Castellina in Chianti Villas - Best Villa Castellina in Chianti 2026

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Our top choices for Castellina in Chianti villas

Villa, Air conditioning, Courtyard View | Exterior

Villa Montecastello

Monteriggioni

includes taxes & fees

29 May - 30 May

Rooster House, cooking classes and opera

Toscana

includes taxes & fees

2 Jun - 3 Jun

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

Colle Val D'Elsa

includes taxes & fees

28 May - 29 May

Villa Marcolina

Castelnuovo Berardenga

includes taxes & fees

28 May - 29 May

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

Siena

includes taxes & fees

31 May - 1 Jun

VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.

Florence

Becky F.

NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!

Oltrarno

Giuseppe F.

includes taxes & fees

14 Jun - 15 Jun

Villa Il Signorino

GREVE IN CHIANTI

Avi A.

includes taxes & fees

28 May - 29 May

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Top Castellina in Chianti Hotel Reviews

The Hoxton Florence

10/10 Excellent

"This was my favorite stay during a two week trip to Italy. The staff were extremely helpful and friendly from the moment we arrived through checkout. Though the room was small, it was comfortable and the aesthetic was nice. Breakfast at the cafe was tasty, the terrace was lovely for just relaxing or having an aperitif. I highly recommend this hotel."

Hotel Albani Firenze

10/10 Excellent

"Everything was great including the breakfast. Also lunch, dinner, snack and cocktail options. Older building so not handicap accessible for all so be aware but no negativity on property. Only think I did not like was my balcony had no good view but I was down low. Great location. I would give a 4.5."

25hours Hotel Florence Piazza San Paolino

4/10 Poor

"The check in was chaotic. Even though I had cancelled 1 room in my itinerary within the time frame that allowed free cancellation and received confirmation email from hotels.com, the staff gave us hard time about that. I had to chat with an agent , soentb30 minutes just to find out that they don’t have any proof of me canceling the room, sent the email confirmation copy yet the agent couldn’t help. I’m verifying disappointed. One front desk person was very rude, she’s the face of the hotel and should at least try to out a positive attitude. She needs to be trained more. I’m not going to stay at this hotel in the near future. "

Art Hotel Villa Agape

10/10 Excellent

"We had a junior suite facing the garden on one side where the patio is. The staff were outstanding on every level. The shuttle was a great advantage as we would park and get a ride down. Having somewhere to put bathroom items would be great. I know we should pack lighter but will never happen."

aparto Florence Manifattura

10/10 Excellent

"My mom and I stayed here two nights and it was a great experience. There is a lot of people speaking english here that were able to help us get transportation. There is a bus stop right outside the stay. It is 10-15 minutes from the city center and the FLR airport. It was a very modern stay with fun restaurants and shops near by."

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews	27
Accommodation	1915 Villas
Lowest Price	€124
Highest Price	€11,800

Frequently asked questions

How much do villas in Castellina in Chianti cost?

Villas in Castellina in Chianti range between €124 and €11,800 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 1915 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.

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Treat yourself

Be picky

Check prices for these dates

Our top choices for Castellina in Chianti villas

Villa Montecastello

Rooster House, cooking classes and opera

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

Villa Marcolina

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

VILLA in FLORENTINE HILLS. 220+ EXCELLENT REVIEWS. 100% travelers recommend.

NEW Dreaming in Pian dei Giullari Villa with private stunning swimming Pool!

Villa Il Signorino

Casa dei Renai by Rentbeat

My Exclusive Italy - Classic Suite in a Luxury Wine Estate

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

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

Villa Capanna: A Window onto Tuscany

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

Villino Serena Di Lapigio Florence: Mountain View, Private Garden

Villa Torre Among the Hills of Siena

My Exclusive Italy - Exclusive Suite with view in a Luxury Wine Estate

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

AGRITURISMO in FLORENTINE HILLS-CHIANTI. 100% Travelers Recommend.

Villa 'Cascina Gretaio' with Mountain View, Private Pool and Wi-Fi

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Top Castellina in Chianti Hotel Reviews

The Hoxton Florence

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Frequently asked questions

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