Castiglione del Bosco Holidays from £320

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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.
Via Del Santo

Via Del Santo

1 out of 5
Price was £592, price is now £320 per person
£320
per person
7 Sept - 11 Sept
found 1 day ago
Return flight included
London (LON) to Pisa (PSA)
8.8/10 Excellent! (43 reviews)
Excellent location. Great property

Reviewed on 18 Jul 2026

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £1,556, price is now £871 per person
£871
per person
21 Sept - 27 Sept
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
8.6/10 Excellent! (493 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

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £645, price is now £366 per person
£366
per person
11 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Florence (FLR)
7.6/10 Good! (1,010 reviews)
La chambre est bien équipée

Reviewed on 18 Jul 2026

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £639, price is now £364 per person
£364
per person
11 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Florence (FLR)
7.4/10 Good! (1,017 reviews)

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was £4,317, price is now £2,499 per person
£2,499
per person
11 Sept - 18 Sept
found 24 hours ago
Return flight included
London (LON) to Florence (FLR)
9.6/10 Exceptional! (147 reviews)
Magical location, pools, staff, property.

Reviewed on 19 Jul 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 £1,464 per night from 2 Aug to 3 Aug
£1,464
2 Aug - 3 Aug
includes taxes & fees
Castiglion del Bosco, A Rosewood Hotel
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

5 out of 5
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
The price is £315 per night from 26 Jul to 27 Jul
£315
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (618 reviews)
"The staff was wonderful. The service was beyond my expectations. They even have a pillow menu. It is close to shopping, and restaurants. Everything was clean and beautiful."

Reviewed on 20 Jul 2026

Grand Hotel Continental Siena – Starhotels Collezione
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
The price is £136 per night from 21 Aug to 22 Aug
£136
21 Aug - 22 Aug
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"Great hotel with helpful staff. Restaurant was really good definitely recommend."

Reviewed on 21 Jul 2026

Hotel Athena
See all 3,375 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 £320. 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.

* 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.