A stone castle with battlements overlooking a lush valley with vineyards.

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24 Aug - 25 Aug
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28 Aug - 30 Aug
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Top Gaiole in Chianti Hotel Reviews

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

10/10 Excellent
"Incredible property, steeped in history. The rooms are beautifully traditional and the staff incredibly friendly. A beautiful place to unwind for a few days in Tuscany! We would re-book in a heartbeat."
Natasha 4-night trip
Posted 23 hours ago
Villa Casagrande Resort & SPA
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back"
Tyler 1-night trip
Posted 5 days ago
Grand Hotel Continental Siena – Starhotels Collezione
 "Villa Torre in Chianti"  Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C

10/10 Excellent
"This was our 50th wedding anniversary celebration, and the it all went very smoothly. Thanks to Beatrice and Jacopo for their help!"
Anonymous traveler 7-night trip
Posted 6 days ago
"Villa Torre in Chianti" Vrbo Vacation Rental of the Year 2026- 8 bedrooms A/C
Hu Firenze Camping In Town

Hu Firenze Camping In Town

10/10 Excellent
"Very family friendly! Pools were amazing! Great food at the restaurant. Convenient place with nearby laundry area, bar, and grocery store. Super friendly staff."
Arianne April 2-night trip
Posted 6 days ago
Hu Firenze Camping In Town
Hotel Athena

Hotel Athena

10/10 Excellent
"We had a superior room, which was very comfortable. We had dinner in the restaurant several times, and the food and drink was excellent. One evening we just enjoyed the cocktail bar, and the staff were fun! Breakfast buffet has everything one could want, and was always fresh. Free parking! You will have an uphill walk to the town centre, but no matter where you go in Siena it’s either up or down. Highly recommended."
Christopher 7-night trip
Posted 7 days ago
Hotel Athena
Castello di Tornano Wine Resort

Castello di Tornano Wine Resort

8/10 Good
"We really like this place. Pool was very nice and staff were mostly helpful. Its a pretty good location to visit multiple areas as well. Room air conditioner did an ok job upstairs in bedroom loft but struggled to keep it cool in the sitting area on main level. The view from the tower is awesome but its a climb"
John 6-night trip
Posted 11 days ago
Castello di Tornano Wine Resort
La Certosa di Pontignano

La Certosa di Pontignano

10/10 Excellent
"Great property with unique setting being an old monastery. We thought we had booked a room with A/C but there wasn’t. They moved us to a room with A/C at no additional cost."
Frederic 4-night trip
Posted 3 weeks ago
La Certosa di Pontignano