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Holiday houses in Sierra de Guadarrama

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Top-rated holiday rentals in Sierra de Guadarrama

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A circular stone table is surrounded by several iron chairs, set against a backdrop of lush green fields and distant mountains. The open sky overhead is bright blue, with a few wispy clouds scattered throughout.
Apartment in El Boalo

El Sonido del Silencio, P.N Guadarrama, La Pedriza

El alojamiento es una pequeña casita, hecha con materiales ecológicos en su mayor parte y amueblada y decorada con cariño para que la estancia en ella sea lo más cómoda y agradable posible. La casita está dentro de nuestro jardín, pero es independiente. La parcela tiene vistas directas al Parque Nacional de Guadarrama y es un lugar muy tranquilo, de belleza espectacular. Está a 5 minutos en coche de La Pedriza, a 20 minutos del Puerto de Navacerrada y a 35 minutos de Plaza de Castilla (Madrid).

4.97 out of 5 average rating, 300 reviews
Top Guest favourite
An overview of a stone house surrounded by lush greenery is captured from above. The building features a traditional tiled roof, arched columns on the patio, and a circular stone seating area in the landscaped garden.
Cottage in La Estación

Villa with pool and mountain views

Disfruta de la Sierra de Madrid en nuestra preciosa casa de piedra rodeada de vegetación. Te despertarás cada mañana con vistas a un increíble jardín con árboles frutales y flores y podrás tomar el desayuno en una gran terraza mirando el monte. Detalles como la escalera de caracol o los arcos de piedra hacen de nuestra casa un sitio especial y diferente. La piscina es súper refrescante durante estos meses y tiene iluminación nocturna para que puedas disfrutar de un baño bajo las estrellas.

4.97 out of 5 average rating, 130 reviews
Top Guest favourite
The exterior of a charming house is covered in vibrant autumn leaves, creating a striking contrast against a soft blanket of snow. Stone steps lead to the entrance, flanked by greenery and lampposts, while the landscape is adorned with seasonal colors.
Cottage in Miraflores de la Sierra

Increíble jardín y encantadora villa en la sierra

Preciosa casa de los 60 rehabilitada, en una gran parcela de 1500m con piscina privada y grandes árboles. Tranquilidad y privacidad en el corazón del bosque en uno de los pueblos más bonitos de la sierra de Madrid. Podrás caminar durante días por los bosques y montañas del parque nacional de Guadarrama desde la misma puerta de casa. Ideal para compartir dos familias. Totalmente equipado con mucho encanto. Chimenea, Barbacoa de gas, ping-pong, cama elástica, tobogán, canasta basket, wi-fi...

4.91 out of 5 average rating, 327 reviews
Top Guest favourite
A rustic wooden stairway leads to a cozy area featuring a modern kitchen and a heated pool. A large screen displays a calming fireplace, enhancing the relaxed ambiance. Soft lighting from candles illuminates the space, highlighting the textured stone walls and wooden accents.
Tiny home in Burgohondo

La Casita de Mi Abuela

En un pintoresco pueblo del Valle del Alberche, a los pies de la Sierra de Gredos, La Casita de Mi Abuela es el refugio ideal para parejas. Acogedora y única, cuenta con piscina climatizada con hidromasaje en su interior, perfecto para relajarse y disfrutar. Rodeada de rutas de senderismo y cerca del río Alberche, donde podrás refrescarte en verano, esta casita combina el encanto rural con la comodidad moderna. Un lugar especial para desconectar y vivir una escapada inolvidable en pareja.

4.96 out of 5 average rating, 203 reviews
Guest favourite
Cottage in Caballar

COVA Caballar. Gran jardín y preciosos atardeceres

ESTRENAMOS GRAN COCINA junto al jardín, Porche y Barbacoa. La COVA está situada en Caballar, Segovia. Totalmente reformada. Dispone de 5 dormitorios, 2 grandes cocinas equipadas, terraza, jardín con porche, 2 salones independientes, 3 baños, un aseo, y conexión WiFi. Está a 5 km de Turégano. Y también muy próxima a lugares como las Hoces del Duratón, La Granja, Pedraza, Valsaín y Segovia Capital. Aforo sujeto a normativa epidemiológica vigente. Número de Registro C.R.-40/720

