Some info has been automatically translated. Show original language

Cottage vacation rentals in Montalcino

Find and book unique cottages on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Montalcino 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, 70 reviews

Romantic House in Tuscany with jacuzzi

JosephRating, 5 stars2 weeks ago
Davide and Annalisa's cottage was absolutely gorgeous, exactly as the pictures showed. It was the perfect place for us to relax and enjoy our last week in Italy. Breakfast out on the patio with the birds chirping and surrounded by nature was a great way to start the day. Davide lit the heater for the hot tub for us and we were able to enjoy a wonderful evening relaxing. Davide and Annalisa were full of good recommendations for restaurants and local places to visit. The cottage is within driving distance of so much - Pisa, Florence, Siena and of course San Gimignano just to name a few. All the amenities we needed were included, the WIFI was great and the cottage was very comfortable. I would highly recommended staying here and if we are ever in the vicinity we would certainly stay here again.
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
4.93 out of 5 average rating, 223 reviews

From Simone, podere santi Lucia and Pietro

LesleyRating, 5 stars8 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.
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" farmhouse with swimming pool.

EliotRating, 5 stars7 months ago
Very good, it was perfect The host were so friendly Thank you very much
Superhost
A gravel pathway leads through an archway adorned with blooming roses, framed by lush olive trees. The entrance is marked by wooden gates that open into the property, inviting guests to explore the serene surroundings.
Cottage in Paciano

NEW Leccino home pool&Jacuzzi a Fontanaro Property

AgnėRating, 5 stars11 months ago
We stayed at the wonderful Fontanaro villa in the village of Paciano, and it was truly a soul-refreshing experience. Lucia is an incredibly caring host, and Pam, who looked after our stay, was a real treasure. She not only provided excellent recommendations on places to visit but also took care of reservations, ensuring we had nothing to worry about. This was not just an ordinary stay; it was a unique experience. We had the opportunity to participate in an olive oil tasting and a cooking class—both activities left an indelible impression. The villa we stayed in was not only stunningly beautiful but also boasted an impressive wine cellar with an extraordinary collection. Overall, our stay at Fontanaro villa exceeded all expectations. It was more than just accommodation—it was an experience we will never forget.
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
4.62 out of 5 average rating, 13 reviews

Tuscany Villa Girasole

DavidRating, 5 stars1 week ago
What a great place to stay. Everything we needed during our stay was available, from a cot for our baby to an iron and a full kitchen etc. The location was great for Tuscany, with Siena, Montelpulciano and others an easy drive away. The pool was just what we needed in the afternoons to cool down and relax after spending our mornings out and about. We hosted a dinner with family in the large dining table overlooking the pool, a lovely end to our stay at a superb family spot.
Guest favorite
A stone villa is surrounded by a lush green lawn, with a pathway leading to the entrance. Sun loungers are positioned nearby for relaxation. The landscape includes distant hills, complementing the serene outdoor environment.
Cottage in Reggello
5 out of 5 average rating, 10 reviews

Independent cottage with private spa

MarcRating, 5 stars10 months ago
Dreamy and beautiful place! You can't ask for better. A breathtaking view, nothing is missing inside, comfortable bed, etc. Not to mention Elena's warm welcome and the good wine 🍷 she left us as well as a large bottle of water.
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
4.96 out of 5 average rating, 90 reviews

EcoLodge – modern design in quiet panoramic location

ChrisRating, 5 stars1 week ago
Third time at this beautiful place! As always a nice surprise
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
5 out of 5 average rating, 60 reviews

Panoramic view & outdoor jacuzzi - Pienza

AmandaRating, 5 stars2 weeks ago
Golly where to start - my husband and I are from New Zealand and used to peace and quiet and this is 100% what we were after. We were literally blown away from the moment we arrived and walked up the path of jasmines to sitting in the spa when it cooled off and watching the fireflies and listening to the bells ringing from the local monastery and churches. It was perfect for two people. You will need to be able to cope with a fairly tight drive in! And another word of advice is make sure you have some bug spray as it’s located in an area of rich agriculture and as such the mosquitos are about not awful but they are there.

