Top Chalets in Community of Madrid in 2026

A grand, illuminated building with intricate architecture, a prominent clock tower, and a fountain in front.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Top Cities in Community of Madrid

A mountainous landscape with rocky terrain and sparse vegetation.

Our top choices for Community of Madrid chalets

A residential property with a swimming pool, a covered patio with outdoor furniture, and a view of the surrounding neighborhood.

1. La Higuera, in Valdelaguna, for 10/15 people with Swimming Pool

Valdelaguna

Carolina M.

A house with a stone facade, a well-maintained lawn, and a large tree in the foreground.

2. Luxury Chalet: LA CASA DE INES

Alcalá de Henares

Tod S.

A rooftop pool area with a white canopy and a view of a residential neighborhood.

3. La Parra: Country House for 2, with Private Pool near Chinchón

Valdelaguna

MANUELA

A balcony with a sofa, two bar stools, and two large barrels.

4. Large family country house in Rascafría,1 h from Madrid, 12 to 24 people

Rascafría

Rafael E.

A yellow building with balconies, surrounded by green trees and bushes.

5. Chalet Ciudad Lineal 3HH M (MIS57)

Ciudad Lineal

Reina

A residential property with a well-maintained lawn, a wooden fence, and a modern house with a flat roof.

6. Chale A Estrenar!! Piscina Chimenea Y BBQ

Griñón

oscar

A staircase leading to a building with stone steps and metal railings.

7. Suyoluce, Chalet con Piscina Privada El Escorial

El Escorial

Christine M.

A rustic stone building with a wooden staircase leading to an interior space.

8. Retiro Park Industrial House

Retiro

Julia

A modern house with a stone wall, white exterior, and a pool area.

9. Design villa in the mountains of Madrid

Guadarrama

Alan M.

A two-story house with a patio area, surrounded by greenery and a mountain in the background.

10. The Brick House. Ideal for families with garden and swimming pool.

San Martín de Valdeiglesias

A multi-story building with a tiled roof, a small tree in the front yard, and a hedge along the sidewalk.

11. Oasis with private pool in Madrid!

Carabanchel

An outdoor brick oven barbecue with a bench, set against a concrete wall.

12. House with pool, Villa Alarilla

Urbanización Alarilla

A stone building with a tiled roof, surrounded by trees.

13. Ideal for FAMILIES up to 15 People in San Martín de Valdeiglesias Madrid

San Martín de Valdeiglesias

Amaya G.

A courtyard with trees, a white building, and a swimming pool.

14. Villa la Roca + la casita

Guadarrama

A black door with a stone wall and lush greenery surrounding it.

15. (SAB52) Spacious 3-bedroom villa with terrace

Fuencarral-El Pardo

"Plusieurs difficultés rencontrées lors du séjour et absence de réponses de l'hébergeur.Literie incomplète et impossibilité de récupérer l'équipement nécessaire : 4 couchages préparés au lieu de 5. Matériel de base manquant dans le logement : absences de condiments, pas de linge de maison, produits d'hygiène non réapprovisionnés (bouteilles vides dans la salle de bain).Qualité du mobilier à revoir dont le système des lits superposés qui demeure peu solide, avec des vis manquantes, une échelle...

carine F.

A narrow stone pathway leading to a small outdoor seating area with a table and chairs.

16. Rustic House in Cercedilla

Cercedilla

Álvaro E.

A modern two-story house with a paved driveway, a covered porch, and a hammock.

17. Espectacular Alojamiento, Piscina, Barbacoa,para Disfrutar en Familia o Amigos

Nuevo Baztán

"Overall we had a rough experience here and due to that I will no longer be using VRBO. It was hard to communicate with the host, the place wasn't as advertised (it only slept 16 when the ad said 20), and the place was dirty, we had to clean the pool, outdoor area, kitchen, and there was garbage sitting in bags in the front. We expressed our concerns about to the host and she said if we didn't like it we could cancel. Rough experience and the host dropped in unannounced our first morning. Overall...

Will R.