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Cottage vacation rentals in Montepulciano

Find and book unique cottages on Airbnb

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Popular amenities for Montepulciano cottage rentals

Cottage rentals with a hot tub

Top guest favorite
A stone cottage is surrounded by lush greenery, featuring a rustic facade with wooden accents. Potted plants are placed near the entrance, and the roof is topped with a small chimney. A pathway of stones leads to the door, inviting guests to explore.
Cottage in San Gimignano
4.97 out of 5 average rating, 66 reviews

Romantic House in Tuscany with jacuzzi

RobertRating, 5 stars5 months ago
We stayed at this lovely cottage in late November and we were delighted with every aspect of the stay. The cottage was clean and comfortable, and was well equipped. The hot-tub was wonderful and sitting there on a chilly night with a view of SG was amazing. Annalisa and Davide were really nice and friendly and very helpful- great hosts. It was about 35 minutes to walk to the town, so quite walkable, and wonderfully quiet and rural (one morning there were 3 deer walking past the window). We had a very nice day out in Sienna which was easy to drive to. I would definitely recommend this place as somewhere really special.
Superhost
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
4.93 out of 5 average rating, 223 reviews

Da Simone, podere santi Lucia e Pietro

LesleyRating, 5 stars6 months ago
Lovely, peaceful, spacious place with a kind and generous host in Simone. He met us as we arrived and used his wagon to help move our luggage into the cottage. Big rooms, lots of space, many handy supplies in the kitchen. Good shower, comfortable bed. Enough bench space in the bathroom to put your things. Simone was really helpful with local recommendations for restaurants and where to park the car. One day he made a delicious tart and bought us in half. Would recommend staying at his place.
Guest favorite
The exterior of the property features a rustic stone façade complemented by wrought iron details. A spacious terrace is equipped with a large umbrella and an outdoor dining area, surrounded by lush greenery, enhancing the natural setting.
Cottage in Radicondoli
4.92 out of 5 average rating, 132 reviews

Splendido fienile ristrutturato in Toscana

RachelRating, 5 stars2 months ago
Beautiful spot in a peaceful setting. Gloria was a fantastic host. We had a wonderful stay.
Superhost
A glass-enclosed veranda offers a view of the private garden and pool area. A round dining table with decorative tiles is surrounded by iron chairs. Light filters through the glass, enhancing the rustic charm of the exposed stone walls.
Cottage in Trequanda
4.75 out of 5 average rating, 142 reviews

"Rosso Poggiolo" casale con piscina.

AliceRating, 5 stars5 days ago
Margherita è stata un host impeccabile, sempre molto gentile e disponibile nelle risposte! Mi ha fornito di tutte le info necessarie e di ottimi consigli. La casa è molto accogliente e funzionale, grandi spazi sia interni che esterni. La casa si trova in un ottima posizione. Spero di poterci ritornare. Grazie Margherita.
The two-story villa features a rustic exterior with a tiled roof and brick accents. A private pool is visible in the foreground, surrounded by well-maintained grass. A staircase leads to the upper level, and large windows allow for natural light. Lush greenery frames the property.
Cottage in Montepulciano
4.58 out of 5 average rating, 12 reviews

Tuscany Villa Girasole

ShariRating, 5 stars8 months ago
Charming home with amazing pool and a great location Massimo was so helpful and always quick to respond offering restaurant reccos as well The ac was great and the bedrooms stay completely dark if you close the shutters which was nice to sleep a little later despite the morning light There were paper towels, salt oil even some coffee and filters, many basics provided We did not hear cars or highway sounds, just owls, roosters and quiet, it truly is a special place
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
4.95 out of 5 average rating, 86 reviews

EcoLodge – modernes Design in ruhiger Panoramalage

NatalieRating, 5 stars5 days ago
Die Eco Lodge ist ein wahres Schmuckstück und Ulla & Ralf sind sehr bemüht und hilfsbereit. Absolute Empfehlung!
Guest favorite
A private outdoor jacuzzi is presented in the foreground, with bubbling water inviting relaxation. In the background, a rustic cottage made of stone is framed by flowering plants and a large olive tree, amidst the scenic landscape of Tuscan rolling hills.
Cottage in Castelmuzio
5 out of 5 average rating, 53 reviews

Panoramic view & outdoor jacuzzi - Pienza

BronwynRating, 5 stars6 months ago
We had a wonderful stay at Orto Cottage. The cottage is very comfortable, the views are divine and the surrounding area is beautiful. We were in our own private world. Frank and Phil are great hosts, very friendly, responsive to any requests and helpful with suggestions. We loved their Private Guidebook. It was packed with great suggestions of places to visit, great restaurants and activities. Orto Cottage is highly recommended if you would like a lovely place to stay in the Tuscan hills that is private and an easy drive to all that the area has to offer.

