Apartments in Sierra de Guadarrama and Houses - Holiday Lettings - Holiday Rentals Sierra de Guadarrama

Close

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

83 Holiday homes

(17) Excellent 

    24

    San Lorenzo de El Escorial holiday apartment rental

    Community of Madrid / San Lorenzo de El Escorial

    3 6 3 nights min

    • 3 bedrooms
    • sleeps 6
    • 3 nights min
    • Child friendly
    • Car not necessary
    • Ask about pets

    from £84 / night

    £517 / week

    Book View

    Responds fast!
    avg. 1 hour 16 minutes

    from £84 / night

    (4) Excellent 

      12

      Holiday cottage in Valdemorillo

      Community of Madrid / Valdemorillo

      4 8 3 nights min

      • 4 bedrooms
      • sleeps 8
      • 3 nights min
      • Beach / lakeside relaxation
      • Swimming pool
      • Child friendly

      from £252 / night

      £1,511 / week

      Book View

      from £252 / night

        19

        Holiday home in Collado Villalba

        Community of Madrid / Collado Villalba

        3 6 3 nights min

        • 3 bedrooms
        • sleeps 6
        • 3 nights min
        • Swimming pool
        • Child friendly
        • Air conditioning

        from £172 / night

        £1,203 / week

        Book View

        Responds fast!
        avg. 3 hours 57 minutes

        from £172 / night

        (1) Excellent 

          18

          Alpedrete holiday chalet rental

          Community of Madrid / Alpedrete

          3 8 2 nights min

          • 3 bedrooms
          • sleeps 8
          • 2 nights min
          • Swimming pool
          • Child friendly
          • Car not necessary

          from £98 / night

          £588 / week

          Book View

          from £98 / night

            4

            Holiday private room in San Lorenzo de El Escorial

            Community of Madrid / San Lorenzo de El Escorial

            1 2 2 nights min

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

            from £40 / night

            £276 / week

            Book View

            Responds fast!
            avg. 3 hours 49 minutes

            from £40 / night

              24

              Holiday villa in El Escorial

              Community of Madrid / El Escorial

              3 6 7 nights min

              • 3 bedrooms
              • sleeps 6
              • 7 nights min
              • Child friendly
              • Ask about pets

              from £146 / night

              £1,021 - £1,219 / week

              Book View

              Responds fast!
              avg. 2 hours 41 minutes

              from £146 / night

              (1) Very Good 

                14

                Las Dehesas holiday villa rental

                Community of Madrid / Las Dehesas

                2 4 min stay varies

                • 2 bedrooms
                • sleeps 4
                • min stay varies
                • Beach / lakeside relaxation
                • Nearest beach 1 km
                • Swimming pool

                Pricing unknown

                Book View

                Pricing unknown

                  24

                  El Escorial holiday home rental

                  Community of Madrid / El Escorial

                  3 6 min stay varies

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

                  from £125 / night

                  £742 - £1,066 / week

                  Book View

                  Responds fast!
                  avg. 1 hour 19 minutes

                  from £125 / night

                    18

                    Robledo de Chavela holiday studio rental

                    Community of Madrid / Robledo de Chavela

                    Studio 3 min stay varies

                    • Studio
                    • sleeps 3
                    • min stay varies
                    • Child friendly
                    • Air conditioning
                    • Pet friendly

                    from £83 / night

                    £533 / week

                    Book View

                    Responds fast!
                    avg. 2 hours 54 minutes

                    from £83 / night

                      38

                      Ski villa to rent in Alpedrete

                      Community of Madrid / Alpedrete

                      6 12 5 nights min

                      • 6 bedrooms
                      • sleeps 12
                      • 5 nights min
                      • Beach / lakeside relaxation
                      • Swimming pool
                      • Ski

                      from £697 / night

                      £3,490 / week

                      Book View

                      Responds fast!
                      avg. 2 hours 54 minutes

                      from £697 / night

                        12

                        Ski home to rent in Manzanares el Real

                        Community of Madrid / Manzanares el Real

                        4 8 2 nights min

                        • 4 bedrooms
                        • sleeps 8
                        • 2 nights min
                        • Beach / lakeside relaxation
                        • Ski
                        • Child friendly

