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

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Check availability on Chianti Region Winery Hotels

Tonight
21 Aug - 22 Aug
Tomorrow
22 Aug - 23 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Chianti Region hotels with winery

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.
A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.
An interior corridor with arches, columns, and a brick wall.
A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

1. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
United States
Edyta
£64
includes taxes & fees
8 Sept - 9 Sept
La Certosa di Pontignano
A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.
A stone building with a courtyard, a covered seating area, and a small bell tower.
A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and lush greenery, overlooking a valley.
A cozy living room with a stone fireplace, striped sofas, and a coffee table.

2. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
United States
Alejandro
£103
includes taxes & fees
13 Sept - 14 Sept
Borgo di Pietrafitta Relais
A wicker chair, a lantern, and a vase of flowers on a balcony with a mountain view.
A spacious living room with a high ceiling, large windows with diamond-patterned blinds, a sofa set, a coffee table, and a painting on the wall.
A rustic stone building with a tiled roof, surrounded by lush greenery and white flowers.
A pool area with a view of a hilly landscape.

3. Borgo Del Cabreo

Borgo Del Cabreo
Greve in Chianti
United Kingdom
joseph
£178
includes taxes & fees
23 Aug - 24 Aug
Borgo Del Cabreo
A narrow stone pathway leading to a rustic building with a wooden door and a window.
A cozy living room with a striped sofa, a wooden coffee table, and a bookshelf.
A cozy living room with a fireplace, wooden beams, and comfortable seating.
A stone building with wooden shutters, a bench, and hanging purple flowers.

4. Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
United States
Giancarlo
£140
includes taxes & fees
25 Aug - 26 Aug
Castello di Fonterutoli Wine Resort
A pool with a view of a lush valley and distant buildings.
A bedroom with a large arched window, a bed, a hanging light fixture, and a view of a green landscape.
A terraced vineyard with stone walls and a stone pathway leading to a seating area with metal chairs and tables.
A courtyard with stone buildings, arched doorways, and potted plants.

5. Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
United States
Shane
£198
includes taxes & fees
27 Aug - 28 Aug
Castello Vicchiomaggio
A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.
A rustic stone building with a garden in front.
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.
A poolside area with lounge chairs and a view of the night sky.

6. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
United Kingdom
Jess
£117
includes taxes & fees
24 Aug - 25 Aug
Belvedere di San Leonino
A couple dining at an outdoor table with a view of the countryside.
A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.
A narrow street with buildings on either side, a flag, and a bench.
A spacious room with high arched ceilings, a wooden dining table, chairs, and a bookshelf.

7. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
Canada
Elizabeth
£147
includes taxes & fees
23 Aug - 24 Aug
Palazzo Leopoldo Dimora Storica & Spa
A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.
A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.
A stone building with a wooden door, outdoor seating, and a pergola with vines.
A pool surrounded by lush greenery and vineyards, with a stone building in the background.

8. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
United States
Paula
£110
includes taxes & fees
27 Aug - 28 Aug
Agriturismo San Sano
An indoor courtyard with stone flooring, arched columns, and tables set up for dining.
A historic building with a stone facade, arched entrance, and a wooden balcony.
A modern spa area with a wooden sauna, a glass-enclosed shower, and a marble-floored pool.
An indoor swimming pool with clear glass walls, wooden beams, and large windows.

9. Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
Figline e Incisa Valdarno
United States
Jason
£129
includes taxes & fees
22 Aug - 23 Aug
Villa Casagrande Resort & SPA
A building with a stone facade, a central arched doorway, and a window with a decorative frame.
A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.
A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.
A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

10. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
Canada
Nicole
£257
includes taxes & fees
25 Aug - 26 Aug
Dievole Wine Resort
View all properties

Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

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."
Justin 4-night trip
Posted 1 hour ago
Castello Vicchiomaggio
Borgo Vescine

Borgo Vescine

10/10 Excellent
"Had an amazing time. Rooms can be a bit hot at times but everything else was spectacular. Highly recommended"
Gabrielle 3-night trip
Posted 2 days ago
Borgo Vescine
Park Hotel Chianti

Park Hotel Chianti

10/10 Excellent
"A clean hotel, we got upgraded so no issues on room was updated and pleasant, AC could have been stronger but was ok, nice buffet breakfast with good assortment of food:) Front desk ladies were helpful in giving restaurant suggestions in the surrounding area 👌"
vincy 2-night trip
Posted 2 days ago
Park Hotel Chianti
Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

10/10 Excellent
"A beautiful hotel in a lovely little town. The staff were amazing, so helpful. The rooms were very clean and comfortable. I didn’t use the indoor pool or spa facilities so can’t comment on them. The outdoor pool is across the road and up a steep hill, so great if you have a car but not so much if you are on foot! Overall a very good stay."
Jonathan 2-night trip
Posted 3 days ago
Villa Casagrande Resort & SPA
Belvedere di San Leonino

Belvedere di San Leonino

10/10 Excellent
"The most beautiful and breathtaking place to stay. The staff were lovely, the rooms were quiet, the views were exceptional. The breakfast was perfect. Idyllic!"
Jess 3-night trip
Posted 10 days ago
Belvedere di San Leonino
Hu Norcenni Girasole Village

Hu Norcenni Girasole Village

10/10 Excellent
"Two large pool sites. Helpful staff. Lots of entertainment. Restaurant options and a well stocked reasonably priced food market."
Katie 5-night trip
Posted 2 weeks ago
Hu Norcenni Girasole Village
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"
Ashley 2-night trip
Posted 2 weeks ago
Castello di Spaltenna- Small Luxury Hotels of the World
Hotel Toscana Ambassador

Hotel Toscana Ambassador

10/10 Excellent
"Room was clean, staff was helpful and easy to park."
Jennifer 3-night trip
Posted 2 months ago
Hotel Toscana Ambassador
COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent
"Great staff!"
Philip 1-night trip
Posted 2 months ago
COMO Castello Del Nero

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