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
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Castellina in Chianti holiday rentals

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 HK$709
HK$815 total
includes taxes & fees
28 Jul - 29 Jul
Mariani Bed & Breakfast
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 HK$956
HK$1,106 total
includes taxes & fees
21 Aug - 22 Aug
Casa Vacanze Squarcialupi
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 HK$1,001
HK$1,137 total
includes taxes & fees
28 Jul - 29 Jul
Residenzia del Sogno
Aerial view

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 HK$1,911
HK$2,120 total
includes taxes & fees
7 Aug - 8 Aug
Riserva di Fizzano Residence
Property grounds

Villa with large garden in the Chianti hills

Villa with large garden in the Chianti hills
Siena
9.6 out of 10, Exceptional, (81 reviews)
"It was a little tricky finding the villa but worth it. Better instructions would be helpful. The home was lovely. The gardens wonderful. A great respite fromThe city."
United States
Julie H.
Villa with large garden in the Chianti hills
Exterior

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 HK$734
HK$1,183 total
includes taxes & fees
28 Jul - 29 Jul
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
TV

Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is HK$2,071
HK$2,552 total
includes taxes & fees
29 Jul - 30 Jul
Casa Marisa in Castellina in Chianti
Property grounds

Casa Antico Roseto - cottage with swimming pool

Casa Antico Roseto - cottage with swimming pool
Castellina in Chianti
8.8 out of 10, Excellent, (3 reviews)
"The borgo was perfect for our family of 6 adults. The views from the pool were spectacular. We had what we needed in kitchen and we grilled one night. The stone structure set on mountainside gave natural coolness for comfort with amazing views- even from the shower! There is AC which we didn’t use but good idea for peak summer. We walked to a great restaurant and also walked to winery for wine tasting. We shared the property but it felt private with our own outdoor dining areas. Maurizio was...
United States
Lisa S.
Casa Antico Roseto - cottage with swimming pool
Outdoor dining

The Arch Among the Hills of Castellina

The Arch Among the Hills of Castellina
Topina
The price is HK$1,993
HK$2,340 total
includes taxes & fees
2 Aug - 3 Aug
The Arch Among the Hills of Castellina
Property grounds

Casa Belvedere cottage with swimming pool in the heart of Chianti

Casa Belvedere cottage with swimming pool in the heart of Chianti
Castellina in Chianti
Casa Belvedere cottage with swimming pool in the heart of Chianti
Interior

Apartment 'La Casa Della Gina' with Wi-Fi

Apartment 'La Casa Della Gina' with Wi-Fi
Castellina in Chianti
The price is HK$4,280
HK$4,673 total
includes taxes & fees
31 Jul - 1 Aug
Apartment 'La Casa Della Gina' with Wi-Fi
Egyptian cotton sheets, premium bedding, down duvets

Sette Angeli Rooms

Sette Angeli Rooms
Historic Centre of Florence
8.8 out of 10, Excellent, (674 reviews)
"Good clean rooms and very close to the city center as well as the train station"
United Kingdom
VISHAL
The price is HK$643
HK$814 total
includes taxes & fees
30 Jul - 31 Jul
Sette Angeli Rooms
Premium bedding, down duvets, in-room safe, blackout curtains

Maison Ginori Guelfa

Maison Ginori Guelfa
Historic Centre of Florence
10.0 out of 10, Exceptional, (36 reviews)
"This was an incredible stay. The host was a phenomenal communicator and the property is as beautiful as pictured. If you want to be downtown in the heart of Florence, this is the perfect place to be and it is also far enough from the standard noise. I had peaceful nights and peaceful days, if I chose a late morning. It was literally near everything and I walked to every place I wanted to see. It was safe and easy to get to. I would absolutely stay at this property again and couldn’t have asked...
United States
Joyce
The price is HK$1,280
HK$1,515 total
includes taxes & fees
31 Jul - 1 Aug
Maison Ginori Guelfa
Room amenity

San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
9.8 out of 10, Exceptional, (444 reviews)
"Clean, friendly staff. Great location. "
United States
Jeannette
The price is HK$1,167
HK$1,391 total
includes taxes & fees
28 Jul - 29 Jul
San Giuliano Inn - Adults Only
Free daily buffet breakfast

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 HK$2,430
HK$2,708 total
includes taxes & fees
2 Aug - 3 Aug
Terre di Baccio
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (96 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 HK$527
HK$615 total
includes taxes & fees
2 Aug - 3 Aug
Domus il Palio B&B
Exterior

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 HK$3,335
HK$3,739 total
includes taxes & fees
9 Aug - 10 Aug
Borgo Argenina
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 HK$903
HK$1,029 total
includes taxes & fees
28 Jul - 29 Jul
B&B Il Corso
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (467 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 HK$1,015
HK$1,152 total
includes taxes & fees
11 Aug - 12 Aug
Siena Vip
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 HK$943
HK$1,073 total
includes taxes & fees
26 Aug - 27 Aug
La Terrazza Sul Campo Rooming House
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

Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

10/10 Excellent
"Nice stay"
Brianna 3-night trip
Posted 1 hour ago
Radisson Blu Hotel, Florence

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 of 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 27 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, Buondonno Winery and City Hall Castellina In Chianti 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.