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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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Superhost
An ancient stone tower is surrounded by lush greenery and flowering shrubs, featuring a wide staircase leading to a glass entrance. The outdoor area includes a small stone patio with seating, offering views of the mountains in the background.
Castle in Piuro
4.83 out of 5 average rating, 355 reviews

Torre Scilano, Chalet Baita in vineyardChiavenna

On top of a hill, surrounded by vineyards stands the "Torre Scilano" lovely place located along the "Bregaglia" bike path whose background are the waterfalls dell'Acquafraggia. Site not only natural but also historical as the tower stands on the remains of ancient Piuro, thriving city buried by a terrible landslide in September 1618. The Tower Scilano offers: - 2 Double room (4 beds total) - Kitchen - Living room with panoramic view - Room Dining - Bathroom with showe - Arbour external - Mountain bikes available - Parking available - Private garden with vineyard - Barbecue in the garden

Top guest favorite
A terrace offers a scenic view of mountains and valleys bathed in the warm hues of a sunset. A small table is positioned on the wooden deck, surrounded by lush greenery and the silhouette of distant peaks.
Cabin in Ardenno
5.0 out of 5 average rating, 153 reviews

Splendid Chalet in Valtellina, Lombardy Mountains

The stars of a luxury hotel don't always count, try counting the ones you see from the panoramic terrace of our fantastic chalet at 1100 m above sea level, in the heart of the beautiful Valtellina, a short distance from Val Masino, 'Ponte nel Cielo', Valgerola, Lake Como and the Bernina Express -Red Train. In a sunny position all year round, it is ideal for admiring the Alps and enjoying absolute tranquility and privacy. Are you ready to stop and listen to the silence and the chorus of nature?

Top guest favorite
Vacation home in Chiavenna
5.0 out of 5 average rating, 13 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.

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, 42 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.

Guest favorite
A modern jacuzzi shares a panoramic view of Lake Como, surrounded by scenic mountains. Sunlight reflects off the water, creating a serene atmosphere. The jacuzzi is positioned on a wooden deck, with glass railings offering unobstructed vistas of the lush landscape.
Condo in Perledo
4.94 out of 5 average rating, 425 reviews

Resort Style Apartment with Lake Views

Marvel at the natural beauty surrounding this prestigious hilltop estate. The luxe home features antique furnishings & decor, a private terrace, BBQ area, a private spa, including jacuzzi and sauna for the exclusive use of the guests Garden with palm trees and vegetable patch The exclusive spot boasts mesmerizing views of Lake Como The property is close to the town of Varenna, facing Bellagio, just 5 kilometers away Typical restaurants and shops nearby Public bus & taxi available.

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.

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

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

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, 35 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
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.

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.

Superhost
A warm wooden interior features two spacious beds with light-colored bedding arranged parallel to each other. Natural light enters through a window, highlighting the rustic wooden beams and paneling. A cozy fireplace stands against one wall, enhancing the comfortable atmosphere.
Apartment in Isola
4.68 out of 5 average rating, 22 reviews

Suite 101 - Isola Madesimo

SUITE 101 is located inside the historic inn of Cardinello. Our guests will be able to enjoy an abundant breakfast at our restaurant (during the opening periods of the same). A sauna and e-bike rental are available upon request. In a few minutes walking you can reach the lake beach, a large children's play area and the bus station with the main connections (Chiavenna station, ski slopes)

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.