Romantic Hotels & Resorts in Castellina in Chianti from NZ$223

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Castellina in Chianti Romantic Hotels

Our top choices for Castellina in Chianti romantic hotels

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 NZ$223
includes taxes & fees
3 Jan - 4 Jan 2026
Borgo di Pietrafitta Relais

PODERE 1384

PODERE 1384
Castellina in Chianti
The price is NZ$1,129
includes taxes & fees
9 Jan - 10 Jan 2026
PODERE 1384

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (200)
"Clean room, courteous staff, and good winery"
United States
Sangchun
The price is NZ$359
includes taxes & fees
14 Dec - 15 Dec
Castello di Fonterutoli Wine Resort

Art Hotel Villa Agape

Art Hotel Villa Agape
4.0 star property
Oltrarno
9.8 out of 10, Exceptional, (1003)
"A beautiful hotel, extremely clean and with stunning gardens."
United Kingdom
Elizabeth
The price is NZ$257
includes taxes & fees
7 Jan - 8 Jan 2026
Art Hotel Villa Agape

Orto De Medici Hotel

Orto De Medici Hotel
4.0 star property
Historic Centre of Florence
9.6 out of 10, Exceptional, (1006)
"We had a wonderful time staying and close to a lot of wonderful spots to visit. "
United States
JoAnn
The price is NZ$247
includes taxes & fees
11 Jan - 12 Jan 2026
Orto De Medici Hotel

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

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 NZ$740
includes taxes & fees
13 Dec - 14 Dec
Torre di Bellosguardo

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

Hotel Lungarno - Lungarno Collection

Hotel Lungarno - Lungarno Collection
5.0 star property
Historic Centre of Florence
9.6 out of 10, Exceptional, (599)
"Excellent location! Truly a 5 star hotel ! Great service, breakfast, and service . Bedrooms were clean! Bathrooms were excellent!"
Canada
Pam
The price is NZ$1,139
includes taxes & fees
13 Dec - 14 Dec
Hotel Lungarno - Lungarno Collection

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
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.

Top Castellina in Chianti Hotel Reviews

Explore a world of travel with Expedia

Frequently asked questions

Searching for romantic hotels in Castellina in Chianti?
If you and your partner need a romantic escape, we'd like to help you plan for it. 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'd like to stay close to a particular destination, you can sort by neighbourhood and proximity to top sights, so you'll be able to see everything on your list.
How many romantic hotels are there 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, take a look at these details about year-round temperatures in Castellina in Chianti: The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Castellina in Chianti is 935 mm.
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 Peretola Airport (FLR), which is the closest major airport located 23.2 mi (37.4 km) from the city centre. If you'd like to explore around the area, consider renting a car to explore more sights.