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Cottage vacation rentals in Castellina in Chianti

Find and book unique cottages on Airbnb

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Popular amenities for Castellina in Chianti cottage rentals

Cottage rentals with a hot tub

Top guest favorite
Cottage in San Gimignano
4.97 out of 5 average rating, 69 reviews

Romantic House in Tuscany with jacuzzi

KrisRating, 5 stars1 week ago
This small cottage offers a great view of the town and surrounding area. It is very quiet and private just outside of town. The living areas are comfortable and well appointed. The kitchen had a really nice gas range and oven along with all of the necessary cooking items a person could want. I loved using the moka pot for my morning coffee! We took advantage of the outdoor patio dining area to enjoy our meals several times. There were several books and maps provided as great resources. We especially appreciated the book on common Italian birds and maps for hiking. Davide was very responsive as a host and provided good recommendations during our stay. We had one issue with a leaky faucet during our stay, which was fixed promptly.
Guest favorite
Cottage in Sovicille
4.93 out of 5 average rating, 223 reviews

From Simone, podere santi Lucia and Pietro

LesleyRating, 5 stars7 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
Cottage in Trequanda
4.75 out of 5 average rating, 142 reviews

"Rosso Poggiolo" farmhouse with swimming pool.

EliotRating, 5 stars6 months ago
Very good, it was perfect The host were so friendly Thank you very much
Superhost
Cottage in Paciano

NEW Leccino home pool&Jacuzzi a Fontanaro Property

AgnėRating, 5 stars10 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.
Cottage in San Quirico - Pescia
4.42 out of 5 average rating, 19 reviews

Cottage in San Quirico with pool

NicoleRating, 5 stars14 months ago
Beautiful views, 20 min by car from the nearest town, not accessible without a car. The communication went great, the house was easy to find with navigation & the area is very nice
Guest favorite
Cottage in Seggiano
4.96 out of 5 average rating, 89 reviews

EcoLodge – modern design in quiet panoramic location

TatianaRating, 5 stars2 weeks ago
This place is truly a 10/10. I’ve stayed at dozens of BNBs over this year and I have to say that this is one of my absolute favorites. Every detail, from the decor to the cleanliness to the nature to the spaciousness, is phenomenal. I cannot recommend this place highly enough! One thing to keep in mind is that it’s nestled quite far into the mountains so whenever we went on day trips like to Pienza or Pitigliano, it was always around an hour drive or more.
Guest favorite
Cottage in Castelmuzio
5 out of 5 average rating, 58 reviews

Panoramic view & outdoor jacuzzi - Pienza

JamesRating, 5 stars4 days ago
If you want to experience the Tuscany of your dreams, then this is the place to stay! The pictures are accurate but do not do justice to the beauty you will experience. Birds chirping and bees buzzing around the fragrant jasmine and roses bring peace and calm as you gaze out over the olive grove to the surrounding hillsides with views of Pienza, other towns and a retired monastery. Frank and Phil are incredibly gracious hosts and will not steer you wrong with recommendations, including wonderful restaurants, beautiful churches and abbeys, and wineries. The garden cottage is quite private and you will have no intrusions. Sitting on the patio with a glass of wine, some local cheese, and a good book was our favorite escape.
Guest favorite
Cottage in Campiglia D'orcia
4.94 out of 5 average rating, 32 reviews

Val D’Orcia Eco Cottage - Exclusive Retreat

ErwinRating, 5 stars2 weeks ago
What a fantastic cottage overlooking the valley (UNESCO heritage). Super quiet area, within walking distance of a nice village with various possibilities. We had a great time here and would book it again in a heartbeat!!

Pet-friendly cottage rentals

Superhost
Cottage in Pian di SCO
4.83 out of 5 average rating, 12 reviews

Country Cottage

AurelienRating, 5 stars4 months ago
beautiful place to rest in the middle of the nature. Location perfect to reach different cities liked Florence and Arezzo.
Superhost
Cottage in Castiglione della Pescaia
4.69 out of 5 average rating, 16 reviews

Seaside villa, 2 bedrooms, garden, parking

ManuelaRating, 5 stars8 months ago
Jacopo was a great host! Available and kind, he immediately worked to solve small problems encountered when we arrived, wifi did not work x the modem fault, a small pot was missing x heat the milk (ruined by previous guests) and the bedroom did not have the curtain x darken the light, the day after he had already resolved the wifi failure, bought a new pot and also a new moka and put the curtain in the room. The house is in a quiet location, of course I can hear the cars passing but the new windows perfectly isolate the rooms and you can sleep without problems, the outdoor veranda where you can eat is very nice, the garden is large and fenced, our dog really appreciated. The house is equipped with a/c although in reality it is always fresh. The only downside is the lack of a small microwave or air fryer, to be able to heat or cook fast dishes, but this certainly did not ruin our vacation, we naturally adapted with the fires.
Superhost
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”.
Superhost
Cottage in Bagno A Ripoli
5 out of 5 average rating, 30 reviews

Borgo Spedaletto 3 – Dolcevita Holiday

MathewRating, 5 stars1 month 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.
Guest favorite
Cottage in Capannori
4.91 out of 5 average rating, 46 reviews

