Best Resorts in Chianti Region Resort

A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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Our top choices for Chianti Region resorts

1. Villa Svetoni Wine Resort

Montepulciano

Matthew

includes taxes & fees

1 Sept - 2 Sept

2. Villa Petriolo

Cerreto Guidi

Nicholas

includes taxes & fees

30 Aug - 31 Aug

3. Monsignor della Casa Country Resort & Spa

Borgo San Lorenzo

Michael

includes taxes & fees

30 Aug - 31 Aug

4. Cortona Resort Spa

Cortona

Candice

includes taxes & fees

26 Aug - 27 Aug

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Top Chianti Region Hotel Reviews

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."

Castello Vicchiomaggio

8/10 Good

"We had mixed feelings about our stay. The property and vineyard are beautiful, with fantastic Tuscan views. Our villa was spacious and private, the AC worked extremely well, and the semi-private pool was great with a small child. We booked through Expedia expecting more of a hotel/resort experience, but the villas operate as self-catering rentals. There was no daily housekeeping, fresh towels/linens, or replenishment of basics. We received three coffee pods and were directed to nearby grocery stores for additional provisions, so plan to stock up after arrival. We were surprised that villa guests could not use the main castle pool and were largely separate from the hotel areas. The four villas are in their own chain-link-fenced compound, which felt secluded from the otherwise beautiful property. Cleanliness could have been better: we found quite a bit of hair on arrival, and the shower flooded the bathroom with each use. We chose not to raise this during our stay. The pool itself is gorgeous, but the surrounding area felt unfinished, with loungers on gravel or long grass/weeds, few tables, and limited shade when multiple families were there. Overall, the villa has a lot going for it. Just arrive expecting a self-catering villa rather than the services and amenities of the hotel."