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

Castellina in Chianti Holiday Rentals

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Castellina in Chianti holiday rentals

A room with a window featuring sheer curtains, a radiator below, and a view of a green landscape.

1. 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 HK$718
HK$825 total
includes taxes & fees
30 Oct - 31 Oct
Mariani Bed & Breakfast
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

2. 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 HK$898
HK$1,040 total
includes taxes & fees
29 Nov - 30 Nov
Casa Vacanze Squarcialupi
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

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 HK$999
HK$1,134 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
9.8 out of 10, Exceptional, (16 reviews)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is HK$1,032
HK$1,170 total
includes taxes & fees
1 Nov - 2 Nov
Residenzia del Sogno
A stone-paved entrance with a grill, potted plants, and a door leading to an interior space.

5. 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
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
An aerial view of a rural estate with stone buildings, a tennis court, and surrounding greenery.

6. 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.

7. Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is HK$1,885
HK$2,357 total
includes taxes & fees
2 Nov - 3 Nov
Casa Marisa in Castellina in Chianti
A rustic outdoor dining area with a stone wall, wooden furniture, and potted plants.

8. 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 bed, bedside tables, a dresser, a window with curtains, and wall-mounted lights.

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

Apartment 'La Casa Della Gina' with Wi-Fi
Castellina in Chianti
10.0 out of 10, Exceptional, (1 review)
"We loved our 13 night stay in Castellina in Chianti! The apartment was clean, spacious and well appointed! From the apartment you step out right onto the pedestrian street with shops, bars and restaurants. The grocery is a couple of minutes walking and everyone in town is so friendly! The host is very friendly and helpful and things could not have been better! I highly recommend the apartment for your stay in Tuscany and we were sad to leave!"
United States
Diane W.
Apartment 'La Casa Della Gina' with Wi-Fi
A stone building with a gravel path, outdoor seating, and greenery.

10. The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is HK$1,885
HK$2,226 total
includes taxes & fees
2 Nov - 3 Nov
The Arch Among the Hills of Castellina
An aerial view of a rural estate with stone buildings, a tennis court, and surrounding greenery.

11. 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.

12. 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 HK$1,473
HK$1,691 total
includes taxes & fees
31 Oct - 1 Nov
Borgo Argenina
A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

13. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (82 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 HK$2,114
HK$2,360 total
includes taxes & fees
30 Oct - 31 Oct
Terre di Baccio
A villa with a swimming pool, outdoor seating, and a tennis court.

14. Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (82 reviews)
"Beautiful resort in the hills, lovely and charming room, incredibly spacious."
United States
Deanna
The price is HK$1,026
HK$1,163 total
includes taxes & fees
30 Oct - 31 Oct
Villa Curina Resort
A hot tub with two glasses of a beverage.

15. Villa di Sotto

Villa di Sotto
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (40 reviews)
"Great spot"
Canada
Philippe
The price is HK$1,314
HK$1,446 total
includes taxes & fees
30 Oct - 31 Oct
Villa di Sotto
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, (60 reviews)
"We booked this last - minute and were really impressed with the whole experience. The property and grounds are beautiful. Staff was so friendly and helpful. The rooms were well appointed and quiet. Beds were too firm for our liking, but it was easy to overlook as the entire stay was really great. Good options in the restaurant too. The block of hotel rooms is in a retirement resort, which I think is a wonderful idea! Very much enjoyed our stay. We had a car and parking was free."
United States
Heidi
The price is HK$760
HK$871 total
includes taxes & fees
3 Nov - 4 Nov
Guild Living Siena Senior Resort & Residence
A table with two wine glasses, a bottle, and a book.

17. Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (102 reviews)
"Very nice place. Nice people, clean and just nice"
Denmark
Leo
The price is HK$595
HK$690 total
includes taxes & fees
1 Nov - 2 Nov
Domus il Palio B&B
A white mobile home with blue shutters, a red roof, and a small deck with white chairs.

18. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (91 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is HK$415
HK$483 total
includes taxes & fees
30 Oct - 31 Oct
Camping Boschetto Di Piemma
A narrow street with buildings on either side, featuring arched windows and a pedestrian walkway.

19. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (218 reviews)
"Very clean and comfortable, great location and staff"
United States
Heather
The price is HK$575
HK$667 total
includes taxes & fees
2 Nov - 3 Nov
B&B Il Corso
A stone building with a patio area featuring a table and chairs under a large umbrella.

20. Relais Villa Olmo - Place of Charme

Relais Villa Olmo - Place of Charme
Impruneta
9.6 out of 10, Exceptional, (274 reviews)
"Great property and staff. Highly recommend!"
United States
Michael
The price is HK$729
HK$828 total
includes taxes & fees
29 Nov - 30 Nov
Relais Villa Olmo - Place of Charme
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

Villa Neroli - Place of Charme

Villa Neroli - Place of Charme

10/10 Excellent
"Great stay"
Bridgette 1-night trip
Posted 15 hours ago
Villa Neroli - Place of Charme

Find out more about Castellina in Chianti

Search for holiday rentals in Castellina in Chianti on Expedia! You can easily find your home rentals, villas, holiday apartments in Castellina in Chianti using one of the methods below:

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Look no further and take a look at our great range of rental properties in Castellina in Chianti!

Frequently asked questions

Are there holiday rentals in Castellina in Chianti?

Yes, there are holiday rentals close to the most popular sights in Castellina in Chianti, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Castellina in Chianti has to offer?

Villa La Stella - Casa per Ferie: This holiday 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 holiday 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 holiday rentals will I find in Castellina in Chianti?

With 31 Expedia holiday rentals, you're guaranteed 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 holiday rental in Castellina in Chianti like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castellina in Chianti. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for families.