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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 32 Cottages in Chianti Region with updated reviews, rates, and availability.

Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle
Outdoor pool

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

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
Happy holidays in Chianti, among olives and vineyards, From Florence
Property grounds

Happy holidays in Chianti, among olives and vineyards, 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, among olives and vineyards, From Florence
Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities
Outdoor pool

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

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.
Panorama Nest - Countryside charm with private pool
Outdoor dining

Panorama Nest - Countryside charm with private pool

10.0 out of 10, Exceptional, (1)
"Hallo , Liebe Leser, nachdem wir die ca. 600m holprige, steinige Straße hinter uns hatten, sahen wir die Unterkunft. Wir hatten 10 wunderschöne Tage in der Toskana und dem schönen Panorama Nest mit unserem Hund. Ruhig gelegen und nur ca. 6 km von Einkaufsmöglichkeiten entfernt. Alles, Perfekt, Sauber, eingezäuntes Grundstück, gut, wenn man mit Hund kommt. Der Ausblick von der Terrasse ist Traumhaft. Auch das Schwimmbad erfüllt seinen Zweck auch wenn es nicht so groß ist, hatten wir viel Spaß....
Panorama Nest - Countryside charm with private pool
Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani
Terrace/patio

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
Casa il Cipresso, in the heart of Chianti with swimming pool
Pool

Casa il Cipresso, in the heart of Chianti with swimming pool

Casa il Cipresso, in the heart of Chianti with swimming pool
Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property
Pool

Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property

8.4 out of 10, Very Good, (10)
"The property's location is much more remote than advertised.. We booked it as we were attending a wedding close to Gaiole and the property description says "15 minutes from Gaiole". The 2.5 km forest road took at least 10 min to get to the main road and from there it's a minimum of 20 min to Gaiole ( if you drive Italian style). No taxi or transportation company will go to the property, so forget having a drink somewhere in town. Also, no wifi at the property and the cellular reception is also...
Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property
Charming Farmhouse with Private Pool among Vineyards
Aerial view

Charming Farmhouse with Private Pool among Vineyards

9.4 out of 10, Exceptional, (50)
"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
Casa Belvedere cottage with swimming pool in the heart of Chianti
Pool

Casa Belvedere cottage with swimming pool in the heart of Chianti

Casa Belvedere cottage with swimming pool in the heart of Chianti
Exceptionally pretty cottage with pool, views, in walking distance from Panzano
Pool

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
Typical country house with garden near Florence Siena Pisa San Gimignano
Outdoor dining

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
La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Fridge, oven, stovetop, dishwasher

La Quercia, apartment with garden for 6/8 people in the heart of Chianti

10.0 out of 10, Exceptional, (2)
"We had a wonderful 7 day stay. The location is perfect. It is an easy drive to all the towns in Tuscany. The property is beautiful and quiet. The views are amazing. Patrizia was a great host and very helpful with restaurant and winery recommendations."
La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Casa Antico Roseto - cottage with swimming pool
Dining

Casa Antico Roseto - cottage with swimming pool

8.0 out of 10, Very Good, (1)
"The villa is lovely. The property is amazing. Check-in and out were easy and the owners are very kind. The only complaint we really had with our stay was that it is probably not the best place to stay during the summer months when it is 95+ outside. The villa has no air conditioning and even the fans they provided us did not prepare us for the heat inside even late at night. When we opened the windows we had a lot of mosquitoes and other bugs enter the house so we were forced to close up most of...
Casa Antico Roseto - cottage with swimming pool
La Misura, cottage with garden and swimming pool on the hills of Chianti
Outdoor dining

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
La Chiantinelle - La Grange
Property grounds

La Chiantinelle - La Grange

La Chiantinelle - La Grange
Cottage Polvereto S. Andrea a Cellole a beautiful hilltop Castle sleeps two
Outdoor pool

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
Villa Gaia
Property grounds

Villa Gaia

Villa Gaia
Cottage "Podere in Volpaia" with Garden & Wi-Fi
Outdoor dining

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
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

Hu Norcenni Girasole Village
Exterior

Hu Norcenni Girasole Village

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

Relais Villa Olmo

9.4 out of 10, Exceptional, (202)
"It is just amaizing!!!!!"
The price is AED 448
AED 504 total
includes taxes & fees
2 Apr - 3 Apr
Relais Villa Olmo
Riserva di Fizzano Residence
Outdoor pool, pool umbrellas, sun loungers

Riserva di Fizzano Residence

3.0 star property
10.0 out of 10, Exceptional, (13)
"Amazing stay and experience. The property is well maintained and very peaceful. Everyone on the staff is friendly and very excited to have you as a guest. Food was wonderful. 5 stars all around. Convenient location for day trips or to just relax by the pool. Highly recommend"
Riserva di Fizzano Residence
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.