50 Best Vacation Rentals in Sierra de Guadarrama - Holiday Lettings - Cabins

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Sierra de Guadarrama

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72 Vacation rentals

(4) Excellent 

12

Vacation 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
First of all, we want to show you a video from the cottage that was recorded some months ago (go to vimeo and look for "casa nacho y pino") 1500 square meter garden with a private swimming pool, nice trees, barbecue, canoe, a cozy porch at a private urbanization with 2 …see more

from $310 / night

$1,859 / week

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from $310 / night

18

Alpedrete Vacation 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
THE PROPERTY IS LOCATED 40 KMS FROM MADRID (25 MINUTES DRIVING) IN THE MOUNTAIN AREA. THE HOUSE IS A 3000 M2 PARCEL WITH TENNIS COURT AND SWIMMING POOL. HAS THREE LEVELS PERFECTLY COMUNICATED: GROUNDWITH THE KITCHEN AND BATHROOM, SECOND 80M2 SALON, THIRD ROOMS AND TWO B …see more

from $149 / night

$620 / week

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from $149 / night

(16) Excellent 

24

San Lorenzo de El Escorial Vacation apartment rental

Community of Madrid / San Lorenzo de El Escorial

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets
Situated five minutes walk from the town centre, the fully furnished flat is in an ideal location for restaurants, bars, shops and local amenities. The flat is on the top floor of a four storey building with views of the mountain sierra. There is parking outside the bui …see more

from $106 / night

$651 / week

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Responds fast!
avg. 3 hours 44 minutes

from $106 / night

14

Vacation 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
Rooms to rent in Madrid a Bus and train ride from the central; keys will be given to guests for the room. The house is in a really good location for tourists. Especially if you want to get away to relax. We also have numerous bars, restaurant, markets, supermarket, ph …see more

from $210 / night

$1,470 / week

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Responds fast!
avg. 3 hours 41 minutes

from $210 / night

(1) Very Good 

14

Las Dehesas Vacation 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 mi
  • Swimming pool
The Villa Rosalva is a apartment-complex with a warm and familial atmosphere. We are perfectly situated in Las Dehesas with a spectacular view on the mountains and the Teide, the city of Puerto and the Atlantic Ocean. Within walking-distance you can reach the beach, the …see more

Pricing unknown

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4

Vacation 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
Our place is close to the historic part of town, several restaurants and dining options, and has great views of the mountains. You’ll love our home because of the location, easy access to both the historic centre and the surrounding natural space. Our place is good for …see more

from $50 / night

$347 / week

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from $50 / night

(7) Excellent 

15

Vacation apartment in Cercedilla

Community of Madrid / Cercedilla

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
It is located in the heart of the village of Cercedilla, in the Plaza Mayor, where you can enjoy its restaurants, bars, shops and stroll through its streets. Ideal for couples, families with children and athletes. The village environment, Las Dehesas Cercedilla Puerto d …see more

from $69 / night

$406 / week

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Responds fast!
avg. 2 hours 22 minutes

from $69 / night

(2) Very Good 

22

Vacation villa in Los Molinos

Community of Madrid / Los Molinos

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Detached villa in the Sierra de Madrid with a view to the mountain in the town of Los Molinos, 1 km. From the center of the village, 3 floors, 4 bathrooms, 4 bedrooms, garage and terrace - garden with barbecue, room games, billiard, darts, etc. Computer, free Wi-Fi. Swi …see more

from $273 / night

$1,363 / week

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Responds fast!
avg. 3 hours 25 minutes

from $273 / night

(3) Very Good 

12

Vacation apartment rental

Community of Madrid / Moralzarzal

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
prime location in the city, with easy access (1-3 min. walk) to supermarkets, medical center, pharmacy, bus station, entertainment area ... Free public parking. WIFI. The apartment is located in a natural environment. Not surprisingly, the municipality is within the R …see more

from $62 / night

$372 / week

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from $62 / night

(1) Excellent 

12

Puerto de Navacerrada ski apartment to rent.

