Castellina in Chianti Villas Rentals

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

Bundle & Save
Get more, spend less whenever you see Bundle & Save deals
OneKeyCash
Earn OneKeyCash on all your eligible bookings
Upfront pricing
We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks

In two months

In three months

In four months

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

Tavarnelle Val di Pesa

$143 nightly

Oct 17 - Oct 18

Total with taxes and fees

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

2. Villa Montecastello

Monteriggioni

Alvaro

$173 nightly

Oct 12 - Oct 13

Total with taxes and fees

A stone building with a swimming pool, wooden deck, and a tall tree.

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

Radda in Chianti

Amber M.

$1,665 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

Gaiole in Chianti

Bernard K.

$2,041 nightly

Nov 3 - Nov 4

Total with taxes and fees

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.

5. Villa Il Signorino

GREVE IN CHIANTI

Avi A.

$502 nightly

Oct 11 - Oct 12

Total with taxes and fees

A brick building with a gravel courtyard, a staircase, and potted plants.

6. GuestHost - Porta Romana Elegant House with Private Parking!

Siena

Kathleen M.

$260 nightly

Oct 11 - Oct 12

Total with taxes and fees

A covered balcony with a brick railing, a bench, and a view of lush greenery.

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

Certaldo - Firenze

Kelly C.

$653 nightly

Oct 11 - Oct 12

Total with taxes and fees

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

Vico dʼArbia

$1,822 nightly

Nov 2 - Nov 3

Total with taxes and fees

A rustic stone building with a tower, covered walkways, and a grassy courtyard.

9. Villa Torre Among the Hills of Siena

Vico dʼArbia

$1,747 nightly

Oct 17 - Oct 18

Total with taxes and fees

An outdoor patio with a wooden pergola, a table set for breakfast, and a view of the surrounding garden.

10. Villa Bellavista - Homelike Villas

Montegonzi

An outdoor dining area with a table and chairs, overlooking a historic town with a prominent tower and buildings.

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

Toscana

$3,067 nightly

Oct 18 - Oct 19

Total with taxes and fees

An outdoor patio with a table and chairs, surrounded by greenery and a view of distant hills.

12. Luxury Villa in the Florentine hills

Florence

melissa r.

$364 nightly

Nov 1 - Nov 2

Total with taxes and fees

A large building surrounded by dense trees and a clear sky.

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

Gambassi Terme

$4,827 nightly

Oct 19 - Oct 20

Total with taxes and fees

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

Montespertoli

Krista G.

$2,172 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

Montespertoli

$6,055 nightly

Oct 14 - Oct 15

Total with taxes and fees

A stone building with a large arched entrance, potted plants, and outdoor seating.

16. Exclusive Estate | Personal Concierge & Heated Pool

impruneta

Oli P.

$1,249 nightly

Oct 19 - Oct 20

Total with taxes and fees

17. Villa Sunset, in the heart of Chianti area

Greve in Chianti

elisa b.

A building with a large entrance, potted plants, and a statue in the foreground.

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

Montespertoli

Scott M.

$2,016 nightly

Nov 7 - Nov 8

Total with taxes and fees

A person in a swimming pool with a view of a vineyard and hills.

19. "A Casa di Franca Villa con piscina"

Gambassi Terme

"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...

Anonymous traveler

$1,571 nightly

Oct 11 - Oct 12

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Villas

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Castellina in Chianti Hotel Reviews

Hotel Paris

10/10 Excellent

"This hotel was very nice, clean and quite full of history. The buildings in Florence are old but this one was very well maintained and a beautiful hotel with character and charm. Breakfast had good choices and variety. The rooms are big compared to more modern buildings and takes you back in time. And the staff were friendly and helpful. We were centrally located and everything was easy to get to. I would love to stay here again."

Hotel Albani Firenze

8/10 Good

"We were very pleased with our stay at this hotel. Our goal was to stay in a decent hotel with an elevator and near the SMNovella train station, and we hit it spot on! From there you can walk to or take a short bus ride to anywhere. The hotel itself was really nice and the staff were all friendly, helpful and spoke English well, and it’s nice to have a buffet breakfast with a good selection every day! The AC was adequate. They put us on the top floor with no view, just a skylight which we didn’t mind. Our only complaint was our bathroom, though very large, only had a tub. It was difficult to shower, especially if you’re older like us, It had a hand-held shower and the pressure was weak, But with all things considered it’s still a good place to stay and the building itself is very nice and classic."

IQ Hotel Firenze

8/10 Good

"The room was small but manageable. Location was good and walkable if you don’t mind 20 min walks which is a long time if you’re trying to get some where. Staff was extremely helpful. Breakfast had a large variety. Dinner was good. Limited choices though. Loved the cool water in the automatic fountains. Went Sept 8-10. Hotel was a bit pricey for my taste but cute hotel. Had a gym but didn’t use it. The beds were 2 twin size and we pushed them together. We were too tired to ask for a full size or queen. Loved the bidet, the bidet towels and intimate wash. Shower was amazing. The offered some sort of spa service wish we had time to partake. Pros- GYM, spa if you have time, breakfast- many selections even cappuccino, savory and sweet breakfast. Shower nice and spacious!! Bathroom was large. Extremely helpful and kind staff. Water coolers in the hallway to help you stay hydrated. It was very refreshing. Saw microwaves near vending machines in case you had leftovers from dinner. Cons- few selections for dinner, 20-25 min walk from famous sites."

Villa Neroli

10/10 Excellent

"Great and affordable hotel outside Florence so we could have a pool to cool down in. Lovely restaurant on site, didn’t explore food options in walking distance. Helpful staff who explained bus routes etc into Florence Bus route with various app really easy to follow and buy ticket. Took about 20 mins to get into centre. We travelled in August and it was late 30’s temp wise each day so was a relief to come back to the hotel each afternoon to cool off in air con and pool. The family room we had was two enormous Rooms very spacious. Second room had space for three kids. Wonderful hotel would recommend and return if I was ever going back to Florence"

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Number of reviews	3
Accommodation	1829 Villas
Lowest Price	$193
Highest Price	$193

Frequently asked questions

How much do villas in Castellina in Chianti cost?

Villas in Castellina in Chianti range between $193 and $193 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.

Explore a world of travel with Expedia

Things to do in Castellina in Chianti

Book Villas in Castellina in Chianti on Expedia.it

Room 1

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Castellina in Chianti villas

1. Rooster House, cooking classes and opera

2. Villa Montecastello

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

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

5. Villa Il Signorino

6. GuestHost - Porta Romana Elegant House with Private Parking!

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

8. Villa Capanna: A Window onto Tuscany

9. Villa Torre Among the Hills of Siena

10. Villa Bellavista - Homelike Villas

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

12. Luxury Villa in the Florentine hills

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

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

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

16. Exclusive Estate | Personal Concierge & Heated Pool

17. Villa Sunset, in the heart of Chianti area

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

19. "A Casa di Franca Villa con piscina"

Find vacation rentals that suit your style

Top Castellina in Chianti Hotel Reviews

Hotel Paris

Hu Firenze Camping In Town

Hotel Albani Firenze

Art Hotel Villa Agape

IQ Hotel Firenze

Plus Florence - Hostel

Villa Neroli

Grand Hotel Cavour

Grand Hotel Baglioni

Find out more about Castellina in Chianti

Castellina in Chianti Villas information

Frequently asked questions

Explore a world of travel with Expedia