Holiday rentals in Guadarrama

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Top-rated holiday rentals in Guadarrama

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

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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

4.96 out of 5 average rating, 24 reviews

The Rascafria granary

Desconecta de la rutina en este alojamiento único en la Sierra de Guadarrama, IG @elpajarderascafria. Situado en el precioso pueblo de Rascafría, desde donde salen las mejores rutas hacia Peñalara. Ideal para descansar en familia en todas las épocas del año. También organizamos retiros (IG @nkalmaretreats) para grupos o celebraciones con diversos talleres. La piscina cuenta con un banco de masajes, en verano. En invierno se puede disfrutar de la chimenea. A una hora de Madrid y de Segovia.

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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 Los Angeles de San Rafael

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.

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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.

LocationFamilyNearby

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, 125 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.

LocationFamilyCleanliness

Guest favourite

A serene garden area is presented, featuring a stone well surrounded by vibrant hydrangea flowers. A stone bench provides a peaceful seating spot, while lush greenery frames the scene, creating a secluded and inviting atmosphere. Natural light enhances the tranquility of the space.

Cottage in Guadarrama

4.92 out of 5 average rating, 50 reviews

No, without

La Bila was built in 1947, in a stone house colony. Its interior is completely renovated. It has a spectacular swimming pool for the summer and a garden to enjoy at all times of the year. The plot is completely fenced and away from the road, it is very quiet. Thanks to its isolation, both in summer and winter the interior temperature is very pleasant. The kitchen is well-equipped in terms of kitchenware and utensils, and its spaciousness is also noteworthy.

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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

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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

4.98 out of 5 average rating, 124 reviews

Villa with pool and mountain views

Enjoy the Sierra de Madrid in our beautiful stone house surrounded by greenery. You'll wake up every morning to an incredible garden with fruit trees and flowers, and you can have breakfast on a large terrace overlooking the mountain. Details such as the spiral staircase or the stone arches make our house a special and different place. The pool is super refreshing during these months and has night lighting so you can enjoy a swim under the stars.

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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, 245 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.

LocationFamilyPool

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

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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, 161 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.

LocationFamilyBiking

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, 119 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.

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Top guest favourite

Cottage in Los Molinos

4.99 out of 5 average rating, 231 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.

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