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House holiday rentals in Sierra de Guadarrama

Find and book unique houses on Airbnb

Top-rated house rentals in Sierra de Guadarrama

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

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Superhost
A spacious living area is highlighted by a large mural depicting a lakeside village. A comfortable sofa adorned with orange cushions faces a wooden dining table, while a small workspace and decorative plants add to the inviting ambiance.
Home in San Martín de Valdeiglesias
4.79 out of 5 average rating, 109 reviews

Nature in the San Juan swamp

In the middle of nature, surrounded by pine trees and 200 meters from the Bungalows beach. First floor: living room with terrace with wonderful views of the pine forest and the surroundings of the swamp. Double bedroom, bedroom with two beds, bathroom and kitchen. Ground floor: large multifunctional living room with bar, ping pong, billiards, dartboard and an apartment with two beds. A place that invites you to relax with the possibility of doing nautical and multi-adventure activities in the swamp area.

Guest favourite
The house features a modern A-frame design with large windows, situated amidst lush greenery. Pine trees surround the property, adding to the natural setting. A pathway leads to the entrance, blending harmoniously with the landscaped garden.
Home in San Martín de Valdeiglesias
4.91 out of 5 average rating, 117 reviews

Casa Salamandra. With swimming pool, next to the swamp

A privileged environment, surrounded by pine trees next to a marsh, located between three of the most representative cities in Spain: Toledo, Avila and Madrid. Very interesting design house in the shape of an A, with lots 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 Martin de Valdeiglesias (where all kinds of services are available). Ability to carry out diversity of water activities.

Top 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
5 out of 5 average rating, 19 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.

Top guest favourite
A rustic house, featuring a mix of wooden and stone exteriors, is surrounded by lush greenery and tall trees. The structure displays a layered roof with clay tiles, while the natural landscape provides a serene backdrop, emphasizing the connection with nature.
Home in Arroyo de la Parra
4.97 out of 5 average rating, 39 reviews

Cabaña del Burguillo

Idyllic environment surrounded by wild nature, located in a pinewood on the edge of the lake with direct access to the beach. Ideal for couples, the house consists of a spacious living room, fully equipped kitchen, bedroom with double bed and extra bed or optional cradle, bathroom and large terrace overlooking the lake. Place that invites you to rest, with the possibility of carrying out nautical and sports activities. Pets are allowed, except february, march & april due to pine processionary.

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, 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.

Guest favourite
The image depicts a rustic orange house surrounded by tall pine trees and a rocky wall. A green gate provides access to the property. Rolling hills are visible in the background under a clear blue sky, showcasing the natural landscape.
Home in Cenicientos
4.86 out of 5 average rating, 162 reviews

House in the countryside to disconnect in Madrid. Animals

Old rehabilitated guard house, 150 m2, with a hall, living room with fireplace, two bedrooms, two bathrooms and a kitchen. The house is part of a 4-hectare estate, with elements of an old farm: garden, woodshed, henhouse, dovecote, two waterwheels, laundry, old fruit trees, etc. Ideal for relaxing, celebrating or enjoying stays with children, who can learn and participate in the tasks of caring for the animals and the farm. There are several walking routes nearby.

Guest favourite
An outdoor patio area features a stone structure with wooden beams. A small white table and two chairs are positioned on a stone floor. Colorful flowers bloom in the background, and a lush green lawn extends beyond the patio.
Home in Palancares
4.89 out of 5 average rating, 200 reviews

Apartamento Ocejón I mean Parents

Places of interest: Valverde de los Arroyos, Tamajón, Incredible views, Hayedo Tejera Negra. Lush oak forests, Pico Ocejón, Las Chorreras Despeñalagua, the route of the Black Villages, light, the comfort of the bed, the cozy space. You'll love my place because it's newly opened, all designed to be very comfortable, incredible views and very individual. Ideal for couples getaways. My accommodation is good for couples, adventurers, and pets.

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

Guest favourite
A spacious terrace features a comfortable seating arrangement with soft cushions, overlooking a stunning lake and surrounding mountains. The reflection of the landscape shimmers in the infinity pool, creating a serene connection between the outdoor space and nature.
Home in Ávila‎
4.87 out of 5 average rating, 75 reviews

Spectacular views one hour from Madrid

Disconnect and enjoy a paradise just an hour from Madrid. Spectacular views, infinity pool, fireplace, garden with barbecue, walking access to the lake and everything you need to enjoy with your family or friends. No parties. No smoking. No pets allowed. Late check-out ONLY WITH PRIOR NOTICE: 120 euros Tourist license: CRU05005000026499 According to Decree 933, we will request guest data in accordance with this regulation.

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, 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!

Guest favourite
Home in San Martín de Valdeiglesias
4.91 out of 5 average rating, 163 reviews

Romantic Triplex with Jacuzzi + Musical Thread

Descubre Casa Capricho, un espacio pensado para disfrutar ✨ Su gran protagonista es el jacuzzi privado en la habitación principal, disponible todo el año, acompañado de hilo musical en toda la casa 🎶 A menos de 1 hora de Madrid, es ideal para escapadas en pareja, con amigos o en familia. Relájate, desconecta y crea el ambiente perfecto en cada momento 💫

Guest favourite
A private swimming pool is presented alongside a well-maintained garden area. The pool features a light blue water surface, surrounded by a paved deck and bordered by a black metal fence. The charming house in the background showcases a stone facade and manicured trees.
Home in Ávila‎
4.95 out of 5 average rating, 108 reviews

A little house in the countryside within the city

A beautiful country house in the city of Ávila. Ideal, cozy house with careful details designed for you to enjoy an independent stay in the middle of nature and at the same time discover the walled city. Feel at home and disconnect in the countryside, or enjoy just a 10-minute walk from the World Heritage City.

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