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Vacation rentals in Madesimo

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Madesimo

  • Total vacation rentals

    Explore 50 vacation rentals in Madesimo

  • Nightly prices starting at

    Madesimo vacation rentals start at G$2,091 GYD per night before taxes and fees

  • Verified guest reviews

    Over 650 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    40 of Madesimo vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Madesimo rentals

  • 4.8 Average rating

    Madesimo stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated vacation rentals in Madesimo

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

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Guest favorite
A cozy living area is highlighted by an angled ceiling and wooden paneling. A spacious sofa with colorful cushions faces a stone fireplace, while a TV is set on a stand nearby. Natural light enters through a small window, enhancing the inviting ambiance.
Apartment in Madesimo
4.95 out of 5 average rating, 21 reviews

Grazioso trilocale a Madesimo

Trilocale in mansarda immerso nel silenzio. Ideale per chi cerca la tranquillità e l'atmosfera di montagna. A due passi dal centro e dagli impianti. Confortevole appartamento di 85mq: Ampio soggiorno con divano letto matrimoniale davanti al camino, zona pranzo, cucina con piastra ad induzione, forno elettrico, frigo. Camera da letto matrimoniale. Cameretta con due letti a castello e armadio Bagno con vasca/doccia, lavello, bidet. Stoviglie, biancheria iniziale, asciugamani inclusi Box auto

Superhost
A cozy living area with wooden beams on the ceiling showcases two soft seating options and a patterned area rug. A simple stone fireplace is flanked by bookshelves, while warm lighting creates a relaxed ambiance.
Apartment in Madesimo
4.57 out of 5 average rating, 23 reviews

La Primula, accogliente e spaziosa mansarda

Ampia mansarda di montagna situata in zona centralissima, ma allo stesso tempo silenziosa e tranquilla, a soli 50 metri dal principale impianto di risalita, vicino a negozi, bar e ristoranti. L'appartamento ha 3 camere da letto, 2 bagni (uno con doccia e uno con vasca), e ospita comodamente 6 persone. Elettrodomestici moderni e WI-FI gratuito. Forniamo la biancheria e gli asciugamani (costo compreso nelle spese di pulizia). Box auto privato nello stesso edificio e parcheggio condominiale.

Superhost
Condo in Madesimo
5.0 out of 5 average rating, 9 reviews

New alpine lodge

L'atmosfera ed il calore della montagna abbinati al comfort del tutto nuovo: un mix perfetto per la vacanza perfetta! Splendida vista sulle montagne grazie alle ampie vetrate. Appartamento ideale per famiglie. Perfettamente integrato nel piccolo borgo di Isola – Madesimo. Punto di partenza ideale per tante belle passeggiate a piedi o in bicicletta. Balcone, giardino e garage privato. Relax e silenzio assicurati...dove la routine quotidiana non è mai stata così lontana! CIR 014035 CNI 00049

Top guest favorite
A well-lit hallway features a series of black and white framed photographs along one wall. A round mirror is positioned over a wooden console table, which holds a woven basket. Light wood flooring extends toward the living area visible in the background.
Condo in Madesimo
4.95 out of 5 average rating, 43 reviews

Rosina apartment - Madesimo centro, car parking

appartamento ristrutturato recentemente (settembre 2024), arredato con un ottimo mix tra design e tradizione a 100mt dal inizio della zona pedonale di Madesimo, 150mt dalla cabinovia larici, 250mt dalla seggiovia arlecchino e 50mt dal supermercato. Camera con 1 letto a castello per 2 persone, soggiorno con letto a scomparsa matrimoniale, cucina completa, 2 balconi, garage privato per una piccola/media automobile nella stessa struttura dove poter depositare anche sci ,scarponi e biciclette.

Top guest favorite
Vacation home in Chiavenna
5.0 out of 5 average rating, 15 reviews

Al Crotto - Casa vacanze

Nel cuore di Chiavenna, a pochi passi dal centro storico, questo appartamento finemente ristrutturato dal proprietario architetto nasce all’interno di un antico Crotto alpino. La pietra a vista e il legno naturale dialogano con linee contemporanee, creando un ambiente intimo e armonioso, tra tradizione e comfort moderno. In posizione strategica tra montagne e laghi, vicino a Madesimo, St. Moritz e al Lago di Como, è immerso nel verde e ideale per un soggiorno rigenerante in ogni stagione.

