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

Castellina in Chianti Vacation Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Castellina in Chianti vacation rentals

A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

1. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.2 out of 10, Wonderful, (5 reviews)
"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "
United States
Jeffrey
The price is AED 401
AED 466 total
includes taxes & fees
11 Nov - 12 Nov
Casa Vacanze Squarcialupi
A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

2. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."
United States
Frank
The price is AED 319
AED 367 total
includes taxes & fees
15 Oct - 16 Oct
Mariani Bed & Breakfast
A stone building with multiple windows and a chimney.

3. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is AED 469
AED 532 total
includes taxes & fees
8 Nov - 9 Nov
Agriturismo La Ferrozzola
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

4. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.6 out of 10, Exceptional, (15 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is AED 484
AED 549 total
includes taxes & fees
14 Oct - 15 Oct
Residenzia del Sogno
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

5. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (42 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is AED 634
AED 706 total
includes taxes & fees
19 Oct - 20 Oct
Riserva di Fizzano Residence
A stone-paved entrance with a grill, potted plants, and a door leading to an interior space.

6. Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi

Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
Castellina in Chianti
The price is AED 340
AED 546 total
includes taxes & fees
10 Nov - 11 Nov
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
A stone staircase leading up to a historic building with a tower, surrounded by lavender fields.

7. Istrice cosy apartment in the Chianti garden swimming pool, tennis and wifi

Istrice cosy apartment in the Chianti garden swimming pool, tennis and wifi
Toscana
Istrice cosy apartment in the Chianti garden swimming pool, tennis and wifi
A brick building with a garden, a metal fence, and a clear sky.

8. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is AED 885
AED 1,106 total
includes taxes & fees
18 Oct - 19 Oct
Casa Marisa in Castellina in Chianti
A rustic outdoor dining area with a stone wall, wooden furniture, and potted plants.

9. La Misura, cottage with garden and swimming pool on the hills of Chianti

La Misura, cottage with garden and swimming pool on the hills of Chianti
Castellina in Chianti
10.0 out of 10, Exceptional, (2 reviews)
"What a beautiful stay in the enchanting Tuscan countryside! Every detail was attended to and we could not have felt more at home. We can only dream of returning sometime!"
United States
Jami B.
La Misura, cottage with garden and swimming pool on the hills of Chianti
A bedroom with a double bed, a dresser, a nightstand, and a door leading to another room.

10. Apartment 'La Casa Della Gina' with Wi-Fi

Apartment 'La Casa Della Gina' with Wi-Fi
Castellina in Chianti
The price is AED 1,770
AED 1,992 total
includes taxes & fees
10 Nov - 11 Nov
Apartment 'La Casa Della Gina' with Wi-Fi
A stone building with a gravel path, outdoor seating, and greenery.

11. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is AED 984
AED 1,143 total
includes taxes & fees
2 Nov - 3 Nov
The Arch Among the Hills of Castellina
A stone staircase leading up to a historic building with a tower, surrounded by lavender fields.

12. Rondine cosy apartment in the Chianti garden pool tennis wifi

Rondine cosy apartment in the Chianti garden pool tennis wifi
Toscana
Rondine cosy apartment in the Chianti garden pool tennis wifi
A stone building with a garden in front.

13. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (28 reviews)
"What an amazing place. We enjoyed it so much."
United States
Tatevik
The price is AED 690
AED 792 total
includes taxes & fees
26 Oct - 27 Oct
Borgo Argenina
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

14. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (80 reviews)
"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."
United States
Gage
The price is AED 1,040
AED 1,161 total
includes taxes & fees
19 Oct - 20 Oct
Terre di Baccio
A villa with a swimming pool, outdoor seating, and a tennis court.

15. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (80 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is AED 429
AED 488 total
includes taxes & fees
19 Oct - 20 Oct
Villa Curina Resort
An outdoor swimming pool with a wooden pergola, lounge chairs, and a stone wall backdrop.

16. Guild Living Siena Senior Resort & Residence

Guild Living Siena Senior Resort & Residence
Scacciapensieri
8.8 out of 10, Excellent, (55 reviews)
"Amazing! Thank you!"
United Kingdom
Lucy
The price is AED 510
AED 577 total
includes taxes & fees
8 Nov - 9 Nov
Guild Living Siena Senior Resort & Residence
A bakery display with pastries and a coffee station.

17. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (215 reviews)
"We enjoyed our stay very much. Staff was very friendly and offered great advise on places to eat. The rooms had great charm to them. We were delighted with our selection of where to stay."
United States
Enrique
The price is AED 269
AED 313 total
includes taxes & fees
9 Nov - 10 Nov
B&B Il Corso
A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

18. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is AED 613
AED 674 total
includes taxes & fees
21 Oct - 22 Oct
Villa di Sotto
A spacious hotel room with a large bed, a sitting area with chairs, and a view through an arched doorway to another room.

19. La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (254 reviews)
"Great stay. Thanks for the hospitality and kindness."
United Kingdom
Agnieszka
The price is AED 470
AED 533 total
includes taxes & fees
2 Nov - 3 Nov
La Terrazza Sul Campo Rooming House
A bathroom with a window view of a historic building and a tiled roof.

20. Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (490 reviews)
"Great location right in the heart of everything and next to an escalator that takes you to the main plaza. Very comfortable bed, friendly staff. Convenient parking option very close by."
United States
Heather
The price is AED 407
AED 465 total
includes taxes & fees
2 Nov - 3 Nov
Siena Vip
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

Bernini Palace

Bernini Palace

10/10 Excellent
"Absolutely amazing hotel. The room was incredible. The hotel staff were so beyond friendly. And the hotel is in a great location! Definitely recommend."
Kaylin 1-night trip
Posted 4 hours ago
Bernini Palace

Frequently asked questions

Are there vacation rentals in Castellina in Chianti?

Yes, you can find vacation rentals near the most popular attractions in Castellina in Chianti, or you can go with a more remote option if you're looking for relaxation. Visitors to Castellina in Chianti speak positively about the countryside and wineries in this destination. Make sure you have time to check out the forests while you're in the area.

What are some of the best vacation home rentals in Castellina in Chianti?

Villa La Stella - Casa per Ferie: This vacation home rental outside Castellina in Chianti is located near the airport and has a garden, a library, and air-conditioning to put you at ease in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind. Some other top choices in Castellina in Chianti are Villa with large garden in the Chianti hills and Farmhouse in the heart of the real chiantishire.

How many vacation rentals will I find in Castellina in Chianti?

With 31 Expedia vacation rentals, you're sure to find just the right place for your Castellina in Chianti stay.

What’s there to see and do in Castellina in Chianti?

While exploring the area, visit family-friendly sights like Chianti Observatory, or get outside and enjoy nature at Chianti Sculpture Park. While here, City Hall Castellina In Chianti and Castellina Fortress are other places worth a visit.

What’s a vacation rental in Castellina in Chianti like?

A vacation rental is a private property you can stay in for several days or longer in Castellina in Chianti. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can provide a sense of seclusion away from shared hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for family gatherings.