                        from £175 / night

                        £965 - £1,058 / week

                        Book View

                        Responds fast!
                        avg. 2 hours 54 minutes

                        from £175 / night

                          35

                          Holiday villa rental

                          Community of Madrid / Hoyo de Manzanares

                          6 12 min stay varies

                          • 6 bedrooms
                          • sleeps 12
                          • min stay varies
                          • Swimming pool
                          • Child friendly
                          • Private garden

                          from £558 / night

                          £3,906 / week

                          Book View

                          Responds fast!
                          avg. 25 minutes

                          from £558 / night

                          (1) Excellent 

                            42

                            Home rental in Valdemorillo

                            Community of Madrid / Valdemorillo

                            4 8 2 nights min

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

                            from £279 / night

                            £1,068 / week

                            Book View

                            from £279 / night

                            (1) Very Good 

                              53

                              Holiday finca with swimming pool in Valdemorillo

                              Community of Madrid / Valdemorillo

                              4 18 2 nights min

                              • 4 bedrooms
                              • sleeps 18
                              • 2 nights min
                              • Swimming pool
                              • Child friendly
                              • Air conditioning

                              from £418 / night

                              £1,858 / week

                              Book View

                              Responds fast!
                              avg. 3 hours 30 minutes

                              from £418 / night

                              (8) Very Good 

                                13

                                Holiday apartment in San Lorenzo de El Escorial

                                Community of Madrid / San Lorenzo de El Escorial

                                1 4 1 night min

                                • 1 bedroom
                                • sleeps 4
                                • 1 night min
                                • Suitable for children age 5+
                                • Car not necessary
                                • Ask about pets

                                from £47 / night

                                £233 / week

                                Book View

                                Responds fast!
                                avg. 1 hour 17 minutes

                                from £47 / night

                                (1) Excellent 

                                  29

                                  Holiday chalet in Colmenar Viejo

                                  Community of Madrid / Colmenar Viejo

                                  4 8 2 nights min

                                  • 4 bedrooms
                                  • sleeps 8
                                  • 2 nights min
                                  • Ask owner if suitable for children
                                  • Ask about pets

                                  from £157 / night

                                  £980 / week

                                  Book View

                                  Responds fast!
                                  avg. 3 hours 13 minutes

                                  from £157 / night

                                    25

                                    Holiday private room in Colmenar Viejo

                                    Community of Madrid / Colmenar Viejo

                                    1 1 2 nights min

                                    • 1 bedroom
                                    • sleeps 1
                                    • 2 nights min

                                    from £23 / night

                                    £135 / week

                                    Book View

                                    Responds fast!
                                    avg. 2 hours 45 minutes

                                    from £23 / night

                                    (1) Excellent 

                                      15

                                      Holiday apartment in Santa Maria de la Alameda

                                      Community of Madrid / Santa Maria de la Alameda

                                      2 6 min stay varies

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

                                      from £84 / night

                                      £465 / week

                                      Book View

                                      Responds fast!
                                      avg. 34 minutes

                                      from £84 / night

                                        26

                                        Holiday chalet with swimming pool in Robledo de Chavela

                                        Community of Madrid / Robledo de Chavela

                                        4 16 min stay varies

                                        • 4 bedrooms
                                        • sleeps 16
                                        • min stay varies
                                        • Swimming pool
                                        • Child friendly
                                        • Pet friendly

                                        from £231 / night

                                        £1,617 / week

                                        Book View

                                        from £231 / night

                                          14

                                          Holiday home in Manzanares el Real

                                          Community of Madrid / Manzanares el Real

                                          3 6 1 night min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 1 night min
                                          • Child friendly

                                          from £91 / night

                                          £632 / week

                                          Book View

                                          Responds fast!
                                          avg. 3 hours 20 minutes

                                          from £91 / night

                                          (9) Excellent 

                                            15

                                            Holiday apartment in Cercedilla

                                            Community of Madrid / Cercedilla

                                            1 4 2 nights min

                                            • 1 bedroom
                                            • sleeps 4
                                            • 2 nights min
                                            • Child friendly
                                            • Car not necessary

                                            from £51 / night

                                            £302 - £432 / week

                                            Book View

                                            Responds fast!
                                            avg. 1 hour 57 minutes

                                            from £51 / night

                                              50

                                              Cercedilla ski finca to rent.

