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 Historic Hotels

Tonight
Oct 9 - Oct 10
Tomorrow
Oct 10 - Oct 11
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Chianti Region historic hotels

A clear swimming pool with a view of a lush green landscape and distant hills.
A courtyard with outdoor seating, a gravel path, and a building covered in ivy.
A bar area with a fireplace, bar stools, a table with bottles, and a shelf with glasses.
A garden with pink roses, a lawn, and a white umbrella.

1. Villa Le Barone

Villa Le Barone
Greve in Chianti
Canada
Tereza
￥39,381
￥44,381 total
includes taxes & fees
Oct 25 - Oct 26
Villa Le Barone
An outdoor dining area with a pool, potted plants, and umbrellas.
A restaurant with a table set for two, overlooking a scenic landscape.
An outdoor dining area with a table set for two, overlooking a pool and vineyard.
A villa with a swimming pool, outdoor seating, and a garden.

2. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
United States
Ali
￥27,287
￥35,449 total
includes taxes & fees
Oct 22 - Oct 23
Relais Vignale & Spa
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.
A rustic dining area with a wooden table, blue chairs, a brick floor, a sofa, and a fireplace.
An outdoor patio with a round table and chairs, surrounded by stone walls and a tall tree.
A rustic dining area with a wooden table and chairs, a fireplace, and a brick floor.

3. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
Canada
James
￥14,292
￥28,097 total
includes taxes & fees
Oct 13 - Oct 14
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
A stone building with a terrace, a table with chairs, and a red umbrella.
A living room with a high wooden ceiling, a blue sofa, a white armchair, a small table with a candle, and a desk with a lamp and candlesticks.
A vineyard with terracotta pots and stone walls, overlooking a hilly landscape with vineyards and distant hills.
A courtyard with stone buildings, a gravel path, and potted plants.

4. CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
Ruffoli
United States
Caleb M.
￥22,301
￥47,080 total
includes taxes & fees
Oct 13 - Oct 14
CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
A rectangular swimming pool with a wooden deck, surrounded by lush greenery and a clear sky.
A two-story building with a balcony, surrounded by palm trees and a well-maintained garden with red flowers.
A stone pathway leading to a building with a yellow facade and green shutters.
A hot tub with two glasses of champagne and a tray of strawberries.

5. Deluxe Room Nero su Bianco with A/C and Private Bathroom in Villa le Facezie B&B

Deluxe Room Nero su Bianco with A/C and Private Bathroom in Villa le Facezie B&B
Terranuova Bracciolini
United States
Lynn P.
￥23,363
￥23,894 total
includes taxes & fees
Oct 13 - Oct 14
Deluxe Room Nero su Bianco with A/C and Private Bathroom in Villa le Facezie B&B
A narrow stone alley with arched doorways, potted plants, and hanging flower baskets.
A staircase with a stone wall on one side and a dark wooden door on the other.
A bedroom with a stone wall, a bed with a headboard, a chair, and two bedside lamps.
A modern kitchen with white cabinets, a gas stove, a microwave, and a dining area with a table and chairs.

6. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
United States
Kathleen F.
￥18,319
￥22,213 total
includes taxes & fees
Oct 18 - Oct 19
Old medieval apartment
A rectangular swimming pool with a wooden deck, surrounded by lush greenery and a clear sky.
A spiral staircase with a metal railing, a white chair, and framed pictures on the wall.
Outdoor spa tub
A buffet table with various food items, plates, and utensils.

7. Superior Settimo Cielo with A/C and Private Bathroom in Villa le Facezie B&B

Superior Settimo Cielo with A/C and Private Bathroom in Villa le Facezie B&B
Terranuova Bracciolini
￥23,894
￥26,814 total
includes taxes & fees
Oct 10 - Oct 11
Superior Settimo Cielo with A/C and Private Bathroom in Villa le Facezie B&B
A stone building with a courtyard, outdoor seating, and potted plants.
A bedroom with a large bed, wooden ceiling beams, a dresser, a mirror, and a chair.
A cozy living room with a fireplace, a floral armchair, a white sofa, and large windows.
A kitchen with wooden cabinets, a stove, a large window, and a recycling bin.

