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

Historic Hotels & Resorts in Chianti Region from NZ$252

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Check availability on Chianti Region Historic Hotels

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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
Ali
NZ$378
includes taxes & fees
26 Oct - 27 Oct
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 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
Tereza
NZ$487
includes taxes & fees
17 Oct - 18 Oct
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
NZ$321
includes taxes & fees
5 Oct - 6 Oct
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 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.
NZ$530
includes taxes & fees
5 Oct - 6 Oct
CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
A view through a large arched window of a stone patio with a table and chairs, an umbrella, and lush greenery.
A rustic dining area with a stone wall, wooden door, and a wooden table with chairs.
A kitchen with a large window, wooden cabinets, and a dining table with chairs.
A rectangular pool with a stone border, surrounded by a grassy area and a row of sun loungers with umbrellas.

5. 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.
NZ$294
includes taxes & fees
20 Oct - 21 Oct
Glicini 1, holiday home with pool 30' from Florence
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 rustic dining area with a wooden table and chairs, a fireplace, and a large cabinet with glass doors.
A cozy living room with a fireplace, a floral armchair, a white sofa, and large windows.

6. Wonderful Tuscan farmhouse with large spaces and panoramic views

Wonderful Tuscan farmhouse with large spaces and panoramic views
impruneta
United States
Christine F.
NZ$504
includes taxes & fees
21 Oct - 22 Oct
Wonderful Tuscan farmhouse with large spaces and panoramic views
A poolside setting with two glasses of red drink, a tray with snacks, and a white umbrella.
A compact kitchen with wooden cabinets, a built-in microwave, a gas stove, and a sink.
A stone patio with a round table and four chairs, an umbrella, and potted plants.
A garden with flowering plants and a view of a mountainous landscape.

7. House in the Florentine hills with swimming pool, free parking and wifi

House in the Florentine hills with swimming pool, free parking and wifi
Reggello provincia Firenze
United States
Peter L.
House in the Florentine hills with swimming pool, free parking and wifi
A poolside setting with two drinks, a tray with snacks, and a white umbrella.
A table set outdoors with a view of a lush green landscape and mountains in the background.
A lush green landscape with a variety of trees and a clear blue sky.
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.
Appartment with swimming pool 30 min of Florence, private garden, parking, WiFi
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 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.

9. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
United States
Kathleen F.
NZ$252
includes taxes & fees
8 Oct - 9 Oct
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 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.

10. 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.
NZ$271
includes taxes & fees
5 Oct - 6 Oct
Deluxe Room Nero su Bianco with A/C and Private Bathroom in Villa le Facezie B&B
View all properties

Top Chianti Region Hotel Reviews

Hotel Toscana Ambassador

Hotel Toscana Ambassador

8/10 Good
"Close to train station"
Marian 1-night trip
Posted 22 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
"From the moment we checked in, This place was a Gem. From the friendly and helpful staff to the beautiful grounds, we were so impressed. Its hard to put into words how wonderful this Hotel is. The food, and drinks were incredible. We also celebrated my wife's birthday at this resort and they did a very special dinner for us to enjoy. Along with Campaign and a personalized Birthday dessert. Special thanks to Noamie (hope i got that right). She was absolutely wonderful. I could go on forever about this Resort. So easy to explore the region while calling this a comfortable landing spot. Can't thank the team enough for a wonderful stay."
Niel 2-night trip
Posted 23 hours ago
Castello di Spaltenna- Small Luxury Hotels of the World
Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

8/10 Good
"Under renovation so it could have been better"
Kimberli 1-night trip
Posted 2 days ago
Villa I Barronci Resort & Spa
Relais Vignale & Spa

Relais Vignale & Spa

10/10 Excellent
"In a convenient location."
MELISSA 2-night trip
Posted 4 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 5 days ago
Villa Le Barone
Hotel Villa Campomaggio

Hotel Villa Campomaggio

10/10 Excellent
"Great hotel"
Dario 2-night trip
Posted 9 days ago
Hotel Villa Campomaggio
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
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 3 weeks ago
Borgo Vescine

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