Castellina in Chianti Villas ￥23,367

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

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

1. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

￥23,367 total

includes taxes & fees

Oct 3 - Oct 4

A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

2. Villa Montecastello

Monteriggioni

Alvaro

￥29,778 total

includes taxes & fees

Oct 4 - Oct 5

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

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

Radda in Chianti

Amber M.

￥285,900 total

includes taxes & fees

Nov 1 - Nov 2

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

Gaiole in Chianti

Bernard K.

￥124,681 total

includes taxes & fees

Oct 3 - Oct 4

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

GREVE IN CHIANTI

Avi A.

￥80,267 total

includes taxes & fees

Oct 2 - Oct 3

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

Certaldo

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

Siena

Ron M.

￥1,251,021 total

includes taxes & fees

Oct 2 - Oct 3

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

Montespertoli

￥1,070,937 total

includes taxes & fees

Oct 14 - Oct 15

A stone building with a large glass door, a wooden deck, and a stone wall.

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

San Gimignano

￥947,129 total

includes taxes & fees

Oct 5 - Oct 6

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

Vico dʼArbia

￥305,548 total

includes taxes & fees

Oct 28 - Oct 29

A rustic stone building with a tower, covered walkways, and a grassy courtyard.

11. Villa Torre Among the Hills of Siena

Vico dʼArbia

￥305,548 total

includes taxes & fees

Oct 17 - Oct 18

An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

12. Villa Bellavista - Homelike Villas

Montegonzi

A brick building with a gravel courtyard, a staircase, and potted plants.

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

Siena

Kathleen M.

￥54,745 total

includes taxes & fees

Oct 5 - Oct 6

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

Toscana

￥487,487 total

includes taxes & fees

Oct 18 - Oct 19

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

Certaldo - Firenze

Kelly C.

￥103,979 total

includes taxes & fees

Oct 3 - Oct 4

An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

16. Luxury Villa in the Florentine hills

Florence

melissa r.

￥59,219 total

includes taxes & fees

Nov 1 - Nov 2

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~

Impruneta

Maria H.

￥66,924 total

includes taxes & fees

Oct 13 - Oct 14

An outdoor patio with a round table, chairs, a sofa, and a potted plant.

18. Molino In Chianti - Villa with Private Pool

Mercatale Val Di Pesa

￥247,387 total

includes taxes & fees

Oct 3 - Oct 4

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

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 traveler

￥204,448 total

includes taxes & fees

Oct 6 - Oct 7

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

Firenze

￥2,323,671 total

includes taxes & fees

Oct 8 - Oct 9

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Top Castellina in Chianti Hotel Reviews

Hu Firenze Camping In Town

10/10 Excellent

"Très bien situe juste en face d’un arrêt de bus, qu’on à pu prendre pour se rendre dans le centre. Au retour des visites on à profite de l’une des 3 piscines. En plus il y à 2 resto sur le site et une épicerie. Tout était parfait."

Art Hotel Villa Agape

8/10 Good

"Beautiful property. The restaurant and breakfast are great. Rooms are cozy and quaint. To consider there shuttle is only to get you to the bridge and walk or cab from there to wherever you’re going. It’s the distance from places such as stores restaurants be prepared for any extra needs of expenses such as bottled water or snacks. Make sure the wine card you prepay for self serve you return for credit it’s $10 a glass and it’s about three sips. But beautiful place and great for quiet and privacy."

Radisson Blu Hotel, Florence

8/10 Good

"Everything was great, staff were helpful. A couple comments I do have are: One of the staff let themselves into our room in the morning while I was still sleeping then saw me and said “sorry” and turned around and walked out. Weird. Also the room had a lot of thick cob webs and didn’t seem that they dust the room. Other than that, it was a very nice room and clean comfortable beds. Handicap accessible room needs some type of shower curtain to contain the water or the whole bathroom becomes a shower and it doesn’t dry which can be very slippery and everything is wet in there. The rest of the hotel was very nice and updated."

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews	177
Accommodation	1830 Villas
Lowest Price	￥23,367
Highest Price	￥2,323,671

Frequently asked questions

How much do villas in Castellina in Chianti cost?

Villas in Castellina in Chianti range between ￥23,367 and ￥2,323,671 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 1830 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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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Castellina in Chianti villas

1. Rooster House, cooking classes and opera

2. Villa Montecastello

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

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

5. Villa Il Signorino

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

7. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

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

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

10. Villa Capanna: A Window onto Tuscany

11. Villa Torre Among the Hills of Siena

12. Villa Bellavista - Homelike Villas

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

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

18. Molino In Chianti - Villa with Private Pool

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

20. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

Hu Firenze Camping In Town

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Frequently asked questions

Explore a world of travel with Expedia