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Check prices for these dates

In two weeks
16 Jan - 18 Jan
In two months
27 Feb - 1 Mar
In three months
27 Mar - 29 Mar
In four months
24 Apr - 26 Apr

Our top choices for Castellina in Chianti holiday rentals

Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, pool loungers
Residenzia del Sogno

Townhouse in Castellina in Chianti

Residenzia del Sogno
9.8 out of 10, Exceptional, (14)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is Rp2.562.507
Rp2.897.604 total
includes taxes & fees
2 Jan - 3 Jan 2026
Residenzia del Sogno
Seasonal outdoor pool
Agriturismo La Ferrozzola

Holiday Home in Castellina in Chianti

Agriturismo La Ferrozzola
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
Panoramic Apartment, Hill View (4) | Terrace/patio
Casa Vacanze Squarcialupi

Apartment in Castellina in Chianti

Casa Vacanze Squarcialupi
8.0 out of 10, Very good, (2)
"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 Rp2.032.068
Rp2.353.544 total
includes taxes & fees
7 Jan - 8 Jan 2026
Casa Vacanze Squarcialupi
Chalet | In-room safe, cots/infant beds, bed sheets
Hu Firenze Camping In Town

Camping in Florence

Hu Firenze Camping In Town
8.8 out of 10, Excellent, (1613)
"It was a grt place to stay"
United States
Sunitha
Hu Firenze Camping In Town
Exterior detail
Villa il Fedino

Townhouse in San Casciano in Val di Pesa

Villa il Fedino
9.6 out of 10, Exceptional, (97)
"Great people, great location great service"
Canada
James
The price is Rp2.459.470
Rp2.784.262 total
includes taxes & fees
9 Jan - 10 Jan 2026
Villa il Fedino
Courtyard
Relais la Corte di Cloris

Townhouse in Santissima Annunziata

Relais la Corte di Cloris
9.2 out of 10, Wonderful, (336)
"The room was clean, the staff wasm"
United States
Melissa
The price is Rp1.646.666
Rp2.047.872 total
includes taxes & fees
6 Jan - 7 Jan 2026
Relais la Corte di Cloris
Birthday party area
Siena Vip

Townhouse in Siena City Centre

Siena Vip
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
The price is Rp2.351.414
Rp2.665.401 total
includes taxes & fees
30 Dec - 31 Dec
Siena Vip
32-inch Smart TV with digital channels, TV, streaming services
B&B Il Corso

Townhouse in Siena City Centre

B&B Il Corso
9.8 out of 10, Exceptional, (192)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso
Lobby lounge
ApartHotel Anghel

Apartment in Siena

ApartHotel Anghel
8.4 out of 10, Very good, (335)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is Rp1.047.372
Rp1.230.955 total
includes taxes & fees
8 Jan - 9 Jan 2026
ApartHotel Anghel
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

Residence in Siena City Centre

La Terrazza Sul Campo Rooming House
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Bar (on property)
Il Battistero Siena - Residenza d'Epoca

Residence in Siena City Centre

Il Battistero Siena - Residenza d'Epoca
9.6 out of 10, Exceptional, (194)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Grand Apartment with Garden | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Regis Condo

Apartment in Siena City Centre

Regis Condo
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
Exterior
PALAZZO DEL PAPA

Townhouse in Siena City Centre

PALAZZO DEL PAPA
9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is Rp3.225.534
Rp3.626.933 total
includes taxes & fees
30 Dec - 31 Dec
PALAZZO DEL PAPA
Seasonal outdoor pool, open 8 AM to 8 PM, pool umbrellas, pool loungers
Tenuta Sant'Ilario

Townhouse in Gambassi Terme

Tenuta Sant'Ilario
9.4 out of 10, Exceptional, (33)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario
Outdoor pool, pool umbrellas, pool loungers
Chianti Village Morrocco

Residence in Barberino Tavarnelle

Chianti Village Morrocco
3.0 star property
8.6 out of 10, Excellent, (108)
"Spacious room in large resort style complex, set up as fully self contained with kitchen and dining furniture. Peaceful location with lovely views. Very pleasant staff and exceptional breakfast. "
France
Richard
Chianti Village Morrocco
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

Solo Experience Hotel

Solo Experience Hotel

10/10 Excellent
"Staff, clean and comfort, location, breakfast"
kevin 2-night trip
Posted 2 days ago
Solo Experience Hotel

Find out more about Castellina in Chianti

Search for holiday rentals in Castellina in Chianti on Expedia.co.id! 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?

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.

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

With 29 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 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.