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Top Chianti Region Luxury Hotels

COMO Castello Del Nero

5.0 star property
Barberino Tavarnelle
9.6 out of 10, Exceptional, (132)
"Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car). "
United States
Matthew
$835 nightly
The price is $928
Dec 14 - Dec 15
Total with taxes and fees
COMO Castello Del Nero

Palazzo Leopoldo Dimora Storica & Spa

4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (274)
"We loved it was easy to get to wineries or small towns we wanted to visit"
United States
Carol
$104 nightly
The price is $121
Dec 16 - Dec 17
Total with taxes and fees
Palazzo Leopoldo Dimora Storica & Spa

Relais Della Rovere

4.0 star property
Colle di Val d'Elsa
9.0 out of 10, Wonderful, (243)
"Quietly located hotel with modern rooms and very good dinner option in the courtyard. Spacious pool to relax after long sightseeing days in the countryside."
Germany
Alexander
$146 nightly
The price is $163
Dec 24 - Dec 25
Total with taxes and fees
Relais Della Rovere

Hotel Borgo San Luigi

4.0 star property
Monteriggioni
9.2 out of 10, Wonderful, (402)
"Beautiful location with clean rooms and wonderful staff. Really enjoyed the breakfast too! Recommended! "
United States
Allyson
$128 nightly
The price is $147
Dec 14 - Dec 15
Total with taxes and fees
Hotel Borgo San Luigi

Villa La Borghetta Resort

4.0 star property
Figline e Incisa Valdarno
7.8 out of 10, Good, (88)
"Beautiful experience!"
United States
ANGEL
$113 nightly
The price is $127
Dec 9 - Dec 10
Total with taxes and fees
Villa La Borghetta Resort

Villa Sabolini

4.0 star property
Colle di Val d'Elsa
9.2 out of 10, Wonderful, (188)
"Beautiful location and hotel Staff were excellent - thank you"
United Kingdom
Amit
$125 nightly
The price is $141
Dec 8 - Dec 9
Total with taxes and fees
Villa Sabolini

Hotel Il Piccolo Castello

4.0 star property
Monteriggioni
8.6 out of 10, Excellent, (335)
"We enjoyed our stay"
United States
Joshua
$106 nightly
The price is $122
Dec 8 - Dec 9
Total with taxes and fees
Hotel Il Piccolo Castello

Hotel Borgo di Cortefreda Relais

4.0 star property
Barberino Tavarnelle
9.4 out of 10, Exceptional, (477)
"The views were spectacular and the grounds were so peaceful"
United States
Michelle
$95 nightly
The price is $112
Jan 6 - Jan 7, 2026
Total with taxes and fees
Hotel Borgo di Cortefreda Relais

Hotel Palazzo San Lorenzo & SPA

4.0 star property
Colle di Val d'Elsa
9.4 out of 10, Exceptional, (432)
"Beautiful hotel and spa. Excellent amenities and modern luxuries. "
United States
George
$107 nightly
The price is $120
Dec 10 - Dec 11
Total with taxes and fees
Hotel Palazzo San Lorenzo & SPA

Hotel Villa Cesi

4.0 star property
Impruneta
8.6 out of 10, Excellent, (70)
"We had a wonderful stay."
United Kingdom
Kanhaiya
Hotel Villa Cesi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find out more about Chianti Region

Chianti Regionand its attractions for luxury travelers

In the enchanting Chianti Region of Italy, luxury travelers can indulge in a range of exquisite experiences. Begin your journey at the historic Castello di Brolio, where you can tour the stunning vineyards and enjoy exclusive wine tastings of some of the finest Chianti Classico. Next, explore the picturesque village of Radda in Chianti, known for its charming cobblestone streets and artisan shops, perfect for leisurely strolls and gourmet dining at Michelin-starred restaurants. For art enthusiasts, a visit to the Villa Medici in Poggio a Caiano offers a glimpse into Renaissance history and beautifully manicured gardens. Adventure seekers can enjoy private hot air balloon rides, gliding over the breathtaking rolling hills and vineyards at sunrise, an experience that truly encapsulates the beauty of Tuscany. Finally, consider staying at the luxurious Rosewood Castiglion del Bosco, where opulent suites and a world-class spa await, alongside personalized service that caters to every need. This region not only offers a taste of refined Italian culture but also ensures a memorable stay filled with sophistication and comfort.

Top Chianti Region Hotel Reviews

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