A stone building with a clock tower, steps leading up to it, and people walking around.

Search Castellina in Chianti Villa Accommodation

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Castellina in Chianti villas

A stone building with a swimming pool, wooden deck, and a tall tree.

1. 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 AU$1,559
includes taxes & fees
18 Sept - 19 Sept
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

2. 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 AU$270
includes taxes & fees
19 Sept - 20 Sept
Villa Montecastello
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

3. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is AU$215
includes taxes & fees
17 Sept - 18 Sept
Rooster House, cooking classes and opera
A stone building with a wooden door, surrounded by greenery and overlooking a valley.

4. Stunning villa with large pool in the heart of Chianti 12km from Siena

Stunning villa with large pool in the heart of Chianti 12km from Siena
Radda in Chianti
8.0 out of 10, Very good, (1 review)
"We spent a great family time at Adme’s house.The house has everything. Was very clean and well maintained . Will highly recommend."
United States
ana r.
The price is AU$1,182
includes taxes & fees
14 Oct - 15 Oct
Stunning villa with large pool in the heart of Chianti 12km from Siena
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

5. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
Siena
The price is AU$7,834
includes taxes & fees
16 Sept - 17 Sept
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

6. "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 AU$3,888
includes taxes & fees
4 Oct - 5 Oct
"Villa Erbolino" with Private Garden, Outdoor Stone Tub, and Wi-Fi
A two-story building with a stone staircase leading to a wooden door. There is a small outdoor table and a potted plant on the porch.

7. 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 AU$729
includes taxes & fees
27 Sept - 28 Sept
Villa Il Signorino
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

8. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is AU$2,953
includes taxes & fees
16 Oct - 17 Oct
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

9. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is AU$2,953
includes taxes & fees
16 Oct - 17 Oct
Villa Torre Among the Hills of Siena
A swimming pool with blue lounge chairs and umbrellas, surrounded by greenery and a view of distant hills.

10. "Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi

"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Certaldo
The price is AU$8,936
includes taxes & fees
13 Oct - 14 Oct
"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
A stone building with a tiled roof, surrounded by trees and potted plants.

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

Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (1 review)
The price is AU$1,324
includes taxes & fees
4 Oct - 5 Oct
Villino Tre Pini | Panoramic Private Pool, Nature & Privacy
A villa with a swimming pool, surrounded by lush greenery and vineyards.

12. Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests

Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Montespertoli
The price is AU$9,714
includes taxes & fees
14 Oct - 15 Oct
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
An outdoor patio with a round table, chairs, a sofa, and a potted plant.

13. Molino In Chianti - Villa with Private Pool

Molino In Chianti - Villa with Private Pool
Mercatale Val Di Pesa
The price is AU$2,244
includes taxes & fees
21 Sept - 22 Sept
Molino In Chianti - Villa with Private Pool
An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

14. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
A stone building with a large glass door, a wooden deck, and a stone wall.

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is AU$8,591
includes taxes & fees
17 Sept - 18 Sept
Villa "Arnilù" with Private Pool & Wi-Fi
A covered balcony with a brick railing, a bench, and a view of lush greenery.

16. 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 AU$943
includes taxes & fees
1 Oct - 2 Oct
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

17. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (149 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
The price is AU$532
includes taxes & fees
12 Oct - 13 Oct
Luxury Villa in the Florentine hills

18. Villa Sunset, in the heart of Chianti

Villa Sunset, in the heart of Chianti
Greve in Chianti
8.0 out of 10, Very good, (1 review)
"La casa é spaziosa ed accogliente e molto pulita in una posizione e strategica e comoda per visitare Firenze e i borghi della zona. "
Italy
elisa b.
Villa Sunset, in the heart of Chianti
An outdoor patio with a wooden table and chairs, a hanging lantern, and a view of the surrounding landscape.

19. 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 AU$1,798
includes taxes & fees
12 Oct - 13 Oct
Villa 'Agriturismo Podere Terrena' with Mountain View, Private Pool and Wi-Fi
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

20. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
The price is AU$21,076
includes taxes & fees
16 Sept - 17 Sept
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castellina in Chianti Hotel Reviews

Hotel Horto Convento

Hotel Horto Convento

10/10 Excellent
"The staff at the front desk were amazing especially M who worked in the afternoon. Only recommendation is to upgrade rooms with new mattresses."
Celinda 3-night trip
Posted 1 hour ago
Hotel Horto Convento

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
3
Accommodation
1571 Villas
Lowest Price
AU$270
Highest Price
AU$270

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Prepare to pay between AU$270 and AU$270 per night for a villa in Castellina in Chianti. No matter your budget, a perfect stay is only a few clicks away on Expedia. This price was 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?
Lock in your holiday dates and then choose from 1571 villas in Castellina in Chianti. For a family trip, a couple's getaway and everything in between, Expedia can help you find the perfect space in a few easy clicks.
What is there to do near my villa in Castellina in Chianti?
Castellina in Chianti has enough activities and experiences to keep you on the go for weeks (or months!), starting with Monteriggioni Castle. Meleto Castle, Castello di Radda Winery and Castello di Albola are other impressive attractions. If you're hanging around a while, Badia a Coltibuono and Isole e Olena Winery will add the finishing touches to your itinerary.