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Holiday houses in Sierra de Guadarrama

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Top-rated holiday rentals in Sierra de Guadarrama

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Guest favourite
Rental unit in San Martín de Valdeiglesias
4.96 out of 5 average rating, 116 reviews

Apartamentos de Carmen, Apartment with a double bed...

Todo para desconectar de la rutina, el apartamento Paraíso San Juan es único y muy relajante. Ideal para parejas. Una habitación privada con cama de 150 cms. Llegada autónoma: accede al alojamiento con la cerradura inteligente. Salón: sofá cama, Smart tv y chimenea eléctrica decorativa. Cocina: vitro, frigorífico y micro. Red wifi apta para trabajar. Dispone de terraza con comedor y sofá-banco chill out con vistas. Mascotas máx.8kg. La reforma ha creado una atmósfera muy natural y acogedora. La rejilla, la madera con la beta vista y los textiles vaporosos, refuerzan esta sensación de serenidad y “Slow Life”. Apartamento que cumple con la legislación vigente inscrita en el Registro de empresas turísticas de la Comunidad de Madrid con. ¿Qué hay en este alojamiento? Vistas panorámicas vistas al lago vistas a la montaña vistas al parque Wifi zona para trabajar cocina ropa de cama elementos básicos TV calefacción frigorífico patio o balcón comedor al aire libre café. Incluso existe una Cala Nudista cerca de la Senda del Yelmo para los que prefieran un baño más libre. Aunque la zona del pantano de San Juan es conocida por su increíble vino (después de todo, estamos en una región vinícola), la amplia escena gastronómica de la sierra oeste entusiasma tanto como para visitarla. Heredera de una gran tradición vinícola que se remonta al siglo XII y que aparece en los textos literarios de Jorge Manrique, Tirso de Molina o Cervantes. Si eres una persona aventurera, deportista, o simplemente te gusta divertirte, en este pequeño paraíso encontrarás todo tipo de actividades que te sorprenderán y harán que pases un día inolvidable. Las más conocidas son la senda del Canto del Guarro, donde habitan jabalíes y conejos, con numerosas encinas, olivares, pinos y viñedos, donde en otoño suelen abundar los níscalos. La senda del cerro de Valdenoches, de 14 km, es muy interesante desde el punto de vista medioambiental. La vía abandonada a Pelayos de la Presa, de 13 km., cómoda y con pocos desniveles. Hay recorridos increíbles en San Martín de Valdeiglesias, pero no siempre es fácil saber adónde ir. Subidas, bajadas, lineales… Estas rutas en bici son muy variadas. Sabemos que hay muchos amantes del ciclismo, por lo que hemos hecho un repaso de nuestra colección de Rutas en MTB en San Martín de Valdeiglesias para seleccionar las mejores. Para los pequeños y no tan pequeños… Estos lugares son perfectos para soltar adrenalina, reír y pasarlo en grande. Una vez que pruebes esa sensación, ¡estarás deseando volver! Amantes de los animales y apasionados de la naturaleza, éste es vuestro lugar. Aquí hallarás distintas ubicaciones en las cuales podrás disfrutar de unas increíbles rutas a caballo. Estos majestuosos e increíbles animales tienen la capacidad de calmar y mejorar habilidades sociales, confianza, seguridad, autoestima y controlar el estrés, entre otras tantas. La equinoterapia ayuda a superar miedos y, ¿quién no quiere superar los suyos? ¿Amante de la navegación o solo quieres pasar un día increíble con los tuyos? Sea como sea, te enseñamos diferentes puertos deportivos en los cuales encontrarás la opción de disfrutar de clases de vela, alquiler de botes y rutas, entre otras.

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
4.97 out of 5 average rating, 126 reviews

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.

Superhost
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
4.94 out of 5 average rating, 129 reviews

Dreamy treehouse

Discover the magic of this charming wooden house, an oasis of tranquility surrounded by trees and nature. Its unique design integrates modernity with the natural environment. Here, you will wake up to the sound of birds and the breeze through the trees, enjoying a cozy and sophisticated atmosphere. A few meters away, you will find hiking trails that cross landscapes where you can see horses, bulls and the beauty of the countryside. Perfect for disconnecting and relaxing.

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
4.95 out of 5 average rating, 190 reviews

My Grandmother's Little House

In a picturesque village in the Alberche Valley, at the foot of the Sierra de Gredos, La Casita de Mi Abuela is the ideal getaway for couples. Cozy and unique, it has a heated pool with hydromassage inside, perfect for relaxing and enjoying. Surrounded by hiking trails and near the Alberche River, where you can cool off in summer, this house combines rural charm with modern comfort. A special place to disconnect and experience an unforgettable getaway as a couple.

