Castellina in Chianti Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

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, (32 reviews)
"Great place to stay in Tuscany! Very nice breakfast also!"
United States
Janet
The price is HK$1,785
HK$1,982 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$1,057
HK$1,199 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$741
HK$851 total
includes taxes & fees
16 Jun - 17 Jun
Mariani Bed & Breakfast
Property grounds

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
Property grounds

Casa il Cipresso, in the heart of Chianti with swimming pool

Casa il Cipresso, in the heart of Chianti with swimming pool
Castellina in Chianti
10.0 out of 10, Exceptional, (1 review)
"Beautiful setting with a rustic and friendly vibe. The place was clean and well-kept. We enjoyed every minute! A bonus was that the nights were cool (did t need the AC), and we slept with the windows open, despite the heat during the day."
Canada
Jon M.
Casa il Cipresso, in the heart of Chianti with swimming pool
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$1,153
HK$1,323 total
includes taxes & fees
25 Jun - 26 Jun
Casa Vacanze Squarcialupi
Interior

Casa Marisa in Castellina in Chianti

Casa Marisa in Castellina in Chianti
Castellina in Chianti
The price is HK$1,951
HK$2,439 total
includes taxes & fees
14 Jun - 15 Jun
Casa Marisa in Castellina in Chianti
Property grounds

CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL

CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
Castellina in Chianti
10.0 out of 10, Exceptional, (1 review)
"Lovely visit. The views are amazing. "
United States
lyndon s.
CASA DEGLI ULIVI - COTTAGE WITH SWIMMING POOL
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$771
HK$1,226 total
includes taxes & fees
12 Jul - 13 Jul
Apartment 'Poggio Della Capannina Di Castellina in Chianti' with Private Garden and Wi-Fi
Property grounds

Casa Antico Roseto - cottage with swimming pool

Casa Antico Roseto - cottage with swimming pool
Castellina in Chianti
8.0 out of 10, Very good, (2 reviews)
"The house was very charming 16th century stay. The gated patio off the bedroom was very convenient for morning coffee and evening wine. Such a beautiful countryside. The house is filled with antiques and furnishings, however, it’s time to update the mattresses. Taking the trash 6 minutes away to the indicated bins was a bit of an inconvenience as well. Very centrally located to Olive Oil and Chianti vineyards, a few towns from Panzano and Greece, gorgeous views and sunsets. "
United States
Brenna H.
Casa Antico Roseto - cottage with swimming pool
Outdoor dining

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
Property amenity

hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.2 out of 10, Very good, (74 reviews)
"Good location. The bed and pillows not so good ! "
United States
Sebastian
The price is HK$480
HK$555 total
includes taxes & fees
15 Jun - 16 Jun
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, (320 reviews)
"Beautiful place for family "
Canada
Ismail
The price is HK$510
HK$588 total
includes taxes & fees
17 Jun - 18 Jun
Hu Norcenni Girasole Village
Seasonal outdoor pool

Camping Village Panoramico Fiesole

Camping Village Panoramico Fiesole
3.0 star property
Fiesole
8.4 out of 10, Very good, (129 reviews)
"Loved that place. Only downside is the little roads getting there. Otherwise, all good. Thank you!"
United Kingdom
Jean-Pierre Olivier Paul
The price is HK$415
HK$493 total
includes taxes & fees
15 Jun - 16 Jun
Camping Village Panoramico Fiesole
Tasting room

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (211 reviews)
"Friendly staff and good location."
Canada
Yongseok
The price is HK$1,057
HK$1,199 total
includes taxes & fees
7 Jul - 8 Jul
Il Battistero Siena - Residenza d'Epoca
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (91 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$609
HK$706 total
includes taxes & fees
3 Jul - 4 Jul
Domus il Palio B&B
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.6 out of 10, Exceptional, (204 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is HK$827
HK$946 total
includes taxes & fees
3 Jul - 4 Jul
B&B Il Corso
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, (246 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$960
HK$1,092 total
includes taxes & fees
10 Jul - 11 Jul
La Terrazza Sul Campo Rooming House
Lobby lounge

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (339 reviews)
"Great stay highly recommend!!"
United States
jon
The price is HK$724
HK$833 total
includes taxes & fees
23 Jun - 24 Jun
ApartHotel Anghel
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (453 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$998
HK$1,134 total
includes taxes & fees
11 Jul - 12 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castellina in Chianti Hotel Reviews

Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

8/10 Good
"The hotel is just off a main road, very easy to drive to from the airport. There is parking onsite which is free. It's a good stopover if you don't need to go into Florence city centre and are driving onto elsewhere in Tuscany. Very much a business hotel. The interior of the hotel was modern and artistic. Rooms were very clean. The king bed is super comfortable. The bath is can be difficult to get in and out of as the glass comes out a lot and where you step into the bathtub is slanted so it can be dangerous, especially when wet! We expected the water to be restocked everyday after room cleaning but this was not the case however."
Yuenkie 2-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:

  • View our selection of featured holiday rentals in Castellina in Chianti
  • Use the map to find apartments and other holiday homes in the Castellina in Chianti neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Castellina in Chianti while they last

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?

Farmhouse in the heart of the real chiantishire: This highly rated holiday home rental in Castellina in Chianti is located in a rural location, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Some other homes for rent in Castellina in Chianti include Villa with large garden in the Chianti hills and 12km North of Siena with a stunning view pool &tennis 3ensuite bedrooms sleep 6.

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 Borgo di Vescine - Tenute di Castelvecchi, or get outside and enjoy nature at Chianti Sculpture Park. While here, City Hall Castellina In Chianti and Walls of Monteriggioni 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.