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

Villas in Castellina in Chianti

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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
$177 nightly
The price is $198
Oct 24 - Oct 25
Total with taxes and fees
Villa Montecastello
A stone building with a swimming pool, wooden deck, and a tall tree.

2. 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.
$1,667 nightly
The price is $1,671
Nov 2 - Nov 3
Total with taxes and fees
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

3. Rooster House, cooking classes and opera

Rooster House, cooking classes and opera
Tavarnelle Val di Pesa
$144 nightly
The price is $147
Oct 22 - Oct 23
Total with taxes and fees
Rooster House, cooking classes and opera
A terrace with wicker furniture, a stone planter with flowers, and a view of vineyards and hills.

4. 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.
$2,041 nightly
The price is $2,045
Nov 3 - Nov 4
Total with taxes and fees
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

5. VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31

VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
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.
$7,864 nightly
The price is $7,864
Oct 21 - Oct 22
Total with taxes and fees
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
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.
$499 nightly
The price is $503
Oct 21 - Oct 22
Total with taxes and fees
Villa Il Signorino
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

7. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
$1,822 nightly
The price is $1,826
Nov 2 - Nov 3
Total with taxes and fees
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

8. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
$1,822 nightly
The price is $1,826
Nov 2 - Nov 3
Total with taxes and fees
Villa Torre Among the Hills of Siena
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.
$654 nightly
The price is $654
Oct 21 - Oct 22
Total with taxes and fees
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

10. Villa Mami: A Tuscan retreat full of elegance and charm

Villa Mami: A Tuscan retreat full of elegance and charm
Toscana
10.0 out of 10, Exceptional, (1 review)
$3,073 nightly
The price is $3,073
Oct 21 - Oct 22
Total with taxes and fees
Villa Mami: A Tuscan retreat full of elegance and charm
A modern house with a swimming pool, outdoor seating, and a view of mountains.

11. Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany

Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
Vaggio
$677 nightly
The price is $680
Nov 9 - Nov 10
Total with taxes and fees
Isolotto degli Angeli – Villa with Pool, Hot Tub & Garden in Tuscany
An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

12. Luxury Villa in the Florentine hills

Luxury Villa in the Florentine hills
Florence
9.8 out of 10, Exceptional, (152 reviews)
"The villa is a nicely restored rustic home with a beautiful landscape. I would definitely stay there again!"
United States
melissa r.
$371 nightly
The price is $376
Nov 1 - Nov 2
Total with taxes and fees
Luxury Villa in the Florentine hills
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

13. 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.
$2,173 nightly
The price is $2,177
Nov 3 - Nov 4
Total with taxes and fees
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.

14. 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.
$1,258 nightly
The price is $1,262
Oct 25 - Oct 26
Total with taxes and fees
Exclusive Estate | Personal Concierge & Heated Pool
A villa with a swimming pool, surrounded by lush greenery and vineyards.

15. 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
$6,054 nightly
The price is $6,059
Oct 21 - Oct 22
Total with taxes and fees
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
An outdoor patio with a round table and chairs, surrounded by a wooden fence and a large canopy.

16. Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany

Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
Vaggio
$1,159 nightly
The price is $1,162
Nov 3 - Nov 4
Total with taxes and fees
Villa 'Dimora degli angeli' – An Exclusive Experience in the Heart of Tuscany
A building with a large entrance, potted plants, and a statue in the foreground.

17. Villa Milani with Shared Pool, Private Terrace & Wi-Fi

Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"The Villa was charming and absolutely bursting with character. We loved exploring the house and the grounds! It was quiet and relaxing, but still only a short drive from Florence, Sienna, San Gimignano and other favorite towns of Tuscany. A memorable stay in an absolutely unique villa!"
United States
Scott M.
$1,816 nightly
The price is $1,819
Nov 1 - Nov 2
Total with taxes and fees
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
Outdoor dining

18. Villa Sunset, in the heart of Chianti area

Villa Sunset, in the heart of Chianti area
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 area
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

19. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
$14,606 nightly
The price is $14,606
Oct 27 - Oct 28
Total with taxes and fees
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A person in a swimming pool with a view of a vineyard and hills.

20. "A Casa di Franca Villa con piscina"

"A Casa di Franca Villa con piscina"
Gambassi Terme
10.0 out of 10, Exceptional, (1 review)
"Pros: La estancia en la casa fue muy bonita. Estaba cerca de Florencia, Siena, Sant Gimigano, etc. Viajamos toda la familia y los propietarios fueron muy acogedores. La piscina es un sitio perfecto para relajarse y bañarse después de ver la Toscana. Nuestros hijos y sobrinos jugaron porque tenían de todo. La casa muy equipada y limpia con televisión en todas las habitaciones. Los propietarios además nos ayudaron con un pequeño contratiempo que tuvimos. Nos sentimos como en casa, muchas...
Spain
Anonymous traveler
$1,709 nightly
The price is $1,713
Nov 3 - Nov 4
Total with taxes and fees
"A Casa di Franca Villa con piscina"
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

Hotel Paris

Hotel Paris

10/10 Excellent
"Staff were friendly and helpful, beautiful building and situated in the heart of where you want to be."
William 3-night trip
Posted 2 hours ago
Hotel Paris

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
331
Accommodation
1829 Villas
Lowest Price
$147
Highest Price
$14,606

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between $147 and $14,606 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 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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