Guest favourite
A spacious living area features natural wood beams and a large window offering views of the greenery outside. Seating includes a wooden chair, a large round coffee table, and a long couch with cushions, providing a comfortable and inviting space.
Chalet in Orejanilla
4.95 out of 5 average rating, 101 reviews

Old barn, renovated

Old stone barn completely renovated. We have respected its rustic spirit by integrating it with a modern architectural design intervention and warm decoration. Take the opportunity to stay in a unique space and environment. Idyllic setting to disconnect from the city in a small village that is secluded but very close to the monumental town of Pedraza, which is a 3 km walk away. There are numerous hiking, cycling, and other activity trails in the surrounding area.

Guest favourite
A serene outdoor space showcases a modern swimming pool framed by a stone patio. A vibrant sunset casts warm hues across the sky, while a hammock and sun loungers invite relaxation. Lush greenery and mountains provide a picturesque backdrop.
Chalet in Segovia
4.98 out of 5 average rating, 123 reviews

A chalet with a pool and dreamy sunsets

Enjoy a special getaway in our cozy villa, 45 minutes from Madrid, in the private development Los Angeles de San Rafael (Segovia). A home with charm and modern design, with 3 bedrooms: 2 with a 1.50 bed and 1 with a double bed. It has 2 bathrooms, one en-suite with a dressing room. Everything is ready for you to live a few unique days. Private salt chlorination pool with thermal canvas, barbecue grill and air conditioning in all rooms for your maximum comfort.

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
4.93 out of 5 average rating, 247 reviews

The Casita de El Montecillo

Charming and fully equipped mountain house. Located in a unique natural setting: a private 65-hectare estate full of holm oaks, with a lake and a hermitage, perfect for walking, hiking in the mountains... You will be in the middle of the Sierra de Guadarrama, surrounded by mountains and nature. The perfect place for a romantic weekend, with a fireplace and jacuzzi for two. Perfect for coming with children. NO PETS ALLOWED. NO SMOKING ALLOWED.

Top Guest favourite
A wooden terrace is shown with a red hammock suspended between two trees. Surrounding greenery features various trees and shrubs, creating a serene natural setting. The distant mountains and a sunset sky add a peaceful ambiance to the scene.
Cottage in Cadalso de los Vidrios
4.98 out of 5 average rating, 122 reviews

Mountain Views with Panoramic Terrace

Less than an hour from Madrid, escape the city's noise and reconnect with the essence of nature. A haven where you can enjoy breathtaking sunsets, breakfasts with endless views, and dinners under the stars, with the absolute privacy that only a detached house can offer. Here, luxury isn't about sophistication, but about silence, fresh air, and a terrace that seems to float above the Sierra de Gredos mountains.

Guest favourite
A spacious bedroom is highlighted by large glass doors that open to a patio and garden. A comfortable bed is adorned with light linens. The outdoor area features a small table and chairs surrounded by greenery, providing a peaceful and relaxing view.
Home in Uceda
4.96 out of 5 average rating, 161 reviews

Rural Boutique with Jacuzzi and Garden

Welcome to the Pertenera house. Immerse yourself in the luxury of our stone-surrounded Jacuzzi for two, where elegance and good taste are present in every detail of this charming house. From the comfortable bed, you can gaze at the stars through the window on clear nights. Relax in our charming courtyard with a cactus garden. Your perfect getaway less than an hour from Madrid, where style meets rural!

Top Guest favourite
Cottage in Los Molinos
4.99 out of 5 average rating, 232 reviews

Recoveco Cottage

Lovely cottage, completely detached, located in the northern mountains of Madrid. Just a 5-minute walk from Los Molinos train/suburban station. And from downtown. The house is fully equipped and has 1G fiber, making your stay a perfect place for leisure, rest, or teleworking. Your perfect choice to enjoy nature with all the amenities the city can offer. No pets allowed.

Guest favourite
A transparent dome structure is nestled among trees, revealing an interior with a spacious bed and soft lighting. Surrounding greenery and flowers create a natural, serene setting, enhancing the unique design of this accommodation.
Dome in Soto del Real
4.91 out of 5 average rating, 209 reviews

Transparent Dome Room Madrid - Natura Domo

Do you want to be at one with nature as you've always dreamed of? Stay in this unique place and enjoy the sounds of nature while looking at the stars. We are the only transparent dome to enjoy with your partner in the Sierra de Madrid, just 40km from the city, with an ecosystem that surrounds it to have an unforgettable experience.

Guest favourite
The exterior of a modern house is illuminated at dusk, showcasing large windows and a spacious terrace. Surrounding greenery adds to the tranquil setting, with trees framing the scene against a clear evening sky.
Home in Collado Mediano
4.93 out of 5 average rating, 188 reviews

Detached house with terrace in a natural setting

Get away from the routine at this unique and relaxing stay, a house with lots of natural light and glazed with beautiful views in the middle of the Sierra de Madrid, a natural enclave surrounded by trees and mountains, 10 minutes from Navacerrada on foot

Popular amenities for Sierra de Guadarrama holiday rentals

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.