8. Wonderful Tuscan farmhouse with large spaces and panoramic views

Wonderful Tuscan farmhouse with large spaces and panoramic views
impruneta
United States
Christine F.
￥14,159
￥44,955 total
includes taxes & fees
Oct 21 - Oct 22
Wonderful Tuscan farmhouse with large spaces and panoramic views
A poolside setting with two drinks, a tray with snacks, and a white umbrella.
A room with a wooden ceiling, a bed with white bedding, a dining table with chairs, and a wooden cabinet.
A bedroom with a wooden bed, two bedside tables with lamps, a chandelier, and a wardrobe.
A lush green landscape with a variety of trees and a clear blue sky.

9. Appartment with swimming pool 30 min of Florence, private garden, parking, WiFi

Appartment with swimming pool 30 min of Florence, private garden, parking, WiFi
Reggello
France
Jean-marc L.
￥14,159
￥17,699 total
includes taxes & fees
Oct 10 - Oct 11
Appartment with swimming pool 30 min of Florence, private garden, parking, WiFi
A view through a large arched window of a stone patio with a table and chairs, an umbrella, and lush greenery.
A two-story building with a yellow facade, multiple windows, and a garden in front.
A rustic dining area with a stone wall, wooden door, and a wooden table with chairs.
A rectangular pool with a stone border, surrounded by a grassy area and a row of sun loungers with umbrellas.

10. Glicini 1, holiday home with pool 30' from Florence

Glicini 1, holiday home with pool 30' from Florence
Tavarnelle Val di Pesa
United States
Joe M.
￥25,907
￥25,907 total
includes taxes & fees
Oct 20 - Oct 21
Glicini 1, holiday home with pool 30' from Florence
View all properties

Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"A unique stay with a picturesque view. Breakfast, lunch, and dinner were fantastic. The property was great for relaxing at but also a good launching spot for exploring some of the nearby towns and sites."
Frank 4-night trip
Posted 18 hours ago
Castello Vicchiomaggio
Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

8/10 Good
"Beautiful views, good location, nice restaurants nearby, friendly staff, lovely breakfast. The heated pool is a nice touch but was always busy, even now, out of season. Sadly, the place felt a little bit run down in the outdoor areas, broken / rotten outdoor furniture and a lot of rubbish dumped around the car park. Beware the huge ants if you plan to stay in the ‘treehouse’; which we felt would benefit from a little renovation, redecoration and sealing better against insects."
Mr Thomas 1-night trip
Posted 22 hours ago
Villa I Barronci Resort & Spa
Borgo Vescine

Borgo Vescine

10/10 Excellent
"The staff was amazing and incredibly kind."
Natalie 2-night trip
Posted 7 days ago
Borgo Vescine
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."
Sonja 3-night trip
Posted 7 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
Hotel Toscana Ambassador

Hotel Toscana Ambassador

8/10 Good
"Close to train station"
Marian 1-night trip
Posted 8 days ago
Hotel Toscana Ambassador
Relais Vignale & Spa

Relais Vignale & Spa

10/10 Excellent
"In a convenient location."
MELISSA 2-night trip
Posted 11 days ago
Relais Vignale & Spa
Villa Le Barone

Villa Le Barone

10/10 Excellent
"Charming place in Tuscany! Everything was absolutely perfect. We highly suggest to dine at the villa, it was exceptional. Breakfast was delicious as well."
Tereza 2-night trip
Posted 11 days ago
Villa Le Barone
Hotel Villa Campomaggio

Hotel Villa Campomaggio

10/10 Excellent
"Great hotel"
Dario 2-night trip
Posted 2 weeks ago
Hotel Villa Campomaggio
Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

8/10 Good
"Restaurant was great. Towels have too much use"
Ana 3-night trip
Posted 2 weeks ago
Villa Casagrande Resort & SPA

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