Cottages in Healdsburg and Cabins - Holiday Lettings - Holiday Rentals Healdsburg

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242 Holiday homes

    52

    Healdsburg holiday home rental

    Sonoma County / Healdsburg

    3 8 min stay varies

    • 3 bedrooms
    • sleeps 8
    • min stay varies
    • Child friendly
    • Car not necessary
    • Air conditioning

    from £375 / night

    £2,625 / week

    Book View

    Responds fast!
    avg. 1 hour 20 minutes

    from £375 / night

    (5) Excellent 

      22

      Holiday home in Healdsburg

      Sonoma County / Healdsburg

      3 8 min stay varies

      • 3 bedrooms
      • sleeps 8
      • min stay varies
      • Child friendly
      • Air conditioning
      • Pet friendly

      from £395 / night

      £2,484 - £2,760 / week

      Book View

      from £395 / night

        10

        Healdsburg holiday home rental

        Sonoma County / Healdsburg

        1 2 2 nights min

        • 1 bedroom
        • sleeps 2
        • 2 nights min
        • Swimming pool
        • Pet friendly
        • Private garden

        from £373 / night

        £2,606 / week

        Book View

        from £373 / night

        (4) Very Good 

          29

          Holiday home in Healdsburg

          Sonoma County / Healdsburg

          5 12 min stay varies

          • 5 bedrooms
          • sleeps 12
          • min stay varies
          • Swimming pool
          • Child friendly
          • Pet friendly

          from £1,095 / night

          £6,898 - £7,665 / week

          Book View

          from £1,095 / night

          (14) Excellent 

            31

            Holiday home in Healdsburg

            Sonoma County / Healdsburg

            4 8 min stay varies

            • 4 bedrooms
            • sleeps 8
            • min stay varies
            • Child friendly
            • Air conditioning
            “Cecilia's Vineyard” This is a wonderful house in a great location. If you are looking for a place where you can cook, relax, and drink the wine from your daily tastings this is the place. It's conveniently located just outside of Healdsburg, but you would never know it. It's just a short drive to Big John's which has everything you might need for cooking in, rather than going out. The view is beautiful, the amenities great, and you can even watch planes take off from the local airport. We were so busy, we didn't even get to really take advantage of the great entertainment room.

            from £784 / night

            £4,939 / week

            Book View

            from £784 / night

              15

              Holiday home rental

              Sonoma County / Healdsburg

              3 6 4 nights min

              • 3 bedrooms
              • sleeps 6
              • 4 nights min
              • Nearest beach 40 km
              • Child friendly
              • Air conditioning

              from £608 / night

              £3,934 / week

              Book View

              from £608 / night

              (22) Excellent 

                24

                Holiday villa in Healdsburg

                Sonoma County / Healdsburg

                4 10 min stay varies

                • 4 bedrooms
                • sleeps 10
                • min stay varies
                • Swimming pool
                • Child friendly
                • Air conditioning
                “Perfect!” Perfect weather, great space, great location. Wish I could be back there now :(

                from £1,095 / night

                £6,209 - £6,898 / week

                Book View

                from £1,095 / night

                (5) Excellent 

                  25

                  Healdsburg holiday home rental

                  Sonoma County / Healdsburg

                  4 8 min stay varies

                  • 4 bedrooms
                  • sleeps 8
                  • min stay varies
                  • Child friendly
                  • Air conditioning

                  from £657 / night

                  £4,139 - £4,599 / week

                  Book View

                  from £657 / night

                    20

                    Holiday home in Healdsburg

                    Sonoma County / Healdsburg

                    10 3 nights min

                    • sleeps 10
                    • 3 nights min
                    • Nearest beach 10 km
                    • Child friendly
                    • Air conditioning

                    from £745 / night

                    £4,380 / week

                    Book View

                    from £745 / night

                      25

                      Holiday home in Healdsburg

                      Sonoma County / Healdsburg

                      3 8 min stay varies

                      • 3 bedrooms
                      • sleeps 8
                      • min stay varies
                      • Child friendly

                      from £254 / night

                      £1,779 / week

                      Book View

                      Responds fast!
                      avg. 37 minutes

                      from £254 / night

                        26

                        Holiday villa in Healdsburg

                        Sonoma County / Healdsburg

                        3 8 3 nights min

                        • 3 bedrooms
                        • sleeps 8
                        • 3 nights min
                        • Child friendly
                        • Air conditioning

