire View

                                                from £153 / night

                                                (1) Very Good 

                                                  20

                                                  Holiday home in Helmsley

                                                  North Yorkshire / Helmsley

                                                  4 8 3 nights min

                                                  • 4 bedrooms
                                                  • sleeps 8
                                                  • 3 nights min
                                                  • Child friendly
                                                  • Pet friendly
                                                  • Private garden

                                                  from £136 / night

                                                  £487 - £1,477 / week

                                                  Enquire View

                                                  from £136 / night

                                                    14

                                                    Helmsley holiday home rental

                                                    North Yorkshire / Helmsley

                                                    3 5 3 nights min

                                                    • 3 bedrooms
                                                    • sleeps 5
                                                    • 3 nights min
                                                    • Child friendly

                                                    from £102 / night

                                                    £375 - £1,048 / week

                                                    Enquire View

                                                    from £102 / night

                                                    (4) Excellent 

                                                      13

                                                      Home rental in Nawton

                                                      Helmsley / Nawton

                                                      3 5 3 nights min

                                                      • 3 bedrooms
                                                      • sleeps 5
                                                      • 3 nights min
                                                      • Child friendly
                                                      • Private garden

                                                      from £110 / night

                                                      £328 - £944 / week

                                                      Enquire View

                                                      from £110 / night

                                                      Great rentals within 20 miles that match your search

                                                      Distance approx 3.99 miles from Helmsley Show on Map

                                                      (11) Very Good 

                                                        21

                                                        Holiday cottage with golf nearby in Ampleforth

                                                        North Yorkshire / Ampleforth

                                                        1 3 3 nights min

                                                        • 1 bedroom
                                                        • sleeps 3
                                                        • 3 nights min
                                                        • Nearest beach 50 km
                                                        • Suitable for children age 5+
                                                        • Private garden

                                                        from £86 / night

                                                        £413 / week

                                                        Book View

                                                        Responds fast!
                                                        avg. 1 hour 39 minutes

                                                        from £86 / night

                                                        Distance approx 9.17 miles from Helmsley Show on Map

                                                        (6) Very Good 

                                                          13

                                                          Bungalow rental in Crayke

                                                          Easingwold / Crayke

                                                          1 2 1 night min

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • 1 night min
                                                          • Child friendly
                                                          • Pet friendly

                                                          from £75 / night

                                                          £401 / week

                                                          Book View

                                                          Responds fast!
                                                          avg. 1 hour 58 minutes

                                                          from £75 / night

                                                          Distance approx 19.06 miles from Helmsley

                                                          (2) Very Good 

                                                            14

                                                            Holiday cottage in Hackness

                                                            Scarborough / Hackness

                                                            3 6 min stay varies

                                                            • 3 bedrooms
                                                            • sleeps 6
                                                            • min stay varies
                                                            • Child friendly
                                                            • Pet friendly
                                                            • Private garden

                                                            from £121 / night

                                                            £659 - £899 / week

                                                            Book View

                                                            from £121 / night

                                                            Distance approx 14.06 miles from Helmsley

                                                            (1) Excellent 

                                                              12

                                                              Holiday home in Topcliffe

                                                              North Yorkshire / Topcliffe

                                                              4 7 5 nights min

                                                              • 4 bedrooms
                                                              • sleeps 7
                                                              • 5 nights min
                                                              • Child friendly
                                                              • Private garden

                                                              from £109 / night

                                                              £576 / week

                                                              Book View

                                                              Responds fast!
                                                              avg. 1 hour 16 minutes

                                                              from £109 / night

                                                              Distance approx 15.72 miles from Helmsley

                                                              (11) Excellent 

                                                                18

                                                                Holiday barn in Great Ayton

                                                                North Yorkshire / Great Ayton

                                                                2 4 7 nights min

                                                                • 2 bedrooms
                                                                • sleeps 4
                                                                • 7 nights min
                                                                • Nearest beach 15 km
                                                                • Child friendly
                                                                • Private garden

                                                                from £54 / night

                                                                £376 - £687 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 1 hour 24 minutes

                                                                from £54 / night

                                                                Distance approx 19.84 miles from Helmsley

                                                                (1) Excellent 

                                                                  10

                                                                  York holiday apartment rental

                                                                  North Yorkshire / York

                                                                  1 3 3 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 3
                                                                  • 3 nights min
                                                                  • Child friendly
                                                                  • Car not necessary

                                                                  from £115 / night

                                                                  £498 - £682 / week

                                                                  Book View

                                                                  from £115 / night

                                                                  Distance approx 5.42 miles from Helmsley Show on Map

                                                                    26

                                                                    Holiday cottage rental

                                                                    North Yorkshire / Kirkbymoorside

                                                                    2 4 3 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 4
                                                                    • 3 nights min
                                                                    • Nearest beach 40 km
                                                                    • Child friendly
                                                                    • Pet friendly

                                                                    from £65 / night

                                                                    £453 - £567 / week

                                                                    Book View

                                                                    Responds fast!
                                                                    avg. 2 hours 55 minutes

