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
Sep 11 - Sep 12
Tomorrow
Sep 12 - Sep 13
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Chianti Region historic hotels

An outdoor dining area with a pool, potted plants, and umbrellas.
A villa with a swimming pool, outdoor seating, and a garden.
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.

1. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
United States
Maaya
￥27,508
￥35,736 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 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.
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
Aditi
￥36,412
￥41,129 total
includes taxes & fees
Oct 11 - Oct 12
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.
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.

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

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
Canada
James
￥14,408
￥28,325 total
includes taxes & fees
Sep 15 - Sep 16
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 living room with a tiled floor, a blue sofa, a beige armchair, a small round table, a television, and a wooden ceiling beam.
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
Lorna M.
￥22,481
￥47,996 total
includes taxes & fees
Sep 21 - Sep 22
CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
A narrow stone alley with arched doorways, potted plants, and hanging flower baskets.
A bedroom with a stone wall, a bed with a headboard, a chair, and two bedside lamps.
A cozy living room with a stone wall, a staircase, and a view of the outside through a window.
A staircase with a stone wall on one side and a dark wooden door on the other.

5. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
United States
Kathleen F.
￥20,519
￥24,445 total
includes taxes & fees
Oct 9 - Oct 10
Old medieval apartment
A rectangular swimming pool with a wooden deck, surrounded by lush greenery and a clear sky.
A hallway with a wooden archway, a bench, a rug, and a table with a book and flowers.
A two-story building with a balcony, surrounded by palm trees and a well-maintained garden with red flowers.
A hot tub with two glasses of champagne and a tray of strawberries.

6. 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.
￥24,533
￥25,068 total
includes taxes & fees
Sep 16 - Sep 17
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 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.
￥14,274
￥43,536 total
includes taxes & fees
Sep 28 - Sep 29
Wonderful Tuscan farmhouse with large spaces and panoramic views
A poolside setting with two glasses of red drink, a tray with chips and olives, and a white umbrella.
A patio with a table and chairs, surrounded by greenery and a view of hills.
A yellow building with a balcony, surrounded by green grass and flowering trees.
A kitchen with white cabinets, a red sofa, and a dining table with chairs.

8. Tuscany countryside appartment with pool

Tuscany countryside appartment with pool
Reggello FI
￥16,058
￥18,021 total
includes taxes & fees
Sep 14 - Sep 15
Tuscany countryside appartment with pool
A narrow cobblestone street with historic buildings, a chain-link fence, and a wooden door with a number plaque.
A hallway with a herringbone floor pattern, grey walls, and a wooden ceiling beam.
A modern kitchen with white cabinets, a microwave, and a glass dining table with blue chairs.
A modern bathroom with a bidet, toilet, and glass-enclosed shower.

9. Colle di Val d'Elsa - Siena - Apt Blue - C

Colle di Val d'Elsa - Siena - Apt Blue - C
Colle di Val d'Elsa
United States
ALLAN
￥14,340
￥26,888 total
includes taxes & fees
Oct 11 - Oct 12
Colle di Val d'Elsa - Siena - Apt Blue - C
A rectangular swimming pool with a wooden deck, surrounded by lush greenery and a clear sky.
A bedroom with a bed, a nightstand, a lamp, a closet with shelves, and a spiral staircase.
A buffet table with various food items, plates, and utensils.
A spiral staircase with a metal railing, a white chair, and framed pictures on the wall.

10. 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
￥24,979
￥28,012 total
includes taxes & fees
Sep 23 - Sep 24
Superior Settimo Cielo with A/C and Private Bathroom in Villa le Facezie B&B
View all properties

Top Chianti Region Hotel Reviews

Borgo Vescine

Borgo Vescine

10/10 Excellent
"⭐️⭐️⭐️⭐️⭐️ We genuinely did not want to leave Borgo Vescine was everything we hoped a stay in Tuscany would be. The property is absolutely stunning, incredibly peaceful, and so beautifully cared for that once we arrived, we honestly didn’t want to leave. What made the experience even more special was the staff. Everyone we encountered was warm, welcoming and genuinely delightful. The hospitality never felt forced or overly formal. We simply felt very well taken care of throughout our stay. We had dinner at the property and the restaurant was excellent, which made staying in for the evening an easy decision. Breakfast was included with our stay and was such a delicious treat each morning. Being able to wake up somewhere this beautiful, have a wonderful breakfast and then simply enjoy the property was exactly the kind of Tuscan experience we were looking for. The grounds themselves are gorgeous and meticulously maintained, with beautiful views and so many quiet little areas to sit and take everything in. Despite everything the property offers, it still feels serene, intimate and wonderfully quiet. Borgo Vescine is the kind of place that makes you reconsider whatever plans you had for the day because you would rather just stay there. One of our favorite stays in Tuscany and a property I would happily return to. Highly recommend."
Nadege 1-night trip
Posted 14 hours ago
Borgo Vescine
Villa Le Barone

Villa Le Barone

10/10 Excellent
"Excellent stay with wonderful , friendly staff!"
Kathleen 3-night trip
Posted 2 days ago
Villa Le Barone
Hotel Villa Campomaggio

Hotel Villa Campomaggio

10/10 Excellent
"This resort is one of the most beautiful properties I have ever stayed in. Free use of the spa just was icing on the cake! Great breakfast spread and our dinner in the restaurant was delicious! We will be back!!"
Jayni 2-night trip
Posted 2 days ago
Hotel Villa Campomaggio
Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"Very nice place in the heart of Chianti Pool and premises are extraordinary"
Maryse 3-night trip
Posted 5 days ago
Castello Vicchiomaggio
Belvedere di San Leonino

Belvedere di San Leonino

10/10 Excellent
"Staff is great. Room clean. Property beautiful and dinner was delicious"
Seong Won 1-night trip
Posted 10 days ago
Belvedere di San Leonino
Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA

10/10 Excellent
"Incredible property, steeped in history. The rooms are beautifully traditional and the staff incredibly friendly. A beautiful place to unwind for a few days in Tuscany! We would re-book in a heartbeat."
Natasha 4-night trip
Posted 3 weeks 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
"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 1 month 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 3 months ago
Hotel Toscana Ambassador
COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent
"Great staff!"
Philip 1-night trip
Posted 3 months ago
COMO Castello Del Nero

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