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Cottage vacation rentals in Sierra Oeste

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Sierra Oeste

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

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Guest favorite
Cottage in Cerro Matallera
4.91 out of 5 average rating, 148 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).

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 Los Angeles de San Rafael
4.96 out of 5 average rating, 168 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, 240 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

Superhost
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 Los Angeles de San Rafael
4.88 out of 5 average rating, 129 reviews

House with beautiful views. VUT-40/868

A house with beautiful views and a garden, modern construction, ideal for disconnecting in nature. Los Angeles de San Rafael development, with entertainment for all ages, golf, horse riding, water sky cable, inflatable slides, water sports, adventure sports, spa, lake and swimming pools. 20 minutes from Segovia and El Escorial and next to the Sierra de Guadarrama. Please don't hesitate to ask any questions or information about the activities available in the area!!!

Guest favorite
The exterior of a two-story red house features a stone foundation and decorative railings on the upper level. Windows are framed with white shutters, and a wooden door is centered beneath the balcony. A paved pathway leads to the entrance.
Cottage in Maello
4.86 out of 5 average rating, 129 reviews

Casa Rosita: Enjoy the rural setting

Casa Rosita is a charming house in the middle of town. It has two floors with 4 spacious and bright rooms (3 with a double bed and 1 with 2 single beds), 2 full bathrooms with shower, fully equipped kitchen (with dining area and laundry room) and full living room with sofa bed. The village where it is located has a swimming pool, paddle tennis court, children's playground and numerous spaces for activities and outdoor walks. Enjoy and relax in an unbeatable setting!

Superhost
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
4.85 out of 5 average rating, 192 reviews

Peguerinos: house with jacuzzi, fireplace and garden

Disconnect and relax 1 hour from Madrid, in an authentic village in the Sierra de Guadarrama. "La Margarita" is a charming, very cozy house, built on an old stone barn completely renovated 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, horse or donkey riding, mushroom picking. Ideal for romantic getaways, relaxing or enjoying as a family.

Guest favorite
A private pool surrounded by lush greenery offers a refreshing retreat. Two lounge chairs, one in red and one in black, are positioned beside the pool, inviting relaxation. A large umbrella provides shade, and the tranquil atmosphere is enhanced by the natural setting.
Cottage in Miraflores de la Sierra
4.91 out of 5 average rating, 313 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

Top guest favorite
A cozy living area features a large stone fireplace and a flat-screen television. Comfortable black sofas are arranged thoughtfully around a coffee table. Expansive glass doors provide a view of the natural landscape outside, allowing soft light to fill the space.
Cottage in Higuera de las Dueñas
4.95 out of 5 average rating, 79 reviews

Spectacular Private Estate with Views of Gredos

A unique refuge in the heart of nature, where the most exquisite comfort blends with the most absolute tranquility. A 10-hectare estate, the house is very well located, with stunning views of the Sierra de Gredos, ideal for those seeking privacy, peace and connection with the natural environment. Immerse yourself in the calm from the spectacular pool, perfect for watching magical sunrises, unforgettable sunsets, or just enjoying the sun in total privacy.

Guest favorite
Cottage in Toledo
4.91 out of 5 average rating, 129 reviews

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

PADEL /HEATED POOL/ PICKLETBALL To preserve the peaceful environment and the neighbors' peace, in this house *no parties, celebrations, gatherings, loud music, shouting, or any behavior that causes bothersome noise are allowed, either during the day or, especially, at night.* It has a heated pool, paddle court, Pickleball, barbecue, ping pong, pool table. All the exclusive use of the renters. It is accessed from a 5.5 km dirt track it takes 10 to 20min

Top guest favorite
Cottage in La Estación
4.97 out of 5 average rating, 118 reviews

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.

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, 237 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 and wood cabin nestled in a lush green landscape, surrounded by oak and pine trees. A winding path leads to the entrance, which features a round window and flower pots. Sunlight filters through the trees, casting gentle shadows on the ground.
Cottage in Gavilanes
4.98 out of 5 average rating, 83 reviews

Room with a view of the Stars

A stone and wood house in a mountain shelter style, nestled south of the Gredos foothills, in the beautiful Tietar Valley. 8000-meter estate, surrounded by nature, oak trees, cork oaks, pine and chestnut trees... An area of mycological and hornitological interest, with night sky observation, routes, trails... If you are looking for tranquility, inspiration, to disconnect from the world... WELCOME TO LA BORRIQUITA.

Popular amenities for Sierra Oeste cottage rentals

When is the best time to visit Sierra Oeste?

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Avg. priceﺩ.ﺇ852ﺩ.ﺇ848ﺩ.ﺇ804ﺩ.ﺇ793ﺩ.ﺇ808ﺩ.ﺇ951ﺩ.ﺇ973ﺩ.ﺇ962ﺩ.ﺇ859ﺩ.ﺇ830ﺩ.ﺇ848ﺩ.ﺇ859
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Quick stats about cottage rentals in Sierra Oeste

  • Total vacation rentals

    Explore 60 vacation rentals in Sierra Oeste

  • Nightly prices starting at

    Sierra Oeste vacation rentals start at ﺩ.ﺇ147 per night before taxes and fees

  • Verified guest reviews

    Over 2,570 verified reviews to help you choose

  • Family-friendly vacation rentals

    60 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    40 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Sierra Oeste vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Sierra Oeste rentals

  • 4.9 Average rating

    Sierra Oeste stays are highly rated by guests—averaging 4.9 out of 5!

Destinations to explore

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