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Vacation rentals in Sierra de Guadarrama

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Top-rated vacation rentals in Sierra de Guadarrama

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

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Guest favorite
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.

Superhost
A wooden terrace showcases two armchairs and a small table, surrounded by lush greenery. The scenic view of rolling hills and trees highlights the natural beauty of the area, providing a peaceful setting for relaxation.
Cottage in Río Cofio
4.84 out of 5 average rating, 241 reviews

Cozy and bright country house. 22-meter terrace

CLOSED PLOT WITH ANTI CATERPILLAR TREATMENT Murmur of the river..Nature at its best..Relax..Evenings in the company of the moon... Unique skies.. Clear views of the majestic mountain of Sta Catalina. Eagles... walks to the river that is 50 meters away... smell of greenery... cozy house... Paraguayan hammocks... barbecue... swimming pool in the development... cool nights... pure air... quiet mornings and also everything you need: wifi, air conditioning, coffee, TV, board games

Guest favorite
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, 113 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 favorite
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, 169 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 favorite
Cottage in Miraflores de la Sierra
4.91 out of 5 average rating, 315 reviews

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

Superhost
A spacious terrace is equipped with comfortable seating and a low table, offering a perfect spot for relaxation. Lush greenery and scenic mountain views surround the area, creating a serene outdoor space. Soft lighting accents are unobtrusively integrated, enhancing the tranquil atmosphere.
Vacation home in Mijares
4.85 out of 5 average rating, 111 reviews

Gredos Starlight House | Mountain Views

Are you looking for a perfect place to explore the Sierra de Gredos? Our house is the ideal place for you We are located in Mijares, a small town at the foot of the Sierra. An incomparable natural environment of mountains, forests and rivers. In the house you will find everything you need for a comfortable and relaxing stay. The ideal place to rest with family, partner or pets. Book your stay and enjoy an unforgettable vacation among mountains and stars.

Top guest favorite
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, 241 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 favorite
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, 158 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 favorite
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, 111 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 favorite
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, 150 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 favorite
Cottage in Los Molinos
4.99 out of 5 average rating, 228 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 favorite
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, 204 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.

Popular amenities for Sierra de Guadarrama vacation rentals

Frequently Asked Questions

  • 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.

  • What is the history of Sierra de Guadarrama?

    Sierra de Guadarrama’s history includes Roman-era trade routes, centuries of pastoral traditions, and forest conservation practices dating back generations. Its mountain parks now preserve cultural and ecological heritage while supporting outdoor recreation.

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