Search Villas in Castellina in Chianti

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Check prices for these dates

Next weekend
25 Apr - 27 Apr
In two weeks
2 May - 4 May
In one month
16 May - 18 May
In two months
13 Jun - 15 Jun

Featured Villas in Castellina in Chianti and around

Your panoramic house in Tuscany between vineyards and olive groves.
Exterior

Your panoramic house in Tuscany between vineyards and olive groves.

9.8 out of 10, Exceptional, (34)
"We had such a nice stay and only wish it had been longer! Enrico & Simona were excellent hosts and we loved the cooking class they did for us and our 3 college students who learned to make pasta for the first time. The views are spectacular and it’s a perfect location for trips to the many surrounding towns and wineries. We’d love to come back in the summer and stay longer!"
Your panoramic house in Tuscany between vineyards and olive groves.
Panoramic villa in the Tuscan hills, near Florence, Wi-Fi and costs included.
Terrace/patio

Panoramic villa in the Tuscan hills, near Florence, Wi-Fi and costs included.

9.8 out of 10, Exceptional, (67)
"We stayed in this beautiful villa for days- it was peaceful and perfect for a group. We were on iur 30th wedding anniversary trip which included a few weeks in Italy. This villa worked for our large group of family and friends. Nicola was informative and kept in contact with us making sure our stay was good. We took advantage of Lorenzo and his wine tour and dinner services- it was an amazing experience."
Panoramic villa in the Tuscan hills, near Florence, Wi-Fi and costs included.
Luxury converted barn with hilltop views in chianti wine region, Tuscany
Outdoor pool, a heated pool

Luxury converted barn with hilltop views in chianti wine region, Tuscany

10.0 out of 10, Exceptional, (88)
"We felt so at home and at peace here. Everything was perfect and location is ideal for day trips around Tuscany. Highly recommend!"
Luxury converted barn with hilltop views in chianti wine region, Tuscany
VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.
Outdoor pool

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

9.8 out of 10, Exceptional, (27)
"We loved our stay at this authentic farmhouse ! The family was very , very warm and welcoming and attentive to our needs / questions. If you don’t have a car ( we didn’t ) you need transport and we had a driver / tour one day . We loved the home cooked meals by Barbara and the pre- stocked groceries. It is quite bare bones - don’t expect any paper towels , any extras at all , not even those you might expect past guests have left . There is literally nothing provided so you must purchase ....
VILLA in FLORENTINE HILLS. 300+ EXCELLENT REVIEWS. 100% travelers recommend.
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Exterior

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

10.0 out of 10, Exceptional, (55)
"A+"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
CountryHouse con Piscina Privata 5 min dal centro
Indoor pool, a heated pool

CountryHouse con Piscina Privata 5 min dal centro

9.8 out of 10, Exceptional, (9)
"The property was outstanding and our family had a blast. It was a nice get away from the crowds in the city to enjoy the animals and greenery of the house on the farm. "
The price is €606
includes taxes & fees
22 Apr - 23 Apr
CountryHouse con Piscina Privata 5 min dal centro
Luxury Villa in the Florentine hills
Fridge, microwave, oven, stovetop

Luxury Villa in the Florentine hills

9.8 out of 10, Exceptional, (136)
"Our family of 4, incl 2 teens really enjoyed the quick commute to the countryside after a busy day in Florence. House had 2 bathrooms, large bedrooms and enough space to spread out. Backyard view and patio space made meals outside a treat! Cable TV was a hit with the teens. Owner was very responsive…"
The price is €459
includes taxes & fees
22 Apr - 23 Apr
Luxury Villa in the Florentine hills
Authentic Tuscan country house, dating back to around the year 1000
Outdoor pool

Authentic Tuscan country house, dating back to around the year 1000

9.6 out of 10, Exceptional, (50)
"Beautiful place and a very friendly and helpful host. Authentic Tuscan farmhouse with no frills. Lovely views all round, especially from the terrace. Excellent bar/ restaurant within walking distance. It was very hot when we were there, so the location of the pool across the road was a problem. Otherwise,great."
Authentic Tuscan country house, dating back to around the year 1000
Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence
Exterior

Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence

9.6 out of 10, Exceptional, (46)
"We had a great stay here. All of us really enjoyed the location!"
Charming Villa w/ pool nestled in Chianti vineyards, with AC, close to Florence
Villa Franchetti - Luxurious Florentine Villa with Swimming Pool
Outdoor pool

Villa Franchetti - Luxurious Florentine Villa with Swimming Pool

10.0 out of 10, Exceptional, (11)
"We enjoyed this beautiful property It was just like in the pictures!!! Everything worked perfect"
Villa Franchetti - Luxurious Florentine Villa with Swimming Pool
Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside
Outdoor pool

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

10.0 out of 10, Exceptional, (69)
"everything about the villa is totally wonderful. perfect location, perfect grounds, perfect view, perfectly comfortable. and bianca is the dream host. i would definitelycome back!"
Exclusive 7BR-8BA Villa with pool, a few mins from town, yet in the countryside
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Outdoor pool, pool loungers

Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!

