
Holiday houses in Sierra de Guadarrama
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Top-rated holiday rentals in Sierra de Guadarrama
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Casa Salamandra. With swimming pool, next to the swamp
Privileged environment, surrounded by pine forests next to the swamp, located between three of the most representative cities of Spain: Toledo, Ávila and Madrid. Very interesting design house in the shape of an A, with a lot of light, in the middle of nature, with views of the lake and mountains. Private garden of 1500 m2 with private pool. Furnished terrace with BBQ. 7 km from San Martín de Valdeiglesias (where all kinds of services are available). Possibility of carrying out a variety of aquatic activities.

COVA Caballar. Large garden and beautiful sunsets
WE HAVE A GREAT KITCHEN next to the garden, porch and barbecue. La COVA is located in Caballar, Segovia. Fully renovated. It has 5 bedrooms, 2 large equipped kitchens, terrace, garden with porch, 2 independent living rooms, 3 bathrooms, a toilet, and WiFi connection. It is 5 km from Turégano. And also very close to places like the Hoces del Duratón, La Granja, Pedraza, Valsaín and Segovia Capital. Capacity subject to current epidemiological regulations. Registration Number C.R.-40/720

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.

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.

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.

Amazing garden and charming villa in the mountains
A beautiful renovated house from the 60s on a large 1500m plot with a private pool and large trees. Tranquility and privacy in the heart of the forest in one of the most beautiful villages in the Sierra de Madrid. You can walk for days through the forests and mountains of Guadarrama National Park from your doorstep. Great for two families to share. Totally charmingly equipped. Fireplace, gas BBQ, ping-pong, trampoline, slide, basketball basket, Wi-Fi, and more

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.

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.

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.

El Covanchon Rural House
Cozy country house on the outskirts of a village in Segovia. Built in wood and stone and surrounded by a beautiful garden with excellent views. The location is ideal as it is within the village but maintains privacy by being on the outskirts and you can walk to many routes in the area. The village has a municipal swimming pool located in a magnificent juniper forest 5 minutes from the house.

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.

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.
Popular amenities for Sierra de Guadarrama holiday rentals
Other great holiday rentals in Sierra de Guadarrama

Casa Josephine Riofrío - retreat 1 hour from Madrid

The Rascafria granary

La Favorita (Mataelpino)

Lovely place with a pool in summer

House with indoor pool in Rascafría, 1 hour from Madrid

A nice chalet with an indoor fireplace and views.

House next to the Pantano de Burguillo

House with a garden and pool in Navacerrada
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
- Santiago Bernabéu Stadium
- Parque Warner Madrid
- Chueca
- El Retiro Park
- Metropolitano Stadium
- La Latina
- Plaza Mayor
- Feria de Madrid
- Las Ventas Bullring
- WiZink Center
- Royal Palace of Madrid
- Teatro Lope de Vega
- Faunia
- Complutense University of Madrid
- Aqueduct of Segovia
- Parque de Atracciones de Madrid
- Teatro Real
- Matadero Madrid
- Madrid Río
- Mercado De San Miguel
- Puerta de Toledo
- Parque Europa
- Círculo de Bellas Artes
- Caja Mágica