                                              Community of Madrid / Cercedilla

                                              5 12 min stay varies

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

                                              from £314 / night

                                              £2,055 - £2,056 / week

                                              Book View

                                              Responds fast!
                                              avg. 1 hour 37 minutes

                                              from £314 / night

                                                10

                                                Holiday private room rental

                                                Community of Madrid / Alpedrete

                                                1 2 1 night min

                                                • 1 bedroom
                                                • sleeps 2
                                                • 1 night min

                                                from £38 / night

                                                £186 - £316 / week

                                                Book View

                                                from £38 / night

                                                (5) Excellent 

                                                  32

                                                  Ski apartment to rent in Matalpino

                                                  Community of Madrid / Matalpino

                                                  2 4 2 nights min

                                                  • 2 bedrooms
                                                  • sleeps 4
                                                  • 2 nights min
                                                  • Swimming pool
                                                  • Ski
                                                  • Child friendly

                                                  from £105 / night

                                                  £729 / week

                                                  Book View

                                                  from £105 / night

                                                  (21) Excellent 

                                                    27

                                                    Holiday home with golf nearby in Robledo de Chavela

                                                    Community of Madrid / Robledo de Chavela

                                                    6 20 2 nights min

                                                    • 6 bedrooms
                                                    • sleeps 20
                                                    • 2 nights min
                                                    • Child friendly
                                                    • Pet friendly
                                                    • Private garden

                                                    from £428 / night

                                                    £2,993 / week

                                                    Book View

                                                    from £428 / night

                                                      45

                                                      Holiday condo in Colmenar Viejo

                                                      Community of Madrid / Colmenar Viejo

                                                      4 7 1 night min

                                                      • 4 bedrooms
                                                      • sleeps 7
                                                      • 1 night min

                                                      from £86 / night

                                                      £598 / week

                                                      Book View

                                                      Responds fast!
                                                      avg. 2 hours 44 minutes

                                                      from £86 / night

                                                        15

                                                        Holiday b&b rental

                                                        Community of Madrid / San Lorenzo de El Escorial

                                                        50 2 1 night min

                                                        • 50 bedrooms
                                                        • sleeps 2
                                                        • 1 night min
                                                        • Car not necessary

                                                        from £65 / night

                                                        £453 / week

                                                        Book View

                                                        from £65 / night

                                                        (1) Excellent 

                                                          21

                                                          Holiday home in San Lorenzo de El Escorial

                                                          Community of Madrid / San Lorenzo de El Escorial

                                                          3 6 7 nights min

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • 7 nights min
                                                          • Beach / lakeside relaxation
                                                          • Swimming pool
                                                          • Child friendly

                                                          from £56 / night

                                                          £325 / week

                                                          Book View

                                                          from £56 / night

                                                            12

                                                            Ski chalet to rent in Alpedrete

                                                            Community of Madrid / Alpedrete

                                                            5 2 2 nights min

                                                            • 5 bedrooms
                                                            • sleeps 2
                                                            • 2 nights min
                                                            • Ski

                                                            from £37 / night

                                                            £194 - £324 / week

                                                            Book View

                                                            from £37 / night

                                                              5

                                                              San Lorenzo de El Escorial holiday apartment rental

                                                              Community of Madrid / San Lorenzo de El Escorial

                                                              2 4 2 nights min

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

                                                              from £70 / night

                                                              £488 / week

                                                              Book View

                                                              from £70 / night

                                                              (11) Very Good 

                                                              Certificate of Excellence

                                                                29

                                                                Apartment rental in San Lorenzo de El Escorial with shared pool

                                                                Community of Madrid / San Lorenzo de El Escorial

                                                                1 4 min stay varies

                                                                • 1 bedroom
                                                                • sleeps 4
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Swimming pool
                                                                • Child friendly

                                                                Certificate of Excellence

                                                                from £55 / night

                                                                £370 - £435 / week

                                                                Book View

                                                                Responds fast!
                                                                avg. 1 hour 29 minutes

                                                                from £55 / night

                                                                  4

                                                                  Valdemorillo holiday home accommodation

                                                                  Community of Madrid / Valdemorillo

                                                                  4 8 7 nights min

                                                                  • 4 bedrooms
                                                                  • sleeps 8
                                                                  • 7 nights min
                                                                  • Swimming pool
                                                                  • Child friendly

