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 5 - Oct 6
Tomorrow
Oct 6 - Oct 7
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Chianti Region historic hotels

An outdoor dining area with a pool, potted plants, and umbrellas.
A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.
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.

1. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
United States
Ali
￥25,751
￥33,780 total
includes taxes & fees
Oct 8 - Oct 9
Relais Vignale & Spa
A clear swimming pool with a view of a lush green landscape and distant hills.
A restaurant with multiple tables set for dining, featuring wooden beams and a chandelier.
A garden with pink roses, a lawn, and a white umbrella.
A bar area with a fireplace, bar stools, a table with bottles, and a shelf with glasses.

2. Villa Le Barone

Villa Le Barone
Greve in Chianti
Canada
Tereza
￥39,530
￥44,549 total
includes taxes & fees
Oct 25 - Oct 26
Villa Le Barone
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.
A rustic dining area with a wooden table and chairs, a fireplace, and a brick floor.
An outdoor patio with a round table and chairs, surrounded by stone walls and a tall tree.

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

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
Canada
James
￥14,346
￥28,203 total
includes taxes & fees
Oct 6 - Oct 7
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 vineyard with terracotta pots and stone walls, overlooking a hilly landscape with vineyards and distant hills.
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 living room with a tiled floor, a blue sofa, a beige armchair, a small round table, a television, and a wooden ceiling beam.

4. CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
Ruffoli
United States
Caleb M.
￥22,385
￥47,257 total
includes taxes & fees
Oct 8 - Oct 9
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 stone pathway leading to a building with a yellow facade and green shutters.
A hallway with a wooden archway, a bench, a rug, and a table with a book and flowers.
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.
￥23,451
￥23,984 total
includes taxes & fees
Oct 6 - Oct 7
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 modern kitchen with white cabinets, a gas stove, a microwave, and a dining area with a table and chairs.
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.

6. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
United States
Kathleen F.
￥18,388
￥22,297 total
includes taxes & fees
Oct 8 - Oct 9
Old medieval apartment
A stone building with a courtyard, outdoor seating, and potted plants.
A kitchen with wooden cabinets, a stove, a large window, and a recycling bin.
A cozy living room with a fireplace, a floral armchair, a white sofa, and large windows.
A rustic dining area with a wooden table and chairs, a fireplace, and a large cabinet with glass doors.

7. Wonderful Tuscan farmhouse with large spaces and panoramic views

Wonderful Tuscan farmhouse with large spaces and panoramic views
impruneta
United States
Christine F.
￥14,390
￥44,948 total
includes taxes & fees
Oct 21 - Oct 22
Wonderful Tuscan farmhouse with large spaces and panoramic views
A view through a large arched window of a stone patio with a table and chairs, an umbrella, and lush greenery.
A kitchen with a large window, wooden cabinets, and a dining table with chairs.
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.

8. 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.
￥25,995
￥25,995 total
includes taxes & fees
Oct 20 - Oct 21
Glicini 1, holiday home with pool 30' from Florence
A rectangular swimming pool with a wooden deck, surrounded by lush greenery and a clear sky.
Outdoor spa tub
A bedroom with a bed, a nightstand, a lamp, a closet with shelves, and a spiral staircase.
A spiral staircase with a metal railing, a white chair, and framed pictures on the wall.

9. 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
￥23,984
￥26,915 total
includes taxes & fees
Oct 6 - Oct 7
Superior Settimo Cielo with A/C and Private Bathroom in Villa le Facezie B&B
A poolside setting with two drinks, a tray with snacks, and a white umbrella.
A lush green landscape with a variety of trees and a clear blue sky.
A table set outdoors with a view of a lush green landscape and mountains in the background.
A room with a wooden ceiling, a bed with white bedding, a dining table with chairs, and a wooden cabinet.

10. 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.
￥14,213
￥17,766 total
includes taxes & fees
Oct 6 - Oct 7
Appartment with swimming pool 30 min of Florence, private garden, parking, WiFi
View all properties

Top Chianti Region Hotel Reviews

Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

8/10 Good
"We quite enjoyed the heated pool and views. Thank you for having us."
Dianna 1-night trip
Posted 18 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 3 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 3 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 4 days ago
Hotel Toscana Ambassador
Relais Vignale & Spa

Relais Vignale & Spa

10/10 Excellent
"In a convenient location."
MELISSA 2-night trip
Posted 7 days ago
Relais Vignale & Spa
Hotel Villa Campomaggio

Hotel Villa Campomaggio

10/10 Excellent
"Great hotel"
Dario 2-night trip
Posted 12 days 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 13 days ago
Villa Casagrande Resort & SPA
COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent
"The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back."
Lauren 3-night trip
Posted 3 weeks ago
COMO Castello Del Nero

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