                        from £697 / night

                        £4,875 / week

                        Book View

                        Responds fast!
                        avg. 37 minutes

                        from £697 / night

                        (1) Excellent 

                          26

                          Home rental in Healdsburg

                          Sonoma County / Healdsburg

                          3 6 2 nights min

                          • 3 bedrooms
                          • sleeps 6
                          • 2 nights min
                          • Beach / lakeside relaxation
                          • Child friendly

                          from £307 / night

                          £2,190 - £2,558 / week

                          Book View

                          from £307 / night

                            14

                            Holiday home accommodation

                            Sonoma County / Healdsburg

                            3 6 2 nights min

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

                            from £565 / night

                            £3,955 / week

                            Book View

                            from £565 / night

                              23

                              Healdsburg holiday home rental

                              Sonoma County / Healdsburg

                              4 8 3 nights min

                              • 4 bedrooms
                              • sleeps 8
                              • 3 nights min
                              • Swimming pool
                              • Child friendly
                              • Air conditioning

                              from £1,052 / night

                              £5,256 / week

                              Book View

                              from £1,052 / night

                              (3) Excellent 

                                25

                                Healdsburg holiday home rental

                                Sonoma County / Healdsburg

                                3 6 min stay varies

                                • 3 bedrooms
                                • sleeps 6
                                • min stay varies
                                • Swimming pool
                                • Child friendly

                                from £697 / night

                                £4,387 - £4,875 / week

                                Book View

                                from £697 / night

                                (4) Very Good 

                                  37

                                  Healdsburg holiday home rental

                                  Sonoma County / Healdsburg

                                  3 8 3 nights min

                                  • 3 bedrooms
                                  • sleeps 8
                                  • 3 nights min
                                  • Ask owner if suitable for children
                                  • Air conditioning
                                  • Ask about pets

                                  from £789 / night

                                  £4,730 / week

                                  Book View

                                  from £789 / night

                                    22

                                    Holiday home in Healdsburg

                                    Sonoma County / Healdsburg

                                    2 6 min stay varies

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

                                    from £197 / night

                                    £1,380 / week

                                    Book View

                                    Responds fast!
                                    avg. 37 minutes

                                    from £197 / night

                                      25

                                      Holiday home in Healdsburg

                                      Sonoma County / Healdsburg

                                      2 6 2 nights min

                                      • 2 bedrooms
                                      • sleeps 6
                                      • 2 nights min
                                      • Child friendly
                                      • Air conditioning

                                      from £346 / night

                                      £2,180 - £2,422 / week

                                      Book View

                                      from £346 / night

                                      (1)  

                                        78

                                        Holiday home in Healdsburg

                                        Sonoma County / Healdsburg

                                        2 6 min stay varies

                                        • 2 bedrooms
                                        • sleeps 6
                                        • min stay varies
                                        • Child friendly
                                        • Car not necessary
                                        • Air conditioning

                                        from £86 / night

                                        £601 / week

                                        Book View

                                        Responds fast!
                                        avg. 1 hour 20 minutes

                                        from £86 / night

                                          18

                                          Holiday home in Healdsburg

                                          Sonoma County / Healdsburg

                                          3 8 min stay varies

                                          • 3 bedrooms
                                          • sleeps 8
                                          • min stay varies
                                          • Air conditioning

                                          from £522 / night

                                          £3,366 - £3,368 / week

                                          Book View

                                          Responds fast!
                                          avg. 1 hour 34 minutes

                                          from £522 / night

                                          (5) Very Good 

                                            20

                                            Holiday home with swimming pool in Healdsburg

                                            Sonoma County / Healdsburg

                                            3 8 2 nights min

                                            • 3 bedrooms
                                            • sleeps 8
                                            • 2 nights min
                                            • Swimming pool
                                            • Child friendly
                                            • Pet friendly

