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Holiday houses in Guadarrama Pass

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Top-rated holiday rentals in Guadarrama Pass

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

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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 El Espinar
4.96 out of 5 average rating, 170 reviews

The corner of your dreams.

Isolation, peace, and enjoyment in its purest state. A unique experience, a magical feeling of having your own wooden house in the middle of the mountain. A 3000m2 private oak wood house (for you) within a community with 24-hour security, swimming pools, hiking trails, golf courses, horseback riding, restaurants, a supermarket, a lake with water activities, and a spa. Each season offers its possibilities, from its cozy fireplace to its barbecues, through a spring full of flowers.

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
4.95 out of 5 average rating, 22 reviews

The Rascafria granary

Escape the daily grind at this unique accommodation in the Sierra de Guadarrama, IG @elpajarderascafria. Located in the beautiful town of Rascafría, the starting point for the best trails to Peñalara. Perfect for a family holiday at any time of the year. We also organise retreats (IG @nkalmaretreats) for groups or celebrations, featuring a range of workshops. The pool has a massage bench in summer. In winter you can enjoy the fireplace. One hour from Madrid and Segovia.

Superhost
The exterior area is softly illuminated at dusk, highlighting a pool surrounded by landscaped gardens. A large rock feature adorned with white stones is showcased in front, and the ambient light enhances the tranquil atmosphere of the outdoor space.
Home in Guadarrama
4.94 out of 5 average rating, 90 reviews

Luxury villa in the Sierra de Madrid with no steps

Spectacularly designed and detached villa, unique in the area. Built in 2007. 2000-square-meter plot with pool, barbecue grill, and kennels. No architectural barrier on the entire property! Residential Complex "Las Cabezuelas", Municipality of Guadarrama (Madrid). Near downtown Alpedrete, next to Sierra de Guadarrama and Navacerrada. Several TV programs have been recorded at the villa, such as: Married with the naked eye, consensual exchange, come to dinner with me, etc.

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
4.95 out of 5 average rating, 119 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
An outdoor space features a grill and a dining table surrounded by green chairs. A seating area with a sofa and a jacuzzi enhances relaxation. Lush grass and potted plants create a natural atmosphere, complemented by a shaded area for comfortable gatherings.
Home in El Espinar
4.99 out of 5 average rating, 71 reviews

El Espinar: BBQ and winter Jacuzzi

Bienvenidos a nuestra casa en El Espinar, entre Ávila, Segovia y Madrid, y muy cerca de los paisajes más bonitos de la Sierra Norte. Recién reformada, es un lugar cómodo y tranquilo, ideal para teletrabajar, pasar unas vacaciones o simplemente desconectar unos días. Cuenta con barbacoa de gran capacidad, paellero a gas, jacuzzi, piscina, wifi de alta velocidad, zona de trabajo, smart TV en salón y dormitorio, chillout con sofá y tumbonas. Uso totalmente privado.

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
4.84 out of 5 average rating, 64 reviews

Lovely place with a pool in summer

Beautiful home, registered in Registry E. T. ref. no. VT-14878, two bedrooms (one double), two bathrooms, full kitchen. Separate entrance. It is the ground floor of a two-story villa (the owners live on the upper floor). Pets are allowed (max 2 medium) at an additional cost of €5 per day/pet. Independent access to the garden. Residential area. Downtown Los Molinos with all amenities a 7-minute walk away, two buses and commuter train connect with Madrid

Top 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
4.94 out of 5 average rating, 244 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.

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
5 out of 5 average rating, 20 reviews

Casa Josephine Riofrío - retreat 1 hour from Madrid

Casa Josephine Riofrío B&B is a capsule of peace and rest one hour from Madrid, in a quiet village in a protected landscape at the foot of the mountain. A place where time passes differently. A retreat, a space to create, rest, or work at a different pace. A house completely renovated in 2022 with an architectural and interior design project based on geometry, materials and proportions, signed by Casa Josephine Studio. License VUT 40/718

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
4.99 out of 5 average rating, 160 reviews

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.

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
4.97 out of 5 average rating, 117 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.

Top Guest favourite
A spacious living area features wooden ceilings and large windows that provide views of the outdoors. Comfortable seating is arranged around a central coffee table, while a wood stove adds warmth. A dining area is visible in the background, enhancing the inviting atmosphere.
Cabin in Pajares de Pedraza
5 out of 5 average rating, 37 reviews

The Pillars of the Sierra

Discover this cozy cabin by the Cega River! With a privileged location, enjoy a retreat in the middle of nature, which combines the charm of the rustic with modern comfort and a short distance from the historic village of Pedraza. Equipped with all the amenities and a charming Nordic touch, it is the perfect retreat to escape the urban hustle and enjoy the tranquility of the natural environment.

Top Guest favourite
Cottage in Los Molinos
4.99 out of 5 average rating, 230 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.

Popular amenities for Guadarrama Pass holiday rentals

  1. Airbnb
  2. Spain
  3. Castile and León
  4. Segovia
  5. Guadarrama Pass