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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Castellina in Chianti

Fullino Nero
Stroll through a serene courtyard surrounded by lush greenery and mature trees, featuring a stone pathway and a traditional building with a sloped roof.

Fullino Nero

9.6 out of 10, Exceptional, (46)
"Good place."
The price is AU$172
includes taxes & fees
20 Aug - 21 Aug
Fullino Nero
agriturismo la roggiola
Situated in a peaceful natural setting, this traditional building offers a serene escape.

agriturismo la roggiola

9.6 out of 10, Exceptional, (105)
"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
Relax under the shade of a large umbrella, surrounded by lush greenery and a beautifully manicured lawn.

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

9.8 out of 10, Exceptional, (66)
"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
Typical Tuscan Countryside Cottage near Florence
Standalone property with a traditional pitched roof and attached structure.

Typical Tuscan Countryside Cottage near Florence

10.0 out of 10, Exceptional, (28)
"Had a great stay with another couple staying upstairs and my wife and and in the downstairs. Host was amazing and her dog, Gustavino, checked in on us each morning! I wish there had been a vineyard with tasting room within walking distance but there were many within 15 minutes by car. Host set us up with restaurant options and they were all excellent. "
Typical Tuscan Countryside Cottage near Florence
Santo Pietro Resort
Escape to a serene Mediterranean villa surrounded by lush greenery and rolling hills, with a spacious courtyard and picturesque views.

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
FALCO: Peaceful farmcottage close to Tuscany 's treasures, 1 mile from shops
Enjoy a serene retreat with a large pool and lush surroundings.

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

9.4 out of 10, Exceptional, (18)
"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
Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle
Experience a historic stay amidst lush greenery and rolling hills, with a swimming pool and guest rooms available.

Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle

9.6 out of 10, Exceptional, (20)
"More than we imagined for our Tuscany vacation. Spacious, well appointed and clean. Marzio was an excellent host with knowledge of the area and its history. He gave wonderful suggestions for wines, restaurants and touring excursions. We highly recommend this historical villa for a Tuscany vacation!"
Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle
TUSCAN COTTAGE WITH PRIVATE GARDEN AND PANORAMIC POOL. 1 KM WALK TO THE VILLAGE.
Relax by the serene pool surrounded by lush greenery and picturesque views.

TUSCAN COTTAGE WITH PRIVATE GARDEN AND PANORAMIC POOL. 1 KM WALK TO THE VILLAGE.

9.8 out of 10, Exceptional, (31)
"This beautiful holiday house iis located at a beautiful county side in Casole d'elsa and is closeby to Florence, Chianti, Siena and Umbria. It is also easily accessible and you can take a train to Florence in less than an hour. Owner is friendly and you will feel like home once you walk in. They are also helpful in giving advise on interesting places to visit and even planning for your trip if you need it."
TUSCAN COTTAGE WITH PRIVATE GARDEN AND PANORAMIC POOL. 1 KM WALK TO THE VILLAGE.
COTTAGE WITH 2 BEDROOMS AND 2 ENSUITE BATHROOMS.PANORAMIC POOL.1 KM TO THE TOWN
Relax by the rectangular pool surrounded by lush greenery and shaded lounge chairs.

COTTAGE WITH 2 BEDROOMS AND 2 ENSUITE BATHROOMS.PANORAMIC POOL.1 KM TO THE TOWN

9.8 out of 10, Exceptional, (40)
"Everything was very satisfactory"
COTTAGE WITH 2 BEDROOMS AND 2 ENSUITE BATHROOMS.PANORAMIC POOL.1 KM TO THE TOWN
Happy holidays in Chianti, among olives and vineyards, From Florence
Relax in a serene garden setting, surrounded by lush greenery and a charming wooden pergola.

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

9.6 out of 10, Exceptional, (18)
"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
Charming Farmhouse with Private Pool among Vineyards
Enjoy a meal under the shade of a pergola, surrounded by lush greenery and comfortable seating.

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
Relax on the patio surrounded by lush greenery and enjoy the scenic views.

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
Relax in a serene outdoor setting with a comfortable lounge chair and table, surrounded by lush trees and a charming pergola.

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

10.0 out of 10, Exceptional, (3)
"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
Relax in a traditional setting with a well-maintained lawn and outdoor seating areas.

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.
Traditional architecture with a secure entrance and stone walls.

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
Experience the charm of a traditional Mediterranean home with a central entrance, windows with shutters, and a cozy outdoor seating area.

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
Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities
Experience the serenity of this historic estate, surrounded by lush greenery and rolling hills, with a traditional bell tower and expansive views of the countryside.

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

9.8 out of 10, Exceptional, (31)
"This is a great location to experience the beauty of Tuscany. People interested in history find this place even more interesting and mystical. Check out the history on their website. Owners did an incredible job restoring the beauty of this place. The entire family lives on site , so it so convenient to seek their advise. They are very helpful and knowledgeable and for us it felt like we were with family. I would definitely recommend this place to my friends and family members. We loved our 5...
Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities
Tuscan Charm: Frassini Cottage
Guests can enjoy a peaceful retreat in this charming building with a pitched roof and attached pergola, surrounded by lush trees and a well-maintained outdoor space.

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
Cottage in San Donato With Pool & Scenic Views
Stroll through the charming courtyard, surrounded by historic stone buildings and lush greenery.

Cottage in San Donato With Pool & Scenic Views

Cottage in San Donato With Pool & Scenic Views
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 AU$273
includes taxes & fees
18 Aug - 19 Aug
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
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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Frequently asked questions

How much do cottages in Castellina in Chianti cost?
You can expect to pay between AU$172 and AU$273 per night for cottages in Castellina in Chianti. Whatever your budget, a wonderful stay is just a click or two away on Expedia. This price was 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?
Claim your holiday time and pick from 160 cottages in Castellina in Chianti. Picturing a place where you can surround yourself with nature? Expedia will help you find the ideal property in just a click or two.
What is there to do in Castellina in Chianti near my cottage?
Castellina in Chianti has enough experiences and activities to keep you entertained for weeks (or months!), beginning with Monteriggioni Castle. Meleto Castle, Castello di Radda Winery and Castello di Albola are other wonderful attractions. If you're sticking around a while, Badia a Coltibuono and Isole e Olena Winery will put the finishing touches on your itinerary.