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 12 - Oct 13
Tomorrow
Oct 13 - Oct 14
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Chianti Region romantic hotels

A rustic outdoor dining area with a stone wall, wooden benches, and a table set for two.
A building with a brick facade, arched entrance, and multiple windows covered in green ivy.
A bathroom with a bathtub, a window with a view of a vineyard, and a small table with a bottle and glasses.
A table set with wine glasses and a candle, viewed through a window with string lights.

1. Tenuta CorteDomina

Tenuta CorteDomina
Radda in Chianti
United States
Edgar
₩238,552
₩268,412 total
includes taxes & fees
Nov 12 - Nov 13
Tenuta CorteDomina
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.
A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.
An interior corridor with arches, columns, and a brick wall.
An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

2. 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 pool with a view of a lush valley and distant buildings.
A garden with neatly trimmed hedges, a gravel path, and a stone barrel.
A courtyard with stone buildings, arched doorways, and potted plants.
A bedroom with a large arched window, a bed, a hanging light fixture, and a view of a green landscape.

3. 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 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 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.
A poolside area with lounge chairs and a view of the night sky.

4. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
United States
Michelle Reene
₩143,825
₩167,215 total
includes taxes & fees
Oct 16 - Oct 17
Belvedere di San Leonino
An indoor courtyard with stone flooring, arched columns, and tables set up for dining.
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.
A modern reception area with a stone counter, a sign for SPA VILLA CASAGRANDE, and a staircase leading to a glass door.

5. 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 couple dining at an outdoor table with a view of the countryside.
A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.
A spacious room with high arched ceilings, a wooden dining table, chairs, and a bookshelf.
A room with a view of a valley, a stone shelf with flowers, a wooden bench, and a fireplace.

6. 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 historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.
A courtyard with stone buildings, outdoor tables set for dining, and a gravel ground.
A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.
A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a tray of items, and a window with curtains.

7. 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 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.

8. 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 12 - Nov 13
Villa I Barronci Resort & Spa
A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.
An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.
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.

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 pool area with a view of a hilly landscape.
A rustic stone building with a tiled roof, surrounded by lush greenery and white flowers.
A bedroom with a large bed, a bedside table, and a chair.

10. Borgo Del Cabreo

Borgo Del Cabreo
Greve in Chianti
United States
Brian
₩319,333
₩357,268 total
includes taxes & fees
Oct 18 - Oct 19
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 1 day 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 4 days ago
Castello Vicchiomaggio
Borgo Vescine

Borgo Vescine

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

Relais Vignale & Spa

10/10 Excellent
"In a convenient location."
MELISSA 2-night trip
Posted 2 weeks 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 2 weeks ago
Villa Le Barone
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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