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Check prices for these dates

In two weeks
17 Apr - 19 Apr
In two months
29 May - 31 May
In three months
26 Jun - 28 Jun
In four months
24 Jul - 26 Jul

Our top choices for Castellina in Chianti holiday rentals

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 2.619.945 ₫
3.003.411 ₫ total
includes taxes & fees
17 Apr - 18 Apr
Mariani Bed & Breakfast
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
The price is 3.332.815 ₫
3.787.446 ₫ total
includes taxes & fees
6 Apr - 7 Apr
Agriturismo La Ferrozzola
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 3.581.103 ₫
4.121.581 ₫ total
includes taxes & fees
7 Apr - 8 Apr
Casa Vacanze Squarcialupi
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 3.405.989 ₫
3.868.029 ₫ total
includes taxes & fees
3 May - 4 May
Residenzia del Sogno
Aerial view

Riserva di Fizzano Residence

Riserva di Fizzano Residence
3.0 star property
Castellina in Chianti
9.8 out of 10, Exceptional, (25 reviews)
"Perfect location on the top of a hill surrounded by the beautiful vineyards of Chianti. Enjoy the view by the pool or the fabulous sunset with a glass of wine. The staff were friendly and the restaurant was 5 star. I highly recommend a stay to fulfill all your Tuscan dreams. "
United States
Eileen
The price is 4.696.242 ₫
5.226.541 ₫ total
includes taxes & fees
11 Apr - 12 Apr
Riserva di Fizzano Residence
City view from property

Boboli Living

Boboli Living
Historic Centre of Florence
10.0 out of 10, Exceptional, (2 reviews)
"The room was perfect, the location is near to all main attractions of the city and is 15 minutes away from the train station."
United States
Rustinko
The price is 6.382.885 ₫
7.385.910 ₫ total
includes taxes & fees
12 Apr - 13 Apr
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, (412 reviews)
"Well located, lovely kind staff beautifully appointed. "
Canada
Nancy
The price is 4.700.125 ₫
5.534.873 ₫ total
includes taxes & fees
6 Apr - 7 Apr
San Giuliano Inn - Adults Only
Food court

Home in Florence

Home in Florence
Historic Centre of Florence
9.0 out of 10, Wonderful, (71 reviews)
"Lovely room and the people running the place were friendly and efficient "
United Kingdom
Thomas
Home in Florence
Breakfast meal

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (197 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is 3.076.562 ₫
3.505.797 ₫ total
includes taxes & fees
8 Apr - 9 Apr
B&B Il Corso
Tasting room

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (200 reviews)
"Room was excellent, location was perfect for seeing Siena and restaurant was also excellent"
United Kingdom
John
The price is 3.961.534 ₫
4.479.267 ₫ total
includes taxes & fees
6 Apr - 7 Apr
Il Battistero Siena - Residenza d'Epoca
Double Room | Minibar, desk, blackout curtains, free WiFi

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (98 reviews)
"Great host! The rooms were super clean and comfy. Highly recommend! 5 stars!"
United Kingdom
Amena
The price is 5.129.242 ₫
5.763.746 ₫ total
includes taxes & fees
9 Apr - 10 Apr
PALAZZO DEL PAPA
Room amenity

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (430 reviews)
"Nice place!"
United States
Pavel
The price is 3.021.509 ₫
3.445.239 ₫ total
includes taxes & fees
12 Apr - 13 Apr
Siena Vip
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, (120 reviews)
"Great location and down right elegant!"
United States
William
The price is 5.515.905 ₫
6.188.845 ₫ total
includes taxes & fees
7 Apr - 8 Apr
Residenza d'Epoca Palazzo Borghesi
City view

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (68 reviews)
"Adequate basic clean room in a beautiful area."
United States
Margaret
The price is 2.904.577 ₫
3.316.614 ₫ total
includes taxes & fees
15 Apr - 16 Apr
Regis Condo
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, (64 reviews)
"Excellent host and location!"
United States
Kimberly
The price is 3.259.073 ₫
3.706.330 ₫ total
includes taxes & fees
5 May - 6 May
B&B Palazzo del Magnifico
Suite | 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, (239 reviews)
"Huge room! Great location "
Canada
karen
The price is 4.752.348 ₫
5.349.162 ₫ total
includes taxes & fees
20 Apr - 21 Apr
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, (83 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
The price is 1.889.997 ₫
2.200.576 ₫ total
includes taxes & fees
7 Apr - 8 Apr
Domus il Palio B&B
Lobby lounge

ApartHotel Anghel

ApartHotel Anghel
Siena
8.4 out of 10, Very good, (336 reviews)
"Would recommend staying here and will hopefully be back!"
Canada
Lisa
The price is 2.432.762 ₫
2.797.389 ₫ total
includes taxes & fees
12 Apr - 13 Apr
ApartHotel Anghel
Exterior

Le Mascie Country House

Le Mascie Country House
Casole d'Elsa
9.2 out of 10, Wonderful, (9 reviews)
"We loved our stay. The property is quiet and private but is in close proximity to a small town. Very charming and the pool was an added bonus. "
United States
Misti
Le Mascie Country House
Terrace/patio

Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (99 reviews)
"A nice blend of old world charm and modern conveniences. It is far from "
United States
John
The price is 2.707.041 ₫
3.038.420 ₫ total
includes taxes & fees
26 Apr - 27 Apr
Palazzo Pacini
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

Grand Hotel Cavour

Grand Hotel Cavour

10/10 Excellent
"The hotel was fantastic. Great style, friendly staff and the rooms and bathrooms were lacking nothing as Americans used to hotels back home. Rooftop bar was a nightly visit and The bar staff were great. "
Matt 3-night trip
Posted 5 hours ago
Grand Hotel Cavour

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 28 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 Chianti Observatory, 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.