Best Villas in Castellina in Chianti 2026

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

Change your mind
Book hotels with free cancellation
Treat yourself
Save instantly and earn perks with One Key
Learn about One Key
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

includes taxes & fees

1 Oct - 2 Oct

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

2. Villa Montecastello

Monteriggioni

Alvaro

includes taxes & fees

4 Oct - 5 Oct

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.

additional charges may apply

4 Oct - 5 Oct

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.

additional charges may apply

6 Oct - 7 Oct

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.

includes taxes & fees

1 Oct - 2 Oct

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

includes taxes & fees

22 Oct - 23 Oct

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.

includes taxes & fees

30 Sept - 1 Oct

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

includes taxes & fees

15 Oct - 16 Oct

View all properties

Find holiday rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Top Castellina in Chianti Hotel Reviews

c-hotels Ambasciatori

10/10 Excellent

"Great location."

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."

The Social Hub Florence Lavagnini

8/10 Good

"The property is definitely a unique property I didn’t realize prior to booking that it caters to student accommodation which is fine I believe students from USC were checking in same time as the Stanford students were leaving I enjoyed the property my only reason for giving 4 out of five stars was my room was like a dorm room very small bed was not comfortable. But I really liked the property the staff were all helpful and professional."

Hotel Horto Convento

10/10 Excellent

"Absolutely amazing hotel. Beautiful grounds and building in a nice, quiet part of the neighborhood, but still so walkable and close to churches, museums, restaurants, etc. Cherish at check-in gave us some great recommendations for food nearby. Had some of the best baked goods I've ever had at breakfast each morning, and had the most beautiful and delicious cocktails and spritz from the bar in the evening. If we come back to the city, we'd 100% want to stay here again."

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews	177
Accommodation	1785 Villas
Lowest Price	£115
Highest Price	£11,177

Frequently asked questions

How much do villas in Castellina in Chianti cost?

Villas in Castellina in Chianti range between £115 and £11,177 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 1785 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.

Explore a world of travel with Expedia

More ways to book

Book Villas in Castellina in Chianti on Expedia.it

Search Villas in Castellina in Chianti

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 holiday rentals that suit your style

Top Castellina in Chianti Hotel Reviews

c-hotels Ambasciatori

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Frequently asked questions

Explore a world of travel with Expedia