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

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78 Holiday homes

(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

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from £222 / night

£1,331 / week

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Responds fast!
avg. 3 hours 44 minutes

from £222 / night

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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

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from £90 / night

£447 / week

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from £90 / night

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(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

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from £76 / night

£470 / week

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Responds fast!
avg. 2 hours 38 minutes

from £76 / night

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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

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from £150 / night

£1,050 / week

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Responds fast!
avg. 3 hours 39 minutes

from £150 / night

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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

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from £36 / night

£251 / week

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Responds fast!
avg. 2 hours 32 minutes

from £36 / night

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(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

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Pricing unknown

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Pricing unknown

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(1) Very Good 

21

Holiday apartment with shared pool, golf nearby in Collado Villalba

Community of Madrid / Collado Villalba

3 5 min stay varies

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

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from £64 / night

£344 - £400 / week

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Responds fast!
avg. 57 minutes

from £64 / night

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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

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from £75 / night

£484 / week

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Responds fast!
avg. 57 minutes

from £75 / night

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21

Cercedilla ski apartment to rent.

Community of Madrid / Cercedilla

1 5 2 nights min

  • 1 bedroom
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Ski
  • Child friendly

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from £62 / night

£420 - £470 / week

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Responds fast!
avg. 57 minutes

from £62 / night

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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

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from £159 / night

£881 - £965 / week

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Responds fast!
avg. 57 minutes

from £159 / night

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(19) Excellent 

9

Collado Mediano ski condo to rent.

Community of Madrid / Collado Mediano

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Ski

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from £47 / night

£275 - £405 / week

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from £47 / night

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(5) Excellent 

Certificate of Excellence

12

Holiday apartment letting

Community of Madrid / Moralzarzal

2 4 2 nights min

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

Certificate of Excellence

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from £45 / night

£268 / week

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Responds fast!
avg. 3 hours 10 minutes

from £45 / night

Book

(1) Very Good 

28

Holiday finca with swimming pool in Valdemorillo

Community of Madrid / Valdemorillo

4 14 2 nights min

  • 4 bedrooms
  • sleeps 14
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

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from £313 / night

£1,788 / week

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Responds fast!
avg. 2 hours 20 minutes

from £313 / night

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(4) Excellent 

18

Robledo de Chavela holiday villa rental

Community of Madrid / Robledo de Chavela

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

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from £224 / night

£983 - £1,140 / week

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Responds fast!
avg. 1 hour 28 minutes

from £224 / night

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(1) Very Good 

56

Holiday home with swimming pool in Manzanares el Real

Community of Madrid / Manzanares el Real

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

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from £108 / night

£701 - £1,204 / week

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from £108 / night

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(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

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from £45 / night

£224 / week

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Responds fast!
avg. 2 hours 6 minutes

from £45 / night

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45

Holiday apartment in Collado Mediano

Community of Madrid / Collado Mediano

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

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from £58 / night

£325 / week

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from £58 / night

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(3) Excellent 

46

Holiday apartment in Galapagar

Community of Madrid / Galapagar

2 6 1 night min

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

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from £23 / night

£222 - £471 / week

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Responds fast!
avg. 2 hours 46 minutes

from £23 / night

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(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

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from £54 / night

£312 / week

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from £54 / night

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(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

Map

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from £268 / night

£1,028 / week

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from £268 / night

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(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

Map

Add to shortlist

from £102 / night

£705 / week

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from £102 / night

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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

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from £67 / night

£470 / week

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from £67 / night

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(18) 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

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from £403 / night

£2,815 / week

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from £403 / night

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(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

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from £50 / night

£293 / week

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Responds fast!
avg. 1 hour 48 minutes

from £50 / night

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(11) Excellent 

24

Holiday home rental

Community of Madrid / Santa Maria de la Alameda

2 6 min stay varies

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

Map

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from £63 / night

£438 / week

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Responds fast!
avg. 1 hour 21 minutes

from £63 / night

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(1) Excellent 

20

Holiday studio in San Lorenzo de El Escorial

Community of Madrid / San Lorenzo de El Escorial

Studio 5 2 nights min

  • Studio
  • sleeps 5
  • 2 nights min
  • Child friendly
  • Private garden

Map

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from £41 / night

£224 - £599 / week

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Responds fast!
avg. 53 minutes

from £41 / night

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(1) Excellent 

24

Holiday apartment in Santa Maria de la Alameda

Community of Madrid / Santa Maria de la Alameda

2 6 2 nights min

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

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from £76 / night

£403 / week

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Responds fast!
avg. 19 minutes

from £76 / night

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(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

Map

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from £50 / night

£291 - £441 / week

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from £50 / night

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31

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

Map

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from £225 / night

£1,572 / week

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from £225 / night

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(6) Very Good 

11

Holiday home in Cercedilla

Community of Madrid / Cercedilla

3 7 2 nights min

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

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Add to shortlist

from £54 / night

£378 - £1,006 / week

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from £54 / night

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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

Map

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from £76 / night

£528 / week

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from £76 / night

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(1) Excellent 

33

Holiday apartment rental

Community of Madrid / Santa Maria de la Alameda

2 6 2 nights min

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

Map

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from £76 / night

£403 / week

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Responds fast!
avg. 19 minutes

from £76 / night

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25

Holiday private room in Colmenar Viejo

Community of Madrid / Colmenar Viejo

1 1 2 nights min

  • 1 bedroom
  • sleeps 1
  • 2 nights min

Map

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from £22 / night

£131 / week

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Responds fast!
avg. 1 hour 1 minutes

from £22 / night

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(3) Excellent 

19

Holiday cottage with swimming pool in Hoyo de Manzanares

Community of Madrid / Hoyo de Manzanares

7 10 2 nights min

  • 7 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden

Map

Add to shortlist

from £382 / night

£1,213 / week

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from £382 / night

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37

Home rental in Robledo de Chavela with shared pool

Community of Madrid / Robledo de Chavela

5 15 2 nights min

  • 5 bedrooms
  • sleeps 15
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

Map

Add to shortlist

from £224 / night

£1,341 / week

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Responds fast!
avg. 3 hours 32 minutes

from £224 / night

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(2) Very Good 

33

Holiday home with swimming pool in Alpedrete

Community of Madrid / Alpedrete

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

Map

Add to shortlist

from £242 / night

£1,162 - £1,251 / week

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Responds fast!
avg. 2 hours 10 minutes

from £242 / night

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(2) Excellent 

31

Holiday home in Cercedilla

Community of Madrid / Cercedilla

3 5 min stay varies

  • 3 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Map

Add to shortlist

from £76 / night

£532 / week

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Responds fast!
avg. 49 minutes

from £76 / night

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(3) Excellent 

44

Holiday chalet in Robledo de Chavela

Community of Madrid / Robledo de Chavela

4 16 2 nights min

  • 4 bedrooms
  • sleeps 16
  • 2 nights min
  • Child friendly
  • Private garden

Map

Add to shortlist

from £405 / night

£2,830 / week

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from £405 / night

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31

Collado Mediano holiday apartment rental

Community of Madrid / Collado Mediano

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

Map

Add to shortlist

from £109 / night

£529 / week

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from £109 / night

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(10) Very Good 

Certificate of Excellence

27

Apartment rental in San Lorenzo de El Escorial with shared pool

Community of Madrid / San Lorenzo de El Escorial

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

Certificate of Excellence

Map

Add to shortlist

from £53 / night

£358 - £420 / week

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Responds fast!
avg. 32 minutes

from £53 / night

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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
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