Castiglione del Bosco Holidays from £249

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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.
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £443, price is now £249 per person
£249
per person
6 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
Highly recommended

Reviewed on 30 Jun 2026

Hotel Bencista

Hotel Bencista

3 out of 5
Price was £1,181, price is now £622 per person
£622
per person
23 Aug - 29 Aug
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
6.8/10 (28 reviews)
Terribile. Esperienza da incubo, ci hanno rovinato la serata. Arriviamo alle 18:00 per il check-in e non c’è nessuno. Nessun messaggio, nessuna email, nessun preavviso con il codice di accesso. Nulla. Siamo costrette a chiamare un numero, restando fuori con tutte le valigie, mentre una persona al telefono ci chiede i documenti prima ancora di darci il codice. Situazione già assurda. Entriamo finalmente in stanza e la televisione non funziona. Zero canali, completamente inutilizzabile. Richiamiamo il numero del check-in e la signorina ci passa un altro numero, dicendo che “ci avrebbero aiutato loro”. Chiamiamo e risponde una persona estremamente scortese e cafona, che invece di scusarsi per il disagio esordisce con: “Innanzitutto chi vi ha dato questo numero? Io non sono nel mio orario lavorativo, prenderò provvedimenti” e subito dopo: “Io non sono un tecnico della televisione”. Nessuna scusa. Nessuna disponibilità. Trattate come se i loro problemi aziendali fossero colpa nostra. A quel punto chiedo il rimborso per poter andare in un’altra struttura. Mi viene risposto che “non hanno potere decisionale” e che la manager mi avrebbe contattata il giorno dopo. Mai sentiti. Spariti. Zero professionalità, zero assistenza, zero rispetto per il cliente. State lontani mille miglia.

Reviewed on 27 Feb 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £1,728, price is now £933 per person
£933
per person
11 Sept - 18 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
9.6/10 Exceptional! (568 reviews)
Very nice and friendly staff, good breakfast, nice and clean hotel

Reviewed on 18 Jun 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £462, price is now £256 per person
£256
per person
6 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Florence (FLR)
7.4/10 Good! (1,014 reviews)
Room was clean, breakfast was decent. In general, it was a good stay. Would likely consider staying again.

Reviewed on 30 Jun 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £1,649, price is now £929 per person
£929
per person
11 Sept - 18 Sept
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
8.6/10 Excellent! (490 reviews)
Very good location. Clean hotel. Our ac was broken but they handled us a new room inmediately. The hotel is confortable and size of the rooms are decent. Bigger than average in the area.

Reviewed on 26 Jun 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 £1,916 per night from 27 Jul to 28 Jul
£1,916
27 Jul - 28 Jul
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 £143 per night from 29 Jul to 30 Jul
£143
29 Jul - 30 Jul
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Excellent service from the staff on reception and the terrace restaurant. The room and balcony was clean and well maintained. Awesome breakfast."

Reviewed on 14 Jun 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 £127 per night from 22 Jul to 23 Jul
£127
22 Jul - 23 Jul
includes taxes & fees
9.4/10 Exceptional! (820 reviews)
"We have always loved staying ar Ravizza (since the 1980s). We like the rooms, the food, anf the view from the rear terrace every afternoon is completely unbeatable in Tuscany. However, the terrace has been invaded by weeds, and the general state of maintenance could use a littke more extra ..."

Reviewed on 28 Jun 2026

Palazzo Ravizza
See all 3,360 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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Stay near popular Castiglione del Bosco attractions

Castiglion del Bosco Winery

9.6/10 (5 reviews)
You can enjoy a tasting or tour at Castiglion del Bosco Winery during your travels to Castiglione del Bosco.
See properties

What to do in Castiglione del Bosco

Montepulciano Gran Tour

Montepulciano Gran Tour

£13
per adult
Montepulciano Gran Tour
Montalcino: Guided Winery Tour and Wine Tasting

Montalcino: Guided Winery Tour and Wine Tasting

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

Frequently asked questions

How much does a Castiglione del Bosco travel package cost?
Tailor make your Castiglione del Bosco travel package from just £249. Pick from any combination of hotels, flights and rental cars to build the trip you've been dreaming about. Remember to add on one or two experiences!
If I'm not able to travel, can I cancel my Castiglione del Bosco travel package?
We understand — life can throw you the odd curveball. If you've locked in a Castiglione del Bosco travel package and need to cancel or change it, we're here to help. It's always worth checking out our Customer Service Portal first for information. But generally speaking, if you've taken out your package within 24 hours, you may be able to cancel and rebook for free. If it's been more than 24 hours, your airline, hotel or car rental company may impose a charge.
How do I get a cheap travel package to Castiglione del Bosco?
Book everything in the one place with our Castiglione del Bosco travel packages. You'll discover deals on flights, hotels and more that'll keep your travel budget happy and your adventurous spirit full. And, with more than 550 partner airlines and 1,000,000 hotels around the globe to pick from, there are endless opportunities to mix and match all you want.
Does Expedia offer Book Now, Pay Later Castiglione del Bosco holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has devised a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book a fantastic getaway without eating away at your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your trip. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month works for you, Klarna can help. Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: If you'd prefer to pay off your escape in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: Clicking the "book now" button is easier with this plan. Put down a small deposit on your holiday and then start working on your travel itinerary.

What are the top hotels in Castiglione del Bosco?
If it's your first time in Castiglione del Bosco, lock in a room at Castello Banfi - Il Borgo or Dimora Delle Muse. Both offer friendly service and are popular options with many travellers.
How far in advance should I book my Castiglione del Bosco holiday?
It depends on the air carrier, but you can normally look up international flights on Expedia nearly a year in advance. While it's generally recommended to book ahead of time, lucky customers occasionally find a cheaper ticket just weeks before the date of departure.
What does an Expedia Castiglione del Bosco travel package include?
Rental cars, hotels and flights — you'll discover them all here. With Expedia, you can shape your Castiglione del Bosco package your way. All you have to do is work out what you need. Once you've made your booking, you can add on extras like tours and activities. The more you bundle, the greater the savings!
What should I know before booking a Castiglione del Bosco travel package?
When you book your hotels, flights and car rentals together, you'll walk away with great discounts. Whether you're planning an outdoor getaway in a chalet or would rather stay in a comfortable hotel in the city, Expedia can make it happen for less.
Can I choose my airline with a Castiglione del Bosco Expedia travel package?
With a travel package, you're in charge. Whether you're looking to fly to Castiglione del Bosco in coach or business class, simply choose from the available airline options. Expedia has access to more than 550 partner airlines across the world.

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.