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

Hotels with connecting rooms in Chianti Region

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Check availability on Chianti Region Hotels with connecting rooms

Tonight
5 Sept - 6 Sept
Tomorrow
6 Sept - 7 Sept
Next weekend
11 Sept - 13 Sept
In two weeks
18 Sept - 20 Sept

Our top choices for Chianti Region hotels with connecting rooms

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 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.
A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

1. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
United States
Malena
S$164
includes taxes & fees
8 Sept - 9 Sept
La Certosa di Pontignano
An outdoor dining area with a pool, potted plants, and umbrellas.
A restaurant with a table set for two, overlooking a scenic landscape.
An outdoor dining area with a table set for two, overlooking a pool and vineyard.
A villa with a swimming pool, outdoor seating, and a garden.

2. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
United States
Maaya
S$299
includes taxes & fees
5 Oct - 6 Oct
Relais Vignale & Spa
A rustic outdoor dining area with a stone wall, wooden benches, and a table set for two.
A white vehicle parked in front of a building with a stone facade and arched windows, surrounded by gravel and greenery.
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.

3. Tenuta CorteDomina

Tenuta CorteDomina
Radda in Chianti
United States
Dustin
S$356
includes taxes & fees
5 Oct - 6 Oct
Tenuta CorteDomina
A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.
An outdoor patio with stone flooring, a table with chairs, and potted plants.

4. Hotel Borgo San Luigi

Hotel Borgo San Luigi
Monteriggioni
Canada
Sara
S$239
includes taxes & fees
9 Sept - 10 Sept
Hotel Borgo San Luigi
A scenic outdoor venue with multiple covered seating areas and a view of the surrounding landscape.
A terraced garden with a pool, outdoor seating, and a view of rolling hills.
A spa room with a massage table, towels, and candles.
A restaurant with white tables and chairs, wine bottles on shelves, and a chandelier.

5. Azienda agricola la camporena

Azienda agricola la camporena
Greve in Chianti
United States
Pawel
S$210
includes taxes & fees
15 Sept - 16 Sept
Azienda agricola la camporena
A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.
A stone building with a wooden door, outdoor seating, and a pergola with vines.
A pool surrounded by lush greenery and vineyards, with a stone building in the background.
A stone building with a window and a light fixture.

6. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
United States
Paula
S$137
includes taxes & fees
6 Oct - 7 Oct
Agriturismo San Sano
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 rustic stone building with a garden in front.
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.

7. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
United States
Seong Won
S$187
includes taxes & fees
10 Sept - 11 Sept
Belvedere di San Leonino
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 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.

8. Villa Le Barone

Villa Le Barone
Greve in Chianti
Canada
Aditi
S$377
includes taxes & fees
13 Sept - 14 Sept
Villa Le Barone
A poolside area with outdoor seating and umbrellas, overlooking a scenic landscape.
A bedroom with a large bed, a view of a green landscape through a sliding door, and a potted plant on the windowsill.
A woman sitting on a chair in a room with a staircase, a wall-mounted light, and a tiled floor.
A pathway lined with wooden fences and benches, leading to a covered seating area with tables and chairs.

9. Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa
San Casciano in Val di Pesa
United States
Juan Antonio
S$223
includes taxes & fees
6 Oct - 7 Oct
Villa I Barronci Resort & Spa
An outdoor patio with tables and chairs, string lights, and hanging glass globes.
A traditional living room with a red sofa, a wooden coffee table, and a bookshelf filled with various items.
A bedroom with a large bed, a wooden ceiling, a wardrobe, and a desk with a lamp.
A dining table set with various dishes, utensils, and a fruit bowl.

10. Bed & Breakfast Le Terrazze del Chianti

Bed & Breakfast Le Terrazze del Chianti
Tavarnelle Val di Pesa
Germany
Robert
S$133
includes taxes & fees
7 Sept - 8 Sept
Bed & Breakfast Le Terrazze del Chianti
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Top Chianti Region Hotel Reviews

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
Villa Le Barone

Villa Le Barone

10/10 Excellent
"Loved staying at Villa Le Barone during my time in Tuscany. The property is beautiful, and super relaxing. Breakfast was delicious, and the space for breakfast and dinner was very nice. Pool was amazing a well. Would recommend and would stay there again!"
Nour 3-night trip
Posted 3 months ago
Villa Le Barone

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