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Holiday houses in Monteriggioni

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Top-rated holiday rentals in Monteriggioni

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

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Top 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, 113 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

FamilyValueBathroom

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
5.0 out of 5 average rating, 343 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni è un antica proprietà del 1600 a gestione familiare situato nelle splendide colline del Chianti in Toscana con la possibilità di organizzare navetta privata e esperienze locali direttamente con la nostra famiglia . L'appartamento è disponibile per 2 adulti con possibilità aggiunta divano letto per 2 bambini sotto i 12 anni . Nel grande cortile esterno troverete una piscina a sale con area relax su terrazza panoramica con vista su castello e vigneti con tramonti unici.

LocationFamilyBarbecue

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, 154 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.

ValueLocationHospitality

Top Guest favourite
An infinity pool reflects a clear blue sky, offering expansive views of rolling hills and lush valleys. A sun umbrella provides shade beside the pool, while a charming rustic structure is positioned nearby, surrounded by trees and Mediterranean flora.
Barn in Castellina in Chianti
5.0 out of 5 average rating, 97 reviews

Cipressini 1 - Swimming pool and stunning view

Ancient stone barn 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. On the GF: Kitchen, large living room with fireplace and double sofa bed. On the LGF: Bedroom with double bed, built-in wardrobes, desk, bathroom with shower, utility room

ValueLocationParking

Guest favourite
Villa in Monteriggioni
4.97 out of 5 average rating, 173 reviews

Villa dei 2 Ulivi (Abbadia Isola)

FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)

LocationFamilyCleanliness

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

Toscana-Monteriggioni- Chianti- Francigena-

L’appartamento è una porzione di casale tipico toscano, anticamente Mulino (la parte più antica risale al 1200 circa) è immerso nella natura e in posizione strategica sulla via Francigena, a 2 km da Monteriggioni, 10 km da Siena e vicino a San Gimignano, Volterra e Firenze. L'appartamento è composto da cucina a vista attrezzata, bagno con doccia, camera con letto matrimoniale e camera con due letti singoli. La zona giorno, dispone di comodo divano letto con tv, wi-fi e aria condizionata

LocationFamilyNearby

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, 290 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.

ValueFamilyAir conditioning

Top Guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.98 out of 5 average rating, 187 reviews

Casa al Gianni - Il Fienile di Simignano

Trasformato da un antico fienile, questo rifugio lussuoso offre 5 camere, 4 bagni, grande cucina attrezzata, ampio living, un ampio giardino privato con parcheggio, hot tub, patio con divani, BBQ, fire pit e cucina esterna. Ideale per chi cerca un'esperienza unica, unisce fascino rustico a comfort moderni. Perfetto per famiglie o gruppi, promette serate magiche sotto le stelle, tra relax nell'hot tub e cene all'aperto. Una fuga memorabile vi aspetta in questo angolo di paradiso!

ValueLocationAir conditioning

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
5.0 out of 5 average rating, 62 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.”

FamilyLocationNearby

Top Guest favourite
Condo in Colle di Val d'Elsa
5.0 out of 5 average rating, 23 reviews

Florence & Siena • Terrace • Private Parking • A/C

Imagine waking up to sunlight filling the apartment and enjoying breakfast overlooking the Tuscan hills. Bright top-floor apartment with elevator, panoramic terrace and 180° open views, between Florence and Siena, in a quiet private area with no through traffic. Perfect for families, with parking, air conditioning, fast Wi-Fi, fully equipped kitchen and all the comforts to explore Tuscany’s villages, wineries, art cities and iconic landscapes.

LocationValueAccuracy

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, 89 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).

LocationValueQuiet

Top Guest favourite
A panoramic view reveals rolling hills adorned with vineyards and olive groves, stretching under a dramatic sky. The tan-coloured buildings of the property are nestled among lush greenery, while a serene pool reflects the surrounding landscape.
Apartment in Quercegrossa
4.97 out of 5 average rating, 77 reviews

Tuscany jem: La Casa del Fattore del Chianti

Questo meraviglioso appartamento appena ristrutturato conserva il fascino dei casolari del Chianti e le comodità di un appartamento moderno. La casa è situata all'interno del complesso della Fattoria di Petroio, azienda vitivinicola del Chianti Classico. Potrete godere della bellezza e della tranquillità delle colline del Chianti, mentre vi immergete nella vita dinamica di un'azienda dedita alla produzione di vini di qualità.

LocationFamilyParking

Popular amenities for Monteriggioni holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Other great holiday rentals in Monteriggioni

Guest favourite
Condo in Colle di Val d'Elsa
4.97 out of 5 average rating, 75 reviews

La Torre di Canonica

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Top Guest favourite
Home in Barberino Tavarnelle
5.0 out of 5 average rating, 82 reviews

Breathtaking Views in Our Chianti Country House

FamilyValueWi-Fi

Top Guest favourite
Condo in Siena
5.0 out of 5 average rating, 19 reviews

Luxury Penthouse overlooking Piazza del Campo

FamilyValueView

Guest favourite
Castle in Tignano
5.0 out of 5 average rating, 25 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

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Top Guest favourite
Apartment in Barberino Val d'Elsa
5.0 out of 5 average rating, 20 reviews

Lorenzo Charme nel Chianti

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Top Guest favourite
Home in Siena
5.0 out of 5 average rating, 20 reviews

Private House for 4P- La Capanna Di Azzurra

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Top Guest favourite
Apartment in Siena
5.0 out of 5 average rating, 16 reviews

Pool Escape Just Outside Siena

FamilyLocationDecor

Top Guest favourite
Two wooden lounge chairs are positioned beneath a large tree, providing shade and comfort. Lush green fields and vineyards are visible in the background, illustrating the serene rural landscape. The scene offers a tranquil spot for relaxation and enjoying the natural surroundings.
Home in Castellina in Chianti
4.97 out of 5 average rating, 30 reviews

Apartment with stunning view on the vineyards

LocationFamilySleep quality

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.

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