The Best Romantic Hotels in Castellina in Chianti from ￥24,524 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

￥14,455

￥27,522 total

includes taxes & fees

Sep 22 - Sep 23

2. CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

Ruffoli

Lorna M.

￥22,555

￥46,184 total

includes taxes & fees

Sep 22 - Sep 23

1 bedroom, iron/ironing board, travel crib, WiFi (free)

Coffee/tea maker, fridge, microwave, oven

3. Old medieval apartment

Tavarnelle Val di Pesa

Kathleen F.

￥20,586

￥24,524 total

includes taxes & fees

Oct 11 - Oct 12

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

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

Colle di Val d'Elsa

ALLAN

￥14,320

￥27,029 total

includes taxes & fees

Oct 13 - Oct 14

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

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

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

Siena

Robyn D.

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

6. 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.

￥81,080

￥96,575 total

includes taxes & fees

Oct 19 - Oct 20

Coffee/tea maker, fridge, microwave, stovetop

7. THE EATER'S NEST - Unique in the Piazza del Campo

Siena City Centre

Benjamin C.

￥16,273

￥27,566 total

includes taxes & fees

Sep 22 - Sep 23

In-room safe, desk, WiFi (free), bed sheets

8. San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

San Gimignano City Centre

Marilyn H.

￥19,297

￥29,207 total

includes taxes & fees

Sep 21 - Sep 22

View all properties

Top Castellina in Chianti Hotel Reviews

Hotel Paris

10/10 Excellent

"This hotel was excellent. I can't praise it enough. The breakfast was wonderful. Staff was the BEST. Central location. Just perfect."

Palazzo Montebello

10/10 Excellent

"Elegant, safe, relaxing property set in residential neighborhood away from the Firenze crowds. But still very close walking distance or tram stop to Duomo, Uffizzi, Academia, Ponte Vechio etc. Beautiful classic + modern decor with lovely gardens for apertivo. AC worked very well and comfortable bed - very restful stay after all the tours and walking. Breakfast is exceptional - delicious, fresh, bountiful with many selections to suit all palettes. Plus great local restaurants and shops within two blocks of property. Felt like I was in a lovely private residence with all the comfort and amenities of an upscale and welcoming home. Highly recommend to property."

Art Hotel Villa Agape

10/10 Excellent

"I would stay here again. Everything was simply incredible !"

Hotel Santa Maria Novella

10/10 Excellent

"Amazing and historical place to stay! Loved everything about it, including the amazing location, helpful stuff, and the historical building."

Hotel Albani Firenze

10/10 Excellent

"Staff were great and the bonus of a lovely breakfast buffet included was wonderful. Perfect location close to Florence Station"

Bernini Palace

10/10 Excellent

"Excellent stay; beautiful breakfast; friendly staff. Very convenient location."

Hotel Delle Nazioni

8/10 Good

"The room were spacious and the location was convenient for tours and trains. However, being on the street next to the street cars and busy train station, the noise was irritable most of the time. Otherwise everything including breakfast was good."

Grand Hotel Cavour

10/10 Excellent

"Lovely hotel and great position in Florence. Staff were friendly and helpful. Breakfast was lovely plenty of choice. Wouldn’t hesitate to stay there again. Perfect for the usual sightseeing !"

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 Castellina Fortress, Walls of Monteriggioni, or Lilliano Estate Winery. 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. Castellina Fortress, Walls of Monteriggioni, and Lilliano Estate 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.

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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