Cottage holiday rentals in Sierra de Guadarrama

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Top-rated cottage rentals in Sierra de Guadarrama

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Top guest favourite

Cottage

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).

Superhost

Cottage

4.9 out of 5 average rating, 119 reviews

Casa de Campo El Encinar-Pool, Paddle Tennis, Barbecue

VUT-45012320553 Single registration. No parties or noise after 11:00 PM. *Ideal for Families.* El Encinar is a 10,000m estate. Located in a natural surroundings of Encinas just 58 kilometers from Madrid and 35 from Toledo. It is accessed from a 5.5 km dirt track exit Santa Cruz del Retamar, 10 to 20min. If it rains, the only access is through the Torre de Esteban de Hambram. We'll let you know the address before we get there. The house is for 8 people but we can accommodate up to 10 sofa beds.

Guest favourite

Cottage

4.96 out of 5 average rating, 156 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 favourite

Cottage

4.9 out of 5 average rating, 105 reviews

Los Nerios Country house with pool

Los Nerios country house with swimming pool (Registered in the Tourist Companies Registry under number VT-13338), on the slopes of Pico de la Miel, a few kilometers from the Atazar reservoir. A house with lots of light, very large spaces and beautiful views of nature. Possibility of enjoying multiple sports activities: kayaking, paddle surfing, horseback riding for all levels (including children), hiking and climbing. Surrounded by a wide variety of gastronomic offerings. 12+1 pax.

Superhost

Cottage

4.91 out of 5 average rating, 288 reviews

Amazing garden and charming villa in the mountains

Beautiful house of the 60 rehabilitated, on a large plot of 1500m with 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 the very door of your home. Ideal for sharing two families. Fully equipped with a lot of charm. Fireplace, BBQ, ping-pong, trampoline, slide, basketball basket, wi-fi...

Guest favourite

Cottage

4.86 out of 5 average rating, 181 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 haystack totally rehabilitated with noble 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

Cottage

4.85 out of 5 average rating, 207 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

Guest favourite

Cottage

4.91 out of 5 average rating, 161 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 out back with a barbecue, stove and mini pool. It is equipped with full kitchen and a wood-fired oven. You can see the available packs in photos.

Guest favourite

Cottage

4.94 out of 5 average rating, 213 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 favourite

Cottage

4.94 out of 5 average rating, 101 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.

Guest favourite

Cottage

4.9 out of 5 average rating, 146 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.

Guest favourite

Cottage

4.96 out of 5 average rating, 100 reviews

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.