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

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78 Vacation rentals

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19

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

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from $196 / night

$1,372 / week

Responds fast!
avg. 3 hours 39 minutes

from $196 / night

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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

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from $288 / night

$1,728 / week

Responds fast!
avg. 3 hours 49 minutes

from $288 / night

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18

Alpedrete Vacation 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

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

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from $116 / night

$691 - $864 / week

from $116 / night

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24

San Lorenzo de El Escorial Vacation 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

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

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from $98 / night

$605 / week

Responds fast!
avg. 2 hours 9 minutes

from $98 / night

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“a lovely appartment in a lovely location”

Reviewed 3 Jan 2012

We stayed in the appartment in San Lorenzo over the christmas period in 2011 - the town of san Lorenzo is in a beautiful location and the appartment itself has wonderful views over the mountains from … More

“Very nice appartment for visit of central Spain”

Reviewed 3 Nov 2011

We enjoyed very much staying in this appartment. We stayed one week. City center is in walking distance, with cafes and shops. One supermarket is there as well, with same value-for-money as the big … More

“Hermoso lugar, excelente apartamento”

Reviewed 11 Jan 2014

Llegamos a santiago de el escorial sin saber que nos encontraríamos, y la verdad que nos sorprendió. El lugar es hermoso, muy turistico, con mucho para dar. La ubicacion del apartamento es excelente,… More

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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

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from $46 / night

$323 / week

Responds fast!
avg. 2 hours 32 minutes

from $46 / night

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21

Vacation 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

This apartment, located in Collado Villalba, is ideal for 5 vacationers. It offers 3 bedrooms, a pool access and a furnished balcony. The lounge is perfect for unwinding after a day of exploration. Curl up on the comfortable sofa and enjoy a good book or take advantage …see more

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from $82 / night

$443 - $515 / week

Responds fast!
avg. 2 hours 4 minutes

from $82 / night

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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

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Pricing unknown

Pricing unknown

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18

Robledo de Chavela Vacation 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

This studio, located in Robledo de Chavela, is ideal for 3 vacationers. It is perfect for unwinding after a day of exploration. Curl up on the comfortable sofa and enjoy a good book. The kitchen is well-equipped for cooking up your favorite meals. Enjoy your feast arou …see more

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from $97 / night

$623 / week

Responds fast!
avg. 2 hours 15 minutes

from $97 / 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

This apartment, located in Cercedilla, is ideal for 5 vacationers. It offers a bedroom. The lounge is perfect for unwinding after a day of exploration. Curl up on the comfortable sofa and enjoy a good book in front of the fireplace. The kitchen is well-equipped for co …see more

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from $80 / night

$542 - $605 / week

Responds fast!
avg. 2 hours 4 minutes

from $80 / 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

This house, located in Manzanares el Real, is ideal for 8 vacationers. It offers 4 bedrooms, a furnished terrace and WiFi. The lounge is perfect for unwinding after a day of exploration. Curl up on the comfortable sofa and enjoy a good book in front of the fireplace or …see more

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from $204 / night

$1,129 - $1,237 / week

Responds fast!
avg. 2 hours 15 minutes

from $204 / night

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35

Vacation villa rental

Community of Madrid / Hoyo de Manzanares

6 13 min stay varies

6 bedrooms
sleeps 13
min stay varies

Swimming pool
Child friendly
Private garden

This villa, located in Hoyo de Manzanares, is ideal for 13 vacationers. It offers 5 bedrooms, a private pool, an enclosed garden and WiFi. The lounge is perfect for unwinding after a day of exploration. Curl up on the comfortable sofa and enjoy a good book in front of …see more

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from $636 / night

$4,452 / week

Responds fast!
avg. 2 hours 46 minutes

from $636 / night

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31

Vacation 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

The villa has two floors and a large garden. On the ground floor we 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. The up …see more

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from $288 / night

$2,016 / week

from $288 / 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

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

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from $288 / night

$1,728 / week

Responds fast!
avg. 3 hours 15 minutes

from $288 / night

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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

