
Holiday houses in Castellina in Chianti
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Top-rated holiday rentals in Castellina in Chianti
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Guest favourite

Guesthouse in Castellina in Chianti
4.86 out of 5 average rating, 193 reviewsIl Giglio Relax in Castellina in Chianti
VanessaRating, 5 stars1 month ago
We and our dog felt very comfortable at the place! Stefano was a very warm host. For example, he took us to the supermarket with his car, shared the fruits and vegetables from his garden with us and made us a great welcome gift with a bottle of wine. If you have any questions, Stefano was always available. His two dogs Theo and Rocky were also very sweet. The apartment is on the outskirts, everything is easily accessible on foot. Everything was clean on site, the garden (and especially the pool) was very nice and you had plenty of space and privacy at the same time. 😊
Superhost

Holiday home in Greve in Chianti
4.9 out of 5 average rating, 20 reviewsCuculo - Rifugium
KlioRating, 5 stars2 months ago
Beautiful apartment in the countryside. Spacious and clean. The access by car was a little difficult but definitely recommended.
Top Guest favourite

Villa in Gaiole in Chianti
5 out of 5 average rating, 24 reviewsMontemarcoli
TorbjørnRating, 5 stars3 weeks ago
We had an amazing stay at the villa. A modern house in a quiet environment with beautiful views. Brigitta was very helpful and responded quickly to our inquiries both before and during the stay.
Top Guest favourite

Home in Poggibonsi
4.92 out of 5 average rating, 59 reviewsAgriturismo Podere San Martino (apartment for two)
LukasRating, 5 stars1 month ago
Everything was just like in the pictures. We had a great time. The view was amazing and Maddalena was really helpful. Thank you!
Top Guest favourite

Farm stay in San Quirico d'Orcia
4.98 out of 5 average rating, 44 reviewsWine Loft in the vineyards
HilaryRating, 5 stars2 weeks ago
The Wine Loft is incredibly peaceful and beautiful. The modern architecture is gorgeous and the views are magical. We traveled by trains and it was easy to take a taxi (arranged by the Wine Loft) from the station. Additionally, we enjoyed walking the country path through the woods and meadow to Bagno Vignoni. We highly recommend this beautiful property. The wines were a phenomenal addition to the stay.
Superhost

Apartment in Castellina in Chianti
5 out of 5 average rating, 4 reviewsLa Querce in Rocca di Castellina
AlfredRating, 5 stars3 weeks ago
We have been visiting Tuscany for about 30 years. This locality is certainly the best we have ever lived in. Martina and her parents are very loving and warm to their guests. We can only recommend this offer and we will certainly come back. Best regards and thank you for the wonderful stay Allfred and Sieglinde
Top Guest favourite

Apartment in San Gimignano
4.98 out of 5 average rating, 42 reviewsHerons Superior Apartment - Splendid view!
MicahRating, 5 stars3 weeks ago
Highly recommend anyone new to Italy to try San gimigano first. Staying here allowed us flexibility to explore other cities and had plenty of great spots in walking distance. Lorenzo provided fantastic recommendations and assisted with everything we asked for.
Guest favourite

Condo in Castelnuovo Berardenga
4.96 out of 5 average rating, 69 reviewsCastello di Orgiale Charme Residenz
ShellRating, 5 stars1 month ago
Property is amazing, host so friendly and helpful… Honestly we spent very little time on the property as we were exploring so much of Tuscany during our stay with the lovely location as our home base. But it was so beautiful to wake to every day and come “home” to late every evening :) During our 6 days, we explored Florence, hung out in Siena, hiked Chianti trails, visiting all over from Monteriggioni to San Gimignano to Volterra… and throughout Val d’Orcia from Montepulciano to Pienza , Pitigliano to Serano… and north to Lucca & Pisa. Just wonderful location :) Thank you so much!
Quick stats about holiday rentals in Castellina in Chianti
Total rentals
60 properties
Nightly prices starting at
$17 NZD before taxes and fees
Total number of reviews
940 reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
30 properties have a pool
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- Cottage rentals Castellina in Chianti
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- Rentals with pools Castellina in Chianti
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- Santa Maria Novella
- Duomo di Firenze
- Lake Trasimeno
- Piazza del Duomo (Pisa)
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Basilica of Santa Maria Novella
- Mugello Circuit
- Ponte Vecchio
- Cala Violina
- Fortezza da Basso
- Uffizi Gallery
- Parco delle Cascine
- Piazza della Repubblica
- Piazzale Michelangelo
- Mercato Centrale
- Pitti Palace
- Stadio Artemio Franchi
- Giardino Bardini
- Cavallino Matto
- Avignonesi Winery Fattoria Le Capezzine
- Medici Chapels
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- The Boboli Gardens
- Pinocchio Park