Castellina in Chianti Villas from SAR 571

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

1. The San Leonino House

Castellina in Chianti

SAR 5,783 total

includes taxes & fees

12 Sep - 13 Sep

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

Radda in Chianti

Amber M.

SAR 4,212 total

includes taxes & fees

17 Sep - 18 Sep

Villa, Air conditioning, Courtyard View | Exterior

3. Villa Montecastello

Monteriggioni

Alvaro

SAR 730 total

includes taxes & fees

13 Sep - 14 Sep

4. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

SAR 571 total

includes taxes & fees

13 Sep - 14 Sep

5. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

Siena

SAR 21,112 total

includes taxes & fees

12 Sep - 13 Sep

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

Gaiole in Chianti

Bernard K.

SAR 10,393 total

includes taxes & fees

18 Sep - 19 Sep

7. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

SAR 1,958 total

includes taxes & fees

13 Sep - 14 Sep

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

Tavarnelle Val di Pesa

SAR 3,614 total

includes taxes & fees

4 Oct - 5 Oct

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Top Castellina in Chianti Hotel Reviews

Grand Hotel Baglioni

8/10 Good

"Property was excellently located across from the main train station. Property lobby was modern with a twist of old. Plenty of shopping around and very close to the Duomo short walk. Centrally located to everything. The hotel itself is very old when you get off your floor. It's very dark rooms are old with old furniture. We had to move our room because the toilet didn't work at first then the shower wouldn't drain, but we moved to a better room on the second floor with a brighter shower tub. There are no USB outlets you have to bring a converter which most of the time did not steadily stay in the plug. There must've been hundreds of rooms. They definitely need updating staff was great. The rooftop was a big draw, although Monday through Friday, there is construction, so you can't really go on the rooftop unless you wanna hear drilling. My son had his welcoming party there on a Saturday thank God. Also breakfast was great. No Pool, or gym . Which my husband was pretty upset about, but you can get a day pass at a local gym, but honestly with all the walking we did I really didn't think he needed it. Overall, for the money, I would say the best thing about this hotel was the location other than that next time I think I would prefer a more modern hotel."

Villa Neroli

10/10 Excellent

"This is overall a great property in every respect. Highly recommended. The only advice to other visitors is to plan for their lunch and dinner if they want more variety. The hotel restaurant is great and we dined there several times. But there are not many other good choices within walking distance from the hotel."

Frequently asked questions

How much do villas in Castellina in Chianti cost?

Villas in Castellina in Chianti range between SAR 571 and SAR 56,927 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 1851 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.

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Treat yourself

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Check prices for these dates

Our top choices for Castellina in Chianti villas

1. The San Leonino House

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

3. Villa Montecastello

4. Rooster House, cooking classes and opera

5. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

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

7. Villa Il Signorino

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

9. Villa Capanna: A Window onto Tuscany

10. Villa Torre Among the Hills of Siena

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

12. Villa Bellavista - Homelike Villas

13. Molino In Chianti - Villa with Private Pool

14. Luxury Villa in the Florentine hills

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

16. Villa Sunset, in the heart of Chianti

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

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

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

20. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

Grand Hotel Baglioni

Bernini Palace

Hotel Horto Convento

IQ Hotel Firenze

Villa Neroli

Grand Hotel Cavour

Hotel Paris

c-hotels Ambasciatori

The Social Hub Florence Lavagnini

Frequently asked questions

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. The San Leonino House

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

3. Villa Montecastello

4. Rooster House, cooking classes and opera

5. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

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

7. Villa Il Signorino

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

9. Villa Capanna: A Window onto Tuscany

10. Villa Torre Among the Hills of Siena

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

12. Villa Bellavista - Homelike Villas

13. Molino In Chianti - Villa with Private Pool

14. Luxury Villa in the Florentine hills

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

16. Villa Sunset, in the heart of Chianti

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

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

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

20. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

Grand Hotel Baglioni

Frequently asked questions