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
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Castellina in Chianti holiday rentals

Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (34 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is 6.514.317 ₫
7.225.953 ₫ total
includes taxes & fees
10 Jul - 11 Jul
Riserva di Fizzano Residence
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers

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 3.521.918 ₫
3.994.517 ₫ total
includes taxes & fees
8 Jul - 9 Jul
Residenzia del Sogno
Lounge

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 2.469.557 ₫
2.836.799 ₫ total
includes taxes & fees
11 Jul - 12 Jul
Mariani Bed & Breakfast
Panoramic Apartment (2) | Terrace/patio

Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
8.8 out of 10, Excellent, (3 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 3.664.902 ₫
4.212.003 ₫ total
includes taxes & fees
2 Aug - 3 Aug
Casa Vacanze Squarcialupi
Courtyard

I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (168 reviews)
"Excelente "
Brazil
Osvaldo
The price is 2.567.963 ₫
3.185.981 ₫ total
includes taxes & fees
12 Jul - 13 Jul
I Parigi Corbinelli
Property amenity

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (83 reviews)
"Good location. The bed and pillows not so good ! "
United States
Sebastian
The price is 1.453.100 ₫
1.688.716 ₫ total
includes taxes & fees
8 Jul - 9 Jul
hu Firenze Certosa camping in town
Exterior

Hu Norcenni Girasole Village

Hu Norcenni Girasole Village
4.0 star property
Figline e Incisa Valdarno
8.6 out of 10, Excellent, (321 reviews)
"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."
United States
Kalinka
The price is 4.390.083 ₫
4.919.398 ₫ total
includes taxes & fees
8 Jul - 9 Jul
Hu Norcenni Girasole Village
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (203 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is 3.046.957 ₫
3.472.059 ₫ total
includes taxes & fees
12 Jul - 13 Jul
B&B Il Corso
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (94 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
The price is 2.025.917 ₫
2.348.805 ₫ total
includes taxes & fees
15 Jul - 16 Jul
Domus il Palio B&B
Lobby lounge

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (341 reviews)
"Great stay highly recommend!!"
United States
jon
The price is 2.291.956 ₫
2.641.558 ₫ total
includes taxes & fees
21 Jul - 22 Jul
ApartHotel Anghel
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (248 reviews)
"The location was amazing. I will never forget the view. Room was huge and access to restaurants and shopping. Also fantastic. We want to go back again already."
United States
Margaret
The price is 3.168.995 ₫
3.606.302 ₫ total
includes taxes & fees
10 Jul - 11 Jul
La Terrazza Sul Campo Rooming House
Double Room | Minibar, desk, blackout curtains, free WiFi

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (108 reviews)
"Fantastic location, walkable to everything, very clean & Hamza was a great host with lots of tips on what to see & where to eat"
United Kingdom
Diane
The price is 4.617.900 ₫
5.200.096 ₫ total
includes taxes & fees
9 Jul - 10 Jul
PALAZZO DEL PAPA
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (463 reviews)
"It’s very close to the historical center but feels quiet and like you are separate from it. I loved our stay"
United States
David
The price is 3.441.382 ₫
3.905.927 ₫ total
includes taxes & fees
8 Jul - 9 Jul
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

Hotel Horto Convento

Hotel Horto Convento

10/10 Excellent
"Beautiful, clean, amazing breakfast, really nice staff. 10/10 recommendation"
Jennifer 5-night trip
Posted 1 hour ago
Hotel Horto Convento

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 25 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.