Castiglione del Bosco Holidays from £371

Book a Hotel + Flight or Car together to unlock savings

Photo by tom owens

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

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.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £746, price is now £371 per person
£371
per person
26 Jul - 31 Jul
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Great location, lots restaurants shops nearby. Easy to access centre. Room modern reasonably clean but very small. Shower like a postage stamp.

Reviewed on 3 Jun 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £777, price is now £380 per person
£380
per person
26 Jul - 31 Jul
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
Clean, modern room w/AC, perfect for me traveling solo. It’s hot in the halls but the room was comfortable. Bonus free cappuccino (and breakfast). Easy and convenient.

Reviewed on 2 Jun 2026

SPLENDIDE RIVIERA

SPLENDIDE RIVIERA

4 out of 5
Save 100% on your flight
Price was £1,764, price is now £1,006 per person
£1,006
per person
8 Aug - 15 Aug
found 1 day ago
Return flight included
London (LON) to Pisa (PSA)
9.8/10 Exceptional! (16 reviews)
The property was very nice, very clean and well maintained. The staff was amazing and always ready to help. Breakfast was great as well!We will definitely return here next year!

Reviewed on 28 May 2026

Castello di Leonina Relais

Castello di Leonina Relais

4 out of 5
Save 100% on your flight
Price was £1,236, price is now £736 per person
£736
per person
19 Aug - 26 Aug
found 23 hours ago
Return flight included
London (LON) to Florence (FLR)
9/10 Wonderful! (129 reviews)
Such a beautiful and relaxing place. Central to many day trip locations in Tuscany. The staff were excellent in all aspects of kindness and professionalism. Would definitely recommend to anyone who asks where the best place to stay would be. Again, thank you to all. Dario

Reviewed on 28 May 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £1,359, price is now £810 per person
£810
per person
6 Aug - 9 Aug
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.6/10 Exceptional! (65 reviews)
Agradable estancia. Excelente servicio. La habitación la mantenían siempre limpia. Todo queda cerca del área. Muy recomendable

Reviewed on 23 May 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
The price is £1,890 per night from 23 Jun to 24 Jun
£1,890
23 Jun - 24 Jun
includes taxes & fees
Castiglion del Bosco, A Rosewood Hotel
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
The price is £174 per night from 4 Jul to 5 Jul
£174
4 Jul - 5 Jul
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Location is good. Large property with good parking. Staff is very helpful and friendly. The hotel aesthetic is bland and utilitarian. Breakfast is good. The rooftop deck is lovely but small."

Reviewed on 26 May 2026

Hotel Athena
Hotel Executive

Hotel Executive

4 out of 5
Via Nazareno Orlandi 32 Siena SI
Fully refundableReserve now, pay when you stay
The price is £71 per night from 7 Jun to 8 Jun
£71
7 Jun - 8 Jun
includes taxes & fees
8.4/10 Very Good! (538 reviews)
"excellent breakfast and very clean"

Reviewed on 27 Apr 2026

Hotel Executive
See all 3,299 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

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

4/5(1 review)

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

Montepulciano Gran Tour

Montepulciano Gran Tour

£13
per adult
Montepulciano Gran Tour
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
Montepulciano: Winery Tour and Tasting

Montepulciano: Winery Tour and Tasting

£30
per adult
100% of travellers recommend
Montepulciano: Winery Tour and Tasting
See all activities in Castiglione del Bosco

Explore a world of travel with Expedia

* 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.