Castellina in Chianti Villas from CA $212

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

CA $2,127 total

includes taxes & fees

Sep 2 - Sep 3

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

Gambassi Terme

CA $6,573 total

includes taxes & fees

Sep 14 - Sep 15

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

Oltrarno

CA $1,393 total

includes taxes & fees

Aug 30 - Aug 31

4. Villa Liberty in The Centre - No Ztl

Siena Historical Center

CA $1,045 total

includes taxes & fees

Sep 20 - Sep 21

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

Radda in Chianti

Amber M.

CA $1,643 total

includes taxes & fees

Sep 17 - Sep 18

Villa, Air conditioning, Courtyard View | Exterior

6. Villa Montecastello

Monteriggioni

Alvaro

CA $292 total

includes taxes & fees

Sep 19 - Sep 20

7. Rooster House, cooking classes and opera

Toscana

CA $212 total

includes taxes & fees

Aug 27 - Aug 28

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

Siena

CA $7,819 total

includes taxes & fees

Aug 26 - Aug 27

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

Gaiole in Chianti

Bernard K.

CA $2,469 total

includes taxes & fees

Sep 11 - Sep 12

10. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

CA $730 total

includes taxes & fees

Sep 7 - Sep 8

11. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

CA $2,850 total

includes taxes & fees

Aug 30 - Aug 31

12. Villa Torre Among the Hills of Siena

Vico dʼArbia

CA $2,850 total

includes taxes & fees

Aug 30 - Aug 31

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

San Gimignano

CA $8,533 total

includes taxes & fees

Sep 7 - Sep 8

14. Villa Bellavista - Homelike Villas

Montegonzi

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

Certaldo - Firenze

Kelly C.

CA $959 total

includes taxes & fees

Aug 26 - Aug 27

16. Lovely apartment in villa with WIFI, A/C, pool, TV, terrace, panoramic view, close to San Gimignano

Montaione

Carole G.

CA $265 total

includes taxes & fees

Aug 28 - Aug 29

17. Luxury Villa in the Florentine hills

Florence

Dawn L.

CA $538 total

includes taxes & fees

Aug 29 - Aug 30

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

Impruneta

Maria H.

CA $563 total

includes taxes & fees

Aug 29 - Aug 30

19. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

Firenze

CA $21,034 total

includes taxes & fees

Aug 29 - Aug 30

20. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

Gaiole in Chianti

"Pros: La casa è sita in una posizione super tranquilla in mezzo al verde e alla natura. Tutto è curato alla perfezione. Nota di merito per il verde e i fiori e per la gentilezza dei proprietari. Cons: La posizione che è un pregio per qualcuno per altri potrebbe non esserlo. In effetti per arrivare al podere ci sono 2 km di strada bianca molto stretta. Una volta arrivati si è però ripagati ampiamente del piccolo disagio!"

Anonymous traveller

CA $1,851 total

includes taxes & fees

Aug 30 - Aug 31

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Top Castellina in Chianti Hotel Reviews

The Social Hub Florence Lavagnini

10/10 Excellent

"Great hotel with helpful amenities: gym, laundry, restaurants plus the tram was just outside so it made getting to the airport extremely easy!"

25hours Hotel Florence Piazza San Paolino

8/10 Good

"Well I loved the theme and the decor of the hotel. I was shocked the pool is locked for hotel guests and a fee to use it with a reservation? Hotel guests should have priority over a day pass and it should be the opposite way around that outside guests need the reservation. It made a normal hotel stay where you randomly may go sit by the pool not a possibility, which was very unfortunate. Also be sure to ask how many people are in the communal reservation for dinner, because I would not have paid 70 euro just to awkwardly sit with one other couple."

Hotel Delle Nazioni

10/10 Excellent

"Breakfast was wonderful. The staff were very helpful and gave excellent instructions about the area and the hotel. The air conditioning worked great and everything in our room was clean and well cared for. We had 2 twins beds side by side that were comfortable and gave the room a lot of space. Location was a plus plus - just under 5 minutes easy walk from the Florence train station (only minus was to exit the train station there were about 20 steps."

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews	176
Accommodation	1829 Villas
Lowest Price	CA $212
Highest Price	CA $21,034

Frequently asked questions

How much do villas in Castellina in Chianti cost?

Villas in Castellina in Chianti range between CA $212 and CA $21,034 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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Search Castellina in Chianti Villa Rentals from CA $212

Change your mind

Treat yourself

Be picky

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. Villa Liberty in The Centre - No Ztl

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

6. Villa Montecastello

7. Rooster House, cooking classes and opera

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

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

10. Villa Il Signorino

11. Villa Capanna: A Window onto Tuscany

12. Villa Torre Among the Hills of Siena

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

14. Villa Bellavista - Homelike Villas

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

16. Lovely apartment in villa with WIFI, A/C, pool, TV, terrace, panoramic view, close to San Gimignano

17. Luxury Villa in the Florentine hills

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

19. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

20. Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi

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