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Holiday houses in Monteriggioni

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Top-rated holiday rentals in Monteriggioni

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Top Guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.93 out of 5 average rating, 281 reviews

Casa al Gianni - Hut

Hi, we're Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism facility located in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: There is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a vacation; it's a return to our roots. This peaceful haven will stay with you in your heart. We look forward to welcoming you!

Top Guest favourite
Home in Monteriggioni
4.97 out of 5 average rating, 37 reviews

Tuscany-Monteriggioni- Chianti- Francigena-

The apartment is a portion of a typical Tuscan farmhouse, formerly a mill (the oldest part dates back to around 1200) and is surrounded by nature and in a strategic position on the Via Francigena, 2 km from Monteriggioni, 10 km from Siena and close to San Gimignano, Volterra and Florence. The apartment consists of an equipped open kitchen, bathroom with shower, bedroom with double bed and bedroom with two single beds. The living area has a comfortable sofa bed with TV, Wi-Fi and air conditioning

Guest favourite
Home in Asciano
4.96 out of 5 average rating, 134 reviews

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Guest favourite
The stone farmhouse, characterized by a rustic façade, features arched doorways and shuttered windows. Lush greenery surrounds the entrance, offering a serene landscape. A gravel driveway leads to the main entrance, highlighting the spaciousness of the property.
Farm stay in Monteriggioni
4.9 out of 5 average rating, 111 reviews

Podere Casalino - Il Gatto

Set in the peaceful countryside near the Monteriggioni Castle, Il Casalino is the result of our love for restoring an old Tuscan farmhouse. My husband and I have carefully created two apartments for our guests: Il Gatto and La Pergola. We want you to feel at home from the very first moment. If you have any questions, feel free to message me: I will reply as quickly as possible. We truly look forward to welcoming you to Il Casalino and sharing this special place with you! Warm regards, Laura

Top Guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano
4.99 out of 5 average rating, 153 reviews

Villa di Geggiano – Guesthouse

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

Top Guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 343 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.

Guest favourite
An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.
Cottage in Monteriggioni
4.95 out of 5 average rating, 289 reviews

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Top Guest favourite
A spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Condo in San Gimignano
5 out of 5 average rating, 60 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Top Guest favourite
An open-concept living area is presented, featuring a hanging chair and stylish black furnishings. Arched doorways lead to the dining space, which is brightened by natural light. Potted plants add greenery to the environment, alongside a cozy rug on the tiled floor.
Apartment in San Gimignano
4.99 out of 5 average rating, 87 reviews

Herons Superior Apartment - Splendid view!

Goditi una vacanza all'insegna dello stile in questo spazio nel centro di San Gimignano. Finemente arredato e con una vista spettacolare sulle colline toscane, Herons Superior Apartment è pronto a ospitarti insieme alle persone che ami. ___________________________________________________ Tassa di soggiorno da pagare sul posto secondo il seguente calcolo: 2,5€ X numero di ospiti sopra gli 11 anni X numero di notti (si pagano al massimo 5 notti).

Top Guest favourite
An infinity pool reflects the sky, surrounded by lush greenery and cypress trees. The pool's edge seamlessly blends into the landscape, overlooking rolling hills and olive groves. Sun loungers are positioned nearby, providing a serene outdoor setting.
Barn in Castellina in Chianti
5 out of 5 average rating, 63 reviews

Cipressini 2 - pool and amazing views

Ancient stone farmhouse adjacent to the main farmhouse dating back to the 17. century, located in the heart of the Chianti Classico on the side of a slope with breathtaking views over the Val d'Elsa. Luxuriously renovated and furnished, equipped with every comfort, it is located in such a way as to guarantee absolute privacy.

Guest favourite
An outdoor pool area is surrounded by olive trees and vineyards, with sun loungers and shaded umbrellas arranged on the deck. Soft sunlight bathes the scene, highlighting the peaceful setting. A gravel path leads around the pool, inviting relaxation amid the natural landscape.
Apartment in Monteriggioni
4.93 out of 5 average rating, 437 reviews

Comfort Apartment in the Chianti Vineyards

Apartment on the upper floor of the structure characterized by a wonderful view of the Chianti hills, olive groves or the patio. Renovated while maintaining the charm of their ancient walls but adding every comfort. It includes a living room, a kitchenette, a double bedroom, a private bathroom with a shower, air conditioning.

