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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Cottages in Castellina in Chianti and around

Fullino Nero
Garden

Fullino Nero

9.6 out of 10, Exceptional, (46)
"Good place."
The price is €102
includes taxes & fees
23 Aug - 24 Aug
Fullino Nero
agriturismo la roggiola
Exterior

agriturismo la roggiola

9.8 out of 10, Exceptional, (106)
"Cute rustic cottage with a beautiful restful view of farm land and forrested hills and a covered outdoor eating area."
agriturismo la roggiola
BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany
Outdoor dining

BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany

9.8 out of 10, Exceptional, (67)
"This is a great property with loveku views and a great welcome. Loved our stay and will be going back."
BRUNELLO - Cozy cottage located in a peaceful & panoramic position in Tuscany
Santo Pietro Resort
Front of property

Santo Pietro Resort

10.0 out of 10, Exceptional, (1)
"Un excellent service à la clientèle. Un gros merci à Chiara pour son accueil et sa rapidité de régler une petite problématique "
Santo Pietro Resort
Charming Farmhouse with Private Pool among Vineyards
Outdoor dining

Charming Farmhouse with Private Pool among Vineyards

9.4 out of 10, Exceptional, (50)
"We stayed here with our family as a large group of 8 adults and 1 infant. The layout of the house worked great, each couple had their own room (even our daughter) and their own bathroom! Our daughter loved the pool and the property had everything we needed. The location was great, our group took day trips to explore Siena, Florence, and wine country. The winery on the property was also fantastic! A great place to say and I highly recommend it!"
Charming Farmhouse with Private Pool among Vineyards
Panorama Nest - Countryside charm with private pool
Outdoor dining

Panorama Nest - Countryside charm with private pool

9.0 out of 10, Wonderful, (4)
"A very quiet und beautiful Place for These looking for siilence and nature.Small House, but clean and excellent equipped.A wonderful terrace with breathtaking view."
Panorama Nest - Countryside charm with private pool
Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani
Outdoor dining

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

10.0 out of 10, Exceptional, (4)
"A slice of Tuscany heaven. Endless views with a pool too! Il Casetto is a loved home and it shows everywhere you look. From lovely decorated rooms to beautiful gardens and a great "cucina" Il Casetto was perfect for our family. The location is just minutes from Castellina in Chianti which is a great home base for touring Tuscany. The VRBO photos are excellent at capturing the home. Every day our family would enjoy sunrise with the aroma of the flowering plants. Jasmin, oleander and others...
Cottage nel Chianti con Piscina. Vista Sulle Colline e sui Vigneti Toscani
Countryside, 10 min from Siena
Exterior

Countryside, 10 min from Siena

9.4 out of 10, Exceptional, (3)
"Thank you Letizia for a lovely two days. The flat is comfortable, tidy and well equipped. The location is peaceful. The road to get to the house is a little bumpy but worth it once you get there. Letizia is friendly and very kind and helpful. Our dog loved his time playing with the other dogs. Grazie mille Letizia"
Countryside, 10 min from Siena
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, (20)
"A great stay in a beautiful part of the world. We go some great recommendations from the host on places to eat and we weren’t disappointed. Just an amazing stay!"
Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.
Glicine, romantic cottage with outdoor patio, on the hills of San Gimignano
Exterior

Glicine, romantic cottage with outdoor patio, on the hills of San Gimignano

7.0 out of 10, Good, (4)
"Loved this quaint cottage. We will be back."
Glicine, romantic cottage with outdoor patio, on the hills of San Gimignano
Tuscan Charm: Frassini Cottage
Exterior

Tuscan Charm: Frassini Cottage

9.0 out of 10, Wonderful, (2)
"Schönes, gastfreundliches Haus, in dem alles für einen typisch italienischen Urlaub vorhanden ist."
Tuscan Charm: Frassini Cottage
Charming Vineyard Escape
Cottage | Exterior

Charming Vineyard Escape

Charming Vineyard Escape
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Exterior

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

10.0 out of 10, Exceptional, (1)
"I can’t say enough about this wonderful Tuscan gem! We were lucky to find such a beautiful spot to stay. The staff were so friendly and helpful and the cooking class was so much fun! The restaurant was also very good! Thank you for a wonderful stay! "
The price is €172
includes taxes & fees
21 Aug - 22 Aug
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Exceptionally pretty cottage with pool, views, in walking distance from Panzano
Outdoor dining

