Cottage holiday rentals in Sierra Oeste

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).

4.91 out of 5 average rating, 129 reviews

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 /PISCINA CLIMATIZADA/ PICKLETBALL Para preservar la tranquilidad del entorno y el descanso de los vecinos, en esta casa *no se permiten fiestas, celebraciones, despedidas, música alta, gritos ni cualquier comportamiento que genere ruido molesto, tanto de día como especialmente por la noche.* Cuenta con Piscina climatizada, Pista de pádel, Pickleball, barbacoa, ping pong, billar. Todo uso exclusivo de los inquilinos. Se accede a ella desde una pista de tierra de 5,5 km se tarda 10 a 20min

4.96 out of 5 average rating, 168 reviews

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

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.

4.84 out of 5 average rating, 240 reviews

A spacious wooden terrace is showcased, featuring comfortable seating and a small coffee table. Lush greenery surrounds the area, with rolling hills visible in the background. The setting captures a peaceful ambiance, ideal for relaxation and enjoying the natural surroundings.

Cottage in Río Cofio

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

4.88 out of 5 average rating, 129 reviews

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

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!!!

4.86 out of 5 average rating, 129 reviews

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!

Cottage in Hoyo de la Guija

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.

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.

Cottage in Miraflores de la Sierra

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.

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

Cottage in Higuera de las Dueñas

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.

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.

4.97 out of 5 average rating, 118 reviews

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.

4.94 out of 5 average rating, 238 reviews

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.

Cottage in Cadalso de los Vidrios

A wooden terrace is shown with a red hammock suspended between two trees. Surrounding greenery features various trees and shrubs, creating a serene natural setting. The distant mountains and a sunset sky add a peaceful ambiance to the scene.

4.97 out of 5 average rating, 108 reviews

Mountain Views with Panoramic Terrace

Less than an hour from Madrid, escape the city's noise and reconnect with the essence of nature. A haven where you can enjoy breathtaking sunsets, breakfasts with endless views, and dinners under the stars, with the absolute privacy that only a detached house can offer. Here, luxury isn't about sophistication, but about silence, fresh air, and a terrace that seems to float above the Sierra de Gredos mountains.

Popular amenities for Sierra Oeste cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

4.88 out of 5 average rating, 16 reviews

The exterior of the chalet is shown, featuring a two-story structure with a warm-colored façade and a tiled roof. A stone wall borders the property, and a covered terrace is visible at the front. Blue skies are present above, enhancing the inviting appearance.

Cottage in Navas del Rey

chalet relax luxury

4.88 out of 5 average rating, 52 reviews

A scenic view reveals a vibrant landscape filled with clusters of purple wildflowers amid lush greenery. A quaint house is nestled in the background, surrounded by trees and rocky features, with mountains rising gently in the distance.

Cottage in Burgohondo

A house with a view

4.84 out of 5 average rating, 19 reviews

A private patio area features a relaxing inflatable jacuzzi surrounded by soft grass. A cozy seating arrangement includes a wooden sofa and a green armchair, with gentle lighting provided by string lights above. Decorative plants enhance the serene atmosphere.

Cottage in Robledillo

Tío Pancho Country House, Outdoor Jacuzzi 4/6 seats

Cottage in Casavieja

4.9 out of 5 average rating, 10 reviews

A beautiful and charming country house

A two-story house with a green façade and stone accents is surrounded by a well-maintained lawn. Outdoor seating arrangements are provided near the pool, which features a wooden deck. Lush trees offer shade, creating a serene outdoor environment for relaxation.

Cottage in Las Herreras

4.7 out of 5 average rating, 125 reviews

Las Herreras 1 Country House

The exterior of a two-story house is shown, featuring a traditional design with a terracotta-tiled roof and stone details. A landscaped yard with green grass and a gated entrance surrounds the property. Several balconies are visible on the upper level, providing access from the second floor.

Cottage in Navaluenga

4.6 out of 5 average rating, 47 reviews

House of the Vines II

5 out of 5 average rating, 21 reviews

A modern living space is presented, featuring an open-plan kitchen and dining area. A sleek table with six black chairs occupies the center. Natural light floods in through two windows, illuminating the adjacent seating area with a gray sofa. Exposed brick walls add textural contrast.

Cottage in Aveinte

House in nature with a spa and large patio.

5 out of 5 average rating, 11 reviews

A spacious bathroom features a rounded jacuzzi with multiple jets, positioned against a light-colored wall. Natural light enters through a window, highlighting the sleek, modern tiles and clean lines of the design.