                                                                    from £65 / night

                                                                    Distance approx 19.4 miles from Helmsley

                                                                    (19) Excellent 

                                                                      23

                                                                      Holiday apartment rental

                                                                      North Yorkshire / York

                                                                      2 5 2 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 5
                                                                      • 2 nights min
                                                                      • Nearest beach 60 km
                                                                      • Child friendly
                                                                      • Car not necessary

                                                                      from £138 / night

                                                                      £916 - £1,117 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 1 hour 2 minutes

                                                                      from £138 / night

                                                                      Distance approx 19.63 miles from Helmsley

                                                                      (44) Excellent 

                                                                      Certificate of Excellence

                                                                        20

                                                                        Holiday townhouse rental

                                                                        York / Central York

                                                                        3 6 min stay varies

                                                                        • 3 bedrooms
                                                                        • sleeps 6
                                                                        • min stay varies
                                                                        • Nearest beach 67 km
                                                                        • Child friendly
                                                                        • Car not necessary

                                                                        Certificate of Excellence

                                                                        from £298 / night

                                                                        £1,374 - £2,061 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 9 minutes

                                                                        from £298 / night

                                                                        Distance approx 19.6 miles from Helmsley

                                                                        (8) Very Good 

                                                                          17

                                                                          Holiday apartment in Central York

                                                                          York / Central York

                                                                          2 4 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • min stay varies
                                                                          • Nearest beach 65 km
                                                                          • Child friendly
                                                                          • Car not necessary

                                                                          from £109 / night

                                                                          £630 - £802 / week

                                                                          Book View

                                                                          from £109 / night

                                                                          Distance approx 19.63 miles from Helmsley

                                                                          (3) Very Good 

                                                                            9

                                                                            Scarborough holiday caravan/mobile home rental

                                                                            Scarborough District / Scarborough

                                                                            2 6 min stay varies

                                                                            • 2 bedrooms
                                                                            • sleeps 6
                                                                            • min stay varies
                                                                            • Nearest beach 16 km
                                                                            • Child friendly
                                                                            • Private garden

                                                                            from £108 / night

                                                                            £539 - £825 / week

                                                                            Book View

                                                                            from £108 / night

                                                                            Distance approx 13.2 miles from Helmsley

                                                                              5

                                                                              Cottage rental in Flaxton

                                                                              York / Flaxton

                                                                              1 2 1 night min

                                                                              • 1 bedroom
                                                                              • sleeps 2
                                                                              • 1 night min
                                                                              • Ask owner if suitable for children

                                                                              from £103 / night

                                                                              £561 / week

                                                                              Book View

                                                                              from £103 / night

                                                                              Distance approx 14.89 miles from Helmsley

                                                                                6

                                                                                Cottage rental in Danby

                                                                                North York Moors National Park / Danby

                                                                                1 2 min stay varies

                                                                                • 1 bedroom
                                                                                • sleeps 2
                                                                                • min stay varies

                                                                                from £97 / night

                                                                                £403 - £482 / week

                                                                                Book View

                                                                                from £97 / night

                                                                                Distance approx 16.72 miles from Helmsley

                                                                                (10) Excellent 

                                                                                  19

                                                                                  Holiday home in Glaisdale

                                                                                  North Yorkshire / Glaisdale

                                                                                  3 6 3 nights min

                                                                                  • 3 bedrooms
                                                                                  • sleeps 6
                                                                                  • 3 nights min
                                                                                  • Child friendly
                                                                                  • Private garden

                                                                                  from £115 / night

                                                                                  £384 - £1,183 / week

                                                                                  Enquire View

                                                                                  from £115 / night

                                                                                  Top Destination reviews

                                                                                  Self Catering 3 Bedroom
                                                                                  perfect place

                                                                                  The locations was very good just a short walk into the town. Parking on the street can be a bit hit and miss as a lot of people park during the day we had no problem in parking just be careful as the traffic warden are very keen. The house itself is very clean good size bedrooms and the bathroom very good lovely towels. The touch about the laundry bag in the room was good. Living area very nice. The dining room was big and lots of book and games and where to go leaflets in date. Kitchen and Utility room plenty of pots and pans, cup plates ect ect. Garden was a lovely surprise very nice . Two very good pubs serving good food with proper Chips. Price were good for the area. We went to Ampleforth for a meal at White Horse was very very nice. Plenty of place to see the castle well worth a visit. Would l stay again yes if in the area. Suits a family or couples we were sister and hubby and our dad who is in his 80s.see more
                                                                                  High Farm, Beadlam Rigg
                                                                                  Great stay

                                                                                  We had a great stay. Caravan is clean and spacious. Lovely being on a working farm with great views and peaceful location. The owners were very friendly and welcoming and showed our children the farm animals which they loved. We will definitely stay again. Thank you! … see more
                                                                                  CASTLE VIEW, pet friendly, character holiday cottage, with a garden in
                                                                                  Beautiful holiday home

                                                                                  A perfect holiday home, clean, spacious and in a quiet part of the lovely village of Helmsley, yet only a 2 minute walk to the main part of the village with all the amenities to hand, shops pubs cafes etc. a really beautiful area and with in easy reach of other attractions. … see more

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