Cottage vacation rentals in Sierra de Guadarrama

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Top-rated cottage rentals in Sierra de Guadarrama

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Guest favorite

A charming house features a combination of stone and wood exteriors, set against a backdrop of a large, textured tree. The structure has a prominent stone chimney and a wooden balcony above a garage area, situated in a natural, rustic landscape.

Cottage in Cerro Matallera

4.91 out of 5 average rating, 139 reviews

Casa Matallera - Mountain Retreat near Madrid

Beautiful house in Sierra de la Cabrera Guadarrama, 40 minutes from Madrid. Hiking, cycling, horse riding, leisure activities for families & a varied gastronomic offer. The loveliest municipal pool is just 10 km away. Very quiet area, ideal for disconnecting, resting, or working remotely. Large dining room, living room. Amazing fireplace and very well-equipped kitchen. Ideal for family gatherings, reduced weddings (30/40 pax) in spring and autumn (events subject to small extra payment to agree).

Top guest favorite

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

4.97 out of 5 average rating, 100 reviews

Villa with pool and mountain views

Disfruta de la Sierra de Madrid en nuestra preciosa casa de piedra rodeada de vegetación. Te despertarás cada mañana con vistas a un increíble jardín con árboles frutales y flores y podrás tomar el desayuno en una gran terraza mirando el monte. Detalles como la escalera de caracol o los arcos de piedra hacen de nuestra casa un sitio especial y diferente. La piscina es súper refrescante durante estos meses y tiene iluminación nocturna para que puedas disfrutar de un baño bajo las estrellas.

Superhost

A terrace features a glass table surrounded by chairs, with a large umbrella providing shade. Scenic views of the Atazar reservoir and surrounding hills can be seen in the background, showcasing the natural beauty of the location during sunset.

Cottage in Cervera de Buitrago

4.88 out of 5 average rating, 153 reviews

Alto de Cervera, spectacular views

Magnificent house with spectacular views of the Atazar reservoir, comfortable house with two floors, 2 bedrooms upstairs and three downstairs. Rooms are opened according to the number of people, common areas are left available throughout the house. A bathroom and toilet downstairs and a bathroom upstairs. Kitchen on both floors. Great terrace where you can enjoy the sunset and the starry sky and glass porch overlooking the reservoir downstairs. We have installed a detachable pool for summer.

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, 158 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 favorite

The exterior of a charming house is covered in vibrant autumn leaves, creating a striking contrast against a soft blanket of snow. Stone steps lead to the entrance, flanked by greenery and lampposts, while the landscape is adorned with seasonal colors.

Cottage in Miraflores de la Sierra

4.91 out of 5 average rating, 290 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

Guest favorite

An open loft area is highlighted by exposed wooden beams and a vibrant wall decoration. A potted plant adds a touch of greenery. Natural light pours in through skylights, illuminating the rustic design that complements the stone walls.

Cottage in Hoyo de la Guija

4.86 out of 5 average rating, 182 reviews

Peguerinos: house with jacuzzi, fireplace and garden

Disconnect and relax 1 hour from Madrid, in an authentic hamlet of the Sierra de Guadarrama. "La Margarita" is a charming house, very cozy, built on an old stone barn, fully restored with fine materials. It has a jacuzzi, fireplace, wifi and a small private garden with barbecue. Very close to a swamp and large pine forests: hiking, mountain biking, horseback riding or donkey, mushroom picking. Ideal for romantic getaways, relaxing or enjoying as a family.

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

4.85 out of 5 average rating, 211 reviews

Cozy and bright country house. 22-meter terrace

CLOSED PLOT WITH ANTI CATERPILLAR TREATMENT Murmullo del Río..Nature tops..Relax..Evening in the company of the moon... Unique skies.. Unique views of the majestic Mount of Sta Catalina. Águilas .. rides to the river that is 50 meters away... smell of green.. cozy house.. umbrella hammocks.. barbecue .....pool in the development ... fresh nights.. pure air... quiet mornings and also everything you need: wifi, air conditioning, coffee, TV, board games

Superhost

A modern dining area is showcased with a wooden table set for a meal. Elegant dishware is arranged alongside glasses, while a stone oven adds character to the background. Decorative elements, such as vases and candles, enhance the inviting ambiance of the space.

Cottage in Valdilecha

4.9 out of 5 average rating, 166 reviews

Your Rural House

Forget the worries in this great home - it's an oasis of tranquility! A wonderful diaphanous apartment that has no lack of detail. It is located in a beautiful village 35km from Madrid. Perfect for recharging batteries in a relaxed atmosphere or spending a romantic weekend as a couple. It has a small garden in the back with a barbecue, stove and mini pool. It is equipped with full kitchen and a wood-fired oven. You can see the Packs available in photos.

Top guest favorite

A scenic view of the casita nestled among lush greenery, surrounded by a diverse variety of trees. The rustic stone structure features a red-tiled roof, harmonizing with the natural landscape of rolling hills and varied vegetation.

Cottage in Los Molinos

4.94 out of 5 average rating, 215 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 favorite

A covered terrace features stylish dark wicker furniture, including two armchairs and a small table. The view overlooks a sprawling landscape of rooftops and greenery under a cloudy sky, enhancing the sense of open space and tranquility.

Cottage in El Espinar

4.88 out of 5 average rating, 112 reviews

House with beautiful views. VUT-40/868

Casita with beautiful views and garden, of modern construction, ideal for disconnecting in nature. Urbanización Los Angeles de San Rafael, with entertainment for all ages, golf, water sky cable, water slides, water sports, adventure sports, spa, lake and pools. 20 minutes from Segovia and El Escorial and next to the Sierra de Guadarrama. Feel free to ask us any questions or information about the activities available in the area!!!

Guest favorite

A bright bedroom features two spacious beds placed against a rustic wooden wall. Each bed is adorned with white linens and colorful decorative pillows. A glass door opens to a small balcony, allowing natural light to fill the room.

Cottage in El Vellón

4.94 out of 5 average rating, 104 reviews

Esencia de Maryvan Rural House

Esencia de Maryvan is a charming country house located in the urban area of the town of El Vellón. Composed of two floors with independent access to each of them. The house will be rented in full. Check the number of people. Enjoy the large outdoor spaces such as the garden, barbecue, pool and large outdoor lounge. The house is located just 47 km from Madrid. You can also enjoy a relaxing stay and environment during your stay.

Top guest favorite

A sleeping area features a spacious bed with a leafy patterned duvet and matching pillows. A lamp is placed beside the bed, providing soft illumination. The room's wooden walls and round mirror add warmth, while a unique window design allows natural light to filter in.

Cottage in Rozas de Puerto Real

4.9 out of 5 average rating, 147 reviews

The Keep

A una hora de Madrid, de Toledo y de Ávila. Junto a su ya famosa Ruta de los Castaños. En el Valle del Tietar , a menos de 15 km de numerosas pozas que permiten el baño y del pantano de San Juan . Ideal para descansar. Ubicado en un entorno rural tranquilo, zona ZEPA, y rodeado de una dehesa, habitada por numerosos animales. Preciosos paseos y rutas, cerca del embalse de los Morales y a los pies del Alto del Mirlo.