                                            from £920 / night

                                            £4,691 / week

                                            Book View

                                            from £920 / night

                                            (4) Excellent 

                                              26

                                              Holiday home in Healdsburg

                                              Sonoma County / Healdsburg

                                              3 8 min stay varies

                                              • 3 bedrooms
                                              • sleeps 8
                                              • min stay varies
                                              • Child friendly
                                              • Air conditioning
                                              • Pet friendly

                                              from £395 / night

                                              £2,484 - £2,760 / week

                                              Book View

                                              from £395 / night

                                                10

                                                Healdsburg holiday home rental

                                                Sonoma County / Healdsburg

                                                4 8 min stay varies

                                                • 4 bedrooms
                                                • sleeps 8
                                                • min stay varies
                                                • Air conditioning
                                                • Private garden

                                                from £1,577 / night

                                                £9,198 / week

                                                Book View

                                                from £1,577 / night

                                                  0

                                                  Holiday home rental

                                                  Sonoma County / Healdsburg

                                                  3 6 min stay varies

                                                  • 3 bedrooms
                                                  • sleeps 6
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Child friendly
                                                  • Car not necessary

                                                  from £348 / night

                                                  £2,435 / week

                                                  Book View

                                                  Responds fast!
                                                  avg. 1 hour 20 minutes

                                                  from £348 / night

                                                    40

                                                    Holiday home in Healdsburg

                                                    Sonoma County / Healdsburg

                                                    4 10 3 nights min

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

                                                    from £701 / night

                                                    £3,504 / week

                                                    Book View

                                                    from £701 / night

                                                      11

                                                      Holiday home in Healdsburg

                                                      Sonoma County / Healdsburg

                                                      5 12 3 nights min

                                                      • 5 bedrooms
                                                      • sleeps 12
                                                      • 3 nights min
                                                      • Swimming pool
                                                      • Child friendly
                                                      • Air conditioning

                                                      from £2,015 / night

                                                      £11,563 / week

                                                      Book View

                                                      from £2,015 / night

                                                      (1) Excellent 

                                                        23

                                                        Holiday home in Healdsburg

                                                        Sonoma County / Healdsburg

                                                        3 8 2 nights min

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

                                                        from £833 / night

                                                        £4,875 / week

                                                        Book View

                                                        from £833 / night

                                                          21

                                                          Holiday home with swimming pool in Healdsburg

                                                          Sonoma County / Healdsburg

                                                          3 8 min stay varies

                                                          • 3 bedrooms
                                                          • sleeps 8
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child friendly

                                                          from £784 / night

                                                          £4,939 - £5,488 / week

                                                          Book View

                                                          from £784 / night

                                                          (7) Average 

                                                            14

                                                            Healdsburg holiday home rental

                                                            Sonoma County / Healdsburg

                                                            2 6 3 nights min

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • 3 nights min
                                                            • Ask owner if suitable for children
                                                            • Air conditioning
                                                            • Ask about pets

                                                            from £350 / night

                                                            £1,836 / week

                                                            Book View

                                                            from £350 / night

                                                              25

                                                              Holiday villa in Healdsburg

                                                              Sonoma County / Healdsburg

                                                              2 4 min stay varies

                                                              • 2 bedrooms
                                                              • sleeps 4
                                                              • min stay varies

                                                              from £395 / night

                                                              £2,484 / week

                                                              Book View

                                                              from £395 / night

                                                                15

                                                                Holiday villa with swimming pool in Healdsburg

                                                                Sonoma County / Healdsburg

                                                                4 10 3 nights min

                                                                • 4 bedrooms
                                                                • sleeps 10
                                                                • 3 nights min
                                                                • Swimming pool
                                                                • Child friendly
                                                                • Air conditioning