Cercedilla / Puerto de Navacerrada

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Ski
  • Child friendly
  • Pet friendly
It is a beautiful apartment in the mountains at 1800 m in the ski resort of Navacerrada in Leeks with amazing views, ideal for lovers of skiing, hiking, biking, or just to unwind and recharge. The nearest supermarket is in Cercedilla 8km, there 4G connection, no wifi, i …see more

from $50 / night

$242 - $539 / week

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from $50 / night

34

Home rental in Collado Villalba

Community of Madrid / Collado Villalba

5 9 2 nights min

  • 5 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
Wonderful villa in the best area of ​​the Sierra de Madrid. Located in one of the most prestigious developments in Collado Villalba, surrounded by nature and indescribable enclave. Nature and Rest 20 minutes from Madrid. More than 5,000 meters of land in the open air, …see more

from $595 / night

$2,478 / week

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from $595 / night

(1) Excellent 

31

Vacation 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
Spend some wonderful days in Cercedilla, the prettiest village in the mountains of Madrid. Three-storey villa, 150m2 home and 120 m2 private garden. Beautiful complex with pool and tennis court and parking 50 km from Madrid. Located in a complex with spectacular mountai …see more

from $118 / night

$824 / week

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Responds fast!
avg. 1 hour 41 minutes

from $118 / 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
Ground floor apartment located in the National Park of the Upper Basin of the Manzanares, with pool and garden shared only with the owner. A place to enjoy nature and perfect for those who want to improve their English in a very special way. The property is let to 4 peo …see more

from $140 / night

$973 / week

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from $140 / night

31

Collado Mediano Vacation 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
Opened in 2007, new account with innovative and modern facilities: hot water and heating during 24 hours a day, phone, Internet, complete and spacious bathrooms, apartments with plenty of natural light in all instances and ceramic floors among other details, all accompa …see more

from $150 / night

$734 / week

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from $150 / night

(8) Very Good 

13

Vacation apartment in San Lorenzo de El Escorial

Community of Madrid / San Lorenzo de El Escorial

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Suitable for children age 5+
  • Car not necessary
  • Ask about pets
Garret rustica in the Centre of San Lorenzo de el Escorial, next to the Town Hall square and 200 metres from the monastery. Opposite the health centre and 50 meters from the municipal market. 500 m from the bus station. 664 and 661 numbers take you from Moncloa station …see more

from $62 / night

$308 / week

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Responds fast!
avg. 1 hour 55 minutes

from $62 / night

(2) Excellent 

19

Vacation 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
Impressive villa in the town of Hoyo de Manzanares. The most representative of the village with stunning views and tranquil area. It is a beautiful plot of 1176 m2 with 490 m2 of housing, consists of 5 bedrooms, of which four have included full bath and also 2 toilets. …see more

from $527 / night

$1,673 / week

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from $527 / night

56

Vacation 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
In the natural park of Pedriza, enjoy this fabulous villa, its beautiful decor, neat garden with orchard, fruit trees and beautiful salt water pool without chlorine. In a relaxing atmosphere, quiet and wonderful views .... and be amazed, unruffled by the capricious rout …see more

from $149 / night

$967 - $1,661 / week

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from $149 / night

(4) Excellent 

18

Robledo de Chavela Vacation villa rental

Community of Madrid / Robledo de Chavela

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa has 250 square meters is located in Robledo de Chavela, mountain town with beautiful mountain walks and hiking. Possibility of horse riding. Tourist visits to the monuments of San Lorenzo de El Escorial. Walking up the Rio Cofi. The villa is an excellent start …see more

from $217 / night

$1,053 - $1,363 / week

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Responds fast!
avg. 1 hour 32 minutes

from $217 / night

(5) Very Good 

22

Puerto de Navacerrada ski condo to rent.

Community of Madrid / Puerto de Navacerrada

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Ski
  • Child friendly
  • Ask about pets
holiday apartment in la sierra, perfect condition in the best area of the puerto de navacerrada, officially recognized as National Park, perfect for lovers of snow, and nature for families or athletes, fully furnished, has garage included in the price, very quiet and wi …see more

from $56 / night

$347 - $521 / week

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Responds fast!
avg. 1 hour 39 minutes

from $56 / night

(2) Excellent 

28

Vacation villa with indoor pool in Becerril de la Sierra

Community of Madrid / Becerril de la Sierra

6 22 Min stay varies

  • 6 bedrooms
  • Sleeps 22
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Samburiel is located in the National Park of the Guadarrama mountain range, it is a detached house with garden, barbecue and games for children. The house has 6 bedrooms, 4 with double bed, 1 with four beds, and 1 with 3 beds. We have 7 beds and 2 extra beds. 3 full bat …see more