4.98 out of 5 average rating, 121 reviews
Guest favourite
A modern bathroom features a freestanding white tub and a glass shower. Natural light enters through a round window, highlighting the smooth, neutral wall textures. A small wooden table holds two glasses, a bottle of wine, and a candle, adding a subtle touch of elegance.
Home in Madrid

Casita de ensueños entre árboles

Descubre la magia de esta encantadora casita de madera, un oasis de tranquilidad rodeado de árboles y naturaleza. Su diseño único integra la modernidad con el entorno natural. Aquí, despertarás con el sonido de los pájaros y la brisa entre los árboles, disfrutando de un ambiente acogedor y sofisticado. A pocos metros, encontrarás rutas de senderismo que atraviesan paisajes donde podrás ver caballos, toros y la belleza del campo. Perfecto para desconectar y relajarte.

4.94 out of 5 average rating, 143 reviews
Top Guest favourite
Cottage in Los Molinos

Recoveco Cottage

Preciosa casa de campo, completamente independiente, ubicada en la sierra norte de Madrid. A escasos 5 minutos andando desde la estación de tren/cercanías Los Molinos. Y del centro del pueblo. La casa está completamente equipada y cuenta con fibra de 1G lo que hace de tu estancia un lugar perfecto para el ocio, el descanso o el teletrabajo. Tu opción perfecta para disfrutar de la naturaleza con todos los servicios que puede ofrecer la ciudad. No se admiten mascotas.

4.99 out of 5 average rating, 237 reviews
Guest favourite
The charming stone exterior of the casita is complemented by a bright red roof. A well-maintained green lawn is bordered by a wrought iron fence. The entrance is framed by decorative gravel and edged with trees, creating a welcoming outdoor space.
Cottage in Los Molinos

La Casita de El Montecillo

Casita de montaña con encanto y completamente equipada. Situada en un entorno natural único: una finca privada de 65 Ha repleta de encinas, con un lago y una ermita, perfecta para pasear, hacer excursiones por la montaña... Estarás en plena sierra de Guadarrama, rodeado de montañas y naturaleza. El sitio perfecto para pasar un fin de semana romántico, con chimenea y jacuzzi para dos personas. Perfecto para venir con niños. NO SE ADMITEN MASCOTAS. NO SE PERMITE FUMAR.

4.93 out of 5 average rating, 253 reviews
Top Guest favourite
A rustic stone house is positioned amid a natural landscape, featuring a wooden staircase leading to the entrance. Lush greenery surrounds the property, with expansive views of the mountains in the background under a clear blue sky.
Chalet in El Boalo

Beautiful rustic house in the mountains of Madrid

Very comfortable rustic house located in the heart of the "Sierra de la Pedriza", that belongs to the Guadarrama regional park, and just half an hour from Madrid. The land of this house has an area of ​​3000 square meters with natural vegetation in the area. 5 minutes walk you will find the beautiful town "El Boalo". Impressive views of the Sierra de Madrid. Possibility of beautiful excursions, horse riding and multiple activities.

4.99 out of 5 average rating, 165 reviews
Guest favourite
A rural house constructed of stone and wood is set against a clear blue sky. Wooden shutters accent the windows, and a spacious garden features a small seating area with tables and chairs. Lush green grass and flowering plants enhance the surroundings.
Cottage in Prádena

Casa Rural El Covanchon

Acogedora Casa Rural a las afueras de un pueblo de Segovia. Construida en madera y piedra y rodeada por un precioso jardín con excelentes vistas. La ubicación es ideal ya que se encuentra dentro de el pueblo pero mantiene una intimidad por estar a las afueras y se puede acceder andando a cantidad de rutas por la zona. El pueblo cuenta con una piscina municipal ubicada en un magnífico bosque de sabinas a 5 minutos de la casa.

