A stone building with a clock tower, steps leading up to it, and people walking around.

Find Romantic Hotels in Castellina in Chianti

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • 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

Seasonal outdoor pool, open 8:00 AM to 7:00 PM, sun loungers

Palazzo Squarcialupi

Palazzo Squarcialupi
4.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (78 reviews)
"We stayed for a week and loved everything about this hotel. The staff went out of their way to make sure everything was perfect and everyone was so friendly. We really enjoyed breakfast each morning on the terrace and we used the pool and spa every day. Very relaxing and walking distance to everything in Castellina. Their pasta restaurant located across the street is also very good."
United States
Jennifer
The price is AED 804
AED 910 total
includes taxes & fees
9 Aug - 10 Aug
Palazzo Squarcialupi
Restaurant

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (179 reviews)
"Excellent place to stay"
United States
Alejandro
The price is AED 521
AED 590 total
includes taxes & fees
31 Jul - 1 Aug
Borgo di Pietrafitta Relais
Front of property

Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
9.8 out of 10, Exceptional, (9 reviews)
"This property has been under renovation for the past few years, with about another year of construction still to go. They are transforming an old winery into what will eventually be a 5- or 6-star resort, complete with a spa and other amenities. We stayed for two nights with our 11- and 13-year-olds and booked a family suite. The master bedroom bed was extremely comfortable, and the kids’ fold-out bed was large and surprisingly comfortable as well. The bathroom was brand new and had a door...
United States
Brian
The price is AED 1,274
AED 1,426 total
includes taxes & fees
19 Jul - 20 Jul
Fattoria di Vegi
Interior entrance

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (123 reviews)
"Friendly staff and walking distance to town"
United States
Scott
The price is AED 455
AED 513 total
includes taxes & fees
26 Jul - 27 Jul
Hotel Colle Etrusco Salivolpi
Exterior

Locanda le Piazze

Locanda le Piazze
4.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (196 reviews)
"Good resort"
United Kingdom
Oluwafunmilayo
The price is AED 1,376
AED 1,538 total
includes taxes & fees
28 Jul - 29 Jul
Locanda le Piazze
Exterior

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (217 reviews)
"Very peaceful and staff was very helpful with reservations for excursions"
United States
Giancarlo
The price is AED 564
AED 638 total
includes taxes & fees
18 Jul - 19 Jul
Castello di Fonterutoli Wine Resort
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (35 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is AED 929
AED 1,031 total
includes taxes & fees
29 Jul - 30 Jul
Riserva di Fizzano Residence
Gift shop

Belvedere di San Leonino

Belvedere di San Leonino
4.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (187 reviews)
"Very clean and amazing staff. And the room is at such a nice and rich location with a beautiful view."
United States
Christopher
The price is AED 645
AED 735 total
includes taxes & fees
10 Aug - 11 Aug
Belvedere di San Leonino
Exterior

Albergo Il Colombaio

Albergo Il Colombaio
3.0 star property
Castellina in Chianti
8.4 out of 10, Very Good, (62 reviews)
"I was a little hesitant about staying outside a "major city," but I'm so glad we did. Very cute hotel and room. It was a short walk to the local town, which had lots of options for dinner and chianti tasting. "
United States
Christine
The price is AED 436
AED 492 total
includes taxes & fees
19 Jul - 20 Jul
Albergo Il Colombaio
Garden

Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
4.0 star property
Castellina in Chianti
9.2 out of 10, Wonderful, (122 reviews)
"Wonderful spot to stop in between cities. Short drive to many vineyards (some require a reso) and Castellina Di Chianti is the beautiful quaint town with the best gelato we have the whole trip (and we went twice a day all around Italy). The pool with the beautiful backdrop was a nice way to slow down. Staff were lovely."
Canada
Makenzie
The price is AED 590
AED 674 total
includes taxes & fees
22 Jul - 23 Jul
Villa Casalecchi Country 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.
View all properties

Top Castellina in Chianti Hotel Reviews

Hotel Albani Firenze

Hotel Albani Firenze

10/10 Excellent
"Great breakfast and good air conditioning"
Eduardo 3-night trip
Posted 2 days ago
Hotel Albani Firenze

Explore a world of travel with Expedia

Frequently asked questions

Searching for romantic hotels in Castellina in Chianti?
If you and your partner need some romantic time away, we'd like to help you plan for it. Couples enjoy Castellina in Chianti for its countryside and wineries. If you want to spend a romantic day sharing a bottle of wine with your love, you might plan a visit to Lilliano Estate Winery, Casa Vinicola Luigi Cecchi, or Buondonno Winery. If you and your sweetheart are looking forward to a relaxing time away or you'd like to be pampered with luxurious amenities and fine dining, you can choose from 5 lodging options in Castellina in Chianti for the ideal romantic vacation.
What's the best hotel for couples in Castellina in Chianti?
Lovely country house in the Chianti region, for 4 persons, near Siena is a favorite country house for couples, and features free WiFi and a garden. Another good option for your romantic getaway is Farmhouse in the Chianti "La Foresta 1" with swimming pool.
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. Castellina Fortress, Archaeological Museum of Chianti, and Buondonno Winery 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.