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8 Aug - 10 Aug
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15 Aug - 17 Aug
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29 Aug - 31 Aug
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26 Sept - 28 Sept

Featured Cottages in Chianti Region and around

Charming Farmhouse with Private Pool among Vineyards
Surrounded by lush greenery, this guesthouse features a serene outdoor setting with a traditional stone building and a tranquil pool area.

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 seating area with a wicker sofa and chairs, a small table, and a candle.

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
Cottage. DEPENDANCE IL BORRACCIO con vista giardino sulla campagna del Chianti.
Enjoy a refreshing swim in the pool surrounded by lush trees and a scenic view.

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

9.0 out of 10, Wonderful, (19)
"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.
Exceptionally pretty cottage with pool, views, in walking distance from Panzano
Relax by the serene pool surrounded by a lush lawn and shaded by a pergola, with breathtaking views of rolling hills.

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
La Misura, cottage with garden and swimming pool on the hills of Chianti
Relax in a serene patio area with a wooden table and chairs, perfect for dining or socializing under a large umbrella.

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
Stone cottage on heritage Chianti estate-pool-tennis
Relax by the serene pool surrounded by lush greenery and a stone wall, featuring a unique fish sculpture.

Stone cottage on heritage Chianti estate-pool-tennis

Stone cottage on heritage Chianti estate-pool-tennis
Casa Antico Roseto - cottage with swimming pool
Traditional kitchen with a classic gas range, wooden cabinet, and dining area leading to a garden.

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
Villa Gaia
Situated in a lush landscape, this cottage offers a welcoming atmosphere with a small porch and well-maintained lawn.

Villa Gaia

Villa Gaia
Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property
Surrounded by lush greenery, this outdoor space features a vibrant flowering shrub and a nearby swimming pool.

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

8.4 out of 10, Very good, (10)
"Marina, Tom und ihre Familie waren super Gastgeber. Für jeden der auf absolute Abgeschiedenheit wert legt ist die Unterkunft perfekt. Nach einer Auffahrt in die toskanischen Hügel fährt man einen nicht befestigten Weg durch den örtlichen Dschungel, an dessen Ende sich die Einfahrt zum Anwesen befindet. Unbedingt ein Fahrzeug mit größerer Bodenfreiheit mitbringen! Vom Haupthaus gehen mehrere kleine Wege zum süß renovierten Capanna. An der Unterkunft hatten wir die 10 Übernachtungen nichts...
Studio in Chianti Villa in heart of Tuscany, super-large pool, 14 ha property
In Chianti along the Francigena - La Voliera Country House
Situated in a lush garden, this charming structure features a chimney and offers a peaceful retreat.

In Chianti along the Francigena - La Voliera Country House

7.4 out of 10, Good, (10)
"Excellent place if you love nature and a quiet place to rest from noisy traffic of bigger cities. You will need a car unless you don’t mind the half mile walk to the medieval town and public transportation. My wife and I enjoyed our stay there with host, Gabrielle and his daughter who were super friendly and helpful. I would stay there again."
In Chianti along the Francigena - La Voliera Country House
Typical country house with garden near Florence Siena Pisa San Gimignano
Sit and unwind in a serene outdoor space surrounded by lush greenery and vibrant flowers.

Typical country house with garden near Florence Siena Pisa San Gimignano

9.6 out of 10, Exceptional, (48)
"We enjoyed some days in this beautiful area"
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
Stroll through the beautifully maintained garden, lined with vibrant flowers and leading to a charming stone building with arched windows.

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
Tuscan Cottage With 2 Pools
Relax by the serene pool surrounded by lush greenery and olive trees, with a panoramic view of rolling hills and distant mountains.

Tuscan Cottage With 2 Pools

Tuscan Cottage With 2 Pools
Beautiful 1-bedroom cottage with garden and views over olive groves, pool
Relax in a serene outdoor setting with a wooden table and two chairs, surrounded by lush greenery and a rustic stone wall.

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
Beautiful 1-bedroom cottage with garden and views over olive groves, pool
Enjoy a casual meal in this outdoor dining area with a rustic stone wall backdrop and comfortable seating for two.

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

Beautiful 1-bedroom cottage with garden and views over olive groves, pool
La Chiantinelle - La Grange
Relax in this inviting room with a comfortable sofa, dining table, and unique arched window overlooking lush flowers.

La Chiantinelle - La Grange

La Chiantinelle - La Grange
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)
"Pros: Jede Menge Platz. Tolle Atmosphäre, idyllisch gelegen. Die Gastgeberin war immer erreichbar und äußerst nett. Der Wein war lecker 😋"
Cottage "Podere in Volpaia" with Garden & Wi-Fi
Casa Belvedere cottage with swimming pool in the heart of Chianti
Relax by the serene pool surrounded by lush evergreen trees and comfortable lounge chairs.

Casa Belvedere cottage with swimming pool in the heart of Chianti

Casa Belvedere cottage with swimming pool in the heart of Chianti
Corte a Bagnano - Ponente
Relax by the serene pool surrounded by lush greenery and scenic views.

Corte a Bagnano - Ponente

Corte a Bagnano - Ponente
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 Chianti Region Hotel Reviews

Hotel Borgo di Cortefreda Relais

Hotel Borgo di Cortefreda Relais

10/10 Excellent
"Great afternoon by the pool. Evening meal menu was odd. I think the chef was trying too hard to be different. The vegetarian chick pea dish was merely a bowl of cooked onions with some vegetable mush- my wife called it baby food. The chicken with truffles was tasty although came with flabby chicken skin. Breakfast was amazingly good in comparison. We had a room with a view of a 6 foot tall hedge, beyond the hedge was a fantastic view of Tuscany we couldn’t see, really strange. Staff were very good, the pool pleasingly cold and refreshing. Good but not a great stay."
Anonymous traveller 1-night trip
Posted 5 days ago
Hotel Borgo di Cortefreda Relais