Pet-friendly cottage rentals

Superhost
A rustic stone building is set amidst a large, green lawn dotted with olive trees. The facade features multiple windows with arched tops, reflecting the characteristic Tuscan architecture. Natural scenery and gentle hills in the background suggest a peaceful, rural atmosphere.
Cottage in Fungaia, Monteriggioni
4.83 out of 5 average rating, 271 reviews

Countryside, 10 min from Siena

RobRating, 5 stars2 weeks ago
een prachtig huis, heerlijke tuin tussen de olijfbomen. en een hele aardige host. de locatie is ruimer dan het op de foto's lijkt. je krijgt een goede omschrijving om er te komen en die heb je wel nodig want ligt heerlijk rustig afgelegen in de natuur
Superhost
An exterior view of a rustic stone structure is presented, featuring a covered porch with a wooden table and benches. Olive trees surround the area, providing shade. A barbecue station is visible nearby, with a pathway leading through the outdoor space.
Cottage in Sinalunga
4.86 out of 5 average rating, 78 reviews

Rustico sulle colline toscane

ErikaRating, 5 stars1 month ago
Alloggio bellissimo ben curato e pulitissimo. Unica pecca l’asciuga capelli piccolissimo e non c’era carta mani in cucina. Del resto tutto ben fornito e posto tranquillissimo
Guest favorite
An outdoor area features a tranquil pool surrounded by neatly arranged lounge chairs and umbrellas. Lush greenery and vibrant flower beds enhance the serene atmosphere, while tall cypress trees create a natural boundary. A dining table is set invitingly, offering a perfect spot for outdoor meals.
Cottage in Bagno A Ripoli
5 out of 5 average rating, 29 reviews

Borgo Spedaletto 3 - Dolcevita Holiday

MathewRating, 5 stars1 week ago
Charming little cottage perfect for a small family in the hills near Florence. Had everything we needed. About 25 minutes drive through the country to central Florence so perfect for day trips in. Lovely walks in the olive groves around the cottage.
Top guest favorite
An outdoor terrace features a rustic wooden ceiling supported by brick columns. Comfortable seating is provided by a light-colored couch and benches, alongside a dining table with chairs. The surrounding greenery and pathways lead to additional buildings, creating a serene and inviting space.
Cottage in Pergine Valdarno
4.77 out of 5 average rating, 57 reviews

Casa Vacanze campagna toscana con piscina

Poussin Bertrand Rating, 5 stars8 months ago
Nous avons passé un très agréable séjour chez Vito. La maison est très bien agencée et propose de nombreux équipements. L’endroit est idyllique entouré de champs d’oliviers et en hauteur permettant une vue exceptionnelle sur la Toscane. La piscine est tout bonnement fantastique, spacieuse et extrêmement entretenue grâce au bras droit de Vito qui prend grand soin de toute la propriété . C’est une adresse à retenir absolument que nous recommandons fortement.
Superhost
A spacious pool is framed by wooden decking, with sun loungers positioned nearby. The view includes a charming stone building with green shutters and lush greenery surrounding the area, creating a serene environment perfect for relaxation.
Cottage in Montespertoli
4.9 out of 5 average rating, 52 reviews

Cottage with panoramic view

PriskaRating, 5 stars7 months ago
We, 2 couples a baby and a dog, enjoyed our week at this lovely location. After a quite rocky and adventurous road, the house is situated in the midst of the beautiful tuscan landscape with wine hills and olive trees. From the lovely pool which was only for us we enjoyed those lovely views. The rooms are spacious and the kitchen is fully equipped, including a nice barbecue ourside. Florence is reachable within about 45 minutes by car and there are two little towns about 10-15 minutes away with big grocery stores, restaurants and gelaterias. Andrea and Gianni were super helpful, responsive and lovely hosts. We would highly recommend Le Spugne.
Guest favorite
Two lounge chairs with cushions are positioned beside a private pool, overlooking rolling hills at sunset. A small table holds a bottle of sparkling beverage, enhancing the serene atmosphere. Lush greenery and trees frame the view, creating a sense of tranquility.
Cottage in San Casciano dei Bagni
5 out of 5 average rating, 15 reviews

