Terraced vineyards on a hillside, a small village, and rolling green hills.

Hotels with connecting rooms in Chianti Region

Dates

November 2026

8

December 2026

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Map of Chianti Region

Our top choices for Chianti Region hotels with connecting rooms

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

1. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

United States

Rodolfo

includes taxes & fees

9 Nov - 10 Nov

A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

2. Belvedere di San Leonino

Castellina in Chianti

Canada

Kevork

includes taxes & fees

15 Nov - 16 Nov

A poolside area with outdoor seating and umbrellas, overlooking a scenic landscape.

3. Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

Canada

Haris

includes taxes & fees

9 Dec - 10 Dec

A pool surrounded by lush greenery and vineyards, with a stone building in the background.

4. Agriturismo San Sano

Gaiole in Chianti

Australia

Glen

includes taxes & fees

10 Nov - 11 Nov

A courtyard with snow-covered plants and a metal railing.

5. Bed & Breakfast Le Terrazze del Chianti

Tavarnelle Val di Pesa

Germany

Janine und Thomas

includes taxes & fees

3 Dec - 4 Dec

A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.

6. Hotel Borgo San Luigi

Monteriggioni

United States

JOHN

includes taxes & fees

10 Nov - 11 Nov

A rustic stone wall with a window, a potted plant, a bust sculpture, and a table with a magazine.

7. Tenuta CorteDomina

Radda in Chianti

United States

piyanut

includes taxes & fees

9 Nov - 10 Nov

An outdoor dining area with a table and chairs, surrounded by greenery and a view of a building in the background.

8. Chiantirooms Guesthouse

Greve in Chianti

Canada

Pasquale

includes taxes & fees

9 Nov - 10 Nov

A historic stone building with a courtyard, surrounded by olive groves and hills.

9. Azienda agricola la camporena

Greve in Chianti

United States

Inna

includes taxes & fees

9 Dec - 10 Dec

A bedroom with a stone wall, a bed, a nightstand, a window, and a mirror.

10. Casale La Gora

Figline e Incisa Valdarno

United States

Roberto

includes taxes & fees

8 Dec - 9 Dec

View all properties

Top Chianti Region Hotel Reviews

A hotel room with a large bed, a vanity with a mirror, and a green archway.

Hotel Certosa Di Maggiano

Siena

10/10 Excellent

Singapore

Oi Kee

A rustic stone wall with a window, a potted plant, a bust sculpture, and a table with a magazine.

Tenuta CorteDomina

Radda in Chianti

10/10 Excellent

Singapore

Alan

A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

Belvedere di San Leonino

Castellina in Chianti

8/10 Good

Singapore

Fatfinger

An opulent room with a grand chandelier, ornate gold detailing, and a large mirror reflecting the luxurious decor.

Villa Cora

Oltrarno

8/10 Good

Everything was perfect, except some minor details. It's related to one particular staff, but details matter when expectations are set so high. (1) I asked to arrange Uffizi tickets, which they kindly did. But there was no mention of any payment method. Eventually, only upon checkout, I was asked to provide cash only. You would think they could have mentioned this to me at the point of booking, otherwise I just assumed that I could pay by credit card to the Uffizi directly on ticket collection,...

Singapore

Doug

A person sitting by a swimming pool with a stone building in the background.

Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

10/10 Excellent

Singapore

Xueling

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