9.8 out of 10, Exceptional, (96)
"Peaceful, quiet, tucked away beautiful in the beautiful Tuscany area. Would stay there again. Excellent property!"
Enchanting Private Villa in Chianti Rolling Hills:Free WiFi,AC,Garden,Pool,View!
Villa with view and private pool
Outdoor pool

Villa with view and private pool

10.0 out of 10, Exceptional, (20)
"We loved the villa and the location. We couldn’t have asked for a better view giving us a wonderful feeling of Tuscany. The closeness to Volterra, coupled with the great supermarket and lovely pizzerias made it special. Guilia was very responsive and helpful at all times. We would come back in a heartbeat. "
Villa with view and private pool
Luxury Villa Tolomei Gucci with Spa
Terrace/patio

Luxury Villa Tolomei Gucci with Spa

Luxury Villa Tolomei Gucci with Spa
Villa Salivolpe - on top of a Chianti hill - Private swimming pool
Outdoor pool

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

9.6 out of 10, Exceptional, (22)
"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
Stunning private villa for 4 guests with pool, WIFI, A/C, TV, terrace and parking
Pool

Stunning private villa for 4 guests with pool, WIFI, A/C, TV, terrace and parking

9.8 out of 10, Exceptional, (28)
"Nice house suitable for a family of 3-4. Two bed rooms, one with a double bed. Living room and well equipped kitchen. Very cozy property a kilometer or so from the town center. The host family lives in another house on the same property, and are very nice and hospitable, while not being intruding in any way. The private church on the property is worth a visit, it was built in 710 a.d. and has frescos from the 1500s inside. The pool is very nice, and there is a nice playground for children. We...
Stunning private villa for 4 guests with pool, WIFI, A/C, TV, terrace and parking
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Outdoor pool

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

10.0 out of 10, Exceptional, (84)
"Alessandro was a fantastic host! He always made us feel right at home. Addressing all of our questions regarding the local area. The property was exactly what we expected. The surrounding area was magnificent. "
San Gimignano villa with pool, 5 rooms en suite, A/C, wi-fi, panoramic view
Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Pool

Villa with private pool on 25 acres in the heart of Chianti, close to Siena

9.8 out of 10, Exceptional, (67)
"The house is well equipped and perfect if you are looking for a quiet and out of the way house. Still a quick drive to Siena where everything can be found. would definitely recommend."
Villa with private pool on 25 acres in the heart of Chianti, close to Siena
Casa Farsetti - Exclusive villa with private pool between Siena and Florence
Terrace/patio

Casa Farsetti - Exclusive villa with private pool between Siena and Florence

9.4 out of 10, Exceptional, (20)
"Wonderful 18th century villa, with farm kitchen. Cooked and cooked, ate and ate."
Casa Farsetti - Exclusive villa with private pool between Siena and Florence
Beautiful Villa With Panoramic Views near San Gimignano
Outdoor pool

Beautiful Villa With Panoramic Views near San Gimignano

9.6 out of 10, Exceptional, (70)
"We had a wonderful stay and this property provided a nice central location from which to explore the region. Information from Steve was timely and extremely helpful. "
Beautiful Villa With Panoramic Views near San Gimignano
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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Other property types in Castellina in Chianti

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Exterior

ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views

10.0 out of 10, Exceptional, (55)
"A+"
ISOLA SERENA Newly Expanded Private Luxury Villa, Tuscany, Infinity Pool & Views
Hu Firenze Camping In Town
Chalet

Hu Firenze Camping In Town

8.8 out of 10, Excellent, (1368)
"Great for families, my kids loved it. Bus to centro in front the property. Market in the property with everything you need, everybody from front desk were speaking English. Swimming pool, playground. We definitely will stay there again."
The price is €94
includes taxes & fees
29 Apr - 30 Apr
Hu Firenze Camping In Town
Forte16
Indoor pool, open 9:00 AM to 8:00 PM, pool loungers

Forte16

9.6 out of 10, Exceptional, (789)
"We were 3 families with 3 kids and our stay was great. is on a walking distance to all the main attractions, close to the public transport, very clean and quiet. it will be our choice again next time when in Florence. Thank you!"
The price is €231
includes taxes & fees
21 Apr - 22 Apr
Forte16
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.

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between €459 and €606 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 1956 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.