Top Guest favourite
A spacious bedroom features a four-poster bed draped with sheer white curtains. Exposed wooden beams adorn the ceiling, while the stone walls add rustic charm. A window with elegant lace curtains offers natural light and a view of the picturesque surroundings.
Condo in Monteriggioni
4.98 out of 5 average rating, 42 reviews

LUNA Romantic bedroom in Monteriggioni

A romantic room in the heart of Monteriggioni, a XII century medieval village on the Francigena way, an ancient walking trail that takes pilgrims from Canterbury to Rome. The room overlooks the main square of the village and offers our guests the unique experience of standing in one of the most beautiful villages in Tuscany!

Popular amenities for Monteriggioni holiday rentals

Frequently Asked Questions

  • What are the best places to stay in Monteriggioni?

    Monteriggioni has stays within its fortified village, country villas surrounded by olive groves, and rustic farmhouses in the countryside. Each setting allows guests to experience the town’s historic atmosphere and scenic vistas.

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

    Families often explore Monteriggioni’s castle walls, try hands-on workshops themed around medieval history, and enjoy village festivals with interactive activities. Open green spaces and guided walks let kids experience the countryside’s nature and stories.

  • What are some of the best things to do in Monteriggioni?

    Stroll the medieval walls of Monteriggioni, discover the historic Porta Franca gate, and explore the main piazza’s small museums. Local wineries and olive groves around Monteriggioni invite tastings and guided visits.

  • How is the weather in Monteriggioni?

    Monteriggioni has mild winters, with temperatures around 36–55°F (2–13°C), and warm, dry summers near 65–90°F (18–32°C). Spring and autumn often bring moderate rainfall and comfortable temperatures, making them appealing seasons for exploring.

  • When is the best time to visit Monteriggioni?

    Late spring and early autumn are often suggested for visiting Monteriggioni, with comfortable temperatures and fewer crowds. This period also brings local festivals, blooming landscapes, and harvest traditions.

  • What are the best places to visit in Monteriggioni?

    Explore Monteriggioni’s medieval walls, the Church of Santa Maria Assunta, and the Armory Museum. The main piazza is a welcoming spot to experience local life and events.

  • What are some hiking trails in Monteriggioni?

    Monteriggioni has scenic trails along sections of the historic Via Francigena and gentle routes through Chianti hills and forests. Walking the footpaths around the village, you may pass vineyards, olive groves, and wildflower meadows.

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

    Families enjoy climbing Monteriggioni’s medieval walls, visiting small museums with interactive displays, and joining local food or craft workshops. Open squares provide space for children to play and experience the village’s traditions.

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

    Many travelers explore nearby hill towns with Etruscan sites, vineyards, and Renaissance art. Popular day trips include visits to historic Siena, local markets, or countryside village festivals.

  • Are there any pet friendly accommodations available in Monteriggioni?

    Monteriggioni has a selection of pet-friendly stays, including apartments, country homes, and traditional villas. Many hosts are happy to welcome travelers with pets, especially in the scenic countryside and village surroundings.

  • What are some local tips for visiting Monteriggioni?

    Start your day early to enjoy Monteriggioni’s quieter atmosphere and bring cash for small artisan shops. Sampling local olive oil and joining a guided village walk are often recommended for a more immersive experience.

  • What is Monteriggioni known for?

    Monteriggioni is known for its striking circular medieval walls, historic towers, and preserved village center. The area has a rich legacy along the Via Francigena pilgrimage route and is often highlighted for its role in regional poetry and history.

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

    Explore Monteriggioni’s quieter medieval alleys, lesser-known artisan workshops, and the ancient Oliveta Abbey nestled around the area. The countryside also has peaceful trails lined with wildflowers and cypress trees.

  • What are the best foods to try in Monteriggioni?

    In Monteriggioni, savor local specialties such as wild boar stew, handmade pici pasta, and pecorino cheese. Many enjoy sharing bruschetta topped with local olive oil, along with traditional Tuscan desserts like cantucci dipped in sweet wine.

  • What should I bring for a trip to Monteriggioni?

    Pack comfortable walking shoes, a sun hat, and layers for changing temperatures, especially in spring or autumn. A small reusable water bottle is practical for wandering medieval streets and exploring the countryside.

  • What is the nightlife in Monteriggioni like?

    Monteriggioni’s nightlife centers on relaxed cafés, wine bars, and live music in the main piazza or historic venues. Warm evenings bring quieter gatherings and seasonal events featuring music and local food.

  • What are the most popular events or festivals in Monteriggioni?

    Monteriggioni’s medieval festival in summer is often highlighted, with reenactments, themed markets, and historical performances. Throughout the year, the village hosts food celebrations, artisan fairs, and music events rooted in local tradition.

  • Are there family friendly vacation rentals in Monteriggioni?

    Monteriggioni has a range of family-friendly vacation rentals, including spacious homes and village apartments with kitchen facilities. Many properties feature easy access to outdoor spaces for children and shared family activities.