Pet-friendly cottage rentals

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
4.78 out of 5 average rating, 58 reviews

Holiday Casa Vacanze Tuscan countryside with swimming pool

Aneta & StefanRating, 5 stars9 months ago
We had a lovely time at Vito's. Great location, great garden and pool. We were able to enjoy our peace and the place was equipped with everything you need. We'd love to come back.
Guest favorite
Two white Adirondack chairs are positioned on a lush green lawn facing the lake, providing a view of the water and a colorful sunset. A firepit is centered between the chairs, adding to the outdoor ambiance. Trees line the edge of the property, enhancing the scenery.
Cottage in Magione
4.96 out of 5 average rating, 92 reviews

Lakehouse in unique position on Lake Trasimeno

JackRating, 5 stars2 weeks ago
The Lakehouse is even better than the pictures, it’s a perfect place to relax or as a base to explore the local area. The villa also has kayaks and paddle boards to explore the lake. The hosts David and Chrissie are the most accommodating organised people I have come across on air bnb. I highly recommend.
Top guest favorite
A wooden swing set is positioned in the lush garden, framed by vibrant greenery and the rustic house in the background, which is partially covered in climbing plants, reflecting the charm of the countryside setting.
Cottage in Lubriano
4.98 out of 5 average rating, 132 reviews

Farmhouse between Orvieto and Civita di Bagnoregio

DorangelliRating, 5 stars1 month ago
The place is as described. It is definitely worth the price. Emi is very nice. We will stay again!!!!
Guest favorite
A stone house is set against a backdrop of green hills and blue sky. The textured facade features warm colors, complemented by a terracotta roof. Surrounding flowers add a natural touch, while the entrance is framed by lush greenery, enhancing the peaceful atmosphere.
Cottage in Santa Fiora
4.86 out of 5 average rating, 22 reviews

Il Seccatoio – a stone house with a panoramic view

FrancescaRating, 5 stars1 month ago
My husband and I stayed two nights in the Chestnut Dryer of the Podere di Maggio. What can I say? A real paradise: nestled in a wonderful valley with Mount Amiata in front of it and the beautiful medieval village of Santa Fiora. We could not ask for more: wonderful structure, well cared for, in detail, priceless peace. The hosts were great, hospitable, and really made us feel at home. In short, everything is perfect, nothing is missing, of course you have to love bucolic life like us ! The only downside? Two nights were too short and we'll definitely be back . Thanks Peter , Rita and sweet Noemi. See you soon
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, 17 reviews

Toscana, Country house with exclusive pool

ThomasRating, 5 stars1 month ago
The view is stunning. The place is very private. Leonardo is very responsive. Definitely worth visiting La Pace, a lovely restaurant 5 mins walk away. 10/10 recommend
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
4.9 out of 5 average rating, 71 reviews

Villetta Belvedere

AndrewRating, 5 stars2 weeks ago
Fantastic stay, incredible views and perfect location. Couldn’t recommend this place highly enough. Thank you Simone :)
Guest favorite
A charming stone cottage is surrounded by lush greenery and flowering plants. The building features a red-tiled roof and distinctive chimney caps, with a welcoming wooden door framed by a gravel pathway. Natural light reflects on the rustic stone exterior.
Cottage in San Casciano In Val di Pesa
4.82 out of 5 average rating, 158 reviews

Chianti Independent barn

SammiRating, 5 stars2 months ago
I wish we could’ve stayed here longer! This was the perfect, cozy, peaceful stay. Daniela and her family were so kind, they made us feel right at home. The grounds were so beautiful, and just a short walk up the hill, through the vineyard, and you get an incredible view. Within a 15 minute drive, there are some great restaurants and vineyards to check out. This was truly a perfect stay for us, we loved everything about it.
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
4.78 out of 5 average rating, 247 reviews

Barn in Chianti

AndreRating, 5 stars4 days ago
Very friendly and helpful hosts. The garden and pool area looks even better in person than in the photos. Price / performance definitely fits and all in all it was a very nice holiday !

Private cottage rentals

Superhost
A stone path winds through lush greenery, flanked by vibrant flowers and tall cypress trees. The landscape in the background showcases rolling hills, providing a serene atmosphere. Soft natural light filters through the trees, creating a calm and inviting scene.
Cottage in Cinigiano
5 out of 5 average rating, 7 reviews

Cottages in Tuscan Country (Spazzacamino)

JanusRating, 5 stars11 months ago
Our stay at Gabriele's place was great and we enjoyed the week we have with him. The house has a cinematic sweeping view of the Tuscan countryside and the pool just like that. The pool is perfect for cooling off on the hot summer days. The house is beautiful, rustic, clean and cool. Air conditioning also helps. We have been a family of 4, with children of 4 and 7 years. We have enjoyed it every day! Gabriele and his wife were very friendly, welcoming and always easy to reach if needed. They helped make our stay just perfect. Thanks to them! We can only recommend a stay with Gabriele and his “Le Capannacce”.
Guest favorite
A tranquil salt-water pool, measuring 10x5 meters, is surrounded by lush greenery and olive trees. Two shaded sun loungers offer a relaxing space to unwind, while an umbrella provides additional shade. Golden stones form the pool deck, reflecting the sunlight.
Cottage in Cavriglia
4.85 out of 5 average rating, 71 reviews

