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Featured Chianti Region Boutique Hotels

Grand Hotel Continental Siena – Starhotels Collezione
Banchi Di Sopra 85 Siena SI
Free Cancellation
Reserve now, pay when you stay
$321 nightly
The price is $360 total per night
$360 total
Dec 24 - Dec 25
Total with taxes and fees
Guests of Grand Hotel Continental Siena – Starhotels Collezione enjoy access to free WiFi in public areas, conference space, and a 24-hour business center. Valet parking is EUR 55 per day if you plan to drive, or hop aboard the airport shuttle (available 24 hours) for EUR 252 per vehicle one-way. Multilingual staff at the 24-hour front desk can assist with concierge services, luggage storage, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury hotel include a computer station, a library, and laundry facilities.
Pet friendly
Free WiFi

Borgo San Felice Resort
San Felice Castelnuovo Berardenga SI
Guests of Borgo San Felice Resort have access to a winery, a full-service spa, and a gym. If you drive, put free parking to good use. The 24-hour front desk has staff standing by to help with luggage storage, dry cleaning/laundry, and tours or tickets. Other amenities at this luxury hotel include a sauna, outdoor tennis courts, and a rooftop terrace.
Pool
Breakfast included

Borgo Livernano
Località Livernano 67/a Radda in Chianti SI
Guests staying at Borgo Livernano enjoy access to a winery, an outdoor pool, and free WiFi in public areas. Free parking is available if you drive. Front-desk staff can assist with securing valuables and luggage storage. Other amenities at this boutique farm stay include meeting rooms, a seasonal outdoor pool, and a library.
Pool
Pet friendly

Villa il Sasso - Dimora d'epoca
Via di Belmonte 27 Bagno a Ripoli FI
Villa il Sasso - Dimora d'epoca features an outdoor pool, WiFi in public areas, and conference space. There's free parking, and an airport shuttle (available 24 hours) for EUR 40 per vehicle roundtrip. The front desk has multilingual staff that can help with securing valuables, concierge services, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury affittacamere include a business center, a computer station, and express check-out.
Pool
Breakfast included

Relais degli Angeli
Via dei Montanini, 83 Siena SI
Free Cancellation
Reserve now, pay when you stay
$195 nightly
The price is $219 total per night
$219 total
Dec 26 - Dec 27
Total with taxes and fees
Guests of Relais degli Angeli enjoy a rooftop terrace, free WiFi in public areas, and meeting rooms. If you plan to drive, free offsite parking is available. The front desk has multilingual staff that can help with luggage storage, securing valuables, and dry cleaning/laundry. Additional amenities include a library, a terrace, and laundry facilities.
Free WiFi
Air conditioning

Hotel Palazzetto Rosso
Via dei Rossi, 38-42 Siena SI
Free Cancellation
Reserve now, pay when you stay
$147 nightly
The price is $162 total per night
$162 total
Jan 23 - Jan 24, 2026
Total with taxes and fees
Renovated in 2014, Hotel Palazzetto Rosso offers free WiFi in public areas, coffee in a common area, and a computer station. Valet parking is available for EUR 49 per night, and there's also limo/town car service. The front desk has multilingual staff that can help with luggage storage, tours or tickets, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this hot springs hotel include a library, express check-in, and express check-out.
Breakfast included
Pet friendly

La Villa di STR
Viale Vittorio Veneto 11 Siena SI
Free Cancellation
$109 nightly
The price is $124 total per night
$124 total
Jan 14 - Jan 15, 2026
Total with taxes and fees
Guests staying at La Villa di STR enjoy free WiFi in public areas, a library, and a garden. Free offsite parking is included with your stay. Front-desk staff can assist with securing valuables and luggage storage.
Pet friendly
Free WiFi

Residenza d'Epoca Relais Campo Regio
via della Sapienza 25 Siena SI
Free Cancellation
Reserve now, pay when you stay
$218 nightly
The price is $245 total per night
$245 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
A local mainstay since 1500, Residenza d'Epoca Relais Campo Regio offers free WiFi in public areas, a library, and free newspapers. The front desk has multilingual staff that can help with tours or tickets, dry cleaning/laundry, and securing valuables. Additional amenities include a terrace, laundry facilities, and a communal living room.
Breakfast included
Free WiFi

Hotel Certaldo
via del Molino, 74 Certaldo FI
Guests of LHP Certaldo Resort have access to an outdoor pool, a 24-hour gym, and free WiFi in public areas. There's free parking, and an airport shuttle (available 24 hours) for EUR 120 per person roundtrip. Multilingual staff at the front desk are standing by 24/7 to help with luggage storage, tours or tickets, and securing valuables. Other amenities at this luxury hotel include a business center, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included
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.
Chianti Region hotels essential information
Accommodation | 4,765 hotels |
|---|---|
Lowest Price | $124 |
Highest Price | $360 |
Popular hotels | Grand Hotel Continental Siena – Starhotels Collezione, Borgo San Felice Resort, Borgo Livernano, Villa il Sasso - Dimora d'epoca, Relais degli Angeli, Hotel Palazzetto Rosso, La Villa di STR, Residenza d'Epoca Relais Campo Regio, Hotel Certaldo |
Recent Boutique Hotels Reviews

Hotel Borgo di Cortefreda Relais
5/5 Excellent
"The hotel and services exceeded my expectations."
A verified traveler stayed at Hotel Borgo di Cortefreda Relais
Posted 3 weeks ago
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