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

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81 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

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from £76 / night

£468 / week

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Responds fast!
avg. 2 hours 9 minutes

from £76 / night

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(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 34 minutes

from £222 / 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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(1) Excellent 

18

Alpedrete holiday chalet rental

Community of Madrid / Alpedrete

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

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from £89 / night

£534 - £668 / week

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from £89 / 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

£250 / 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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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

£482 / week

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Responds fast!
avg. 3 hours 7 minutes

from £75 / night

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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

£342 - £398 / week

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from £64 / 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 £158 / night

£872 - £956 / week

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Responds fast!
avg. 3 hours 7 minutes

from £158 / 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

£419 - £467 / week

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Responds fast!
avg. 3 hours 7 minutes

from £62 / night

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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

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from £493 / night

£3,452 / week

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Responds fast!
avg. 3 hours 7 minutes

from £493 / 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

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from £223 / night

£1,558 / week

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from £223 / night

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10

Holiday private room rental

Community of Madrid / Alpedrete

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min

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from £36 / night

£178 - £303 / week

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from £36 / night

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(19) Excellent 

9

Collado Mediano ski condo to rent.

Community of Madrid / Collado Mediano

1 3 4 nights min

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

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from £47 / night

£275 - £406 / week

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from £47 / 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

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from £267 / night

£1,023 / week

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from £267 / 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

£223 / week

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Responds fast!
avg. 2 hours 6 minutes

from £45 / night

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(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

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from £401 / night

£1,780 / week

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Responds fast!
avg. 3 hours 29 minutes

from £401 / 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

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from £22 / night

£130 / week

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Responds fast!
avg. 2 hours 20 minutes

from £22 / 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

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from £101 / night

£699 / week

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from £101 / night

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(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

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from £143 / night

£890 / week

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Responds fast!
avg. 1 hour 49 minutes

from £143 / 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

£401 / week

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Responds fast!
avg. 19 minutes

from £76 / night

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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

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from £63 / night

£436 / week

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from £63 / 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

£468 / week

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from £67 / 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

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from £85 / night

£592 / week

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Responds fast!
avg. 3 hours 39 minutes

from £85 / 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

Map

Add to shortlist

from £54 / night

£312 / week

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from £54 / night

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50

Cercedilla ski finca to rent.

Community of Madrid / Cercedilla

5 12 2 nights min

  • 5 bedrooms
  • sleeps 12
  • 2 nights min
  • Swimming pool
  • Ski
  • Child friendly

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from £367 / night

£1,979 / week

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from £367 / 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 £49 / night

£291 - £416 / week

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Responds fast!
avg. 1 hour 48 minutes

from £49 / night

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45

Holiday condo in Colmenar Viejo

Community of Madrid / Colmenar Viejo

4 7 1 night min

  • 4 bedrooms
  • sleeps 7
  • 1 night min

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from £82 / night

£574 / week

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Responds fast!
avg. 2 hours 20 minutes

from £82 / night

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15

Robledo de Chavela holiday apartment rental

Community of Madrid / Robledo de Chavela

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

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from £63 / night

£436 / week

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from £63 / night

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(19) 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 £401 / night

£2,804 / week

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from £401 / night

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(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

Map

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from £53 / night

£356 - £419 / week

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Responds fast!
avg. 1 hour 33 minutes

from £53 / night

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29

Robledo de Chavela holiday apartment rental

Community of Madrid / Robledo de Chavela

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

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from £143 / night

£997 / week

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from £143 / 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

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from £223 / night

£1,335 / week

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Responds fast!
avg. 3 hours 15 minutes

from £223 / 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

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from £76 / night

£401 / week

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Responds fast!
avg. 19 minutes

from £76 / night

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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

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from £201 / night

£1,402 / week

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from £201 / night

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(1) Very Good 

46

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 £57 / night

£323 / week

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from £57 / night

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32

Colmenar Viejo holiday private room rental

Community of Madrid / Colmenar Viejo

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min

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from £62 / night

£379 / week

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Responds fast!
avg. 2 hours 20 minutes

from £62 / 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

Map

Add to shortlist

from £23 / night

£223 - £472 / week

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Responds fast!
avg. 2 hours 46 minutes

from £23 / night

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18

Holiday home in Cercedilla

Community of Madrid / Cercedilla

3 7 6 nights min

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

Map

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from £80 / night

£445 / week

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from £80 / night

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29

Private room rental in Colmenar Viejo

Community of Madrid / Colmenar Viejo

2 2 1 night min

  • 2 bedrooms
  • sleeps 2
  • 1 night min

Map

Add to shortlist

from £43 / night

£272 / week

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Responds fast!
avg. 2 hours 20 minutes

from £43 / 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