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 Romantic Hotels

Tonight
Oct 11 - Oct 12
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Oct 12 - Oct 13
Next weekend
Oct 16 - Oct 18
In two weeks
Oct 23 - Oct 25

Our top choices for Chianti Region romantic hotels

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.
An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.
A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.
A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

1. La Certosa di Pontignano - Place of Charme

La Certosa di Pontignano - Place of Charme
Castelnuovo Berardenga
United States
Leslie
₩127,123
₩151,844 total
includes taxes & fees
Nov 2 - Nov 3
La Certosa di Pontignano - Place of Charme
A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.
A poolside area with lounge chairs and a view of the night sky.
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.
A person relaxing in a hot tub with a view of a building and trees in the background.

2. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
United States
Michelle Reene
₩146,951
₩170,655 total
includes taxes & fees
Nov 11 - Nov 12
Belvedere di San Leonino
An indoor courtyard with stone flooring, arched columns, and tables set up for dining.
A modern reception area with a stone counter, a sign for SPA VILLA CASAGRANDE, and a staircase leading to a glass door.
An indoor swimming pool with clear glass walls, wooden beams, and large windows.
A historic building with a stone facade, arched entrance, and a wooden balcony.

3. Villa Casagrande Resort & SPA

Villa Casagrande Resort & SPA
Figline e Incisa Valdarno
United States
Ana
₩144,729
₩162,202 total
includes taxes & fees
Nov 8 - Nov 9
Villa Casagrande Resort & SPA
A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.
A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.
A courtyard with stone buildings, outdoor tables set for dining, and a gravel ground.
A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a tray of items, and a window with curtains.

4. Castello La Leccia

Castello La Leccia
Castellina in Chianti
United States
Eva
₩268,765
₩301,646 total
includes taxes & fees
Nov 2 - Nov 3
Castello La Leccia
A couple dining at an outdoor table with a view of the countryside.
A spacious room with high arched ceilings, a wooden dining table, chairs, and a bookshelf.
A narrow street with buildings on either side, a flag, and a bench.
A room with a view of a valley, a stone shelf with flowers, a wooden bench, and a fireplace.

5. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
Canada
Elizabeth
₩147,665
₩171,439 total
includes taxes & fees
Nov 1 - Nov 2
Palazzo Leopoldo Dimora Storica & Spa
A poolside area with outdoor seating and umbrellas, overlooking a scenic landscape.
A pathway lined with wooden fences and benches, leading to a covered seating area with tables and chairs.
A table with breakfast items, a clear view of the countryside, and a white umbrella.
A woman sitting on a chair in a room with a staircase, a wall-mounted light, and a tiled floor.

6. Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa
San Casciano in Val di Pesa
Canada
Haris
₩103,786
₩123,172 total
includes taxes & fees
Nov 10 - Nov 11
Villa I Barronci Resort & Spa
A rustic outdoor dining area with a stone wall, wooden benches, and a table set for two.
A bathroom with a bathtub, a window with a view of a vineyard, and a small table with a bottle and glasses.
A building with a brick facade, arched entrance, and multiple windows covered in green ivy.
A white vehicle parked in front of a building with a stone facade and arched windows, surrounded by gravel and greenery.

7. Tenuta CorteDomina

Tenuta CorteDomina
Radda in Chianti
United States
Edgar
₩164,653
₩187,123 total
includes taxes & fees
Nov 8 - Nov 9
Tenuta CorteDomina
A pool with a view of a lush valley and distant buildings.
A courtyard with stone buildings, arched doorways, and potted plants.
A garden with neatly trimmed hedges, a gravel path, and a stone barrel.
A terraced vineyard with stone walls and a stone pathway leading to a seating area with metal chairs and tables.

8. Castello Vicchiomaggio

Castello Vicchiomaggio
Greve in Chianti
United States
Mary Margaret
₩244,776
₩269,254 total
includes taxes & fees
Oct 29 - Oct 30
Castello Vicchiomaggio
A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.
A courtyard with a stone building, wooden pergola, and raised garden beds with various plants.
A landscaped garden with a swimming pool, a vineyard in the background, and a stone pathway.
A spa area with stone flooring, wooden chairs, a table with amenities, and a view of a garden through a glass door.

9. Hotel Villa Campomaggio

Hotel Villa Campomaggio
Radda in Chianti
United States
Dario
₩221,084
₩252,200 total
includes taxes & fees
Nov 3 - Nov 4
Hotel Villa Campomaggio
A wicker chair, a lantern, and a vase of flowers on a balcony with a mountain view.
A rustic stone building with a tiled roof, surrounded by lush greenery and white flowers.
A pool area with a view of a hilly landscape.
A spacious living room with a high ceiling, large windows with diamond-patterned blinds, a sofa set, a coffee table, and a painting on the wall.

10. Borgo Del Cabreo

Borgo Del Cabreo
Greve in Chianti
United States
Brian
₩319,343
₩357,282 total
includes taxes & fees
Oct 13 - Oct 14
Borgo Del Cabreo
View all properties

Top Chianti Region Hotel Reviews

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 hours ago
Castello di Spaltenna- Small Luxury Hotels of the World
Castello Vicchiomaggio

Castello Vicchiomaggio

10/10 Excellent
"A unique stay with a picturesque view. Breakfast, lunch, and dinner were fantastic. The property was great for relaxing at but also a good launching spot for exploring some of the nearby towns and sites."
Frank 4-night trip
Posted 3 days ago
Castello Vicchiomaggio
Borgo Vescine

Borgo Vescine

10/10 Excellent
"The staff was amazing and incredibly kind."
Natalie 2-night trip
Posted 9 days ago
Borgo Vescine
Relais Vignale & Spa

Relais Vignale & Spa

10/10 Excellent
"In a convenient location."
MELISSA 2-night trip
Posted 13 days ago
Relais Vignale & Spa
Hotel Villa Campomaggio

Hotel Villa Campomaggio

10/10 Excellent
"Great hotel"
Dario 2-night trip
Posted 3 weeks 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 1 month ago
COMO Castello Del Nero

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