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

10.0 out of 10, Exceptional, (43)
"Superb location / great scenery Lucrezia is a welcoming hostess "
Exceptionally pretty cottage with pool, views, in walking distance from Panzano
Suite indipendent apartment located in Historic Estate from 1600
Exterior

Suite indipendent apartment located in Historic Estate from 1600

10.0 out of 10, Exceptional, (25)
"Loved the stay and the quiet countryside!"
Suite indipendent apartment located in Historic Estate from 1600
Typical Tuscan Cottage with swimming pool and park, five minutes from San Galgano
Exterior

Typical Tuscan Cottage with swimming pool and park, five minutes from San Galgano

10.0 out of 10, Exceptional, (14)
"A great place for a family vacation. An intimate cottage on a hill with a very large garden and a private swimming pool allows for a great rest. A small town with a delicious pizza (Bar L'Incontro) and a great wine bar (Benedetto Vino) A great starting point to Florence, Siena, San Gimignano, Volterre and the seaside (Follonica, Cecina). Very friendly and cordial owner Michele always helpful and providing support in times of need (eg where is the best food, where to go on a trip). I heartily...
Typical Tuscan Cottage with swimming pool and park, five minutes from San Galgano
Stone cottage on heritage Chianti estate-pool-tennis
Outdoor dining

Stone cottage on heritage Chianti estate-pool-tennis

Stone cottage on heritage Chianti estate-pool-tennis
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)
"What a beautiful stay in the enchanting Tuscan countryside! Every detail was attended to and we could not have felt more at home. We can only dream of returning sometime!"
La Misura, cottage with garden and swimming pool on the hills of Chianti
Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC
Exterior

Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC

The price is €155
includes taxes & fees
21 Aug - 22 Aug
Charming double bedroom in cottage in enchanting Monteaperti with WiFi, AC
Traumblick in die Toskana vom Landhaus mit Pool auf Hügel zw. Siena u. Florenz
Property grounds

Traumblick in die Toskana vom Landhaus mit Pool auf Hügel zw. Siena u. Florenz

9.8 out of 10, Exceptional, (28)
"Die Lage der Hütte ist ausgezeichnet.Nur 20min / 10km entfernt von Siena und trotzdem absolute Stille und Natur.Die Sicht in die Hügel von der Terasse vor der Hütte ist wunderbar und wird nicht langweilig.Die Kinder hatten viel Spaß auf den Wiesen um das Haus. Die Hütte ist sehr geräumig und sehr gut ausgestattet. Einziges Manko: die Matrazen im Hangzimmer waren nicht sehr gut.Hinweis: man fährt 5-10min Schotterpiste zur Hütte."
Traumblick in die Toskana vom Landhaus mit Pool auf Hügel zw. Siena u. Florenz
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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Top Castellina in Chianti Hotel Reviews

Ruby Bea Hotel Florence

Ruby Bea Hotel Florence

10/10 Excellent
"Fui en familia, nos encantó todo. El hotel tiene un concepto moderno y cuidan los detalles en todo a su alrededor. El servicio es excelente, todo el equipo nos apoyó en lo que necesitábamos. Rafaella y Marco gentilmente resolvieron nuestras dudas. Su opcion de desayuno es excelente, si les gusta lo fresco, sano y natural. El metro está justo frente a el hotel y las camas son cómodas. Lo recomendaría y repetiría mi estadía. 100 puntos!!!"
Diana 2-night trip
Posted 17 hours ago
Ruby Bea Hotel Florence

Frequently asked questions

How much do cottages in Castellina in Chianti cost?
Expect to pay between €102 and €172 per night for cottages in Castellina in Chianti. No matter your budget, an epic stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Castellina in Chianti?
Take your pick of 147 cottages in Castellina in Chianti. Whether you're travelling with the little ones or planning a weekend break with your besties, Expedia can help you find the perfect place to escape the hustle and bustle.
Are there any family-friendly cottages in Castellina in Chianti?
You bet there are! Book a room at Fullino Nero, a terrific base for exploring the great outdoors in Castellina in Chianti. This family-friendly cottage has a 2-star rating and includes conveniences like laundry facilities and pillow top mattresses. Once you've checked in and dropped off your bags, there are plenty of family-friendly attractions to visit around Castellina in Chianti. Monteriggioni Castle and Castello di Albola promise fun for all ages.