Search Cottages in Chianti Region

Compare 28 Cottages in Chianti Region with updated reviews, rates, and availability.

Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities

9.8 out of 10, Exceptional, (29)
"Most beautiful and quiet setting. Awesome host. I would have given 5 stars across the board but the property is fairly remote down a rough gravel road, but definitely worth the drive for the location and host."
Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities

Apartment/ flat - Barberino val d'ElsaHouse with character

9.8 out of 10, Exceptional, (39)
"We had a lovely 12 day stay in this charming little villa near Tuscany. Loretta was a wonderful host and the location was perfect for us. We enjoyed exploring Sienna, Florence and nearby Poggibonsi, but days in the pool at the villa were hard to beat (especially with the 40 degree heat)."
Apartment/ flat - Barberino val d'ElsaHouse with character

Happy holidays in Chianti, between olives and vines, 35 min. From Florence

9.8 out of 10, Exceptional, (16)
"A lovely little cottage in beautiful surroundings and perfectly situated to discover Tuscany. Elisabeth is lovely and very friendly and helpful and Oliver is brilliant"
Happy holidays in Chianti, between olives and vines, 35 min. From Florence

Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.

9.0 out of 10, Wonderful, (19)
"It was wonderful "
Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.

Charming Farmhouse with Private Pool among Vineyards

9.4 out of 10, Exceptional, (49)
"This property is fantastic if you want to enjoy the real Tuscan life. The Villa, pool is all that is advertised. Olivia is the property manager and makes your stay everything you could hope for. We spent an entire month with 6 guests per week. Morning day trips afternoons by the pool and evenings watching the sunset with the estates wines. It was a month to remember. Cheers Steve Enna"
Charming Farmhouse with Private Pool among Vineyards

Typical country house with garden near Florence Siena Pisa San Gimignano

9.8 out of 10, Exceptional, (47)
"Distant views of olive groves and vineyards. Misty cool mornings, listening to church bells and birdsong. THIS was our home base in Tuscany that we were lucky enough to have discovered. All of the photos and descriptions do not do justice to this beautiful villa 30 minutes outside of Florence! Close to the tram, which brought us into Florence 4 times during our incredible 2 week stay we also took advantage of our rented car to drive the beautiful scenic roads to nearby medieval villages and...
Typical country house with garden near Florence Siena Pisa San Gimignano

Exceptionally pretty cottage with pool, views, in walking distance from Panzano

10.0 out of 10, Exceptional, (43)
"Could not have asked for more the grounds, the house, the hostess, the surroundings . . . All just beautiful and wonderful. Felt like I could have spent a month there. The hostess was so nice and so helpful. On the last night we had the chef and owner from a local restaurant, Mimo come and cook for us. It was like a movie. He was such a good cook, so nice. Sat down and talked to us and had a glass of wine . . . It was wonderful, felt like we had a much better understanding of Italy."
Exceptionally pretty cottage with pool, views, in walking distance from Panzano

FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops

9.6 out of 10, Exceptional, (17)
"We stayed in apartment Falco which has great views over the valley.The apartment is exactly as listed,well equipped and spotlessly clean.It is perfectly placed for visiting all the top Tuscan towns and there are numerous local restaurants within easy reach. Fabio and Annemarie are wonderful hosts and we will definitely be visiting again. Thanks for a wonderful stay."
FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops

Detached house in heart of Chianti Classico,pool,quiet panoramic position,WLAN

10.0 out of 10, Exceptional, (15)
"The situation is secluded and delightful. The only sounds were from the birds and the occasional car. The house was spotlessly clean and the lady owner was charming. We loved exploring the nearby hill-top towns and we ate some delicious food. Because the house is quite high there was a welcome breeze. The pool was exceptional."
Detached house in heart of Chianti Classico,pool,quiet panoramic position,WLAN

Cottage Polvereto S. Andrea a Cellole a beautiful hilltop Castle sleeps two

9.8 out of 10, Exceptional, (10)
"To start we were welcomed by a complimentary bottle of wine to celebrate our new marriage! The host was very attentive, provided restaurant recommendations, wine tour suggestions and local site seeing suggestions. Apartment was clean and cozy with spectacular views with olive trees and host made olive oil! This host goes above and beyond to make their guests feel at home. By far our favourite part of our week was Nelson…. You stole my heart out handsome guard dog. We will 100% be back and...
Cottage Polvereto S. Andrea a Cellole a beautiful hilltop Castle sleeps two

Podere le Fonti

Podere le Fonti

The Arsoli hut .Swimming pool exclusive use.

