Find Romantic Hotels in Castellina in Chianti

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Check availability on Castellina in Chianti Romantic Hotels

Our top choices for Castellina in Chianti romantic hotels

Restaurant
Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais

Castellina in Chianti
9.4 out of 10, Exceptional, (169)
"Wonderful setting."
United Kingdom
Simon
The price is SAR 342
SAR 393 total
includes taxes & fees
8 Jan - 9 January 2026
Borgo di Pietrafitta Relais
Front of property
PODERE 1384

PODERE 1384

Castellina in Chianti
The price is SAR 2,097
SAR 2,333 total
includes taxes & fees
11 Dec - 12 Dec
PODERE 1384
Breakfast, lunch, dinner served; Italian cuisine, garden views
Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort

Castellina in Chianti
9.4 out of 10, Exceptional, (199)
"Clean room, courteous staff, and good winery"
United States
Sangchun
The price is SAR 568
SAR 643 total
includes taxes & fees
11 Dec - 12 Dec
Castello di Fonterutoli Wine Resort
Exterior detail
Art Hotel Villa Agape

Art Hotel Villa Agape

4.0 star property
Oltrarno
9.8 out of 10, Exceptional, (1000)
"A beautiful hotel, extremely clean and with stunning gardens."
United Kingdom
Elizabeth
The price is SAR 433
SAR 537 total
includes taxes & fees
11 Dec - 12 Dec
Art Hotel Villa Agape
Superior Room, Balcony | Balcony
Orto De Medici Hotel

Orto De Medici Hotel

4.0 star property
Historic Centre of Florence
9.6 out of 10, Exceptional, (1004)
"We had a wonderful time staying and close to a lot of wonderful spots to visit. "
United States
JoAnn
The price is SAR 500
SAR 612 total
includes taxes & fees
11 Dec - 12 Dec
Orto De Medici Hotel
View from room
Hotel Ginori al DUOMO

Hotel Ginori al DUOMO

4.0 star property
Historic Centre of Florence
9.2 out of 10, Wonderful, (19)
"Highly recommend. Staff is friendly, everything was clean and the location was great. "
United States
Jenna
Hotel Ginori al DUOMO
Terrace/patio
Cellai Boutique Hotel

Cellai Boutique Hotel

4.0 star property
Historic Centre of Florence
8.2 out of 10, Very Good, (676)
"Great location - good place to stay for price"
United States
Cynthia
Cellai Boutique Hotel
Comfort Double Room | Terrace/patio
Villa Gelsomino Garden

Villa Gelsomino Garden

Oltrarno
9.0 out of 10, Wonderful, (128)
"Great clean hotel not far from central Florence. "
United States
David
Villa Gelsomino Garden
Seasonal outdoor pool
Torre di Bellosguardo

Torre di Bellosguardo

4.0 star property
Oltrarno
9.0 out of 10, Wonderful, (103)
"Beautiful property and wonderful staff."
United States
Brad
The price is SAR 1,403
SAR 1,605 total
includes taxes & fees
8 Jan - 9 January 2026
Torre di Bellosguardo
Deluxe Double Room | 1 bedroom, premium bedding, down comforters, minibar
Opera Boutique B&B

Opera Boutique B&B

San Lorenzo
9.0 out of 10, Wonderful, (143)
"Beautiful quiet space. Lovely room. Easy walking to tourist attractions. Catch the tram just around the corner. Hostess wonderful. "
United States
leslie
Opera Boutique B&B
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.
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Top Castellina in Chianti Hotel Reviews

Hotel Paris

Hotel Paris

10/10 Excellent
"This place is great! They are generous with luggage storage times even after checkout and the room was beautiful. The showers are tiny but everywhere in italy is like that."
Matthew 1-night trip
Posted 3 days ago
Hotel Paris

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Frequently asked questions

Searching for romantic hotels in Castellina in Chianti?
If you and your partner need a romantic vacation, we've got just the thing. Our guests also enjoy Castellina in Chianti for its wineries and countryside. You might consider checking out some of the nearby sights and attractions such as Buondonno Winery, Casa Vinicola Luigi Cecchi, or Castellina Fortress. If you're interested in staying near a particular destination, you can sort by neighborhood or distance to top sights, so you'll be able to see everything on your list.
How many romantic hotels will we find in Castellina in Chianti?
Expedia has 5 romantic Castellina in Chianti hotels for you both to enjoy.
When is the best time of year for a romantic getaway to Castellina in Chianti?
If you're hoping to get lost in the rain on your romantic getaway, check out these details about year-round temperatures in Castellina in Chianti: The hottest months are usually August and July with an average temp of 72°F, while the coldest months are January and February with an average of 44°F. Average annual precipitation for Castellina in Chianti is 37 inches.
What is there to do in Castellina in Chianti?
There's nothing better than experiencing a new destination with your sweetheart, so consider taking time to discover all there is to see and do in Castellina in Chianti. If you and your partner are interested in sampling the area's cuisine, you'll enjoy Castellina in Chianti for its wineries. Buondonno Winery, Casa Vinicola Luigi Cecchi, and Castellina Fortress are worth a stop when you're out and about.
What's the best way to get to Castellina in Chianti and around town during my romantic getaway?
These transportation options in Castellina in Chianti might help your romantic trip get off to a smooth start: Make your way to Castellina in Chianti with a flight to Florence Airport, Peretola (FLR), which is the closest major airport located 23.2 mi (37.4 km) from the city center. If you'd like to explore around the area, consider renting a car to take in more sights.