4.96 out of 5 average rating, 109 reviews
Guest favourite
The stone and wood house features a traditional tile roof, complemented by large windows allowing natural light. Surrounding structures include a stone wall and another building with wooden balcony, under a clear blue sky.
Cottage in Braojos

Rustic house near National Park

DISCOUNT 7 NIGHTS OR MORE 20%, ENTIRE MONTH 47% !!! Rustic house, made of stone and timber. It is localization in a little town, Braojos, 1.200 metres high, in the Central Mountains of Spain. The house is surrounded by mountains and forests, 50 minutes drive from the city of Madrid

4.93 out of 5 average rating, 413 reviews
Guest favourite
A welcoming exterior of a rustic farmhouse is surrounded by a blooming wildflower garden. A wooden table set for outdoor dining and a stone path lead through the lush greenery, framed by mature trees and distant hills, capturing the serene rural setting.
Farm stay in Braojos

Via Fera, with views of nature

Isolated rural space with capacity for 2/3 people, with a 1,000 square meter wild garden and a gazebo over the Lozoya river valley. Located in an old cattle farm. Kilometers of horizon over a score of towns in the Madrid mountains.

4.94 out of 5 average rating, 173 reviews

Popular amenities for Sierra de Guadarrama holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Sierra de Guadarrama

Guest favourite
The wooden house is surrounded by lush greenery and stone landscaping. Sunlight filters through the trees, illuminating the natural elements. A stone seating area is visible in the foreground, with the house featuring large windows and a welcoming porch.
Cottage in Los Ángeles de San Rafael

El rincón de tus Sueños.

4.95 out of 5 average rating, 174 reviews
Guest favourite
A bright and open living space features soft sectional seating in neutral tones, complemented by a small wooden table. A patterned black-and-white wall adds visual interest, while a window with a grid design allows natural light to fill the room, enhancing the overall ambiance.
Home in La Losa

Casa Josephine Riofrío - retiro a 1 h de Madrid

5.0 out of 5 average rating, 22 reviews
Guest favourite
An overhead view captures a serene outdoor space, featuring a lawn bordered by a swimming pool and sun loungers. The rustic stone walls and wooden beams contribute to a harmonious setting, while an umbrella provides shade over a dining area with modern furnishings.
Home in Rascafría

El pajar de Rascafria

4.97 out of 5 average rating, 31 reviews
Guest favourite
A peaceful garden area is displayed, featuring a stone pergola with a wooden table and a hammock. Lush green grass surrounds the space, with a clear view of the pool in the background. A mountain landscape is visible, providing a picturesque backdrop.
Home in Los Molinos

Precioso alojamiento con piscina en verano

4.85 out of 5 average rating, 74 reviews
Top Guest favourite
An outdoor seating area features wooden lounge chairs and a small table placed on a stone surface. In the background, a dining table is visible under a shaded patio, surrounded by greenery and trees, providing a relaxed atmosphere.
Cottage in Mataelpino

La Favorita Mataelpino

4.96 out of 5 average rating, 75 reviews
Guest favourite
Cottage in La Matilla

VillaTua · Piscina climatizada · 6 suites con baño

4.96 out of 5 average rating, 45 reviews
Guest favourite
An open living space features wooden beams and terracotta flooring. Natural light filters through large windows, illuminating the cozy seating area. A rustic dining table is set nearby, complementing the warm, inviting atmosphere of the home.
Cottage in Segovia

El Palomar I - casa de campo para 6 personas

4.98 out of 5 average rating, 65 reviews
Guest favourite
Chalet in Rascafría

Casa con piscina cubierta Rascafría 1h00 de Madrid

4.91 out of 5 average rating, 35 reviews

Frequently Asked Questions

  • Where is Sierra de Guadarrama located?

    Sierra de Guadarrama is a mountainous natural region stretching across the Community of Madrid. Positioned near several small towns and protected parks, it is known for scenic landscapes and forested slopes.

  • When is the best time to visit Sierra de Guadarrama?

    Late spring and summer are often recommended for hiking and outdoor activities, thanks to milder temperatures ranging from about 47–74°F (9–23°C) and lower rainfall. Autumn brings colorful foliage, while winter draws visitors interested in snow sports.

  • What are some things to do near Sierra de Guadarrama?

    Sierra de Guadarrama has opportunities to explore hiking trails, mountain biking routes, and rock climbing spots. Nearby, you can visit traditional villages, nature reserves, and local markets featuring seasonal foods and crafts.

  • How is the weather near Sierra de Guadarrama?

    Winters are cold and damp, with temperatures mostly between 27–42°F (-3–6°C) and frequent rainfall. Summers stay pleasant, often reaching 74°F (23°C) with drier conditions, making outdoor exploration especially inviting.

Destinations to explore