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from $346 / night

$1,325 / week

from $346 / night

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32

Vacation 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

Rural house with charm in the mountains of Madrid. Designed by interior designers and with all the comforts and details for all types of groups: ideal for families, although also designed for groups of friends who want to spend a few days in contact with nature. The hou …see more

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from $231 / night

$1,613 / week

from $231 / night

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21

Vacation 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

Building Gravelines. Urbanización with large green areas. Views of the garden and the monastery. Great social and sports area with restaurant, pool, gym, tennis court, paddle tennis courts, playgrounds, etc. Bus to Madrid at the entrance station. Close to shopping area …see more

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from $69 / night

$402 / week

from $69 / night

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15

Vacation apartment in Cercedilla

Community of Madrid / Cercedilla

1 4 2 nights min

1 bedroom
sleeps 4
2 nights min

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

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from $64 / night

$377 / week

Responds fast!
avg. 1 hour 48 minutes

from $64 / night

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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

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from $130 / night

$902 / week

from $130 / night

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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

Certificate of Excellence

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from $67 / night

$398 / week

Responds fast!
avg. 3 hours 23 minutes

from $67 / night

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20

Vacation 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

It is a studio-flat with all amenities. Very quiet room to rest. perfect to enjoy the countryside and with all amenities nearby and not far from downtown situation. The comfortable and spacious beds. Come to know you'll love. Children are charged from the 2 years as an …see more

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from $58 / night

$346 - $830 / week

Responds fast!
avg. 52 minutes

from $58 / night

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33

Vacation 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

Beautiful house, located in the Berrocales urbanization of Alpedrete, 5 rooms, 3 double rooms with double bed (180cm and 160cm), two double rooms (type twin beds) 3 bathrooms, 1 living room with fireplace, another living room with .Piscina fireplace and sofa bed, barbec …see more

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from $311 / night

$1,497 - $2,281 / week

Responds fast!
avg. 2 hours 10 minutes

from $311 / night

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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

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from $69 / night

$484 - $1,290 / week

from $69 / night

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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

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from $98 / night

$686 / week

Responds fast!
avg. 49 minutes

from $98 / night

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45

Vacation 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

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

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from $74 / night

$418 / week

from $74 / night

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53

Vacation 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

Finca of 3 hectares with luxury house and main natural pool and capacity for 12 people. and a wooden guest house with three bedrooms and capacity for 6 people. Located in a protected park in the Sierra de Madrid, with beautiful views of the mountains and direct access t …see more

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from $519 / night

$2,303 / week

Responds fast!
avg. 2 hours 20 minutes

from $519 / night

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15

Robledo de Chavela Vacation 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

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

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from $81 / night

$565 / week

from $81 / night

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28

Vacation apartment with shared pool in Robledo de Chavela

Community of Madrid / Robledo de Chavela

4 14 min stay varies

4 bedrooms
sleeps 14
min stay varies

Swimming pool
Child friendly
Air conditioning

The Casa Rural Cuarcita is composed of: Large dining room with access to covered porch overlooking the pool and valley 1 Bedroom 2 PAX (1 double) 1 bedroom 5 PAX (1 double + 2 twin) 1 bedroom 5 PAX (2 bunk beds + 1 individual) 1 bedroom 2 PAX (1 double) 2 full bathrooms …see more

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from $254 / night

$1,774 / week

from $254 / night

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29

Vacation chalet in Colmenar Viejo

Community of Madrid / Colmenar Viejo

4 8 2 nights min

4 bedrooms
sleeps 8
2 nights min

Ask about children
Ask about pets

We offer you live a few days with the Prairies where riding Clint Eastwod and Kirk Douglas fought the Romans in the natural settings of films like; “Spartacus”, “El Cid”, “The Good, the Bad. and the Ugly”, “For a Few Dollars More”…and more than 200 movies filmed in th …see more

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from $185 / night

$1,152 / week

Responds fast!
avg. 1 hour 49 minutes

from $185 / night

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4

Valdemorillo Vacation home accommodation

Community of Madrid / Valdemorillo

4 8 7 nights min

4 bedrooms
sleeps 8
7 nights min

Swimming pool
Child friendly

Detached house loft 38 km from Madrid and 13 Km of San Lorenzo del Escorial. Two plants. First floor with large living room and TV area with built-in living room, bedroom and bathroom. Second floor with 3 bedrooms and two bathrooms. separate pool. Terrace of 38 m2 barbe …see more

