Castiglione del Bosco Holidays from £180
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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.
La Villa di STR
Siena Historical Center
£180
per person
2 Dec - 5 Dec
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.2/10 Wonderful! (450 reviews)
We had a great stay at La Villa. We spent 4 days bicycling and our rental company was able to coordinate drop off and pick up without us needing to be involved. They had a storage area for our bikes. Location was away from the crowds but close enough to walk to all of the sites. Breakfast was excellent.
Reviewed on 13 Oct 2026
Aurum Uffizi
Historic Centre of Florence
£423
per person
31 Dec - 3 Jan
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
The staff was excellent, especially Joshua. The room was cleaned daily. Breakfast was ok.
Reviewed on 20 Oct 2026
Monastero di Cortona Hotel & Spa
Cortona Old Town
£541
per person
12 Dec - 18 Dec
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
10/10 Exceptional! (337 reviews)
Amazing service and care. Especially Sara, Mathilda, Fredrico and Allesandro. The manager was so helpful as well. A must stay!
Reviewed on 20 Oct 2026
Eurostars Florence Boutique
Historic Centre of Florence
£362
per person
21 Nov - 27 Nov
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
8.6/10 Excellent! (503 reviews)
The bed was comfortable but low to the floor. The shower was very slippery and could have used a shower mat. The breakfast was great. The staff were very nice and helpful.
Reviewed on 10 Oct 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
Localita Castiglion del Bosco Montalcino SI
Fully refundableReserve now, pay when you stay
£1,034
3 Nov - 4 Nov
includes taxes & fees
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
£107
13 Nov - 14 Nov
includes taxes & fees
Grand Hotel Continental Siena – Starhotels Collezione
Banchi Di Sopra 85 Siena SI
Fully refundableReserve now, pay when you stay
£275
20 Nov - 21 Nov
includes taxes & fees
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.
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.
What to do in Castiglione del Bosco
Montalcino: Guided Winery Tour and Wine Tasting
£39
per adult
Montepulciano: Winery Tour and Tasting
£30
per adult
100% of travellers recommend
Frequently asked questions
How much does a Castiglione del Bosco travel package cost?
Tailor make your Castiglione del Bosco travel package from just £180. 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.
