Castiglione del Bosco Holidays from £315

Book a Hotel + Flight or Car together to unlock savings

Photo by tom owens

  • Plan, book, travel with confidence

  • Better together

    Save up to £335 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 £561, price is now £315 per person
£315
per person
2 Jul - 5 Jul
found 15 hours ago
Return flight included
London (LGW) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
Breakfast was ok but we found it difficult to get healthy food. There seemed to be a finite amount of fruit and yogurt (managed to get a yogurt one morning out of four). That said we opted for 8 am breakfast and might have had more luck earlier. Hotel was well located and felt really secure. I would stay there again.

Reviewed on 13 Apr 2026

EXE Toscana

EXE Toscana

4 out of 5
Lucca Historical Center
Price was £990, price is now £491 per person
£491
per person
27 Jun - 3 Jul
found 16 hours ago
Return flight included
London (LGW) to Florence (FLR)
8.4/10 Very Good! (822 reviews)
Room was run down and the breakfast was included in the past but not now. Staff said that the name change and rebranding was meant to attract business people but there were no working outlets in the room and no usb or other charging outlets apart from one socket in the bathroom. Very inconvenient. The place was much nicer to stay at in the past 15 years but has been let down by its owners sadly.

Reviewed on 14 Apr 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £2,248, price is now £1,124 per person
£1,124
per person
18 May - 25 May
found 24 hours ago
Return direct flight included
Edinburgh (EDI) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
You have a lot of restaurants in a short walking distance. You have a famous sandwich shop you must try. Train station not too far. The hotel is very small. The staff is the best part

Reviewed on 17 Apr 2026

Park Hotel Villa Ariston

Park Hotel Villa Ariston

4 out of 5
Save 100% on your flight
Price was £1,646, price is now £890 per person
£890
per person
20 Jun - 27 Jun
found 1 day ago
Return direct flight included
London (LHR) to Florence (FLR)
8.8/10 Excellent! (128 reviews)
Amazing property with good facilities. Easy access to the beach and local restaurants. Simming pool is excellent and the staff very friendly. You can have a nice and peaceful stay there

Reviewed on 8 Sept 2024

Residenza Florentia

Residenza Florentia

1 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £976, price is now £573 per person
£573
per person
26 May - 29 May
found 1 day ago
Return direct flight included
London (LHR) to Florence (FLR)
8.4/10 Very Good! (48 reviews)
The hotel staff were extremely friendly and highly professional – honestly, I’ve rarely experienced this level of service. The hotel is in a perfect location, right in the city center, which is a huge advantage. Everything was clean, well-maintained, and very comfortable. I would highly recommend this place to anyone looking for quality accommodation.

Reviewed on 6 Apr 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 £1,489 per night from 25 Apr to 26 Apr
£1,489
25 Apr - 26 Apr
includes taxes & fees
10/10 Exceptional! (75 reviews)
If you don’t like th it s place, then there will never be a place on earth that you like.. it’s actually above a 5 star!! Over the top service.. food seasons breakfast fantastic…fell very lucky to have stayed here.. thank you

Reviewed on 8 Apr 2026

Castiglion del Bosco, A Rosewood Hotel
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
The price is £190 per night from 23 Apr to 24 Apr
£190
23 Apr - 24 Apr
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
Cafeteria buffet breakfast. Loads of food. But we didn't come to Italy to eat American-style big breakfasts. Everything else was fine.

Reviewed on 15 Apr 2026

Hotel Athena
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34 Siena SI
Fully refundableReserve now, pay when you stay
The price is £185 per night from 23 Apr to 24 Apr
£185
23 Apr - 24 Apr
includes taxes & fees
9.4/10 Exceptional! (778 reviews)
Excellent all around

Reviewed on 15 Apr 2026

Palazzo Ravizza
See all 3,264 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

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

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
Montepulciano Gran Tour

Montepulciano Gran Tour

£13
per adult
Montepulciano Gran Tour
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.