Castellina in Chianti Villas Rentals

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 villas

1. The San Leonino House

Castellina in Chianti

$1,255 nightly

Aug 24 - Aug 25

Total with taxes and fees

2. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

Gambassi Terme

$4,707 nightly

Sep 15 - Sep 16

Total with taxes and fees

3. Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence

Oltrarno

$984 nightly

Aug 23 - Aug 24

Total with taxes and fees

4. Rooster House, cooking classes and opera

Toscana

$148 nightly

Aug 20 - Aug 21

Total with taxes and fees

Villa, Air conditioning, Courtyard View | Exterior

5. Villa Montecastello

Monteriggioni

Alvaro

$192 nightly

Aug 29 - Aug 30

Total with taxes and fees

6. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

Radda in Chianti

Amber M.

$1,173 nightly

Sep 17 - Sep 18

Total with taxes and fees

7. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

Siena

$5,603 nightly

Aug 20 - Aug 21

Total with taxes and fees

8. "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

Gaiole in Chianti

Bernard K.

$1,585 nightly

Aug 22 - Aug 23

Total with taxes and fees

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Top Castellina in Chianti Hotel Reviews

The Social Hub Florence Lavagnini

10/10 Excellent

"Lovely stay. Will visit again."

Bernini Palace

10/10 Excellent

"The entire stay was perfect, from start to finish. This hotel is to the image of Florence: beautiful and steeped in history. All staff were professional, competent and very pleasant. Our room was comfortable and the all-linen sheets? Dreamy. The breakfast was delicious and suited all tastes. We could not have asked for a better location to explore all that Florence has to offer."

The Hoxton, Florence

8/10 Good

"I loved the hotel decor! And the hotel staff were great! Check-in/check-out was a breeze. Super helpful and knowlegeable staff. The room was a bit small but cozy, clean and a very comfy bed. There is minimal area to store/hang clothing. There was a mini safe in the room. The bar fridge included water and cream for coffee/tea which was provided at no additioal charge. The patio area is quite lovely with a variety of sitting areas, umbrellas and misters. The restaurant staff was great but the food is very pricey and not fabulous. This hotel is located within walking distance to restaurants, shops, farmacias. It was about a $15 EU cab fare from the Florence Santa Maria Novella train station to the hotel."

Radisson Blu Hotel, Florence

10/10 Excellent

"We weren’t sure whether to book our 2 night stay based on other reviews, but we are so glad that we did. We arrived by car and there was ample free parking on site. A car park in Florence was recommended by the lobby staff that was a 15 minute drive and had lots of spaces and not insanely priced, the centre was then a 10 minute walk from there. The hotel was spotless, easy check in, big room. Pool was great, the kids loved the splash area and there was even a FREE arcade room in the basement! The kids loved it. Breakfast was a god buffet with plenty for me as vegetarian and gluten free bread etc for my wife. Plenty of fruit and pastries for the kids! The beds were large and comfortable, air con great. Room has a fridge and some free waters which was a nice touch along with a coffee machine. A really good stay, well priced and I wouldn’t hesitate to stay here again if coming to Florence. There is a shuttle bus that you can book a seat on too, but we didn’t use this as had the car. Great hotel"

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews	176
Accommodation	1829 Villas
Lowest Price	$152
Highest Price	$15,073

Frequently asked questions

How much do villas in Castellina in Chianti cost?

Villas in Castellina in Chianti range between $152 and $15,073 per night. These stays offer the privacy of your own space at a price that doesn't break the bank. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many villas are there in Castellina in Chianti?

You can choose from 1829 villas in Castellina in Chianti. No matter if you're traveling with the family or planning a getaway with your buddies, Expedia will help you find the ideal base for your squad.

Why book your villa in Castellina in Chianti with Expedia?

Reserving a villa in Castellina in Chianti is as simple as deciding on your travel dates and picking the option suited to your needs. In search of something affordable or luxurious, or a property that also has a kitchen and laundry? Use Expedia's search filters to narrow your results and find the perfect pad.

How can I find cheap villas in Castellina in Chianti?

The easiest way to compare cheap villas in Castellina in Chianti is with Expedia's convenient filter tool. Narrow your search by amenities, budget and star rating to nab awesome rates in only a few clicks.

What is there to do near my villa in Castellina in Chianti?

Whatever your interests, Castellina in Chianti has loads to keep you on the hop. Buondonno Winery, City Hall Castellina In Chianti and Casa Vinicola Luigi Cecchi are on most visitors' itineraries. Don't forget to explore Walls of Monteriggioni, Castellina Fortress and Archaeological Museum of Chianti either. With Expedia's Castellina in Chianti hotel deals, you can discover even more terrific attractions like these with the cash you save.

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Radda in Chianti Vacation Rentals

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Villas in Castellina in Chianti

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Upfront pricing

Check prices for these dates

Our top choices for Castellina in Chianti villas

1. The San Leonino House

2. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

3. Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence

4. Rooster House, cooking classes and opera

5. Villa Montecastello

6. Villa 'La Petrosa' with Private Pool, Private Garden and Balcony

7. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

8. "Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi

9. Villa Il Signorino

10. Villino Tre Pini | Panoramic Private Pool, Nature & Privacy

11. Villa Torre Among the Hills of Siena

12. Villa "Arnilù" with Private Pool & Wi-Fi

13. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

14. Villa Mami: A Tuscan Retreat of Elegance and Charm

15. Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany

16. Luxury Villa in the Florentine hills

17. Nice apartment in villa with A/C, WIFI, pool, TV, terrace and panoramic view, close to San Gimig...

18. Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi

19. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

20. Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

The Social Hub Florence Lavagnini

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Frequently asked questions

Explore a world of travel with Expedia