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. UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK
Ruffoli
9.2 out of 10, Wonderful, (28 reviews)
"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...
Canada
James
The price is ¥14,190
¥27,897 total
includes taxes & fees
Oct 27 - Oct 28
UNIQUE LARGE TERRACE WITH VIEWS TO CHAINTI VALLEY AND DRINK

2. CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS
Ruffoli
9.2 out of 10, Wonderful, (31 reviews)
"Such a lovely property with a view that never quits. The pool is so refreshing and did I mention the view? Great place for a small group with the ability to expand to additional rooms on the property with notice. We will definitely be going back!"
United States
Caleb M.
The price is ¥22,141
¥46,743 total
includes taxes & fees
Oct 27 - Oct 28
CHIANTI VINEYARDS OLIVE GROVES FOOD TASTINGS SCENIC VIEWS

3. Old medieval apartment

Old medieval apartment
Tavarnelle Val di Pesa
9.8 out of 10, Exceptional, (9 reviews)
"Very welcoming host, lovely stone wall in the apartment and the beautiful bathroom."
United States
Kathleen F.
The price is ¥18,188
¥22,054 total
includes taxes & fees
Oct 28 - Oct 29
Old medieval apartment

4. APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM

APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM
Monteriggioni
9.8 out of 10, Exceptional, (10 reviews)
"Tutto perfetto: accoglienza, pulizia, bellezza. Proprietari gentilissimi. Un luogo che resta nel cuore. Ci ritorneremo.."
Italy
giuseppe z.
The price is ¥28,309
¥42,191 total
includes taxes & fees
Nov 1 - Nov 2
APARTMENT OF CHARME WITH POOL IN CHIANTI-SHIRE-FLORENCE 40 KM-SIENA 20 KM

5. Farmhouse in Chianti

Farmhouse in Chianti
gaiole in chianti
9.8 out of 10, Exceptional, (6 reviews)
"We absolutely loved the pool and the view. The pool with a deep end and color changing light was our highlight. The hosts were very friendly, helpful and always available if needed, since they live upstairs in the same house. Still, they never complained about us being loud. Everything was perfectly clean, the pool was cleaned regularly during our stay. The road to the property might be rough, but the view is beautiful. Also, we were gifted some delicious wine."
Germany
Johanna K.
The price is ¥71,169
¥87,248 total
includes taxes & fees
Oct 30 - Oct 31
Farmhouse in Chianti

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

San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service
San Gimignano City Centre
9.8 out of 10, Exceptional, (43 reviews)
"Authentic 13th century building with so much character and charm. The room was very unique and opened to a lovely courtyard. The location was great, and very close to the gate. A full Italian breakfast buffet was offered at a reasonable cost. Laundry service was also available. And the hosts were very friendly and helpful."
United States
Marilyn H.
The price is ¥18,029
¥27,519 total
includes taxes & fees
Oct 30 - Oct 31
San Gimignano Apartment in the Heart of Town for 4 People with Fast Wi-Fi and Concierge Service

7. San Gimignano Apartment in the Heart of the City for 3 People: Fast Wi-Fi, Concierge Service

San Gimignano Apartment in the Heart of the City for 3 People: Fast Wi-Fi, Concierge Service
San Gimignano City Centre
9.8 out of 10, Exceptional, (12 reviews)
"Our cosy little part of the palazzo was wonderful and our host sent us to an amazing array of restaurants. We had a wonderful time."
United States
Daniel T.
The price is ¥23,565
¥37,975 total
includes taxes & fees
Oct 27 - Oct 28
San Gimignano Apartment in the Heart of the City for 3 People: Fast Wi-Fi, Concierge Service

8. LA COSTARELLA- central with cozy terrace

LA COSTARELLA- central with cozy terrace
Siena City Centre
8.8 out of 10, Excellent, (5 reviews)
"Great location and great views. But be aware the AC isn’t in the bedroom, just upstairs in the living area. Also, the shower would not drain. So we had to take super fast showers as to not flood the bathroom, which was less than ideal. My husband waited about half an hour after mine and it had mostly drained. But after his shower, it didn’t drain overnight into the next morning when we left. Hopefully it gets fixed!"
United States
Megan D.
The price is ¥15,975
¥25,304 total
includes taxes & fees
Oct 28 - Oct 29
LA COSTARELLA- central with cozy terrace

9. IL NIDO DEL MANGIA - Unico in Piazza del Campo

IL NIDO DEL MANGIA - Unico in Piazza del Campo
Siena City Centre
9.6 out of 10, Exceptional, (14 reviews)
"Comfy bed, great location!"
United States
Benjamin C.
The price is ¥15,975
¥27,062 total
includes taxes & fees
Oct 28 - Oct 29
IL NIDO DEL MANGIA - Unico in Piazza del Campo

10. BANDINI 35 - centrally located with an elevator and air conditioning

BANDINI 35 - centrally located with an elevator and air conditioning
Siena City Centre
9.2 out of 10, Wonderful, (9 reviews)
"We loved our stay here. Located on a quiet street but close to Piazza del Campo."
United States
Nancy H.
The price is ¥15,975
¥30,576 total
includes taxes & fees
Oct 27 - Oct 28
BANDINI 35 - centrally located with an elevator and air conditioning
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

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, Archaeological Museum of Chianti, 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. Castellina Fortress, Archaeological Museum of Chianti, 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.