Toscana, Country house with exclusive pool

JelmerRating, 5 stars7 months ago
Wij hebben bijna twee weken verbleven in het huisje van Leonardo en we hebben heel erg genoten. Het zwembad was voor ons een echte uitblinker. Je hebt het zwembad helemaal voor jezelf alleen en is prive gelegen. De omgeving is erg rustig en het uitzicht vanaf het huisje fantastisch. Wel zal je even in de auto moeten zitten om een grotere supermarkt te bezoeken (~20 minuten) of naar een stadje te gaan (Sienna, Perugia bijvoorbeeld). Wij genoten juist van de rust en het weer en de privacy. Er is op loopafstand een restaurantje wat zeker een aanrader is! Het huisje zelf was erg goed schoongemaakt toen we aankwamen en Leonardo bood ook nieuw beddengoed aan na een week als we dat wilde, heel netjes. Verder is het huisje wel simpel te noemen en het is niet groot, maar alles wat je nodig hebt zit er in (koelkast met vriezer, vaatwasser, goede TV, goed internet, etc) en als je daar op vakantie ben, ga je natuurlijk ook niet binnenzitten... Misschien komen we nog eens terug!
Guest favorite
Cottage in San Casciano In Val di Pesa
4.82 out of 5 average rating, 157 reviews

Chianti Fienile indipendente

AriannaRating, 5 stars6 months ago
Beautiful little cottage! My young daughters (5 & 2) loved being around Daniella’s dog and the beautiful surroundings of olive trees and being able to disconnect with electronics. We even got to see how olives were harvested early in the morning. We were even given a bottle of wine to enjoy during our stay. Daniella was very helpful! And out of all the Airbnbs I’ve stayed in, the beds were very comfortable!! It is very secluded and the road is very curvy so if you get car sick, take your motion sickness meds. Other than that, I would stay here again! My 5 year old loved our stay here and didn’t want to leave. Thank you Daniella!
Superhost
A well-lit living area features a round wooden dining table surrounded by classic chairs. Soft curtains frame the window, and a door opens to a small balcony. A television stands on a wooden stand, while a decorative lamp and a vase of dried flowers add to the ambiance.
Cottage in Montespertoli
4.77 out of 5 average rating, 243 reviews

Fienile nel Chianti

AntonioRating, 5 stars6 months ago
oltre ogni aspettativa, la vista dalle vetrate sui vigneti del chianti è impagabile, appartamento confortevole e pulito, le foto non rendono giustizia, Paola veramente gentile e reattiva. ci torneremo sicuramente consigliatissimo

Private cottage rentals

Superhost
The cozy porch features a wooden table surrounded by comfortable seating, with lush greenery visible beyond. Decorative plants in terracotta pots add a touch of nature, while lanterns provide ambient lighting. The blue wooden beams create a welcoming entrance to the home.
Cottage in Castiglione della Pescaia
4.96 out of 5 average rating, 48 reviews

The Cottage

JuttaRating, 5 stars6 months ago
Das Haus lebt von Gloria, die eine perfekte Gastgeberin und eine Seele von Mensch ist. Sie hat uns persönlich zu der Unterkunft begleitet, uns alles erklärt und mit hausgemachten Köstlichkeiten und toskanischen Spezialitäten verwöhnt: selbstgebackenes Brot und Kekse, Marmelade, frisches Obst, Wasser im Kühlschrank, toskanisches Olivenöl und Kaffee. Weil es bei unserem Aufenthalt im Oktober teilweise ziemlich kühl wurde, hat sie uns zusätzlich noch Holz und Anzünder für den offenen Kamin gebracht. Wir hatten drei gemütliche Tage in dem blauen Gartenhaus, das seinen Charme im Sommer sicher noch mehr entfaltet, wenn man den Garten und die schöne Terrassen nutzen kann. Ans Meer sind es nur ein paar Kilometer mit dem Rad oder dem Auto. Sehr zu empfehlen ist auch das vegetarische Restaurant, das Gloria zusammen mit ihrer Schwester betreibt, etwa 1 km vom Haus entfernt.
Superhost
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
4.88 out of 5 average rating, 83 reviews

dependance mandriola

AndreaRating, 5 stars8 months ago
La dependance è molto bella e accogliente, con uno stile "antico" ma con servizi moderni, arredamento curato, bello e funzionale. Ci siamo trovati molto bene e ci siamo sentiti accolti dai proprietari, che abitando a pochi metri ci hanno invitato a non esitare a disturbarli per ogni evenienza. La posizione è ottima, con vista a 360 gradi sulle colline circostanti, a pochi minuti dal casello dell'autostrada anche se dalla casa è impossibile dirlo. Punto di forza ovviamente la jacuzzi esterna, ottima per il relax serale dopo aver girato tutto il giorno. Ci ha fatto piacere ricevere la visita mentre eravamo nel portico dei vari amici a 4 zampe che sono stati molto coccoloni! Se capita ci tornerò molto volentieri!
Guest favorite
Cottage in San Martino in Grania
5 out of 5 average rating, 41 reviews

