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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Castellina in Chianti villas

A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

1. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is NZ$263
includes taxes & fees
1 Oct - 2 Oct
Rooster House, cooking classes and opera
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 NZ$332
includes taxes & fees
4 Oct - 5 Oct
Villa Montecastello
A stone building with a swimming pool, wooden deck, and a tall tree.

3. 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 NZ$3,608
includes taxes & fees
6 Oct - 7 Oct
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

4. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub 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 NZ$2,938
includes taxes & fees
6 Oct - 7 Oct
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub 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.

5. 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 NZ$905
includes taxes & fees
30 Sept - 1 Oct
Villa Il Signorino
A swimming pool with blue lounge chairs and umbrellas, surrounded by greenery and a view of distant hills.

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

"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
Certaldo
The price is NZ$11,084
includes taxes & fees
12 Oct - 13 Oct
"Villa Bellavista" with Private Pool, Private Whirlpool & Wi-Fi
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

7. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
Siena
10.0 out of 10, Exceptional, (1 review)
"We celebrated our 20th Anniversary with 23 guests, all who stayed at the Property. The location and accommodations could not have been better and the staff and property manager were excellent. I would highly recommend staying here for any Tuscany adventures! Thank you so much to the owner and all involved!Ron and Wendy"
United States
Ron M.
The price is NZ$14,075
includes taxes & fees
3 Oct - 4 Oct
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
A villa with a swimming pool, surrounded by lush greenery and vineyards.

8. 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 NZ$12,049
includes taxes & fees
14 Oct - 15 Oct
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A stone building with a large glass door, a wooden deck, and a stone wall.

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is NZ$10,680
includes taxes & fees
30 Sept - 1 Oct
Villa "Arnilù" with Private Pool & Wi-Fi
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

10. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is NZ$3,438
includes taxes & fees
17 Oct - 18 Oct
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

11. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is NZ$3,438
includes taxes & fees
17 Oct - 18 Oct
Villa Torre Among the Hills of Siena
An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

12. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
A brick building with a gravel courtyard, a staircase, and potted plants.

13. 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.
The price is NZ$616
includes taxes & fees
5 Oct - 6 Oct
GuestHost - Porta Romana Elegant House with Private Parking!
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

14. 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 NZ$5,302
includes taxes & fees
18 Oct - 19 Oct
Villa Mami: A Tuscan Retreat of Elegance and Charm
A covered balcony with a brick railing, a bench, and a view of lush greenery.

15. 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 NZ$1,170
includes taxes & fees
3 Oct - 4 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.

16. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (150 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 NZ$746
includes taxes & fees
12 Oct - 13 Oct
Luxury Villa in the Florentine hills
An open wooden door leading to a balcony with a round table and two chairs, overlooking a garden with trees and flowers.

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

Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
Impruneta
10.0 out of 10, Exceptional, (3 reviews)
"Super quaint, beatiful, designed, comfortable, not lacking anything house and location. Very informative and accessable host. Listen to the instructions on how to go to Firenze. No need to take your car tyere!"
United States
Maria H.
The price is NZ$767
includes taxes & fees
30 Sept - 1 Oct
Firenze‼️~Integer VILLA in hillside 7 places & 4 bathrooms~
An outdoor patio with a round table, chairs, a sofa, and a potted plant.

18. Molino In Chianti - Villa with Private Pool

Molino In Chianti - Villa with Private Pool
Mercatale Val Di Pesa
The price is NZ$2,790
includes taxes & fees
2 Oct - 3 Oct
Molino In Chianti - Villa with Private Pool
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 NZ$2,300
includes taxes & fees
6 Oct - 7 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 NZ$26,201
includes taxes & fees
28 Oct - 29 Oct
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.
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Top Castellina in Chianti Hotel Reviews

c-hotels Ambasciatori

c-hotels Ambasciatori

10/10 Excellent
"Great location."
Wendy 1-night trip
Posted 1 hour ago
c-hotels Ambasciatori

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
177
Accommodation
1547 Villas
Lowest Price
NZ$263
Highest Price
NZ$26,201

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between NZ$263 and NZ$26,201 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 1547 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.
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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