Cottage holiday rentals in Sierra Oeste

Find and book unique cottages on Airbnb

Quick stats about cottage rentals in Sierra Oeste

Total holiday rentals
Explore 50 holiday rentals in Sierra Oeste
Nightly prices starting at
Sierra Oeste holiday rentals start at €35 per night before taxes and fees
Verified guest reviews
Over 2,650 verified reviews to help you choose
Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 30 rentals that welcome pets
Holiday rentals with a pool
30 properties feature pools
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
40 of Sierra Oeste holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Sierra Oeste rentals
4.8 Average rating
Sierra Oeste stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated cottage rentals in Sierra Oeste

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

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Guest favourite

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 Ángeles de San Rafael

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.

LocationValueParks

4.95 out of 5 average rating, 174 reviews

Guest favourite

A rustic stone house features a charming façade with a combination of rough stone and wooden accents. Steps lead up to the entrance, framed by well-maintained greenery. The structure is complemented by traditional tile roofing, evoking a warm and welcoming presence amid the natural surroundings.

Cottage in Madrid

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.

LocationFamilyCheckout

4.92 out of 5 average rating, 125 reviews

Superhost

A stunning sunset casts vibrant hues of orange and pink across the sky, reflecting on the tranquil waters of the pantano. The surrounding mountains create a serene backdrop, enhancing the peaceful ambiance of the natural landscape.

Cottage in El Tiemblo

The Swamp House

The house is located on the banks of the Burguillo swamp with 3000 m2 of private land where you will find a large garden with a pool, barbecue and terrace with spectacular views of the swamp. Everything around it is the Iruelas Valley Nature Reserve, so it is a natural, isolated and quiet environment. Water sports, hiking trails, biking, horseback riding, mushroom picking, chestnuts... The area offers you a taste of the cuisine that is characterized by its rich meats and vegetables.

ValueLocationIndoor spaces

4.86 out of 5 average rating, 125 reviews

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

Country house. 22-metre terrace. It has not been damaged by fire!

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

FamilyLocationHiking

4.84 out of 5 average rating, 256 reviews

Guest favourite

An indoor pool area is highlighted by sleek glass walls and a wooden ceiling with exposed beams. Sunlight filters through the skylights, reflecting off the calm water. Comfortable loungers are positioned alongside the pool, creating a relaxing atmosphere.

Cottage in Toledo

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

PADEL /HEATED POOL/ PICKLETBALL To preserve the tranquillity of the surroundings and the rest of the neighbours, *parties, celebrations, stag/hen dos, loud music, shouting or any behaviour that causes annoying noise are not allowed in this house, both during the day and 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

LocationValueCheck-in

4.9 out of 5 average rating, 135 reviews

Guest favourite

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

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!

ValueFamilyComfort

4.86 out of 5 average rating, 139 reviews

Top guest favourite

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

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

ValueFamilyPets

4.91 out of 5 average rating, 327 reviews

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

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.

LocationFamilyLaundry

4.86 out of 5 average rating, 202 reviews

Guest favourite

A serene garden area is presented, featuring a stone well surrounded by vibrant hydrangea flowers. A stone bench provides a peaceful seating spot, while lush greenery frames the scene, creating a secluded and inviting atmosphere. Natural light enhances the tranquility of the space.

Cottage in Guadarrama

No, without

La Bila was built in 1947, in a stone house colony. Its interior is completely renovated. It has a spectacular swimming pool for the summer and a garden to enjoy at all times of the year. The plot is completely fenced and away from the road, it is very quiet. Thanks to its isolation, both in summer and winter the interior temperature is very pleasant. The kitchen is well-equipped in terms of kitchenware and utensils, and its spaciousness is also noteworthy.

ValueFamilyIndoor spaces

4.92 out of 5 average rating, 53 reviews

Guest favourite

A spacious living area features a light-colored sofa facing a stone fireplace. A wooden coffee table sits in front, while a cabinet along the wall displays decorative items. Natural light enters through a window adorned with a vibrant curtain.

Cottage in Muñana

Estajero Rural House

House of the year 1855 totally rehabilitated in the year 2022. Its 120m2 are distributed in living room with fireplace, fully furnished and equipped kitchen, 2 bathrooms, 2 double bedrooms, a single with option of extra bed, interior patio with barbecue. Heating and wood-burning fireplace (wood drawer for 3-4 days at €12) No parties permitted. The town has a supermarket, butcher, fishmonger, pharmacy, restaurant... polideportivo and municipal pool

ValueLocationAmenities

4.95 out of 5 average rating, 121 reviews

Top guest favourite

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

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.

ValueFamilyAccuracy

4.97 out of 5 average rating, 130 reviews

Guest favourite

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

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.

FamilyLocationParking

4.93 out of 5 average rating, 253 reviews