Romantic Hotels in Chianti Region
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Featured Chianti Region Romantic Getaways & Hotels

VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA.
San Gimignano
At this villa, guests enjoy features like an outdoor pool, a gym, and a sauna. Transportation is made easy with limo/town car service. Helpful staff is there to provide concierge services, as well as offer insight about the area. Other amenities at this family-friendly villa include a hot tub, an arcade/game room, and laundry facilities.
Pool
Hot Tub

Palazzo Leopoldo Dimora Storica & Spa
Via Roma 33 Radda in Chianti SI
Free Cancellation
Reserve now, pay when you stay
$95 nightly
The price is $112 total per night
$112 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
Palazzo Leopoldo Dimora Storica & Spa features a full-service spa, an indoor pool, and an outdoor pool. There's free parking, and an airport shuttle (available 24 hours) for EUR 150 per room one-way. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, tours or tickets, 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 spa hotel include a gym, a sauna, and a rooftop terrace.
Pool
Hot Tub

COMO Castello Del Nero
Strada Spicciano 7 Barberino Tavarnelle FI
Free Cancellation
Reserve now, pay when you stay
$849 nightly
The price is $943 total per night
$943 total
Dec 30 - Dec 31
Total with taxes and fees
Guests staying at COMO Castello Del Nero enjoy access to a full-service spa, a gym, and a sauna. You can take advantage of free parking, along with an airport shuttle for a fee. Multilingual staff at the front desk are standing by 24/7 to help with dry cleaning/laundry, luggage storage, and tours or tickets. 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 outdoor tennis courts, free WiFi in public areas, and a business center.
Pool
Breakfast included

Villa il Poggiale - Dimora Storica
Via Empolese 69 San Casciano in Val di Pesa FI
Free Cancellation
Reserve now, pay when you stay
At Villa il Poggiale - Dimora Storica, guests have access to an outdoor pool, a sauna, and a rooftop terrace. You can take advantage of free parking, along with an airport shuttle (available 24 hours) for EUR 65 per vehicle one way. The front desk has multilingual staff that can help with dry cleaning/laundry, securing valuables, and tours or tickets. Other amenities at this spa property include free WiFi in public areas, a hot tub, and a business center.

Castello di Fonterutoli Wine Resort
Via Puccini 4 Castellina in Chianti SI
Free Cancellation
Reserve now, pay when you stay
$196 nightly
The price is $220 total per night
$220 total
Dec 22 - Dec 23
Total with taxes and fees
Guests of Castello di Fonterutoli Wine Resort enjoy features like a winery, free WiFi in public areas, and refrigerator in a common area. You can take advantage of free offsite parking, along with limo/town car service. The front desk has multilingual staff that can help with tours/tickets and luggage storage. Additional amenities include a meeting room, a library, and wedding services.
Pet friendly
Free WiFi

Hotel Le Fontanelle
SP 408-km 14.7 Castelnuovo Berardenga SI
A local mainstay since 1200, Hotel Le Fontanelle offers a winery, a full-service spa, and an indoor pool. Free valet and self parking are available, and there's also limo/town car service. The 24-hour front desk has multilingual staff ready to assist with securing valuables, dry cleaning/laundry, and tours or tickets. 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 gym, a sauna, and free WiFi in public areas.
Pool
Hot Tub

Cdh Hotel Radda
Loc La Calvana, 138 Radda in Chianti Tuscany
At Cdh Hotel Radda, guests enjoy a full-service spa, an outdoor pool, and a children's pool. Onsite parking is offered for a fee. Multilingual staff at the front desk are standing by 24/7 to help with securing valuables, luggage storage, and dry cleaning/laundry. Other amenities at this spa hotel include a gym, a sauna, and a rooftop terrace.
Pool
Hot Tub

Relais Vignale & Spa
Via Pianigiani 9 Radda in Chianti SI
A full-service spa, a sauna, and a rooftop terrace are featured at Relais Vignale & Spa. You can take advantage of free parking, along with an airport shuttle (available 24 hours) for EUR 135 per vehicle one-way. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, luggage storage, and tours or tickets. 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 spa hotel include free WiFi in public areas, a hot tub, and meeting rooms.
Pool
Hot Tub

Hotel Palazzo San Lorenzo & SPA
Via Gracco Del Secco 113 Colle di Val d'Elsa SI
Free Cancellation
Reserve now, pay when you stay
A full-service spa, a sauna, and free WiFi in public areas are featured at Hotel Palazzo San Lorenzo & SPA. A stay here includes free offsite parking. The front desk is staffed 24/7 to help with dry cleaning/laundry, securing valuables, 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 hotel include a hot tub, meeting rooms, and free newspapers.

Villa San Lucchese
Località San Lucchese, 5 Poggibonsi SI
Free Cancellation
Reserve now, pay when you stay
Villa San Lucchese offers a children's pool, free WiFi in public areas, and an outdoor tennis court. There's free parking, and an airport shuttle (available 24 hours) for EUR 140 per vehicle. The 24-hour front desk has multilingual staff ready to assist with securing valuables, concierge services, and dry cleaning/laundry. Other amenities at this family-friendly hotel include a seasonal outdoor pool, a library, and express check-out.
Pool
Breakfast included

Villa Scacciapensieri Boutique Hotel
Strada di Scacciapensieri 10 Siena SI
Guests of Villa Scacciapensieri Boutique Hotel enjoy a rooftop terrace, free WiFi in public areas, and a seasonal outdoor pool. Free offsite parking is included with your stay. The front desk has multilingual staff on hand 24/7 to help with tours or tickets, securing valuables, and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls, pet-sitting services, and litter boxes. Other amenities at this family-friendly hotel include coffee/tea in a common area, a computer station, and a library.

Grand Hotel Continental Siena – Starhotels Collezione
Banchi Di Sopra 85 Siena SI
Free Cancellation
Reserve now, pay when you stay
$299 nightly
The price is $336 total per night
$336 total
Dec 21 - Dec 22
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.

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.

Villa La Borghetta Resort
Via del Cesto Figline e Incisa Valdarno FI
Free Cancellation
Reserve now, pay when you stay
Guests staying at Villa La Borghetta Resort enjoy access to a full-service spa, an outdoor pool, and a sauna. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, securing valuables, and tours or tickets. Other amenities at this spa hotel include free WiFi in public areas, a hot tub, and conference space.
Pool
Hot Tub
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 | $112 |
Highest Price | $943 |
Popular hotels | VILLA IRIS LUXURY SAN GIMIGNANO, 6 EN-SUITE BEDROOMS, SWIMMING POOL, SPA, SAUNA., Palazzo Leopoldo Dimora Storica & Spa, COMO Castello Del Nero, Villa il Poggiale - Dimora Storica, Castello di Fonterutoli Wine Resort, Hotel Le Fontanelle, Cdh Hotel Radda, Relais Vignale & Spa, Hotel Palazzo San Lorenzo & SPA, Villa San Lucchese, Villa Scacciapensieri Boutique Hotel, Grand Hotel Continental Siena – Starhotels Collezione, Borgo San Felice Resort, Villa La Borghetta Resort, "LA MEZZANA" apartment with private terrace and stunning views |
Recent Romantic Getaways & 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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