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Hotels in Chianti for 2 travelers on a 5-Day Tuscany Culinary and Wine Journey (September 2025)

Hotels in Chianti typically offer charming Tuscan-style accommodations with beautiful vineyard views, perfect for travelers interested in culinary and wine experiences. These hotels often provide easy access to local wineries, cooking classes, and scenic countryside landscapes, ideal for a 5-day Tuscany Culinary and Wine Journey.
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Hotel La Magione
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pin
Via Senese, 293, 53036 Poggibonsi
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Storied Collection:
Chianti
4-star
Breakfast included
Hotel La Magione is an excellent choice for your Tuscany Culinary and Wine Journey, located in Poggibonsi, which is in the heart of the Chianti region. The hotel offers **4-star comfort**, **air-conditioned rooms**, and a **continental or Italian breakfast**, perfect for starting your day of culinary exploration.... Read more
7.9
Good
(109 reviews)
Matched amenities:
ParkingParking
Pets allowedPets allowed
BarBar
24-hour front desk24-hour front desk
Non-smoking roomsNon-smoking rooms
Lowest price
Booking
/night
Available from:Sep 2-5
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95% Match
Soleevino B&B - Exclusively for Adults
starstarstarstar
pin
Località Melazzano, 50022 Greve in Chianti
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Storied Collection:
Chianti
infinity pool
garden
This hotel is perfectly suited for your Tuscany Culinary and Wine Journey as it is located in Greve in Chianti, a prime area for wine lovers. The property offers an **infinity pool** and a **garden** for relaxation, along with **private parking** and **free WiFi**, enhancing your comfort during the stay.... Read more
10.0
Wonderful
(25 reviews)
Matched amenities:
GardenGarden
Free parkingFree parking
Internet servicesInternet services
HeatingHeating
WiFiWiFi
Lowest price
Booking
/night
Available from:Sep 2-5
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85% Match
Palazzo delle Erbe
starstarstar
pin
Via Roma, 66, 53031 Casole dʼElsa
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Storied Collection:
Chianti
Breakfast included
Free WiFi
This bed and breakfast is located in Casole dʼElsa, which is within the Chianti region, making it an excellent base for your Tuscany Culinary and Wine Journey. It offers **air conditioning**, **free WiFi**, and a **continental breakfast**, ensuring a comfortable and convenient stay during your trip.... Read more
9.7
Wonderful
(29 reviews)
Matched amenities:
Pets allowedPets allowed
GardenGarden
TerraceTerrace
Non-smoking roomsNon-smoking rooms
Internet servicesInternet services
Lowest price
Booking
/night
Available from:Sep 2-5
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90% Match
Castello di Montemasso B&B
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via Rubbiana Case Sparse, 37, 50022 Santo Stefano A Tizzano
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Storied Collection:
Chianti
garden
family rooms
This hotel is located in Santo Stefano A Tizzano, within the Chianti region, making it an excellent base for a Tuscany Culinary and Wine Journey. It offers a **garden**, **terrace**, and **family rooms**, providing a comfortable and scenic stay with easy access to local attractions and culinary experiences.... Read more
9.6
Wonderful
(18 reviews)
Matched amenities:
ParkingParking
Pets allowedPets allowed
GardenGarden
TerraceTerrace
Non-smoking roomsNon-smoking rooms
Lowest price
Booking
/night
Available from:Sep 2-5
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90% Match
Relais Casanova
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Località Casanova, 53019 San Gusmè
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Storied Collection:
pool with a view
picnic area
barbecue facilities
Relais Casanova is an excellent choice for your Tuscany Culinary and Wine Journey, offering a **pool with a view** and a **picnic area** perfect for enjoying local delicacies. The farm stay's **barbecue facilities** and proximity to cycling and hiking trails enhance the authentic Tuscan experience.... Read more
8.9
Very Good
(16 reviews)
Matched amenities:
Pets allowedPets allowed
Room serviceRoom service
GardenGarden
Family roomsFamily rooms
Breakfast in the roomBreakfast in the room
Lowest price
8% off
Booking
/night
Available from:Sep 2-5
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