Castellina in Chianti Villas Rentals

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

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

Radda in Chianti

Amber M.

$1,108 nightly

Sep 23 - Sep 24

Total with taxes and fees

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

2. Villa Montecastello

Monteriggioni

Alvaro

$172 nightly

Sep 25 - Sep 26

Total with taxes and fees

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

3. Rooster House, cooking classes and opera

Tavarnelle Val di Pesa

$148 nightly

Sep 20 - Sep 21

Total with taxes and fees

A stone building with a wooden door, surrounded by greenery and overlooking a valley.

4. Stunning villa with large pool in the heart of Chianti 12km from Siena

Radda in Chianti

ana r.

$940 nightly

Oct 16 - Oct 17

Total with taxes and fees

A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

5. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

Siena

$8,093 nightly

Sep 17 - Sep 18

Total with taxes and fees

A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

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

Gaiole in Chianti

Bernard K.

$2,768 nightly

Oct 5 - Oct 6

Total with taxes and fees

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.

7. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

$515 nightly

Sep 17 - Sep 18

Total with taxes and fees

A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

8. Villa Capanna: A Window onto Tuscany

Vico dʼArbia

$1,972 nightly

Oct 17 - Oct 18

Total with taxes and fees

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Top Castellina in Chianti Hotel Reviews

The Social Hub Florence Lavagnini

10/10 Excellent

"It’s totally walkable to center of Fl"

Art Hotel Villa Agape

8/10 Good

"The room, breakfast and front counter staff were excellent. Overall was a nice experience. there was a wedding in the courtyard patio area during our stay on the first night and we couldn’t enjoy certain areas of the property. We would have liked to have been made aware of that. Instead of stumbling into their party and told it was private. Both men and the lady at the desk were extremely helpful and kind. As well as the morning breakfast lady."

Palazzo Montebello

8/10 Good

"Lovely hotel, spotlessly clean and we liked that the location was 15 mins walk away from the super busy chaos of the main tourist areas. Lots of amenities within short walk away and the walk along the river to the centre of Florence was lovely. Front desk staff were very helpful and offered great recommendations for places to eat and visit. The only downsides for us were: 1. the breakfast options which were very basic for how expensive the hotel is per night, the cooked breakfasts were not good so we had to eat elsewhere for a few days. 2. Our room was great but very much let down by the fact there was a huge window which had no cover or curtains to close which let in a lot of light as there happened to be a lamp right outside of it which shined directly in to the room. It meant our room was lit up like Times Square even in the middle of the night and we ended up having to wedge a towel over the window to try and reduce this. The window was also immediately opposite our bathroom so anyone outside could see straight in to it if they wanted to. Not sure if this is relevant for other rooms but it was very annoying for us and seems like it could be an easy fix! Overall we had a really great time and would stay again!"

Villa Neroli

10/10 Excellent

"My cousin and I were on a month trip with many stops in 4 countries. Florence was our 2nd last stop. Villa Nerolli was my favorite overall stay. It was so very relaxing with the scents of roses, bamboo, jasmine and wisteria everywhere. Simply beautiful and a symphony for all the senses. The food, service, pool, and drinks were fabulous 💖 I hope to make it back one day 🙏"

Plus Florence - Hostel

8/10 Good

"This was a GREAT stay. The hotel is very complete, with lots of amenities, and everything was very clean and well maintained. We had a really good experience and would definitely stay here again. My only downside was that the bed was quite hard for my preference, but other than that, everything was great!"

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews	3
Accommodation	1829 Villas
Lowest Price	$193
Highest Price	$193

Frequently asked questions

How much do villas in Castellina in Chianti cost?

Villas in Castellina in Chianti range between $193 and $193 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 1829 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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Villas in Castellina in Chianti

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Upfront pricing

Check prices for these dates

Our top choices for Castellina in Chianti villas

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

2. Villa Montecastello

3. Rooster House, cooking classes and opera

4. Stunning villa with large pool in the heart of Chianti 12km from Siena

5. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

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

7. Villa Il Signorino

8. Villa Capanna: A Window onto Tuscany

9. Villa Torre Among the Hills of Siena

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

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

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

13. Molino In Chianti - Villa with Private Pool

14. Villa Bellavista - Homelike Villas

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

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

17. Luxury Villa in the Florentine hills

18. Villa Sunset, in the heart of Chianti

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

The Social Hub Florence Lavagnini

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Frequently asked questions

Explore a world of travel with Expedia