Top guest favorite
A charming stone building is surrounded by lush greenery and mountains. The structure features wooden shutters and a large balcony overlooking the landscape. Snow-capped peaks are visible in the distance, offering a serene setting for relaxation in nature.
Apartment in Madesimo
4.91 out of 5 average rating, 70 reviews

true alpine rustic

IDEAL FOR SPENDING BEAUTIFUL DAYS IN CLOSE CONTACT WITH NATURE FOR A PRIVATE, RELAXING & REJUVENATING STAY SURROUNDED BY SPECTACULAR MOUNTAINS, GREEN MEADOWS, FRESH STREAM, CRYSTAL-CLEAR LAKES, JUST A FEW MINUTES' WALK FROM THE CENTER OF MADESIMO (SUPERMARKET, BAR, CINEMA, ETC.) A LOCATION THAT BOASTS 60 KM OF SKI SLOPES, VARIOUS SUMMER AND WINTER SPORTS ACTIVITIES, WITH A MYRIAD OF TRAILS (HIKING), A DESTINATION FOR A PLEASANT AND RELAXING HOLIDAY IN PLACES OF INCOMPARABLE BEAUTY.

Guest favorite
Apartment in Madesimo
5.0 out of 5 average rating, 7 reviews

A casa di Anna

The holiday apartment A casa di Anna is located in Madesimo and overlooks the mountain. The 75 m² property consists of a living room, a kitchen, 2 bedrooms and 1 bathroom and can therefore accommodate 4 people. Additional amenities include high-speed Wi-Fi (suitable for video calls) with a dedicated workspace for home office, a TV, a washing machine as well as a dryer. A baby cot and a high chair are also available. This accommodation does not offer: air conditioning.

Top guest favorite
A wooden bedroom is highlighted by natural wood paneling on the walls and ceiling, creating a warm ambiance. A spacious bed sits in the center, flanked by bedside lamps. A small table and chair are positioned nearby, with a cozy rug underfoot, enhancing the room's inviting atmosphere.
Home in Bregaglia
5.0 out of 5 average rating, 36 reviews

Chesa Antica - Historic Charm & Alpine Relax 1601

Chesa Antica is a historic house built in 1601. With its vaulted ceilings and rooms made of larch and Swiss pine, this home fascinates and enchants with its charm. Located at the foot of Piz Lunghin and the Septimer Pass, 10’ from Maloja and 25’ from St. Moritz. A haven for those who love nature and seek beauty and uniqueness. Choose from walks in the woods or along lakes, adventurous hikes, or extreme mountaineering – perfect for families, couples, or friends!

Guest favorite
The bedroom features a spacious bed with a natural wood headboard and soft bedding. A cowhide rug lies beneath, while a cozy armchair and a dark wardrobe are positioned nearby. Soft lighting enhances the inviting atmosphere.
Apartment in Madesimo
4.83 out of 5 average rating, 12 reviews

Apartment Kern-skiing on the doorstep-

Enjoy a stylish experience at this centrally located, charming 2 room apartment. Madesimo invites you with the enchanting mountains in winter to versatile Winter sports, in summer for hiking, climbing and mountain biking. The apartment is characterized by a perfect location: direct access to the ski slope; Ski rental and supermarket across the street. The town center with restaurants, bars and shops is within easy walking distance (200m). CIR 014035-CNI-00072

Guest favorite
A stone house exterior features a large arch window and a wooden terrace with a railing. The facade is accented by wooden details and the surrounding landscape includes mountains and trees. Natural light illuminates the space while the roof is constructed with traditional tiles.
Apartment in Madesimo
4.98 out of 5 average rating, 92 reviews

Panoramic Attic Solee Caterina, Madesimo

Attic apartment with a large panoramic arch window and terrace in a typical stone house. Our House "Solee Caterina - Tradizionecasa" in Madesimo is a third floor attic. The apartment disposes of 55m2 and is divided in two double bedrooms and a bathroom. The living room facade has a large arch window of 5x2,5m and a wooden terrace with a little table and chairs. The view is towards southwest, where you can see the beautiful San Sisto valley and Quadro peak.

Guest favorite
Apartment in Madesimo
5.0 out of 5 average rating, 11 reviews

Casa Greta by Interhome

All discounts are already included, please go ahead and book the property if your travel dates are available. Below please see all the listing details 3-room apartment 88 m2 on 2nd floor, south facing position. Bright, fully renovated in 2025, modern and stylish furnishings: large living/dining room with sliding door, panoramic window with 1 double sofabed and Scandinavian wood stove (only for decoration), dining table and TV. Exit to the terrace.

