Castiglione del Bosco Holidays from £558

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Your Castiglione del Bosco Holiday

Take the guesswork out of travel planning with a Castiglione del Bosco holiday package. A great neighbourhood to stay in this vibrant city is Poggioferro, which is great for views and much more. Like to start exploring your surroundings? Tenuta Greppo Franco Biondi Santi, Fortress of Montalcino and Museum of Brunello are among the top places to visit during your trip to Castiglione del Bosco. That dream Castiglione del Bosco holiday is just clicks away. Search flights, accommodation and more on Expedia for an adventure that's tailored just for you.

Top Castiglione del Bosco Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Alfieri9

Alfieri9

3 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £974, price is now £558 per person
£558
per person
1 Jun - 6 Jun
found 2 hours ago
Return flight included
London (LGW) to Florence (FLR)
9.6/10 Exceptional! (159 reviews)
Hotel was in a nice quiet neighborhood, but still only a short walk to main attractions. The breakfast was excellent. Staff interactions were good.

Reviewed on 5 Dec 2025

Hotel Duomo Firenze

Hotel Duomo Firenze

3 out of 5
Historic Centre of Florence
Price was £1,287, price is now £701 per person
£701
per person
1 Jun - 6 Jun
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.2/10 Wonderful! (1,002 reviews)
Great location, excellent staff service, and the breakfast is fantastic!

Reviewed on 19 Mar 2026

Residenza Florentia

Residenza Florentia

1 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £1,623, price is now £1,016 per person
£1,016
per person
25 May - 30 May
found 24 hours ago
Return flight included
London (LHR) to Florence (FLR)
8.6/10 Excellent! (47 reviews)
Location, accommodations, and communication. Simple but comfortable. A basic facilities, and nice AC, elevator, and luggage storage.

Reviewed on 12 Jun 2025

Hotel Bijou Roof Terrace

Hotel Bijou Roof Terrace

3 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £1,110, price is now £702 per person
£702
per person
1 Jun - 6 Jun
found 2 hours ago
Return flight included
London (LGW) to Florence (FLR)
8.6/10 Excellent! (54 reviews)
Very confortable room for our family of 5! Great breakfast!

Reviewed on 27 Dec 2025

Art Hotel Villa Agape

Art Hotel Villa Agape

4 out of 5
Oltrarno
Save 100% on your flight
Price was £1,453, price is now £947 per person
£947
per person
12 Jun - 19 Jun
found 1 day ago
Return flight included
Birmingham (BHX) to Florence (FLR)
9.8/10 Exceptional! (1,000 reviews)
It was definitely an amazing experience staying in this hotel. Staff were friendly rooms were clean. It was a nice day for the time that I stayed six days. Breakfast was phenomenal and the garden was really beautiful. Me and my wife really enjoyed staying here for a honeymoon.

Reviewed on 2 Mar 2026

Castiglione del Bosco Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Max Temp Winter
10ºC
Max Temp Summer
29ºC
Top Sights
Castello Banfi, Tenuta Greppo Franco Biondi Santi and Capanna of Cencioni

Top hotels in Castiglione del Bosco

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

5 out of 5
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
The price is £1,095 per night from 19 Apr to 20 Apr
£1,095
19 Apr - 20 Apr
includes taxes & fees
Castiglion del Bosco, A Rosewood Hotel
Hotel Chiusarelli

Hotel Chiusarelli

3 out of 5
Viale Curtatone 15 Siena SI
Fully refundableReserve now, pay when you stay
The price is £89 per night from 22 Mar to 23 Mar
£89
22 Mar - 23 Mar
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
Nice staff, very good breakfast and the hotel is located near of the main attractions.

Reviewed on 18 Mar 2026

Hotel Chiusarelli
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34 Siena SI
Fully refundableReserve now, pay when you stay
The price is £96 per night from 27 Mar to 28 Mar
£96
27 Mar - 28 Mar
includes taxes & fees
9.4/10 Exceptional! (763 reviews)
This is a gem and well worth the stay!!! So so amazing

Reviewed on 20 Mar 2026

Palazzo Ravizza
See all 3,271 properties in Castiglione del Bosco
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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Popular places to visit

Tenuta Greppo Franco Biondi Santi

You can enjoy a tasting or tour at Tenuta Greppo Franco Biondi Santi during your travels to Montalcino. Discover the area's countryside and spas.

Tenuta Greppo Franco Biondi Santi

Castiglion del Bosco Winery

You can enjoy a tasting or tour at Castiglion del Bosco Winery during your travels to Castiglione del Bosco.

Castiglion del Bosco Winery

Museum of Brunello

You can spend time studying the exhibits at Museum of Brunello in Montalcino. Discover the area's countryside and spas.

Museum of Brunello

What to do in Castiglione del Bosco

3 Regions in 1 Day from Rome with Tuscany Wine Tasting & Lunch

From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch

£69
per adult
100% of travellers recommend
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
Seggiano: Guided Tour of the Olive Grove and Food Tasting

Seggiano: Guided Tour of the Olive Grove and Food Tasting

£22
per adult
Seggiano: Guided Tour of the Olive Grove and Food Tasting
Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

£39
per adult
Montalcino: Guided Winery Tour and Wine Tasting
See all activities in Castiglione del Bosco

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.