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from $260 / night

$1,814 / week

from $260 / night

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22

Vacation home in Cercedilla

Community of Madrid / Cercedilla

3 5 1 night min

3 bedrooms
sleeps 5
1 night min

Nearest beach 10 mi
Child friendly
Car not necessary

Triplex en el centro de Cercedilla, frente a la Iglesia de San Sebastián. Vistas espectaculares y muy tranquilo. A 5 minutos de autobuses a Madrid, y de rutas de senderismo. Gran azotea con vistas. Muy fresquita. Para una familia con 2 ó tres hijos es fantástica. A tres …see more

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from $80 / night

$460 - $694 / week

from $80 / night

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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

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from $60 / night

$356 - $526 / week

from $60 / night

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13

Vacation 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

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

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from $58 / night

$288 / week

Responds fast!
avg. 2 hours 6 minutes

from $58 / night

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15

Vacation 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

Historic building with spacious, 8 meeting rooms (open, high ceilings and natural light), area of terraces for lunch, and Chapel. Located opposite the Royal Monastery of San Lorenzo of el Escorial, choir and cross of the fallen. Located in the Valle de los Caídos (nati …see more

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from $81 / night

$563 / week

from $81 / night

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12

Ski chalet to rent in Alpedrete

Community of Madrid / Alpedrete

5 2 2 nights min

5 bedrooms
sleeps 2
2 nights min

Ski

RENTAL 2 ROOMS IN VILLA. PRICES ARE OFFERED BREAKFAST. DEPENDING ON THE NUMBER OF ROOMS REQUIRED WILL CHANGE THE PRICE. Located one kilometer ALPEDRETE VILLAGE AND YET kilometer from the town of Collado Villalba. THE DETACHED HOUSE CONSISTS OF 2 ROOMS WITH A LARGE LIVIN …see more

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from $46 / night

$242 - $403 / week

from $46 / night

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27

Vacation 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

Spectacular villa with unique charm and in an environment of great beauty. The house is situated on top of a hill, in a quiet area called the Spanish Switzerland, overlooking beautiful mountains and bucolic valleys under which the singular village of Robledo de Chavela …see more

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from $519 / night

$3,628 / week

from $519 / night

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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

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from $139 / night

$899 - $1,543 / week

from $139 / night

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5

San Lorenzo de El Escorial Vacation apartment rental

Community of Madrid / San Lorenzo de El Escorial

2 4 2 nights min

2 bedrooms
sleeps 4
2 nights min

Child friendly

It is a cozy apartment with 2 bedrooms, a study, two bathrooms, living room, kitchen and small terrace clothesline. There is also a small balcony in the living room and another in the master bedroom. It is a 10-minute walk from the town center -Extensive culture, restau …see more

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from $87 / night

$605 / week

from $87 / night

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29

Robledo de Chavela Vacation 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

El apartamento Madera tiene 175m2 y está enclavado en la planta alta de uno de los edificios que pertenecen a la finca de Roqueo de Chavela. Está distribuido de la siguiente forma: consta de 2 dormitorios dobles, 1 dormitorio con litera, 1 dormitorio individual y un a …see more

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from $184 / night

$1,286 / week

from $184 / night

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46

Vacation apartment in Galapagar

Community of Madrid / Galapagar

2 6 1 night min

2 bedrooms
sleeps 6
1 night min

Child friendly

cozy, very bright because it is south facing. It has as many services around: bus stop (Madrid, El Escorial, Colmenarejo), supermarkets, banks, post office, shops of all kinds ... Galapagar is a strategic point to visit Madrid and surroundings as San Lorenzo del Escoria …see more

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from $29 / night

$287 - $609 / week

Responds fast!
avg. 2 hours 46 minutes

from $29 / night

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18

Robledo de Chavela Vacation 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

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

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from $288 / night

$1,267 - $1,469 / week

Responds fast!
avg. 1 hour 28 minutes

from $288 / night

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