from $44 / night

$304 / week

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Responds fast!
avg. 35 minutes

from $44 / night

(1) Very Good 

28

Vacation 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
  • Private garden
3 hectare farm with luxury and natural pool principal and up to 14 people. Also rent in the same building, wooden house can accommodate 6 people. Located in a protected park in the Sierra de Madrid, with beautiful mountain views and direct access to hiking in the countr …see more

from $434 / night

$2,478 / week

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avg. 3 hours 29 minutes

from $434 / night

(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
Warm apartment in one of the towns best connected with the rest of the Sierra de Madrid, 15 minutes from La Pedriza and the newly created National Park Guadarrama, also has direct connection with Madrid commuter and bus. The house is located near the center of town, wit …see more

from $65 / night

$383 - $565 / week

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from $65 / night

(9) Very Good 

Certificate of Excellence

26

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
Ideal for couples with child in quiet residential area with 50m pool and children's pool, tennis, paddle tennis, playground, sauna, social club and restaurant in very garden located at the foot of Mount Abantos apartment. * If deemed appropriate, a deposit (150 €) will …see more

Certificate of Excellence

from $73 / night

$496 - $583 / week

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Responds fast!
avg. 38 minutes

from $73 / night

19

La Navata Vacation apartment rental

Community of Madrid / La Navata

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
Our apartment is located on the ground floor of the chalet with views to the garden. It has two bedrooms, living room, kitchen and bathroom. You can accommodate 4 people and is located two blocks from bus stop, direct to the Centre of Madrid. The space to enjoy the tra …see more

from $86 / night

$599 / week

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from $86 / night

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
We María Inés and Pedro Dubié and hope that you feel comfortable in our house. Deo Gratias and House of familias.Fue our home and now is home to those looking to relax and have fun with family and friends in a different and original place. The views from the living room …see more

from $372 / night

$1,487 / week

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from $372 / night

15

Robledo de Chavela Vacation apartment rental

Community of Madrid / Robledo de Chavela

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
La Pizarra es un bungalow de 35m2 perfecto para una pareja e incluso para compartir con 1 ó 2 niños. Está compuesto por un dormitorio con cama de matrimonio, un salón-comedor con cocina americana y sofá/cama. Un cuarto de baño con bañera infantil. En su parte exterior …see more

from $87 / night

$607 / week

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Responds fast!
avg. 3 hours 17 minutes

from $87 / night

14

Becerril de la Sierra ski gite to rent.

Community of Madrid / Becerril de la Sierra

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ski
  • Child friendly
  • Pet friendly
House in Madrid Lolita charm built in the 70s in Becerril de la Sierra, this fully updated while retaining the essence of yesteryear. It is characterized as a rural house in Madrid charming, cozy rural accommodation in the Sierra de Madrid with all the amenities you can …see more

from $149 / night

$1,041 / week

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from $149 / night

27

Vacation chalet in Robledo de Chavela

Community of Madrid / Robledo de Chavela

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 2 nights min
  • Child friendly
  • Pet friendly
The villa has two floors and a large garden. On the ground floor we can find the living room with a cozy fireplace and a large table. The kitchen is completely equipped. In addition, on this floor there is a bathroom and a cozy conservatory overlooking the mountains. Th …see more

from $248 / night

$1,735 / week

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from $248 / night

(6) Very Good 

11

Vacation home in Cercedilla

Community of Madrid / Cercedilla

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Ask about pets
Stone house built in 1925, completely renovated, retains some of the original, convenient and comfortable to spend a few days in the Sierra, family room furniture. Features: It has 3 double rooms outside, two bathrooms with shower, living room with sofa bed and TV, kitc …see more

from $75 / night

$521 - $1,388 / week

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from $75 / night

(1) Excellent 

15

Cercedilla Vacation home rental

Community of Madrid / Cercedilla

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Lovely and comfortable house 100 m. in Cercedilla. A 10 minute walk from the train station and 10 meters from the bus to Madrid. They can comfortably sleep up to 6 people. It has all the amenities necessary. It has 2 living rooms, 2 bathrooms, 3 bedrooms, kitchen, 2 gar …see more

