The Best Romantic Hotels in Castellina in Chianti from AED 464 in 2026

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

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Our top choices for Castellina in Chianti romantic hotels

1 bedroom, iron/ironing board, WiFi (free), bed sheets

1. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

Ruffoli

"This is truly a unique and special property providing incredible value . One of the most beautiful views in a spectacular setting hidden away in the Tuscan hills above Panzano. A perfect location for day trips to vinyards, restaurants and the Chianti area. Our apartment was extremely well appointed and beautifully decorated. Spacious and varied outdoor sitting areas and patios with a very nice pool area. Our hostess Babette was extremely accomodating and informative which added to our overall...

James

AED 344

AED 676 total

includes taxes & fees

4 Sep - 5 Sep

2. CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

Ruffoli

Lorna M.

AED 536

AED 1,132 total

includes taxes & fees

7 Sep - 8 Sep

Coffee/tea maker, fridge, microwave, oven

4 bedrooms, iron/ironing board, WiFi, bed sheets

3. Farmhouse in Chianti

gaiole in chianti

"This location provided our blended family an authentic experience in a small village on top of a mountain in Chianti. The house is surrounded by olive groves and wine grapes. The pool was great and the village, literally less than a city block up the road. Folks are incredibly friendly and helpful. Two of the rooms had their own bathrooms and the other two share a bathroom. There is a common kitchen for cooking and eating. We cooked most nights and ate on the outside terrace. Allesandra is a...

Lara W.

AED 1,724

AED 2,117 total

includes taxes & fees

7 Sep - 8 Sep

2 bedrooms, iron/ironing board, WiFi, bed sheets

Smart TV, fireplace, video-game console, DVD player

4. La Senesina, Monteriggioni, Siena. In the best countryside of Tuscany !

Siena

Robyn D.

AED 632

AED 938 total

includes taxes & fees

5 Sep - 6 Sep

5. Glicini 1, holiday home with pool 30' from Florence

Tavarnelle Val di Pesa

Joe M.

AED 703

AED 703 total

includes taxes & fees

19 Sep - 20 Sep

6. THE CASINA OF SANT 'AGOSTINO

Colle di Val d'Elsa

AED 511

AED 648 total

includes taxes & fees

4 Sep - 5 Sep

1 bedroom, in-room safe, travel crib, WiFi (free)

7. Colle di Val d'Elsa - Siena - Apt Blue - C

Colle di Val d'Elsa

ALLAN

AED 549

AED 881 total

includes taxes & fees

30 Sep - 1 Oct

8. Il Melograno, Chianti apartment in farmhouse for 4 people with garden

Montespertoli

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Top Castellina in Chianti Hotel Reviews

Bernini Palace

10/10 Excellent

"We had incredible service from everyone and had a lovely time. I would recommend it to anyone looking for an upscale hotel in Florence."

Hotel Albani Firenze

10/10 Excellent

"Everything was Great! It was a good and hearty breakfast. The rooms were cleaned daily. It is right around the corner from the train station and a central location to the city center."

The Market Urban Hotel

10/10 Excellent

"Staff was very welcoming, nice, and prompt on any request. Great location, just a short 10 minute walk to everything. Would stay again next time in Florence"

Grand Hotel Baglioni

10/10 Excellent

"Beautiful historic building - lovely hotel, very charming staff. Could not have been happier at our choice of hotel! By the way, the rooftop bar is magnificent!"

Hotel Delle Nazioni

10/10 Excellent

"Great staff. Clean hotel with air conditioning. Near the train station and all the attractions. Decent breakfast. I recommend this hotel."

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, Castellina Fortress, or Walls of Monteriggioni. 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.

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. Buondonno Winery, Castellina Fortress, and Walls of Monteriggioni 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.

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Change your mind

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Check availability on Castellina in Chianti Romantic Hotels

Our top choices for Castellina in Chianti romantic hotels

1. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK