Cottage vacation rentals in Monticchiello

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Monticchiello

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

1 of 1 pages1 / 1

Guest favorite

A rustic stone building featuring multiple levels stands in the countryside, surrounded by landscaped gardens. Sun loungers line the grassy area near a refreshing outdoor swimming pool, while shaded umbrellas provide comfort. The property showcases a blend of traditional architecture and serene natural beauty.

Cottage in Radicofani

Charming Tuscan Cottage La Bita in Val d’Orcia

La Bita is a lovely typical Tuscan cottage that overlooks UNESCO's Heritage Orcia Valley. Located in the countryside of the medieval hamlet of Radicofani, it's surrounded by 3 hectares of private land and includes an outdoor swimming pool (open seasonally Jun-Sep), garden, outdoor dining area, BBQ and free parking area (uncovered). The studio flat is part of "Podere Maltaia", a property of 12 independent cottages, each with a private garden and entrance. CIR 052024LTN0064 CIN IT052024C2Y95TV5DS

4.9 out of 5 average rating, 100 reviews

Top guest favorite

The cottage, constructed with Città della Pieve's distinctive red brick, is framed by lush greenery under a clear blue sky. Traditional wooden shutters add character to the windows, while a chimney rises from the roof, suggesting warmth and comfort inside.

Cottage in Città della Pieve

Grove Cottage, Immersed in nature & close to town

Overlooking ancient olive groves, yet just an easy stroll from the vibrant heart of historic Città della Pieve, this top-rated luxury cottage is yours for exclusive use. A rare find for its size and location, the property and expansive landscaped garden offer a private, year-round retreat—perfectly situated for exploring the treasures of both Tuscany and Umbria. Enjoy local palazzos, restaurants, and festivals, or relax while exploring the region's vineyards, famed hilltop towns or thermal spas.

5.0 out of 5 average rating, 54 reviews

Guest favorite

A cozy bedroom features a large bed framed by elegant wrought-iron headboards. Textured stone walls complement the cream-colored backdrop. A small table displays travel brochures and decorative elements, providing a homely touch.

Cottage in Pari

Affittacamere La Casa del Frantoiano -Pari-

Proponiamo ai nostri ospiti un appartamentino a Pari, un grazioso borgo nel cuore della Toscana, nei pressi delle Terme di Petriolo e a metà strada tra Siena e il mare, raggiungibili in circa mezz'ora. Completamente e recentemente ristrutturato, si compone di cucina, ampia camera da letto, bagno, spazio relax all'aperto con tavolo. Dotato di aria condizionata e ogni tipo di comfort, é ieale per 2/3 persone, in cucina è presente un letto singolo. Piscina privata in condivisione con altri ospiti.

4.94 out of 5 average rating, 179 reviews

Top guest favorite

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

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.

4.99 out of 5 average rating, 155 reviews

Guest favorite

A modern stone house is surrounded by lush greenery, nestled against a hillside. Large glass windows provide ample natural light, showcasing the inviting interior. The roof has a gentle slope, reflecting a blend of traditional and contemporary architecture.

Cottage in Seggiano

EcoLodge – modernes Design in ruhiger Panoramalage

Die moderne, ökologische und komfortable EcoLodge liegt ruhig und für sich inmitten von Olivenhainen, Kastanien- und Obstbäumen, Wein und Wiesen. Vor Ihnen die Hügel des Val d’Orcia, im Rücken der Monte Amiata. Hier treffen drei Welten aufeinander: Val d’Orcia, Monte Amiata und Maremma. Die Vielfältigkeit ist ein idealer Ausgangspunkt für Kultur, Wein, Wandern, Mountainbiken, heiße Quellen und Meer – und zugleich ein Ort, um abseits der Touristenströme das toskanische Landleben zu genießen.

4.94 out of 5 average rating, 111 reviews

Top guest favorite

A shaded pergola adorned with grapevines provides a relaxing spot for outdoor dining. A colorful table features a floral design, surrounded by wrought iron chairs. A private jacuzzi sits nearby, with lush greenery and rolling hills visible in the background.