                                                                  from £209 / night

                                                                  £1,463 / week

                                                                  Book View

                                                                  from £209 / night

                                                                    29

                                                                    Robledo de Chavela holiday apartment rental

                                                                    Community of Madrid / Robledo de Chavela

                                                                    4 10 2 nights min

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

                                                                    from £260 / night

                                                                    £1,821 / week

                                                                    Book View

                                                                    from £260 / night

                                                                      29

                                                                      Private room rental in Colmenar Viejo

                                                                      Community of Madrid / Colmenar Viejo

                                                                      2 2 1 night min

                                                                      • 2 bedrooms
                                                                      • sleeps 2
                                                                      • 1 night min

                                                                      from £45 / night

                                                                      £284 / week

                                                                      Book View

                                                                      Responds fast!
                                                                      avg. 2 hours 44 minutes

                                                                      from £45 / night

                                                                        37

                                                                        Home rental in Robledo de Chavela with shared pool

                                                                        Community of Madrid / Robledo de Chavela

                                                                        5 15 min stay varies

                                                                        • 5 bedrooms
                                                                        • sleeps 15
                                                                        • min stay varies
                                                                        • Swimming pool
                                                                        • Child friendly
                                                                        • Pet friendly

                                                                        from £238 / night

                                                                        £1,425 / week

                                                                        Book View

                                                                        Responds fast!
                                                                        avg. 2 hours 8 minutes

                                                                        from £238 / night

                                                                          22

                                                                          Holiday home in Cercedilla

                                                                          Community of Madrid / Cercedilla

                                                                          3 5 1 night min

                                                                          • 3 bedrooms
                                                                          • sleeps 5
                                                                          • 1 night min
                                                                          • Nearest beach 10 km
                                                                          • Child friendly
                                                                          • Car not necessary

                                                                          from £64 / night

                                                                          £371 - £559 / week

                                                                          Book View

                                                                          from £64 / night

                                                                            15

                                                                            Robledo de Chavela holiday apartment rental

                                                                            Community of Madrid / Robledo de Chavela

                                                                            1 4 2 nights min

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • 2 nights min
                                                                            • Swimming pool
                                                                            • Child friendly
                                                                            • Air conditioning

                                                                            from £79 / night

                                                                            £550 / week

                                                                            Book View

                                                                            from £79 / night

                                                                            (1) Excellent 

                                                                              15

                                                                              El Escorial holiday apartment rental

                                                                              Community of Madrid / El Escorial

                                                                              2 4 3 nights min

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

                                                                              from £53 / night

                                                                              £309 - £469 / week

                                                                              Book View

                                                                              Responds fast!
                                                                              avg. 3 hours 18 minutes

                                                                              from £53 / night

                                                                                32

                                                                                Holiday home in Cercedilla

                                                                                Community of Madrid / Cercedilla

                                                                                5 10 2 nights min

                                                                                • 5 bedrooms
                                                                                • sleeps 10
                                                                                • 2 nights min
                                                                                • Swimming pool
                                                                                • Child friendly
                                                                                • Pet friendly

                                                                                from £279 / night

                                                                                £1,951 / week

                                                                                Book View

                                                                                from £279 / night

                                                                                (1) Excellent 

                                                                                  18

                                                                                  Holiday apartment rental

                                                                                  Community of Madrid / Santa Maria de la Alameda

                                                                                  2 6 min stay varies

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

                                                                                  from £86 / night

                                                                                  £475 / week

                                                                                  Book View

                                                                                  Responds fast!
                                                                                  avg. 34 minutes

                                                                                  from £86 / night

                                                                                  Top Destination reviews

                                                                                  ESPECTACULAR VIEWS IN MADRID
                                                                                  Superb

                                                                                  A lovely cottage in an idyllic spot. Pino the owner was fantastic help from the moment we booked to well after we departed. The house itself is beautifully finished with an artistic character and some quirky features, not least the cats and chickens that live there. Don't worry if your not an animal lover though, we were asked in advance if we wanted them removed before we arrived. A great library of books and DVD's was a welcome escape in the evenings. The cottage comes with it's own pool but this is pretty cold at the end of the season and so we mainly swam in the lake, a very short stroll from the house. Cannot recommend the cottage and area enough for a break away from the tourist hotspots.see more
                                                                                  San Lorenzo
                                                                                  Ticked all the boxes

                                                                                  The apartment fully lived up to our expectatiions. Homely and comfortable. A great view from the balcony. Excellent location in San Lorenzo, Ideal for visiting Madrid by train and touring the beautiful Guadarrama Mountains and beyond. Thanks to Elisabet for ensuring the booking process and directions were smooth and simple. R & A Burton.see more

                                                                                  Also consider