@collecottage

Helga Jeanne RRating, 5 stars1 day ago
We had a wonderful stay in this lovely and cosy cottage. Dominick was a great host. We felt at home right away. We also enjoyed the company of Blacky, the house cat, who payed us a visit every morning. There was a bar and some restaurants within walking distance. The perfect spot to explore Tuscany.
Guest favorite
Cottage in San Casciano dei Bagni
5 out of 5 average rating, 16 reviews

Toscana, Country house with exclusive pool

ThomasRating, 5 stars1 week 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
Superhost
Cottage in Massa Marittima
5 out of 5 average rating, 3 reviews

Country cottege olive trees garden near seaside

PatrickRating, 5 stars10 months ago
Giovanni's place fully meets the expectations given by the description and images. We were on site with 3 adults and 3 kids. That is also the maximum and rather very tight but that was clear to us beforehand. The house is a bit remote and about 2.5 km from the place Scarlino. We found it very quiet and in a wonderful location. We took the bike to the bakery in the morning to buy fresh rolls. However, the highlight is the fantastic large pool which was used extensively in the morning and in the afternoon before and after our beach day. Furthermore, you can also rest under a beautiful shade place under the huge palm tree by the pool. The nearest beach is about 10km away in Follonica. The beach is very large and long but of course very crowded during the summer holidays. We looked at and enjoyed almost all the beaches 30min away. The city of Pisa is also easily accessible in 1 hour 45 minutes and is very worth seeing
Guest favorite
Cottage in Pari
4.95 out of 5 average rating, 152 reviews

La Casa del Frantoiano - Pari -

MauraRating, 5 stars3 months ago
Beautiful location! Wonderful stay.

Private cottage rentals

Guest favorite
Cottage in Cavriglia
4.92 out of 5 average rating, 39 reviews

La Loggia, cozy stone cottage for 2 with terrace

AndyRating, 5 stars1 month ago
Wonderful place! Super clean and well-equipped kitchen. Internet was very good, perfect for working from the terrace. Unfortunately, it was still too chilly for the pool. Thanks for the stay!
Superhost
Cottage in Tereglio
4.8 out of 5 average rating, 25 reviews

Cottage Rifustieri with pool

JetteRating, 5 stars8 months ago
Wonderful Airbnb in a great place. The garden is really beautiful. Nicely received and very lovingly helped with our luggage by Lorenza's parents! Highly recommended, and we'd love to come back!
Guest favorite
Cottage in Capannori
4.81 out of 5 average rating, 208 reviews

Lovely cottage in the park of a Renaissance Villa

DaniRating, 5 stars2 weeks ago
The property is quietly located and not directly on the street - you can only get to the property and house through a gate. Loved it! Alessandro is very friendly and always available. Everything was explained to us on arrival. Check in and out was very easy and flexible. The house was very clean and you have everything you need on 2 floors. The location is perfect, you can get everywhere very quickly. We were in Florence, Pisa, Lucca, La Spezia, Siena and some places nearby. There are also some restaurants nearby that are easy to walk to. We will be back to be guests at Alessandro's!
Superhost
Cottage in Paciano
4.84 out of 5 average rating, 67 reviews

Stone cottage in beautiful Umbrian countryside

TimRating, 5 stars5 days ago
Practically perfect in every way - no faults to find at all 😃
Superhost
Cottage in Paciano
4.71 out of 5 average rating, 21 reviews

Casetta Di Pietra 2-bed cottage with private pool.

DawidRating, 5 stars7 months ago
Fiona is a great host. She was really friendly and always eager to help. The house is super cosy and well equipped. The kitchen is great, there was everything we needed to cook delicious Italian dishes. We loved the fire burner. I can highly recommend this quiet place to anyone willing to rest from the bustling city life. The internet connection could be better but this is a very remote location so there’s probably nothing the host can do to improve it. The pool closes in October. It was too cold there to use it but it could have been mentioned in the offer. The quite high (300 eur) deposit for electricity was required and this should have been mentioned as well. It hasn’t been returned to us yet so I can’t say how high the bill for electricity could be. Anyway, this is a really nice place and we had a great time there.
Top guest favorite
Cottage in Impruneta
4.93 out of 5 average rating, 27 reviews

Cottage with private swimming pool

JoeRating, 5 stars8 months ago
My wife and I stayed here as part of our honeymoon and we absolutely fell in love with this place! The scenery is gorgeous, the view from the cottage did not get old! Very private setting in a peaceful neighborhood. Andrea was a fantastic host, along with the help of his lovely parents. He communicated with me at every step of the way making sure all of our needs were taken care of. Could not be happier with our stay and it made our honeymoon very special.
Top guest favorite
Cottage in Città della Pieve
5 out of 5 average rating, 23 reviews

Grove Cottage, Immersed in nature & close to town

CarolRating, 5 stars2 months ago
This is the second time staying at the Grove Cottage and it was as fabulous as the first. After 2 years, the cottage looked exactly the same, everything has been well maintained by the hosts. The garden area has matured providing the most scenic view right outside the front door. Città della Pieve is a charming town and there is a lot to see and do in the area. The hosts are friendly, responsive and a wealth of information.
Guest favorite
Cottage in Pistoia
4.89 out of 5 average rating, 109 reviews

Wonderful Rustic Cottage with Garden-Only Adults

CherylRating, 5 stars3 weeks ago
Comfortable spot for two people. Beautiful garden and friendly neighbors too. Close to Pistoia - with great places to dine. We would definitely return!

Destinations to explore

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  3. Tuscany
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