Cottage in Baterna

Loft-style country house with a JACUZZI

Pet-friendly cottage rentals

Cottage in Becerril de la Sierra

An outdoor seating area features a combination of white-framed benches and chairs with cushions in soft shades. A wooden table sits at the center, surrounded by natural stone walls and greenery. The space offers a cozy atmosphere for relaxation or socializing.

4.95 out of 5 average rating, 20 reviews

Cute and cozy stone cottage

Cottage in Villa del Prado

A scenic view captures a backyard with a spacious swimming pool surrounded by loungers. Planters filled with greenery frame the foreground, while rolling hills and a cloudy sky are visible in the background, enhancing the tranquil setting.

4.66 out of 5 average rating, 35 reviews

House for 12, swimming pool, and barbecue

Cottage in Becerril de la Sierra

A charming red house is positioned on an elevated area with a stone facade. A spacious terrace is supported by wooden railings, featuring multiple blue chairs. A garden area is visible in the foreground, alongside a paved driveway leading to a garage beneath the living space.

4.83 out of 5 average rating, 64 reviews

Country house with Mount Maliciosa view, RobledoII

5 out of 5 average rating, 17 reviews

Cottage in Navahondilla

Villa in San Juan lake with private pool and BBQ

4.98 out of 5 average rating, 60 reviews

An open living space features wooden beams and terracotta flooring. Natural light filters through large windows, illuminating the cozy seating area. A rustic dining table is set nearby, complementing the warm, inviting atmosphere of the home.

Cottage in Segovia

El Palomar I - country house for 6/8 people

5 out of 5 average rating, 11 reviews

Cottage in Hernansancho

La Tinaja: Rural charm with a heated pool

4.71 out of 5 average rating, 48 reviews

Cottage in Toledo

El Paraíso Country house, views VUT45012320812

5 out of 5 average rating, 21 reviews

A rustic well with an ornate iron hook stands in the foreground, complementing the stone house in the background. The house features large windows and a red-tiled roof, surrounded by green trees and natural landscapes illuminated by the soft glow of evening light.

Cottage in Navaluenga

Finca del Carmen

Private cottage rentals

5 out of 5 average rating, 7 reviews

A white, single-story house is set against a backdrop of tall pine trees. A covered porch is visible, adorned with colorful outdoor furnishings. A stone pathway leads to the entrance, framed by natural landscaping and a fence with black gates.

Cottage in El Pimpollar

The river house. Mountains and river in Madrid.

Cottage in San Martín de Valdeiglesias

4.89 out of 5 average rating, 9 reviews

Brick House with Pool and Swamp View

4.88 out of 5 average rating, 82 reviews

A light-filled living area is shown, featuring a spacious sectional sofa with decorative pillows. A wooden coffee table sits at the center, while a bookshelf filled with various items lines one wall. Natural light filters through green curtains, highlighting the inviting atmosphere.

Cottage in La Estación

La osa and el madroño, Robledo de Chavela country house

4.93 out of 5 average rating, 59 reviews

The exterior of a stone house features a terracotta roof and black shutters on the windows. A shaded outdoor dining area with tables and chairs is visible in the foreground. Lush greenery partially frames the house, highlighting its rustic charm and inviting setting.

Cottage in Cercedilla

Refugio del Nogal (Cercedilla)

A compact living area features a white sofa adjacent to a glass dining table. A television is positioned on a dark cabinet, while framed artwork decorates the walls. A staircase leads to the upper floor, and a wooden door is visible at the end of the corridor.

Cottage in Sotillo de la Adrada

4.78 out of 5 average rating, 139 reviews

Sotillo de la Adrada, V. del Tietar, (Toledo & Ávila)

Cottage in San Bartolomé de Pinares

The open-concept kitchen and dining area features modern appliances, including a refrigerator and washing machine. Light wood flooring extends throughout, complemented by a staircase leading to the upper level. A small dining table with stools adds functionality to the space.

4.92 out of 5 average rating, 60 reviews

CASCORRO RURAL HOUSE

4.96 out of 5 average rating, 24 reviews

The single-story house features a spacious outdoor area paved with stone and tile, framed by well-maintained gardens. A large covered porch with dining furniture is visible, inviting outdoor meals, while warm lighting highlights the welcoming facade at dusk.

Cottage in Abades

Country House and Events in Segovia