10.0 out of 10, Exceptional, (23)
"Words can't can't describe how much we enjoyed our stay. Anna became one our family and ours hers. She brought a doctor to the unit so I was able to get a needed prescription. She stopped by daily to say hi and we learned to use translate to communicate which was lots of fun. The grounds offer plenty of privacy. Sienna is not far and Multapulciano"
The Arsoli hut .Swimming pool exclusive use.

Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle

9.6 out of 10, Exceptional, (19)
"First of all, Marzio was hands down the best host we have ever stayed with. He was very helpful with recommendations and giving us information of the area. We ate in some outstanding restaurants on Marzio recommendation and he was right on the mark. The house is exactly what we were looking for, a beautiful Tuscan retreat, close to Florence and Siena. The pool was an added bonus that we used every day to cool off. We would really want to stay again. We did happen to stay in July and it was...
Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle

Beautiful 1-bedroom cottage with garden and views over olive groves, pool

Beautiful 1-bedroom cottage with garden and views over olive groves, pool

Cottage "Podere in Volpaia" with Garden & Wi-Fi

10.0 out of 10, Exceptional, (3)
"Nous avons séjourné 10 jours dans cette charmante maison en Août 2023. Cristina nous a bien accueillie, la maison est très fonctionnelle, Il y a une belle terrasse couverte et un petit coin de verdure privé. La maison est entourée de vignes et d'oliviers, nous avons pu déguster l'huile et le chianti produits sur place. Cristina, la propriétaire, nous a organisé un repas et nous a fait déguster les vins de sa production. Le petit village de Radda est à 10 min en voiture, on y trouve tout ce...
Cottage "Podere in Volpaia" with Garden & Wi-Fi

La Misura, cottage with garden and swimming pool on the hills of Chianti

10.0 out of 10, Exceptional, (2)
"We had a wonderful couple days at La Misura. Niccolò was super nice and helped us get settled. The view was like a painting of Tuscany. It was everything we could have wanted. This is a beautiful location. We will go back soon. Thank you!"
La Misura, cottage with garden and swimming pool on the hills of Chianti

Villa Gaia

Villa Gaia

Beautiful 1-bedroom cottage with garden and views over olive groves, pool

9.2 out of 10, Wonderful, (7)
"Country setting with beautiful views. Low key and a good place to unplug. Good restaurants and villages near by. Simon was helpful and we enjoyed our stay."
Beautiful 1-bedroom cottage with garden and views over olive groves, pool

Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani

10.0 out of 10, Exceptional, (1)
"This was by far the best experience I have EVER had at a VRBO property. The house is absolutely precious and my group of four loved it. Everything was so charming- we kept comparing it to Cameron Diaz in The Holiday. The back porch is perfect for a morning cup of coffee that Eva provides (every single option) or a fabulous glass of wine at the end of the day touring vineyards in Tuscany. We can’t speak more highly about the host, Eva. She was so easy to work with, gave us fabulous restaurant...
Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani

Belvilla by OYO Cottage in Tavarnelle With Garden

Belvilla by OYO Cottage in Tavarnelle With Garden
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Chianti Region

Relais Villa Olmo

9.4 out of 10, Exceptional, (200)
"My family and I stayed there for 2 nights, at the family suite. It was very clean and well decorated & furnished, with private pool and garden. The environment and view were good, staff were helpful, buffet breakfast got lot of choices. Highly recommended this lovely place "
Relais Villa Olmo

Hu Norcenni Girasole Village

4.0 star property
8.6 out of 10, Excellent, (279)
"Everything ok 🙂"
Hu Norcenni Girasole Village

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

10.0 out of 10, Exceptional, (55)
"A+"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.