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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$2,092 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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Top guest favorite
Vacation home in Chiavenna
5.0 out of 5 average rating, 14 reviews

Al Crotto - Vacation home

In the heart of Chiavenna, a short walk from the historic center, this apartment, finely renovated by the architect owner, was created inside an ancient Alpine Crotto. The exposed stone and natural wood interact with contemporary lines, creating an intimate and harmonious environment, between tradition and modern comfort. Strategically located between mountains and lakes, close to Madesimo, St. Moritz and Lake Como, it is surrounded by greenery and ideal for a regenerating stay in every season.

LocationQuietHiking

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

recently renovated apartment (September 2024), furnished with an excellent mix of design and tradition 100 meters from the beginning of the pedestrian area of Madesimo, 150 meters from the larch gondola, 250 meters from the arlecchino chairlift and 50 meters from the supermarket. Bedroom with 1 bunk bed for 2 people, living room with a double foldaway bed, full kitchen, 2 balconies, private garage for a small/medium car in the same building where you can also store skis, boots and bicycles.

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Top guest favorite
Home in Aurogna
4.97 out of 5 average rating, 32 reviews

Bellavista Lake Como Garden View

Svegliati ogni mattina con una vista mozzafiato sul Lago di Como e vivi il piacere di una terrazza panoramica tutta per te! Bellavista Lake Como Garden View è un luogo dove rallentare, respirare e vivere l’autentica bellezza del Lago di Como. Ogni alba, ogni tramonto e ogni momento diventano un ricordo speciale. Nelle vicinanze, è possibile praticare vari tipi di sport, tra cui ciclismo, escursionismo, windsurf, kitesurf e canoa. L'Aeroporto di Milano Orio al Serio dista 90 km.

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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.

LocationValueHeating

A cozy living space features wooden walls and warm lighting. A comfortable black sofa is positioned alongside a bunk bed. A decorative rug rests on the wooden floor, contributing to the room's inviting ambiance. A door and wall-mounted equipment are visible in the background.
Loft in Madesimo
4.64 out of 5 average rating, 11 reviews

Luxury apt 50mt from the skilift max 4people

Enjoy this studio apartment created in the centre of Madesimo, and close to the ski-lifts. Relax in a stylish apartment with beautiful wood interiors entirely handmade but with all the comforts a modern house can offer. You will be close to all the restaurants and bars if you like to go out, or you can stay home with a fully furnished kitchen and taste some of the wines of our cellar. Perfect for kids-has a bank bed, and a big sofa. There is a private ski-room at the basement too.

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

New alpine lodge

The atmosphere and warmth of the mountain combined with the comfort of the brand new: a perfect mix for the perfect vacation! Beautiful mountain views thanks to the large windows. Ideal apartment for families. Perfectly integrated into the small village of Isola – Madesimo. Ideal starting point for many beautiful walks or bike rides. Balcony, garden and private garage. Relaxation and silence assured...where the daily routine has never been so far away! CIR 014035 CNI 00049

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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, 20 reviews

Charming three-room apartment in Madesimo

Three-room attic apartment surrounded by silence. Ideal for those seeking tranquility and a mountain atmosphere. Within walking distance of the center and the facilities. Comfortable 85 sqm apartment: Large living room with double sofa bed in front of the fireplace, dining area, kitchen with induction hob, electric oven, fridge. Double bedroom. Bedroom with two bunk beds and a closet Bathroom with tub/shower, sink, bidet. Dishes, initial linen, towels included Garage

FamilyLocationNearby

Guest favorite
Apartment in Madesimo
5.0 out of 5 average rating, 6 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.

LocationConditionNearby

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.

LocationValueSleep quality

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, cozy and spacious attic

Large mountain attic located in a very central area, but at the same time quiet and peaceful, just 50 meters from the main ski lift, close to shops, bars and restaurants. The apartment has 3 bedrooms, 2 bathrooms (one with shower and one with bathtub), and comfortably accommodates 6 people. Modern appliances and free WIFI. We provide linen and towels (cost included in the cleaning fee). Private garage in the same building and condominium parking.

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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.

LocationGetting aroundKitchen

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

Green house

Charming three-room apartment overlooking the church square. Central but quiet location. The apartment has a large living room with a dining table and a balcony. Double bedroom and bedroom with two bunk beds for a total of 6 beds. The bathroom has a washing machine and bathtub. The kitchen has all the necessary accessories and appliances.

LocationFamilyAccess

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.