                                                                from £1,310 / night

                                                                £9,167 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 37 minutes

                                                                from £1,310 / night

                                                                  44

                                                                  Healdsburg holiday home accommodation

                                                                  Sonoma County / Healdsburg

                                                                  3 8 30 nights min

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

                                                                  from £161 / night

                                                                  £1,125 / week

                                                                  Book View

                                                                  from £161 / night

                                                                    15

                                                                    Home rental in Healdsburg with golf nearby

                                                                    Sonoma County / Healdsburg

                                                                    4 9 min stay varies

                                                                    • 4 bedrooms
                                                                    • sleeps 9
                                                                    • min stay varies
                                                                    • Child friendly
                                                                    • Pet friendly

                                                                    from £1,402 / night

                                                                    £9,811 / week

                                                                    Book View

                                                                    from £1,402 / night

                                                                      24

                                                                      Home rental in Healdsburg

                                                                      Sonoma County / Healdsburg

                                                                      2 4 3 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 4
                                                                      • 3 nights min
                                                                      • Child friendly
                                                                      • Car not necessary
                                                                      • Air conditioning

                                                                      from £425 / night

                                                                      £2,974 - £6,242 / week

                                                                      Book View

                                                                      from £425 / night

                                                                        13

                                                                        Holiday villa in Healdsburg

                                                                        Sonoma County / Healdsburg

                                                                        4 8 min stay varies

                                                                        • 4 bedrooms
                                                                        • sleeps 8
                                                                        • min stay varies
                                                                        • Air conditioning
                                                                        • Private garden

                                                                        from £1,927 / night

                                                                        £13,490 / week

                                                                        Book View

                                                                        from £1,927 / night

                                                                          6

                                                                          Holiday cottage in Healdsburg

                                                                          Sonoma County / Healdsburg

                                                                          2 4 30 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 4
                                                                          • 30 nights min
                                                                          • Nearest beach 29 km
                                                                          • Child friendly
                                                                          • Air conditioning

                                                                          from £219 / night

                                                                          £1,533 / week

                                                                          Book View

                                                                          Responds fast!
                                                                          avg. 3 hours 2 minutes

                                                                          from £219 / night

                                                                          Great rentals within 20 miles that match your search

                                                                          Distance approx 12.12 miles from Healdsburg Show on Map

                                                                            33

                                                                            Cazadero holiday log cabin rental

                                                                            Sonoma County / Cazadero

                                                                            2 4 30 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 4
                                                                            • 30 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Child friendly
                                                                            • Pet friendly

                                                                            from £101 / night

                                                                            £705 / week

                                                                            Book View

                                                                            from £101 / night

                                                                            Distance approx 16.54 miles from Healdsburg Show on Map

                                                                              30

                                                                              Sebastopol holiday studio rental

                                                                              Sonoma County / Sebastopol

                                                                              Studio 2 2 nights min

                                                                              • Studio
                                                                              • sleeps 2
                                                                              • 2 nights min

                                                                              from £114 / night

                                                                              £798 / week

                                                                              Book View

                                                                              from £114 / night

                                                                              Distance approx 6.82 miles from Healdsburg Show on Map

                                                                                4

                                                                                Holiday condo with golf nearby in Windsor

                                                                                Sonoma County / Windsor

                                                                                2 6 7 nights min

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

                                                                                from £438 / night

                                                                                £3,066 / week

                                                                                Book View

                                                                                from £438 / night

                                                                                Distance approx 12.78 miles from Healdsburg Show on Map

                                                                                  20

                                                                                  Monte Rio holiday home rental

                                                                                  Sonoma County / Monte Rio

                                                                                  2 4 min stay varies

                                                                                  • 2 bedrooms
                                                                                  • sleeps 4
                                                                                  • min stay varies
                                                                                  • Beach / lakeside relaxation
                                                                                  • Child friendly
                                                                                  • Pet friendly

                                                                                  from £146 / night

                                                                                  £871 - £976 / week

                                                                                  Book View

                                                                                  from £146 / night

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