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

Find Historic Hotels in Chianti Region

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chianti Region Historic Hotels

Tonight
Oct 21 - Oct 22
Tomorrow
Oct 22 - Oct 23
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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
￥27,400
￥35,596 total
includes taxes & fees
Oct 26 - Oct 27
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
￥39,391
￥44,396 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.
An outdoor patio with a round table and chairs, surrounded by stone walls and a tall tree.
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, 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
￥14,351
￥28,213 total
includes taxes & fees
Oct 22 - Oct 23
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 courtyard with stone buildings, a gravel path, and potted plants.
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.

4. CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
Ruffoli
United States
Caleb M.
￥22,393
￥47,274 total
includes taxes & fees
Oct 22 - Oct 23
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 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.
￥23,459
￥23,992 total
includes taxes & fees
Oct 22 - Oct 23
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 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.
A bedroom with a large bed, wooden ceiling beams, a dresser, a mirror, and a chair.

6. Sorbeto Vacation Home

Sorbeto Vacation Home
impruneta
United States
Christine F.
￥14,040
￥52,606 total
includes taxes & fees
Oct 22 - Oct 23
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.
￥18,394
￥22,304 total
includes taxes & fees
Oct 28 - Oct 29
Old medieval apartment
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 bedroom with a wooden bed, two bedside tables with lamps, a chandelier, and a wardrobe.
A room with a wooden ceiling, a bed with white bedding, a dining table with chairs, and a wooden cabinet.

8. 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.
￥14,218
￥17,772 total
includes taxes & fees
Oct 22 - Oct 23
Appartment with swimming pool 30 min of Florence, private garden, parking, WiFi
A modern bedroom with a curved bed, a large mirror, and a jungle-themed mural.
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.
A narrow cobblestone street with historic buildings, a chain-link fence, and a wooden door with a number plaque.

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

Colle di Val d'Elsa - Siena - White Apartment - D
Colle di Val d'Elsa
￥15,355
￥28,151 total
includes taxes & fees
Oct 22 - Oct 23
Colle di Val d'Elsa - Siena - White Apartment - D
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.
An aerial view of a property with a swimming pool, lounge chairs, and a large house surrounded by greenery.
A bedroom with a metal bed frame, two bedside tables with lamps, a wooden window with shutters, and a wall-mounted light fixture.

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.
￥28,631
￥42,671 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

Hotel Toscana Ambassador

Hotel Toscana Ambassador

10/10 Excellent
"Excellent hôtel qualité-prix, très propre, très beau déjeuner, bien situé"
Nadine 1-night trip
Posted 14 hours ago
Hotel Toscana Ambassador
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 10 days 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 3 weeks 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

Explore a world of travel with Expedia