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

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Check prices for these dates

In two weeks
4 Sep - 6 Sep
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Castellina in Chianti holiday rentals

A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

1. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
9.8 out of 10, Exceptional, (17 reviews)
"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."
Japan
Chie
The price is 2.528.926 ₫
2.903.829 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Mariani Bed & Breakfast
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.

2. 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 3.243.837 ₫
3.690.338 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Residenzia del Sogno
A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

3. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
9.0 out of 10, Wonderful, (4 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 3.473.918 ₫
4.004.323 ₫ total
includes taxes & fees
25 Aug - 26 Aug
Casa Vacanze Squarcialupi
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

4. Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (36 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is 6.113.595 ₫
6.785.952 ₫ total
includes taxes & fees
31 Aug - 1 Sept
Riserva di Fizzano Residence
A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

5. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"
United States
Julia
The price is 8.310.516 ₫
9.263.578 ₫ total
includes taxes & fees
24 Aug - 25 Aug
Terre di Baccio
A stone building with a garden in front.

6. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
9.8 out of 10, Exceptional, (24 reviews)
"A very peaceful and relaxing B&B that I highly recommend, spacious rooms , clean and well maintained! Host were very pleasing and helpful… definitely recommend!!"
Canada
Sabatino
The price is 4.049.937 ₫
4.698.950 ₫ total
includes taxes & fees
23 Aug - 24 Aug
Borgo Argenina
A bakery display with pastries and a coffee station.

7. B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (205 reviews)
"Lovely B&B right in the heart of Siena. Pierre was incredibly helpful and kept me up to date prior to my arrival with suggestions for dining out, shopping and bars. Would highly recommend"
United Kingdom
Katherine
The price is 3.087.500 ₫
3.518.259 ₫ total
includes taxes & fees
23 Aug - 24 Aug
B&B Il Corso
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

IQ Hotel Firenze

IQ Hotel Firenze

10/10 Excellent
"Rooms were clean and nicely laid out. Excellent showers. The in-room refrigerator was kept stocked and was *free*! The included breakfast had lots of tasty options. I would definitely stay there again. Walkable to all the touristy stuff and also very close to the tram line."
James 7-night trip
Posted 3 hours ago
IQ Hotel Firenze

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.

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

With 26 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 Sentierelsa Trail. While here, City Hall Castellina In Chianti and Buondonno Winery 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.