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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 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
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 3.460.304 ₫
3.929.712 ₫ total
includes taxes & fees
16 Mar - 17 Mar
Residenzia del Sogno
Panoramic Apartment (2) | 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 2.923.089 ₫
3.400.203 ₫ total
includes taxes & fees
23 Feb - 24 Feb
Casa Vacanze Squarcialupi
City view from property

Boboli Living

Boboli Living
Historic Centre of Florence
The price is 2.353.512 ₫
2.958.718 ₫ total
includes taxes & fees
18 Feb - 19 Feb
Boboli Living
Deluxe Double Room, City View | 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
Deluxe Double Room (1° floor) | Egyptian cotton sheets, premium bedding, down duvets

Sette Angeli Rooms

Sette Angeli Rooms
Historic Centre of Florence
8.8 out of 10, Excellent, (640 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 1.929.411 ₫
2.492.207 ₫ total
includes taxes & fees
1 Mar - 2 Mar
Sette Angeli Rooms
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
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
Double Room | 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 4.641.710 ₫
5.229.166 ₫ total
includes taxes & fees
23 Feb - 24 Feb
PALAZZO DEL PAPA
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 2.604.327 ₫
2.988.045 ₫ total
includes taxes & fees
17 Feb - 18 Feb
Siena Vip
Property grounds

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (83 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
Domus il Palio B&B
Suite | Living room | Flat-screen TV

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
Superior Double Room, 1 Queen Bed, Private Bathroom, City View | Egyptian cotton sheets, premium bedding, down duvets, minibar

B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (63 reviews)
"Excellent host and location!"
United States
Kimberly
B&B Palazzo del Magnifico
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
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 2.326.697 ₫
3.484.035 ₫ total
includes taxes & fees
28 Feb - 1 Mar
Palazzo al Torrione 2
Garden

Tenuta Quadrifoglio

Tenuta Quadrifoglio
Gambassi Terme
10.0 out of 10, Exceptional, (5 reviews)
"A lovely spot for relaxation .The appartments were lovely and comfortable .the only criticism was you do need a car to get any where. It is totally in the middle of nowhere. "
United Kingdom
Geraldine
The price is 4.959.450 ₫
5.547.828 ₫ total
includes taxes & fees
17 Feb - 18 Feb
Tenuta Quadrifoglio
Deluxe Room, Patio | 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
Free daily buffet breakfast

Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (72 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
Terre di Baccio
Property entrance

Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (99 reviews)
"Great people, great location great service"
Canada
James
The price is 3.845.653 ₫
4.353.504 ₫ total
includes taxes & fees
24 Feb - 25 Feb
Villa il Fedino
View from room

Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Barberino Tavarnelle
8.6 out of 10, Excellent, (112 reviews)
"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

IQ Hotel Firenze

IQ Hotel Firenze

10/10 Excellent
"The hotel was very nice. The staff was very nice, very clean, very cozy. Just a beautiful hotel."
Katherine 3-night trip
Posted 1 day ago
IQ Hotel Firenze

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.