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Check prices for these dates

In two weeks
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 Dec

Our top choices for Castellina in Chianti villas

Exterior

1. The San Leonino House

The San Leonino House
Castellina in Chianti
The price is £1,130
includes taxes & fees
23 Aug - 24 Aug
The San Leonino House
Exterior

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

Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Gambassi Terme
The price is £3,480
includes taxes & fees
14 Sept - 15 Sept
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Exterior

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

Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence
Oltrarno
The price is £737
includes taxes & fees
23 Aug - 24 Aug
Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence
Property grounds

4. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Toscana
The price is £115
includes taxes & fees
17 Aug - 18 Aug
Rooster House, cooking classes and opera
Villa, Air conditioning, Courtyard View | Exterior

5. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is £158
includes taxes & fees
25 Aug - 26 Aug
Villa Montecastello
Pool

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

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is £1,236
additional charges may apply
1 Sept - 2 Sept
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Property grounds

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

"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Best view in TuscanyIt was all new on the inside and very rustic exterior Beautiful villa!!!Great Host "
United States
Bernard K.
The price is £1,173
additional charges may apply
25 Aug - 26 Aug
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
Property grounds

8. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Siena
The price is £4,136
includes taxes & fees
15 Aug - 16 Aug
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30
Exterior

9. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is £415
includes taxes & fees
11 Sept - 12 Sept
Villa Il Signorino
Exterior

10. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is £1,654
includes taxes & fees
30 Aug - 31 Aug
Villa Torre Among the Hills of Siena
Outdoor dining

11. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is £1,654
includes taxes & fees
21 Aug - 22 Aug
Villa Capanna: A Window onto Tuscany
Property grounds

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

Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is £778
includes taxes & fees
27 Aug - 28 Aug
Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Outdoor dining

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

Villa Mami: A Tuscan Retreat of Elegance and Charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is £3,801
includes taxes & fees
9 Sept - 10 Sept
Villa Mami: A Tuscan Retreat of Elegance and Charm
Exterior

14. GuestHost - Porta Romana Elegant House with Private Parking!

GuestHost - Porta Romana Elegant House with Private Parking!
Siena
9.0 out of 10, Wonderful, (4 reviews)
"Excellent location 15 mi minute walk to the center of town. Towels and linens were fresh and fragrant. On site parking was super convenient because of limited parking around the town. The property manager was immediately available by phone and delivered an extra blanket which in 5 minutes of our request."
United States
Kathleen M.
GuestHost - Porta Romana Elegant House with Private Parking!
Exterior

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is £4,535
includes taxes & fees
16 Aug - 17 Aug
Villa "Arnilù" with Private Pool & Wi-Fi
Outdoor dining

16. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (149 reviews)
"Lovely property, nicely appointed, would be happy to stay there again."
United States
David K.
The price is £343
includes taxes & fees
3 Sept - 4 Sept
Luxury Villa in the Florentine hills
Exterior

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

Nice apartment in villa with pool, WIFI, A/C, TV, terrace and panoramic view, close to San Gimig...
Montaione
10.0 out of 10, Exceptional, (5 reviews)
"We spend a great time, marvellous place and people"
United States
Carole G.
The price is £140
includes taxes & fees
28 Aug - 29 Aug
Nice apartment in villa with pool, WIFI, A/C, TV, terrace and panoramic view, close to San Gimig...
Terrace/patio

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

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Certaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
United States
Kelly C.
The price is £507
includes taxes & fees
17 Aug - 18 Aug
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Outdoor dining

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

Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Mercatale Val Di Pesa
The price is £1,185
includes taxes & fees
23 Aug - 24 Aug
Villa 'Molino' with Private Pool, Private Terrace and Wi-Fi
Outdoor dining

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

Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
Gaiole in Chianti
8.0 out of 10, Very good, (1 review)
"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!"
Italy
Anonymous traveller
The price is £1,070
includes taxes & fees
30 Aug - 31 Aug
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
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.
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Top Castellina in Chianti Hotel Reviews

25hours Hotel Florence Piazza San Paolino

25hours Hotel Florence Piazza San Paolino

10/10 Excellent
"Great stay again - love the sauna"
Dave 2-night trip
Posted 5 hours ago
25hours Hotel Florence Piazza San Paolino

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
177
Accommodation
1806 Villas
Lowest Price
£115
Highest Price
£4,535

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between £115 and £4,535 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 1806 villas in Castellina in Chianti. No matter if you're travelling 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.