Castellina in Chianti Villas from SAR 770

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. Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence

Oltrarno

SAR 4,083 total

includes taxes & fees

9 Aug - 10 Aug

2. Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning

Siena

SAR 1,567 total

includes taxes & fees

1 Sep - 2 Sep

3. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

Siena

SAR 20,964 total

includes taxes & fees

15 Aug - 16 Aug

Villa, Air conditioning, Courtyard View | Exterior

4. Villa Montecastello

Monteriggioni

Alvaro

SAR 770 total

includes taxes & fees

6 Aug - 7 Aug

5. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

Vico dʼArbia

Marina O.

SAR 6,100 total

includes taxes & fees

9 Aug - 10 Aug

6. Villa Torre Among the Hills of Siena

Vico dʼArbia

SAR 7,643 total

includes taxes & fees

6 Aug - 7 Aug

7. Villa "Il Fornacino" with Pool, Garden & Wi-Fi

Rapolano Terme

Toon M.

SAR 8,465 total

includes taxes & fees

22 Aug - 23 Aug

8. Villa Marcolina

Castelnuovo Berardenga

SAR 3,502 total

includes taxes & fees

1 Sep - 2 Sep

9. Cosy apartment in villa with pool, WIFI, A/C, TV, terrace, panoramic view, close to San Gimignano

Montaione

Carole G.

SAR 711 total

includes taxes & fees

21 Aug - 22 Aug

10. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

SAR 8,387 total

includes taxes & fees

30 Aug - 31 Aug

11. The three owls of san gimignano

San Gimignano

SAR 671 total

includes taxes & fees

7 Aug - 8 Aug

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

San Gimignano

SAR 25,363 total

includes taxes & fees

31 Aug - 1 Sep

13. Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

San Vivaldo

SAR 7,202 total

includes taxes & fees

6 Aug - 7 Aug

14. Villetta Leonardo: Independence, Garden & Relaxation in Tuscany

Montaione

SAR 1,533 total

includes taxes & fees

28 Aug - 29 Aug

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

Radda in Chianti

Amber M.

SAR 6,728 total

includes taxes & fees

1 Sep - 2 Sep

16. "A Casa di Franca Villa con piscina"

Gambassi Terme

"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...

Anonymous traveler

SAR 4,105 total

includes taxes & fees

24 Aug - 25 Aug

17. 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

SAR 7,271 total

includes taxes & fees

31 Aug - 1 Sep

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

Gaiole in Chianti

"Everything about this house is exquisite and very homey. Decors are really tasteful. Outdoors spaces and the views are absolutely beautiful. Kitchen is really well appointed. There is no shortage of dish-wear, silverware and glasses. Location is very central to explore Tuscany. Our host, Lapo is very welcoming and helpful with all recommendations. He is the kind of host that you want to stay in touch and come back to see him. "

Ravin N.

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

Certaldo - Firenze

Kelly C.

SAR 2,571 total

includes taxes & fees

2 Aug - 3 Aug

20. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Montaione

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Top Castellina in Chianti Hotel Reviews

Hotel Calimala Florence

10/10 Excellent

"Everything in general was absolutely great."

Hotel Paris

10/10 Excellent

"Everything about our stay at Hotel Paris was wonderful. The staff were accommodating. The location was steps from the train station and a 5 minute walk to the Duomo. Our room was spacious and quiet. The breakfast was great with cooked eggs and bacon, with tea and coffee available all day. The shower had great water pressure, was super hot and the wifi was strong. The only complaint I had, but not my son, was the beds were very firm, which doesn’t work well for me. If ever back in Florence, I would stay again!"

Plus Florence - Hostel

10/10 Excellent

"Great hostel. Sayed with my Husband (30s) didn't feel out of place,mixture of ages. Private dbl room,separate building (same complex). Very clean. Our particular room was a weird layout, there were normal windows then some windows at floor level to crawl through to go onto a balcony. Maybe we weren't supposed to go out there?. There was no fridge in the room. Unfortunately the housekeeping ladies kept coming late afternoon to our floor, so we kept having to decline them as we like to chill before going back out in the evening. This meant our room wasnt cleaned for the duration. But if we would have agreed they would have done it. The outdoor bar and pool area are great! Nicely decorated. Music playing. Brilliant to cool off and chill. Cocktails were nice but small. We didn't eat at the restaurant but had a few drinks at the indoor bar where there is a pool table and loads of seating. The bar toilets are very clean. There is a kitchen so we used the fridge a couple of times. 15-20 nice walk to Duomo. Great location. There are a few mini supermarkets very short walk away. Definitely recommend staying here."

Frequently asked questions

How much do villas in Castellina in Chianti cost?

Villas in Castellina in Chianti range between SAR 770 and SAR 3,502 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 1556 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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Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Castellina in Chianti villas

1. Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence

2. Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning

3. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

4. Villa Montecastello

5. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

6. Villa Torre Among the Hills of Siena

7. Villa "Il Fornacino" with Pool, Garden & Wi-Fi

8. Villa Marcolina

9. Cosy apartment in villa with pool, WIFI, A/C, TV, terrace, panoramic view, close to San Gimignano

10. Villa Capanna: A Window onto Tuscany

11. The three owls of san gimignano

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

13. Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

14. Villetta Leonardo: Independence, Garden & Relaxation in Tuscany

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

16. "A Casa di Franca Villa con piscina"

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

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

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

20. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

Hotel Calimala Florence

Il Malaspina

Grand Hotel Baglioni

Hotel Delle Nazioni

Hotel Paris

25hours Hotel Florence Piazza San Paolino

Starhotels Tuscany

Plus Florence - Hostel

Bernini Palace

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. Wonderful Villa Pian dei Giullari with Pool – Elegance and Relaxation in the Heart of Florence

2. Villa 'La Casa Nel Bosco - Antiche Dimore' with Shared Pool, Wi-Fi & Air Conditioning

3. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

4. Villa Montecastello

5. Villa Capannina with Private Pool, Wi-Fi and Air Conditioning

6. Villa Torre Among the Hills of Siena

7. Villa "Il Fornacino" with Pool, Garden & Wi-Fi

8. Villa Marcolina

9. Cosy apartment in villa with pool, WIFI, A/C, TV, terrace, panoramic view, close to San Gimignano

10. Villa Capanna: A Window onto Tuscany

11. The three owls of san gimignano

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

13. Villa 'Eleonora' with Private Pool, Private Garden and Wi-Fi

14. Villetta Leonardo: Independence, Garden & Relaxation in Tuscany

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

16. "A Casa di Franca Villa con piscina"

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

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

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

20. Villetta Brunelleschi: Privacy and Comfort on Two Levels

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

Hotel Calimala Florence

Frequently asked questions