from $124 / night

$868 / week

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from $124 / night

22

Vacation apartment rental

Community of Madrid / Galapagar

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden
new apartments in the Sierra de Madrid, Galapagar. Excellent area for sightseeing, hiking, eating at the best restaurants, activities, entertainment, culture, well connected. The private swimming pool, tennis court, wifi, kitchen and common areas .. Services Tennis cour …see more

from $122 / night

$619 / week

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Responds fast!
avg. 3 hours 26 minutes

from $122 / night

(1) Excellent 

28

Vacation apartment with shared pool in Robledo de Chavela

Community of Madrid / Robledo de Chavela

4 11 Min stay varies

  • 4 bedrooms
  • Sleeps 11
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Quartzite Rural House consists of: large living room with access to the covered porch with view of pool and Valley bedroom quadruple (1 double + 2 single) 1 triple bedroom (bunk + individual) 2 double bedrooms (2 beds in each) 2 bathrooms 1 toilet kitchen fully equipped …see more

from $273 / night

$1,908 / week

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Responds fast!
avg. 3 hours 17 minutes

from $273 / night

10

Apartment rental in Collado Villalba with shared pool

Community of Madrid / Collado Villalba

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
functional and comfortable apartment complete 65 m. upstairs bedroom, bathroom with shower, living room-kitchen, courtyard garden of 25 m., garage, Wifi fiber, gated community, pool and garden. In the heart of the Sierra de Madrid, well connected by A6, cinemas, superma …see more

from $69 / night

$403 / week

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from $69 / night

(4) Very Good 

19

Valdemanco Vacation cottage rental

Community of Madrid / Valdemanco

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
  • Ask about pets
Accommodation consisting of 2 Villa Semidetached houses with 8 seats each, are rented together or separately. Each chalet has 3 bedrooms, 3 bathrooms, rural kitchen with BBQ, very spacious living room, Garden, terrace, kitchen with all the necessary accessories. Each ch …see more

from $248 / night

$1,735 / week

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from $248 / night

(9) Excellent 

24

Vacation 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
Equipment: Fully furnished, kitchen appliances Heating. Appliances: refrigerator, microwave, electric oven, toaster, Dishwasher Audio Video: 4 television, wi-fi Outside: barbecue, outdoor furniture, tables, chairs and deck chairs, fenced private pool, porch linen: blank …see more

from $87 / night

$607 / week

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Responds fast!
avg. 2 hours 37 minutes

from $87 / night

11

San Lorenzo de El Escorial Vacation home rental

Community of Madrid / San Lorenzo de El Escorial

4 6 Min stay varies

  • 4 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Sunny house with private garden in prime location with barbecue, pool and paddle tennis courts in San Lorenzo del Escorial, in a natural setting of great beauty, located on Mount Abantos. The best place for a few days of rest and leisure. A ten minute walk from the hist …see more

from $112 / night

$682 - $1,177 / week

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from $112 / 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
House on one floor with spectacular natural park views. If you're looking to enjoy your family, friends, trips into the countryside, this villa with colonial decor immerses you in calm, relaxation and peace with nature. The space is unique for its views and tranquility. …see more

from $310 / night

$1,215 - $1,425 / week

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from $310 / night

17

Cercedilla Vacation home rental

Community of Madrid / Cercedilla

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Child friendly
  • Private garden
Canadian house with totally individual garden, accessed by main house. Wonderful Hospitality, pure mountain air, ideal hiking and biking. The village offers everything for tourists .. In the house there is a fridge, microwave, kitchenware, linens, towels, TV, Wifi, etc. …see more

from $77 / night

$538 / week

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from $77 / night

(1) Excellent 

15

El Escorial Vacation 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
In the municipality of El Escorial, on the slopes of the Sierra de Guadarrama, I offer a detached single-family housing -including an apartment with separate entrance comprising entrance hall, two large rooms and bathroom with tub. A stay living-dining-kitchen. It has a …see more

from $69 / night

$403 - $611 / week

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Responds fast!
avg. 3 hours 25 minutes

from $69 / night

14

Vacation 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
Excellent location opposite the mountain, river and Chapel of the Sacra rock. Panoramic views and unique completely open and unobstructed mountain and mundo.Privacidad ball and privacy, ideal for relaxation, meditation, relaxation. limpio.Posibilidad fresh air and varie …see more

from $106 / night

$738 / week

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from $106 / night