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Featured Villas in Castellina in Chianti and around

Our top choices for Castellina in Chianti villas

San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

10.0 out of 10, Exceptional, (98)
"The location and views were absolutely spectacular! Alessandro was EXTREMELY helpful and accommodating. He helped arrange for chef and wine tasting at the villa and they were memorable. "
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view

A Panoramic Tuscan Luxury - Villa Maria in Fronzano

10.0 out of 10, Exceptional, (74)
"Beautifully maintained with all necessary amenities. Surprised to find fresh food and wine/ drinks at the house when we arrived with fresh cheese and homemade olive oil. Tommaso is a fantastic host would highly recommend"
A Panoramic Tuscan Luxury - Villa Maria in Fronzano

Villa in Poggiarello-ripa with 3 bedrooms sleeps 5

10.0 out of 10, Exceptional, (110)
"We loved our stay, it was beautiful and relaxing beyond words! Francesca and her team were amazing, providing so many memorable experiences and great support! We will be back! What a wonderful time all around. "
Villa in Poggiarello-ripa with 3 bedrooms sleeps 5

Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

10.0 out of 10, Exceptional, (38)
"Excellent in every way. Highly recommend"
The price is €2,070
includes taxes & fees
28 Aug - 29 Aug
Luxury Villa with Swimmingpool in Chianti/Sleeps 21 - or more in extra suites

Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool

10.0 out of 10, Exceptional, (54)
"We had the trip of a lifetime at this wonderful home. Sherri, the property manager, made sure we had everything we needed upon arrival and organized a truffle hunt and wine tasting with her lovely local connections. She also introduced us to her favorite restaurants nearby (they were amazing) and told us where to shop. And the house itself is stunning- it should be in a movie about Tuscany. Cannot wait to go back!"
Charming Tuscan Villa Near Siena/ Capitivating Private Setting / Lrg Heated Pool

Villa Franchetti - Luxurious Florentine Villa with Swimming Pool

10.0 out of 10, Exceptional, (15)
"We enjoyed this beautiful property It was just like in the pictures!!! Everything worked perfect"
Villa Franchetti - Luxurious Florentine Villa with Swimming Pool

Stunning Villa: 24 guests, private SwimmingPool

9.8 out of 10, Exceptional, (28)
"We had a fantastic time at the house, Fabio was excellent in his communication and help. The house is great with separate areas but big communal spaces. We had a couple of delicious meals cooked for us by Fabio, I would highly recommend this luxury! If I had to say one thing it would be great if the pool seating area was tiled instead of grass, but overall can't fault it."
Stunning Villa: 24 guests, private SwimmingPool

Villa Costa, Stunning Villa in the heart of Tuscany.

10.0 out of 10, Exceptional, (36)
"You have all the amenities of a large, historic villa - and also the real farmland all around you. Sheep, horses, dogs - beautiful, and not in your personal space (unless you want them to be!). Pasqualina and her son Francesco are perfect hosts. Incredibly responsive, even with a language barrier. If I return to Tuscany I would want to stay here again. Thank you so much."
Villa Costa, Stunning Villa in the heart of Tuscany.

BEAUTIFUL VILLA with private Pool in the heart of Chianti

10.0 out of 10, Exceptional, (26)
"We celebrated our baby turning 1 with family and friends and this property was an absolute dream! It comfortably fit our large group! We had a private chef host a dinner for us that Alessandro requested which was incredible! We are grateful for the family memories and would 100% return! Thank you for being such a great host! "
BEAUTIFUL VILLA with private Pool in the heart of Chianti

Villa Salivolpe - on top of a Chianti hill - Private swimming pool

9.6 out of 10, Exceptional, (23)
"The villa was a beautiful home to send our our time in Tuscany, Italy. We enjoyed having our own bedrooms and baths. We had a special meal cooked by a local chef, Rachel. The kitchen worked well for the cooking, and for our breakfasts. The scenery was just breathtaking, and it is just as pictures in books looked like. We very much enjoyed our stay."
Villa Salivolpe - on top of a Chianti hill - Private swimming pool

Luxury Villa Basilio Chianti

Luxury Villa Basilio Chianti

Beautiful private villa for 4 people with A/C, WIFI, pool, TV, terrace and parking

9.8 out of 10, Exceptional, (29)
"Mooie woning met een grote tuin en fijn zwembad. [English translation courtesy of Easy Reserve] Beautiful home with a large garden and lovely pool."
Beautiful private villa for 4 people with A/C, WIFI, pool, TV, terrace and parking

Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside

10.0 out of 10, Exceptional, (79)
"Bianca was the perfect host. She communicated quickly and clearly. She was so eager to help and spend time with us as we inquired about the region. She was super helpful to help arrange transportation and give us good insight to our visit. The property is in a great loction. Close to Florence yet out in the fields of Tuscany. There were ten of us and the villa worked so well. We all would go back to the villa and Bianca."
Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside

Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

10.0 out of 10, Exceptional, (109)
"We had a lovely stay at the villa. The villa was comfortable, well furnished and had a beautiful view of San Gimignano. The owner was very helpful and responsive. We will definitely stay there again if we visit San Gimignano."
Villa with pool, 4 rooms en suite, WiFi A/C, walking distance from San Gimignano

Villa in Chianti with private pool, walking to a restaurant Electric car charger

10.0 out of 10, Exceptional, (15)
"We thoroughly enjoyed this property .it is well off the main road , totally private, and the view is breathtaking .We are happy to recommend this villa to future travelers."
Villa in Chianti with private pool, walking to a restaurant Electric car charger

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (40)
"Very spacious and clean villa in between Florence and Siena in the heart of Chianti. Tremendous hosts that communicated often and met a couple special requests. Have already referred this listing and will definitely come back!"
Your panoramic house in Tuscany between vineyards and olive groves.

Private villa in the heart of chianti with view of siena

10.0 out of 10, Exceptional, (1)
"Fantastiskt boende med underbar trädgård och utsikt, nära vingårdar och historiska städer!"
Private villa in the heart of chianti with view of siena

Quiet and Beautiful Property, Large Pool, Airco in bedrooms

10.0 out of 10, Exceptional, (55)
"The house was fantastic and had more than enough space for our large family. What was particularly great was the large table where we always ate before we went to the very large swimming pool."
Quiet and Beautiful Property, Large Pool, Airco in bedrooms

VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.

9.8 out of 10, Exceptional, (30)
"Friendly hosts. Very beautiful place. Nicely located, near Firenze. The pool and the gardens were amazing. Very clean and we had everything we needed!"
VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.

Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany

10.0 out of 10, Exceptional, (80)
"Great place. Great host Driveway….needs work "
Villa Sabrina - Luxury Villa Rental with private swimming pool in San Gimignano, Tuscany
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Castellina in Chianti Hotel Reviews

Find out more about Castellina in Chianti

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Castellina in Chianti Villas information

Number of reviews
676
Accommodation
2092 Villas
Lowest Price
€2,070
Highest Price
€2,070

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between €2,070 and €2,070 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 2092 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.