Cottage in Castelmuzio

Panoramic view & outdoor jacuzzi - Pienza

‘L’Orto’ sits on a hill facing the 15th century monastery of Sant’Anna in Camprena, which was featured in the Academy Award-winning film ‘The English Patient’. Relax under a vine-covered pergola or in your private outdoor jacuzzi while enjoying panoramic views of idyllic Tuscan countryside, with its rolling hills and winding paths lined with cypress trees. ‘L’Orto’ is ideally located for a visit to the Val d’Orcia, a UNESCO World Heritage site, Pienza, Montalcino, Montepulciano or Siena.

5.0 out of 5 average rating, 81 reviews

Top guest favorite

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

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.

4.95 out of 5 average rating, 298 reviews

Top guest favorite

A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.

Cottage in Osteria delle Noci

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

5.0 out of 5 average rating, 116 reviews

Guest favorite

A rustic stone building is framed by lush greenery and seasonal flowers. Outdoor seating is arranged on a grassy area, including a table and chairs. A swimming pool partially visible in the background invites relaxation. The sky is clear, suggesting a bright day.

Cottage in Fabro

dependance mandriola

La mandriola è la nostra dependance, un vero nido accogliente e affascinante, ristrutturata ed arredata in stile rustico umbro-toscano. Dispone di un ambiente unico pranzo-cucina con caminetto e divano, un'ampia camera da letto con letto a baldacchino, bagno con doccia e lavatrice e un comodo soppalco con letto matrimoniale. Il tutto incastonato in un grande giardino con terrazze panoramiche. Novità 2021: grande jacuzzi privata e casetta sull’ albero per i piccolini!

4.9 out of 5 average rating, 106 reviews

Top guest favorite

An aerial view captures the agriturismo's lush green landscape, featuring neatly arranged cypress trees lining the path. A sparkling swimming pool glimmers amidst the foliage, while sprawling fields extend into the background under a clear sky, showcasing the beauty of the Tuscan countryside.

Cottage in Buonconvento

Tuscan Barn Apartment for 6 with panoramic pool

Panoramic Tuscan apartment converted from an old barn, with direct access to the garden and a shared panoramic swimming pool overlooking the Senese hills. Ideal for families or small groups of friends looking to enjoy for an authentic rural experience, privacy and relax. The apartment features three double bedrooms each with private bathroom, air-conditioning and WI-FI. A perfect place to enjoy nature, silence and unforgettable Tuscan sunsets.

4.89 out of 5 average rating, 100 reviews

Top guest favorite

A spacious area of well-kept grass is seen in the foreground, with a rustic Tuscan farmhouse in the background. The building features a tiled roof and multiple windows. Bare trees and some greenery surround the property, under a clear blue sky with scattered clouds.

Cottage in Sovicille

Da Simone, podere santi Lucia e Pietro

Di recente inaugurazione, la struttura è una porzione di casolare toscano con ingresso indipendente immerso nella campagna senese a soli 10 minuti dal centro storico di Siena. L'appartamento è composto da due camere matrimoniali con due letti matrimoniali ed un letto singolo, bagno con doccia e vasca, soggiorno, cucina. A richiesta un lettino per bambini 60*120 con protezioni. All'esterno è disponibile un'aia comune. Tax di sogg. 1,5€/persona

4.94 out of 5 average rating, 243 reviews

Guest favorite

A stone exterior is presented, showcasing a well-maintained garden with various plants and flowers. A staircase leads from the garden to an entrance, while a wrought-iron gate opens onto a pathway. The structure is flanked by a neighboring building visible in the background.

Cottage in Vescovado

Casa Roberta: una splendida vista sulle Crete!

Casa in pietra, finemente ristrutturata, collocata sulla collina di Vescovado di Murlo. E' ai limiti del centro storico in zona tranquilla dove si sente solo il suono della natura. Due piani con piccolo giardino con vista splendida. Può accogliere quattro ospiti. La casa non è adatta a persone disabili (presenza di scale, vani porta non idonei). Le automobili devono essere parcheggiate all'esterno, nei molti parcheggi del Borgo.

4.83 out of 5 average rating, 161 reviews