Guest favorite
The living area features wooden beams and a cozy atmosphere. Two patterned sofas and a central table are arranged on a colorful rug. Natural light enters through the balcony door, which leads to a quaint outdoor view. Artworks adorn the walls, contributing to the inviting decor.
Apartment in Madesimo
4.83 out of 5 average rating, 18 reviews

Casa verde

Grazioso trilocale affacciato alla piazza della chiesa. Posizione centrale, ma tranquilla. L'appartamento ha un ampio salotto con tavolo da pranzo e balconcino. Camera matrimoniale e camera con due letti a castello per un totale di 6 posti letto. Il bagno dispone di lavatrice e vasca da bagno. La cucina ha tutti gli accessori e gli elettrodomestici necessari.

Popular amenities for Madesimo vacation rentals

Frequently Asked Questions

  • What are the best places to stay in Madesimo?

    Accommodations are concentrated around the town center and near ski lifts, with chalets, apartments, and lodges suited for groups and families. Staying close to main squares has easy access to shops, eateries, and activities.

  • What are the best things to do in Madesimo with kids?

    Kids can enjoy snow activities like sledding in winter, gentle nature trails, and playgrounds around the town. Guided outdoor adventures, bike rentals, and interactive workshops are also available depending on the season.

  • How is the weather in Madesimo?

    Madesimo has cold winters with snow, temperatures from 19–33°F (-7–1°C), and cool, wetter summers averaging 47–65°F (9–18°C). Plan for changing weather, especially in mountain areas, and bring clothing suited for alpine conditions.

  • When is the best time to visit Madesimo?

    Winter draws many visitors for skiing and snow sports, while late spring and summer bring milder temperatures, hiking opportunities, and mountain festivals. Outdoor activities shift with the season, making each time distinct.

  • What are the best places to visit in Madesimo?

    Frequently suggested spots include the town center, the ski area, Lago di Isola, and surrounding mountain valleys. Visitors also explore traditional churches and local artisan workshops for a glimpse of regional culture.

  • What are some hiking trails in Madesimo?

    Madesimo has mountain trails leading through alpine forests and past scenic viewpoints, with routes suited for various skill levels. Popular paths include those to Lago di Isola and trails exploring Valchiavenna landscapes.

  • What are some family activities we can do in Madesimo?

    Families in Madesimo often enjoy guided hikes, skiing, mountain biking, and playgrounds around the town. The area has nature trails and seasonal experiences like sledding or picnicking by mountain streams.

  • What are some of the best day trip ideas from Madesimo?

    Explore nearby alpine villages for local markets or visit scenic lakes and mountain passes. Many guests venture to regional parks or historic towns known for their architecture and local crafts.

  • Are there any pet friendly accommodations available in Madesimo?

    Madesimo has pet-friendly vacation rentals, especially around the town center and mountain foothills. You can find stays where pets are welcomed, making it easy to explore trails and outdoor spots with your companion.

  • What are some local tips for visiting Madesimo?

    Locals suggest booking mountain accommodation early in peak seasons and trying homemade alpine dishes at family-run trattorias. Carry cash for smaller shops and take time to explore the quieter paths around the village.

  • What is Madesimo known for?

    Madesimo is known for its ski resorts, scenic alpine hiking, and welcoming mountain atmosphere. The town frequently attracts outdoor enthusiasts for winter sports and summer trails surrounded by peaks.

  • What are the best hidden gems to explore in Madesimo?

    Explore tranquil mountain paths, discover small alpine churches, and visit local woodcarving workshops. Many guests find quiet spots by streams or in picturesque valleys, often recommended by locals for a peaceful break.

  • What are the best foods to try in Madesimo?

    Visitors often enjoy dishes rooted in local Lombard tradition, such as pizzoccheri, hearty polenta, and alpine cheeses. Madesimo also has mountain-inspired desserts and dishes featuring wild mushrooms or game meats.

  • What should I bring for a trip to Madesimo?

    Pack layered clothing for cool alpine temperatures, comfortable hiking shoes, and a waterproof jacket. In winter, prepare for snow with warm outerwear, while summer visits benefit from sun protection and sturdy outdoor gear.

  • What is the nightlife in Madesimo like?

    Nightlife in Madesimo centers around laid-back venues and cozy mountain bars where guests can enjoy local wines and live music. Many visitors unwind in après-ski lounges or join social evenings after exploring the outdoors.

  • Are there family friendly vacation rentals in Madesimo?

    Madesimo has a range of accommodations that welcome families, including spacious apartments and cozy chalets near winter sports and mountain trails. Look for rentals around the town center to easily access local shops, parks, and activity areas.

  • What are the most popular amenities for Apartment Rentals in Madesimo?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 30 homes with wifi, over 30 homes with a kitchen, over 20 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • How much does it cost to stay in apartment rentals in Madesimo?

    Experience the best of Madesimo with our apartment rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.