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8 Aug - 10 Aug
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29 Aug - 31 Aug
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Cottages in Castelfranco di Sopra

Typical Tuscan Countryside Cottage near Florence
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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
Cottage Pino Rural Tuscan retreat in Stunning Hilltop castle
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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
Happy holidays in Chianti, among olives and vineyards, From Florence
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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
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
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, (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.
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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.
Cottage Murlo stunning hilltop castle peace & quiet countryside near art cities
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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
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
Purgatorio house, a typical Tuscan structure with pool, surrounded by nature.
Outdoor dining

Purgatorio house, a typical Tuscan structure with pool, surrounded by nature.

10.0 out of 10, Exceptional, (9)
"It was a great stay and Laura is a very friendly and helpful host who was also able to give excellent tips for trips. But also the cottage and pool were fantastically beautiful. We enjoyed it very much."
Purgatorio house, a typical Tuscan structure with pool, surrounded by nature.
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
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
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)
"Ruhe und Erholung in toller Lage für Ausflüge und Radtouren mit Freunden "
Traumblick in die Toskana vom Landhaus mit Pool auf Hügel zw. Siena u. Florenz
Casa Antico Roseto - cottage with swimming pool
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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
Property grounds

Villa Gaia

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

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
Cottage Polvereto S. Andrea a Cellole a beautiful hilltop Castle sleeps two
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Cottage Polvereto S. Andrea a Cellole a beautiful hilltop Castle sleeps two

9.8 out of 10, Exceptional, (10)
"Apart from the spacious,well equipped cottage and overall calm and relaxing environment with great pool and outdoor eating area, Marzio, Adela and Mauro were the perfect hosts providing us with very practical advice on what to see and do in the region. Cellole is also very well situated to explore the region, half way between Florence and Sienna it allowed us to visit these cities or explore the many medieval fortress villages close by. The cooking course we did was a real highlight. My daughter...
Cottage Polvereto S. Andrea a Cellole a beautiful hilltop Castle sleeps two
La Quercia, apartment with garden for 6/8 people in the heart of Chianti
Property grounds

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
Cottage | Pool | Outdoor pool

Tuscan Cottage With 2 Pools

Tuscan Cottage With 2 Pools
Beautiful 1-bedroom cottage with garden and views over olive groves, pool
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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
Exterior

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

Beautiful 1-bedroom cottage with garden and views over olive groves, pool
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 Castelfranco di Sopra Hotel Reviews

Grand Hotel Cavour

Grand Hotel Cavour

10/10 Excellent
"Gorgeous hotel with lovely rooms and staff. They were flexible with our check in and out times. Would love to return, highly recommend!"
Sally 1-night trip
Posted 2 days ago
Grand Hotel Cavour