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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
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
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 3.468.185 ₫
3.938.567 ₫ total
includes taxes & fees
4 Jan - 5 Jan
Residenzia del Sogno
Panoramic Apartment, Hill View (4) | Terrace/patio
Casa Vacanze Squarcialupi

Apartment in Castellina in Chianti

Casa Vacanze Squarcialupi
8.8 out of 10, Excellent, (3)
"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 3.184.524 ₫
3.688.320 ₫ total
includes taxes & fees
7 Jan - 8 Jan
Casa Vacanze Squarcialupi
Food and drink
San Giuliano Inn - Adults Only

Townhouse in Historic Centre of Florence

San Giuliano Inn - Adults Only
10.0 out of 10, Exceptional, (406)
"Great inn. "
United States
Carol
San Giuliano Inn - Adults Only
Deluxe Double Room (1° floor) | Egyptian cotton sheets, premium bedding, down duvets
Sette Angeli Rooms

Townhouse in Historic Centre of Florence

Sette Angeli Rooms
8.8 out of 10, Excellent, (636)
"I loved this place and the stuff was very kind <3 "
United Kingdom
romina
The price is 2.138.627 ₫
2.723.030 ₫ total
includes taxes & fees
6 Jan - 7 Jan
Sette Angeli Rooms
Premier Apartment | Private kitchen | Coffee/tea maker, electric kettle
My Guest In Florence

Townhouse in Historic Centre of Florence

My Guest In Florence
9.0 out of 10, Wonderful, (125)
"My kids and I had a wonderful stay. The apartment was very nice and clean. Directions for checking in were clear and the staff was very helpful. "
United States
Susie
My Guest In Florence
Birthday party area
Siena Vip

Townhouse in Siena City Centre

Siena Vip
9.2 out of 10, Wonderful, (423)
"A great location!"
Canada
Cheryl
The price is 3.069.599 ₫
3.500.073 ₫ total
includes taxes & fees
4 Jan - 5 Jan
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
Exterior
PALAZZO DEL PAPA

Townhouse in Siena City Centre

PALAZZO DEL PAPA
9.6 out of 10, Exceptional, (97)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is 3.789.628 ₫
4.292.104 ₫ total
includes taxes & fees
2 Feb - 3 Feb
PALAZZO DEL PAPA
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, (195)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
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
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 1.529.261 ₫
1.805.750 ₫ total
includes taxes & fees
6 Jan - 7 Jan
ApartHotel Anghel
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
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, (34)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario
Terrace/patio
Palazzo Alfieri Residenza d’epoca

Residence in Historic Centre of Florence

Palazzo Alfieri Residenza d’epoca
9.2 out of 10, Wonderful, (728)
"This was such a lovely hotel! It was in a great location with an incredible view. The staff was great and the breakfast was absolutely fantastic! I would highly recommend this hotel "
United States
Christine
The price is 3.795.381 ₫
4.607.389 ₫ total
includes taxes & fees
8 Jan - 9 Jan
Palazzo Alfieri Residenza d’epoca
Terrace/patio
Numa Palazzo San Niccolò

Apartment in Historic Centre of Florence

Numa Palazzo San Niccolò
9.4 out of 10, Exceptional, (176)
"Great stay . Super location"
United States
Kedar
The price is 2.298.269 ₫
2.898.784 ₫ total
includes taxes & fees
7 Jan - 8 Jan
Numa Palazzo San Niccolò
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 Pendini

Hotel Pendini

10/10 Excellent
"Super clean, great service, perfectly located. "
Luis 2-night trip
Posted 1 day ago
Hotel Pendini

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 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.