Il Fienile, characteristic stone cottage for 2

JanRating, 5 stars1 month ago
Beautiful location, remote and quiet. Nice base for city visit (Arezzo, Siena, Florence) Beautiful hike in the Balze made!! Friendly Host!
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
4.87 out of 5 average rating, 83 reviews

Rustic retreat in the Tuscan hills

FedericaRating, 5 stars3 weeks ago
The farmhouse among the olive trees is an oasis of peace, we had a very good time as a group of four with our two dogs in absolute tranquility and with a spectacular view of the hills. There is everything you need in the house. Thank you so much Federica and family
Superhost
Cottage in Fabro
4.88 out of 5 average rating, 86 reviews

dependance mandriola

DesireeRating, 5 stars2 weeks ago
We can only say, that we stumbled upon this find was pure luck. We are nature lovers and this place helped unwind and immerse ourselves in the natural beauty of Tuscany. Thank you Tiziana and Family- esp the fur babies, they become part of our happiest memories.
Superhost
A cascading display of delicate white flowers hangs from intertwined branches, creating a natural canopy. Soft sunlight filters through the blossoms, illuminating the pale petals against a clear blue sky.
Cottage in Scarlino
4.82 out of 5 average rating, 17 reviews

A cottage with a view

JosefRating, 5 stars12 months ago
The house is very clean and simple but conveniently furnished. The access leads the last kilometer over a natural road, which is also easily accessible without an SUV. To mention is the absolute tranquility and the many forest paths, which can be used perfectly for jogging, hiking or mountain biking. The highlight, however, is the pool, which was exclusively available to us. The sea and various beaches (sand or stone) can be reached in about 15 minutes by car. Margeritha is always available if there are any issues or questions and helps quickly and unbureaucratically. (Broken washing machine was replaced within a few hours) All in all, an absolutely positive experience
Top guest favorite
A charming stone house is framed by greenery, with a covered porch featuring wooden beams. Colorful flowers in bloom line a path leading to the entrance, enhancing the natural surroundings. The setting conveys tranquility and a connection to nature.
Cottage in San Venanzo
5 out of 5 average rating, 34 reviews

a small stone house in the woods

CarolineRating, 5 stars5 days ago
Well what can you say about a little piece of heaven! Everything about this lovely house in the woods was perfect for us. If you want peace, tranquility and nature this is just the place! The house is beautifully designed, very well equipped and very well thought out from an environmental perspective as well. Gabriele was so helpful, so respectful and such an interesting person to talk to. By the end of the stay we felt we had made such a lovely new genuine friend. The swimming pool was such a lovely bonus as well. I feel sure we will be back again!
Guest favorite
Cottage in Frattavecchia
4.89 out of 5 average rating, 54 reviews

Casale Poggiolo Basso - The place of silence

CeciliaRating, 5 stars1 month ago
Our family enjoyed a delightful week-long reunion at Cassale Poggio Baggio. Silvia's property provided an ideal setting for relaxation and togetherness, comfortably accommodating guests traveling from various global locations. Its convenient proximity to Castiglione del Lago, Panicale, Paciano, Cortona, and Montepulciano, among other notable destinations, offered ample sightseeing opportunities. The abundance of nearby vineyards further enhanced our experience with wine tasting excursions. The house itself was fully equipped, including a complete kitchen and laundry facilities, along with a generous selection of books and games. Camila's assistance with check-in and check-out, coupled with a tour of her olive orchard and vegetable garden, including a tasting of her produce, exceeded our expectations.
Top guest favorite
An outdoor dining area features a stone table surrounded by wooden chairs, set within a landscaped garden. Lush greenery and trees provide a natural backdrop, while a grill is visible in the distance. The scene is complemented by a gentle gradient of colors in the evening sky.
Cottage in CittĂ  della Pieve
5 out of 5 average rating, 25 reviews

Grove Cottage, Immersed in nature & close to town

GemmaRating, 5 stars1 week ago
We thoroughly enjoyed our stay at the cottage. The cottage and gardens are beautiful and stylishly designed. Leonardo was also a lovely and accommodating host. The local town was approx a 20min walk away with a small supermarket and some lovely restaurants. We recommend Pomario winery for their wine tasting and charcuterie and also Slow Cooking school for a cooking class which is about 25min drive away from the cottage. A local hotel in the area, hotel Vanucci, was also a great place to grab breakfast or for late evening drinks after dinner. Highly recommended booking this beautiful place.

Destinations to explore

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