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

Villas in Castellina in Chianti

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Castellina in Chianti villas

A garden with outdoor seating, a shade structure, and a view of the surrounding landscape.

1. Rooster House, Cooking Classes, and Opera

Rooster House, Cooking Classes, and Opera
Tavarnelle Val di Pesa
$126 nightly
The price is $129
Nov 17 - Nov 18
Total with taxes and fees
Rooster House, Cooking Classes, and Opera
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
7.4 out of 10, Good, (3 reviews)
"RUN as fast as you can. Booked this place and left hours after. Here is why:1. It is actually part of a commune. Numerous other building that don't appear in pictures or description on VRBO2. There are 2 separate units. One up, One down. Require separate entrance3. Downstairs bathroom flooded. Owner admits to a broken pipe in the wall, so says use the other 2 upstairs. So, go outside, upstairs, unlock the door to use the bathroom in the middle of the night? We decide to sleep upstairs with the...
United States
JIm B.
$1,357 nightly
The price is $1,361
Nov 17 - Nov 18
Total with taxes and fees
Villa 'La Petrosa' with Private Pool, Private Garden and Balcony
A stone building with an arched entrance, surrounded by gravel, potted plants, and trees.

3. 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
$315 nightly
The price is $350
Nov 20 - Nov 21
Total with taxes and fees
Villa Montecastello
A landscaped garden with a central fountain, a pool, and a small building with a tiled roof.

4. 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.
$8,355 nightly
The price is $8,355
Nov 15 - Nov 16
Total with taxes and fees
VILLA ASCARA - Sixteen Bedroom Villa, Sleeps 31
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.
$1,709 nightly
The price is $1,713
Nov 15 - Nov 16
Total with taxes and fees
Villa 'Erbolino' with Private Garden, Outdoor Stone Bathtub and Wi-Fi
An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

6. 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)
$2,870 nightly
The price is $2,870
Nov 18 - Nov 19
Total with taxes and fees
Villa Mami: A Tuscan retreat full of elegance and charm
A large estate with a swimming pool, tennis court, and multiple guest rooms.

7. VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36

VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
Colle Val D'Elsa
$13,007 nightly
The price is $13,007
Nov 29 - Nov 30
Total with taxes and fees
VILLA ALTAMIRA - Eighteen Bedroom Villa, Sleeps 36
A covered outdoor patio with a wooden table and chairs, a vase of flowers, and a view of the countryside.

8. Villa Capanna: A Window onto Tuscany

Villa Capanna: A Window onto Tuscany
Vico dʼArbia
$1,636 nightly
The price is $1,640
Nov 15 - Nov 16
Total with taxes and fees
Villa Capanna: A Window onto Tuscany
A rustic stone building with a tower, covered walkways, and a grassy courtyard.

9. Villa Torre Among the Hills of Siena

Villa Torre Among the Hills of Siena
Vico dʼArbia
$1,636 nightly
The price is $1,640
Nov 15 - Nov 16
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.

10. 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.
$1,281 nightly
The price is $1,281
Nov 15 - Nov 16
Total with taxes and fees
Villa in the Heart of Chianti — Peace, Views, and Authentic Tuscany
A dining area with a wooden table, white chairs, and a chandelier.

11. Villa Liberty in The Centre - No Ztl

Villa Liberty in The Centre - No Ztl
Siena Historical Center
$365 nightly
The price is $365
Nov 15 - Nov 16
Total with taxes and fees
Villa Liberty in The Centre - No Ztl
A villa with a swimming pool, surrounded by lush greenery and vineyards.

12. 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
$5,952 nightly
The price is $5,957
Nov 15 - Nov 16
Total with taxes and fees
Villa with Guesthouse: Private Pool, Air Conditioning, 13 Bedrooms for up to 30 Guests
A stone building with a large arched entrance, potted plants, and outdoor seating.

13. Premorae - Tenuta corte dell'Angelo - heated pool and concierge service

Premorae - Tenuta corte dell'Angelo - heated pool and concierge service
impruneta
10.0 out of 10, Exceptional, (117 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.
$1,392 nightly
The price is $1,397
Nov 18 - Nov 19
Total with taxes and fees
Premorae - Tenuta corte dell'Angelo - heated pool and concierge service
A two-story building with a gravel driveway, a wooden door, and a small garden area with potted plants.

14. 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.
$1,543 nightly
The price is $1,548
Nov 29 - Nov 30
Total with taxes and fees
Luxury Villa: Air-Co & Swimmingpool in Chianti/Sleeps 21 or more in extra suites
A multi-story building with a stone pathway leading to the entrance, surrounded by lush greenery and flowering plants.

15. VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37

VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
Firenze
$15,608 nightly
The price is $15,608
Nov 15 - Nov 16
Total with taxes and fees
VILLA ARTIUM - Twenty Bedroom Villa, Sleeps 37
A large, historic building with a tower, multiple arches, and a courtyard with outdoor seating.

16. VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25

VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
Careggi Rifredi
10.0 out of 10, Exceptional, (1 review)
"Staff went over and above for us. Food was wonderful service 5 stars"
United States
robert g.
$10,406 nightly
The price is $10,406
Nov 15 - Nov 16
Total with taxes and fees
VILLA MEDICEA - Seven Bedroom Villa, Sleeps 25
A modern outdoor space with a rectangular pool, a wooden bench, and a well-maintained lawn.

17. 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
$1,310 nightly
The price is $1,313
Nov 15 - Nov 16
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.

18. 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.
$1,786 nightly
The price is $1,788
Nov 19 - Nov 20
Total with taxes and fees
Villa Milani with Shared Pool, Private Terrace & Wi-Fi
A pool area with a stone archway, lounge chairs, and a stone wall with greenery behind.

19. Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi

Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
Rignano sull'Arno
$5,226 nightly
The price is $5,230
Nov 15 - Nov 16
Total with taxes and fees
Villa with a Pool in Florence / Breakfast, Daily Housekeeping, Air Conditioning, Jacuzzi
A clear blue pool with a view of rolling hills and a hedge-lined edge.

20. VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16

VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16
Firenze
$2,341 nightly
The price is $2,341
Nov 15 - Nov 16
Total with taxes and fees
VILLA GRAND MEDICI - Eight Bedroom Villa, Sleeps 16
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castellina in Chianti Hotel Reviews

Hotel Santa Maria Novella

Hotel Santa Maria Novella

10/10 Excellent
"You can walk to just about every major tourist destinations in 10 to 20 minutes. The hotel is well maintained and housekeeping staff keep your room nice and clean. Amenities include standard items such as body soap, shampoo/conditioner but also body cream, shower cap, slippers, bathrobes, etc. They provide a coffee/espresso machine and a kettle. It was nice to see some “decaf “ options. You might consider bringing your own universal plug for the EU style outlets to charge electronics. Breakfast is excellent; lots of options."
Yuka 5-night trip
Posted 1 hour ago
Hotel Santa Maria Novella

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews
178
Accommodation
1812 Villas
Lowest Price
$129
Highest Price
$15,608

Frequently asked questions

How much do villas in Castellina in Chianti cost?
Villas in Castellina in Chianti range between $129 and $15,608 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 1812 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.

Explore a world of travel with Expedia