Crete Senesi - Asciano Capanna Cavoni

ChristophRating, 5 stars7 months ago
perfect place in Tuscany we stayed 7 days and it was perfect to explore Tuscany and to relax at the pool side. The house is very charming in Tuscany style Laura even left us coffee water and Prosecco. One if the best stays during our Italy trip
Guest favorite
The image captures a tranquil pool area surrounded by lush greenery, with vibrant pink flowers framing the view. A shaded lounging area is positioned adjacent to the salt-water pool, inviting relaxation under the sun.
Cottage in Cavriglia
4.92 out of 5 average rating, 38 reviews

La Loggia, cozy stone cottage for 2 with terrace

GüntherRating, 5 stars11 months ago
Urlaub und Entspannung von der ersten Minute an. Schön eingerichtetes Haus mit zwei geräumigen Zimmern sowie Bad und Küchenzeile. Perfekte sonnige Terrasse, auf der man von morgens bis abends seine Zeit verbringen kann. Tisch, Stühle, Sessel und Liegen vorhanden. Gut erreichbar ca. 20 km von der Autobahn. In 15 km Entfernung alle Einkaufsmöglichkeiten.
Guest favorite
Cottage in Pievescola
4.93 out of 5 average rating, 88 reviews

Antico Borgo Ripostena – n. 1 Casa Bertilla

JackRating, 5 stars7 months ago
Fantastic place to stay! A beautiful place nestled away in the countryside. We loved our honeymoon stay, thanks for the wine!
Superhost
A dining table is set outdoors, surrounded by olive trees. Plates and glasses are neatly arranged, along with green and dark bottles of wine. A slender olive tree serves as a centerpiece, blending harmoniously with the serene landscape of the Tuscan countryside.
Cottage in Cortona
4.9 out of 5 average rating, 29 reviews

Casa Gialla, Cortona-sunsets in the olive grove

Hans PeterRating, 5 stars9 months ago
We had a wonderful time. In addition to other reviews let me point this out: good matrasses, working roll-up flyscreens at bedroom windows, Lesley (or Celeste) helped very fast when WiFi was down due to power cut, comfy chairs for garden, cushions for chairs and deck chairs. Apart from that: everybody was nice, everything was as described. We would definitely like to come back.
Superhost
A refreshing swimming pool is framed by a well-maintained lawn, with two stone buildings visible in the background. The adjacent structure displays classic architecture, while the other features inviting windows and a welcoming entrance, surrounded by lush greenery and blooming flowers.
Cottage in Monteriggioni
4.75 out of 5 average rating, 58 reviews

apartment surrounded by greenery

LaurenceRating, 5 stars9 months ago
Nous avons passé un excellent séjour chez Antonello. Il est très accueillant, en dépit du fait qu'il ne parle qu'Italien, et allemand, si je ne me trompe pas. Il a été tres compréhensible sur le fait que nous arrivions plus tôt que l'heure prévue. Nous avons pu déposer nos bagages et la nourriture que nous avions apportée de notre précédent logement, chez lui. A notre retour, nous avons été agréablement surpris de voir qu'il avait tout transféré dans notre location et avait même mis nos bouteilles au réfrigérateur 🤩. La piscine est superbe, à très bonne température, et les transats à disposition, sont confortables, il y a même une douche, ce qui est très bien. Vous pouvez mangez à l'extérieur, à l'ombre, il y a différents espaces à votre disposition. En résumé, nous pouvons dire que nous avons passe un excellent séjour, dans un magnifique environment, calme, aménagé avec goût. Il faut prévoir d'y venir en voiture, si vous souhaitez visiter....
Guest favorite
The exterior features a spacious garden surrounded by greenery, showcasing a variety of plants. A shaded area provides seating with lounge chairs and a large tree offers additional shade. The house structure is visible in the background, with large windows reflecting the landscape.
Cottage in Castelfranco Piandiscò
4.91 out of 5 average rating, 68 reviews

Villetta Belvedere

RicardoRating, 5 stars1 month ago
The place was very nice and well located! The garden with the view of the Tuscan hills is amazing! Simone is very responsive and helpful. The village is peaceful and idyllic with local markets and shops around the corner. The location is perfect to further explore Tuscany. Would definitely recommend Simone’s place!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Montepulciano
  6. Cottage rentals