Castellina in Chianti Vacation 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
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Castellina in Chianti holiday rentals

Front of property

Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
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 RM443
RM515 total
includes taxes & fees
25 Feb - 26 Feb
Casa Vacanze Squarcialupi
Room amenity

San Giuliano Inn - Adults Only

San Giuliano Inn - Adults Only
Historic Centre of Florence
10.0 out of 10, Exceptional, (407 reviews)
"Great inn. "
United States
Carol
San Giuliano Inn - Adults Only
City view from property

Boboli Living

Boboli Living
Historic Centre of Florence
The price is RM357
RM448 total
includes taxes & fees
18 Feb - 19 Feb
Boboli Living
Egyptian cotton sheets, premium bedding, down duvets

Sette Angeli Rooms

Sette Angeli Rooms
Historic Centre of Florence
8.8 out of 10, Excellent, (638 reviews)
"The hotel manager, Maria, was very helpful in guiding us to a trusted overnight parking garage and was very willing in doing us a favor of mailing our package for us! The hotel location was great, very close to many of Florence’s main attractions!"
United States
Alexander
The price is RM360
RM452 total
includes taxes & fees
1 Mar - 2 Mar
Sette Angeli Rooms
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (426 reviews)
"Nice place!"
United States
Pavel
The price is RM395
RM454 total
includes taxes & fees
12 Feb - 13 Feb
Siena Vip
Minibar, desk, blackout curtains, free WiFi

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (97 reviews)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is RM703
RM792 total
includes taxes & fees
25 Feb - 26 Feb
PALAZZO DEL PAPA
Tasting room

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (196 reviews)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
Living room

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (239 reviews)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (82 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
Domus il Palio B&B
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (192 reviews)
"Great location"
United Kingdom
Mina
B&B Il Corso
Lobby lounge

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (335 reviews)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
ApartHotel Anghel
Daily continental breakfast (EUR 20 per person)

Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (116 reviews)
"What a gold mine , perfect location with friendly staff , beautiful hotel "
United States
Malinda
The price is RM679
RM766 total
includes taxes & fees
15 Feb - 16 Feb
Residenza d'Epoca Palazzo Borghesi
Balcony

Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (107 reviews)
"Great location, beautiful room with a terrace and the best breakfast we had in Italy! "
United States
Angel
The price is RM353
RM528 total
includes taxes & fees
18 Feb - 19 Feb
Palazzo al Torrione 2
Frette Italian sheets, premium bedding, minibar, in-room safe

Tenuta Sant'Ilario

Tenuta Sant'Ilario
Gambassi Terme
9.4 out of 10, Exceptional, (34 reviews)
"Amazing location and property! Owner and staff super nice! I am sure we will be back!"
Australia
Ilaria
Tenuta Sant'Ilario
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

Hotel Albani Firenze

Hotel Albani Firenze

10/10 Excellent
"Room was spacious and very clean"
Karen 4-night trip
Posted 4 days ago
Hotel Albani Firenze

Find out more about Castellina in Chianti

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

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

With 31 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.