A stone building with a clock tower, steps leading up to it, and people walking around.

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Castellina in Chianti villas

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

1. Villa Montecastello

Villa Montecastello
Monteriggioni
8.0 out of 10, Very good, (3 reviews)
"Amazing stay! Teh apartment is HUGE and GORGEOUS. The whole villa is amazing. The view , unbeatable. The host , super warm. Highly recommend!"
United States
Alvaro
The price is ￥50,665
￥56,263 total
includes taxes & fees
Oct 20 - Oct 21
Villa Montecastello
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

2. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
The price is ￥19,491
￥23,212 total
includes taxes & fees
Nov 5 - Nov 6
Rooster House, cooking classes and opera
A stone building with a swimming pool, wooden deck, and a tall tree.

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

Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
Radda in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"A dream property come true. Breathtaking views, most accommodating hosts, Perfect Tuscan location."
United States
Amber M.
The price is ￥198,798
￥284,004 total
includes taxes & fees
Nov 6 - Nov 7
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

4. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32

VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
Siena
10.0 out of 10, Exceptional, (1 review)
"We celebrated our 20th Anniversary with 23 guests, all who stayed at the Property. The location and accommodations could not have been better and the staff and property manager were excellent. I would highly recommend staying here for any Tuscany adventures! Thank you so much to the owner and all involved!Ron and Wendy"
United States
Ron M.
The price is ￥1,157,199
￥1,246,028 total
includes taxes & fees
Oct 7 - Oct 8
VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 32
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

5. Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi

Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
Gaiole in Chianti
10.0 out of 10, Exceptional, (9 reviews)
"Best view in TuscanyIt was all new on the inside and very rustic exterior Beautiful villa!!!Great Host "
United States
Bernard K.
The price is ￥319,786
￥324,050 total
includes taxes & fees
Nov 3 - Nov 4
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
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.

6. Villa Il Signorino

Villa Il Signorino
GREVE IN CHIANTI
9.4 out of 10, Exceptional, (3 reviews)
"Nice place 👌 "
United States
Avi A.
The price is ￥55,963
￥79,947 total
includes taxes & fees
Oct 7 - Oct 8
Villa Il Signorino
A stone building with a large glass door, a wooden deck, and a stone wall.

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

Villa "Arnilù" with Private Pool & Wi-Fi
San Gimignano
The price is ￥410,653
￥476,539 total
includes taxes & fees
Oct 12 - Oct 13
Villa "Arnilù" with Private Pool & Wi-Fi
An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

8. Villa Bellavista - Homelike Villas

Villa Bellavista - Homelike Villas
Montegonzi
Villa Bellavista - Homelike Villas
A covered balcony with a brick railing, a bench, and a view of lush greenery.

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

Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
Certaldo - Firenze
2.0 out of 10, (1 review)
"House is very nice and clean , but not equipped for rental, kitchen is poorly equipped, towels are like napkins , no toilet paper, no soap , nothing "
United States
Kelly C.
The price is ￥81,897
￥103,564 total
includes taxes & fees
Oct 7 - Oct 8
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

10. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
The price is ￥250,144
￥289,407 total
includes taxes & fees
Nov 2 - Nov 3
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

11. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
The price is ￥250,144
￥289,407 total
includes taxes & fees
Nov 2 - Nov 3
Villa Torre Among the Hills of Siena
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

12. Villa Mami: A Tuscan Retreat of Elegance and Charm

Villa Mami: A Tuscan Retreat of Elegance and Charm
Toscana
10.0 out of 10, Exceptional, (1 review)
The price is ￥355,318
￥485,542 total
includes taxes & fees
Oct 18 - Oct 19
Villa Mami: A Tuscan Retreat of Elegance and Charm
An outdoor patio with a round table, chairs, a sofa, and a potted plant.

13. Molino In Chianti - Villa with Private Pool

Molino In Chianti - Villa with Private Pool
Mercatale Val Di Pesa
The price is ￥245,690
￥246,401 total
includes taxes & fees
Oct 7 - Oct 8
Molino In Chianti - Villa with Private Pool
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

14. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (151 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
The price is ￥35,532
￥58,450 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Villa in the Florentine hills
A two-story building with a garden, a gazebo, and a statue.

15. Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills

Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
Gambassi Terme
The price is ￥765,568
￥766,101 total
includes taxes & fees
Oct 8 - Oct 9
Villa Borgo Il Castagno – Historic Villa with Private Pool in the Tuscan Hills
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

16. Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites

Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
Montespertoli
10.0 out of 10, Exceptional, (42 reviews)
"Absolutely fabulous! Beautiful location, exceptional host and the Tuscan countryside dream. Room for all 11 of our ladies, dreamy grounds. We all felt like we were living our Eat, Love, Pray best life!"
United States
Krista G.
The price is ￥302,020
￥345,191 total
includes taxes & fees
Nov 1 - Nov 2
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A stone building with a large arched entrance, potted plants, and outdoor seating.

17. Exclusive Estate | Personal Concierge & Heated Pool

Exclusive Estate | Personal Concierge & Heated Pool
impruneta
10.0 out of 10, Exceptional, (115 reviews)
"We had a great time with the family in impruneta. Caterine - the host - was very friendly and made everything to have a perfect stay in the villa. We can absolutely recommend this villa !"
Germany
Oli P.
The price is ￥173,148
￥198,486 total
includes taxes & fees
Oct 25 - Oct 26
Exclusive Estate | Personal Concierge & Heated Pool
Dining

18. Villa Liberty in The Centre - No Ztl

Villa Liberty in The Centre - No Ztl
Siena Historical Center
Villa Liberty in The Centre - No Ztl
A villa with a swimming pool, surrounded by lush greenery and vineyards.

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

Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Montespertoli
The price is ￥1,065,954
￥1,066,665 total
includes taxes & fees
Oct 14 - Oct 15
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
Pool

20. Villa Sunset, in the heart of Chianti

Villa Sunset, in the heart of Chianti
Greve in Chianti
8.0 out of 10, Very good, (1 review)
"La casa é spaziosa ed accogliente e molto pulita in una posizione e strategica e comoda per visitare Firenze e i borghi della zona. "
Italy
elisa b.
Villa Sunset, in the heart of Chianti
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

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

10/10 Excellent
"The hotel was nice, clean, and well-maintained. Our room was spacious and had a beautiful view. We especially loved the rooftop bar! We would definitely stay here again and would also consider trying one of their other locations."
Eniko 1-night trip
Posted 1 hour ago
The Social Hub Florence Lavagnini

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
328
Accommodation
1830 Villas
Lowest Price
￥23,212
Highest Price
￥1,246,028

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between ￥23,212 and ￥1,246,028 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 1830 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.