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 25 - Oct 26
Tomorrow
Oct 26 - Oct 27
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

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.
A villa with a swimming pool, outdoor seating, and a garden.

1. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
United States
Ali
￥27,092
￥35,196 total
includes taxes & fees
Oct 27 - Oct 28
Relais Vignale & Spa
A clear swimming pool with a view of a lush green landscape and distant hills.
A garden with pink roses, a lawn, and a white umbrella.
A restaurant with multiple tables set for dining, featuring wooden beams and a chandelier.
A courtyard with outdoor seating, a gravel path, and a building covered in ivy.

2. Villa Le Barone

Villa Le Barone
Greve in Chianti
Canada
Tereza
￥38,948
￥43,897 total
includes taxes & fees
Oct 31 - Nov 1
Villa Le Barone
A stone building with a gated entrance, terracotta pots with flowers, and a staircase leading up to the door.
A bedroom with a bed under a canopy, wooden beams on the ceiling, and a white door.
A rustic dining area with a wooden table and chairs, a fireplace, and a brick floor.
A rustic dining area with a wooden table, blue chairs, a brick floor, a sofa, and a fireplace.

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

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
Canada
James
￥14,190
￥27,897 total
includes taxes & fees
Oct 26 - Oct 27
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 tiled floor, a blue sofa, a beige armchair, a small round table, a television, and a wooden ceiling beam.
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 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.
￥22,141
￥47,270 total
includes taxes & fees
Oct 26 - Oct 27
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 hot tub with two glasses of champagne and a tray of strawberries.
A two-story building with a balcony, surrounded by palm trees and a well-maintained garden with red flowers.
A hallway with a wooden archway, a bench, a rug, and a table with a book and flowers.

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.
￥23,196
￥23,723 total
includes taxes & fees
Oct 27 - Oct 28
Deluxe Room Nero su Bianco 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.

6. Sorbeto Vacation Home

Sorbeto Vacation Home
impruneta
United States
Christine F.
Sorbeto Vacation Home
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 modern kitchen with white cabinets, a gas stove, a microwave, and a dining area with a table and chairs.
A bedroom with a stone wall, a bed with a headboard, a chair, and two bedside lamps.

7. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
United States
Kathleen F.
￥18,188
￥22,054 total
includes taxes & fees
Oct 28 - Oct 29
Old medieval apartment
A modern bedroom with a curved bed, a large mirror, and a jungle-themed mural.
A narrow cobblestone street with historic buildings, a chain-link fence, and a wooden door with a number plaque.
A modern hotel corridor with a light-colored floor, a wooden ceiling, and a door leading to a bathroom.
A bedroom with a white bed, a nightstand with a red lamp, and a wall mural of tropical leaves.

8. Colle di Val d'Elsa - Siena - White Apartment - D

Colle di Val d'Elsa - Siena - White Apartment - D
Colle di Val d'Elsa
￥15,183
￥27,835 total
includes taxes & fees
Oct 27 - Oct 28
Colle di Val d'Elsa - Siena - White Apartment - D
A rustic kitchen with a wooden table set for dining, a window with curtains, and a radiator.
A large house with a swimming pool, surrounded by a well-maintained lawn and a few lounge chairs.
Property grounds
Exterior

9. Scaletta Apartment in Organic Agriturismo with Panoramic Pool, Tuscany

Scaletta Apartment in Organic Agriturismo with Panoramic Pool, Tuscany
Castelfranco PiandiSco
Scaletta Apartment in Organic Agriturismo with Panoramic Pool, Tuscany
A two-story stone house with a swimming pool, surrounded by greenery and a clear sky.
A lush garden with a pool, a gazebo, and a view of distant trees and hills.
A bedroom with a metal bed frame, two bedside tables with lamps, a wooden window with shutters, and a wall-mounted light fixture.
A stone wall with potted plants and flowers, surrounded by greenery and a stone building in the background.

10. APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM

APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM
Monteriggioni
Italy
giuseppe z.
￥28,309
￥42,191 total
includes taxes & fees
Nov 1 - Nov 2
APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM
View all properties

Top Chianti Region Hotel Reviews

Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

8/10 Good
"Wine area not open"
Mark 4-night trip
Posted 1 day ago
Villa Casagrande Resort & SPA
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."
Michelle 3-night trip
Posted 2 weeks ago
Castello di Spaltenna- Small Luxury Hotels of the World
Borgo Vescine

Borgo Vescine

10/10 Excellent
"The staff was amazing and incredibly kind."
Natalie 2-night trip
Posted 3 weeks ago
Borgo Vescine
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 1 month ago
Villa Le Barone
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 2 months ago
COMO Castello Del Nero

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