Castiglione del Bosco Holidays from £632

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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 Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
per person
10 Oct - 17 Oct
found 13 hours ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
Very small rooms and bathrooms. Breakfast and breakfast staff were awesome and on the top floor. Hotel room small and nothing special. Great location and quiet…but good luck getting out of a car with luggage.

Reviewed on 4 Aug 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
25 Oct - 1 Nov
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on 6 Jun 2025

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
per person
9 Sept - 16 Sept
found 1 day ago
Return flight included
London (LON) to Florence (FLR)
9.4/10 Exceptional! (104 reviews)
The staff were incredibly kind and helpful. I got a flat tire the day I was leaving the hotel and the staff went above and beyond to help me get the tire fixed so I could be on my way. The hotel is beautiful and the food was excellent. I also requested a more private room and the staff changed the room for me right away. Highly recommended for beauty, serene peace and quiet

Reviewed on 19 Jul 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
Save 100% on your flight
per person
10 Oct - 17 Oct
found 13 hours ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
10/10 Exceptional! (1 review)
Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
10 Oct - 17 Oct
found 13 hours ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
8.6/10 Excellent! (468 reviews)
Great little hotel. Everything is within walking distance. The view from the terrace was amazing.

Reviewed on 6 Aug 2025

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

Rosewood Castiglion del Bosco

Rosewood Castiglion del Bosco

5 out of 5
Localita Castiglion del Bosco, Montalcino, SI
Fully refundableReserve now, pay when you stay
The price is £1,654 per night from 12 Aug to 13 Aug
£1,654
12 Aug - 13 Aug
includes taxes & fees
10/10 Exceptional! (65 reviews)
"Beautiful property and great service. Was a little disappointed they charge double the price for wine they make in their back yard then I pay here in Montreal."

Reviewed on 3 Aug 2025

Rosewood Castiglion del Bosco
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundableReserve now, pay when you stay
The price is £124 per night from 10 Aug to 11 Aug
£124
10 Aug - 11 Aug
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Beautiful location overlooking the hills of Tuscany! Right from Martina checking us in, and the beautiful room with views, everything was amazing! Very clean rooms and comfortable bed. Very nice bathroom and all the amenities. We enjoyed the breakfast each morning, nice selection of food to choose ..."

Reviewed on 3 Aug 2025

Hotel Athena
Palazzo Ravizza

Palazzo Ravizza

4 out of 5
Pian dei Mantellini 34, Siena, SI
The price is £94 per night from 8 Aug to 9 Aug
£94
8 Aug - 9 Aug
includes taxes & fees
9.2/10 Wonderful! (682 reviews)
"Amazing property with a back patio to die for. Nothing like eating a superb breakfast and enjoying a view of the hills and city."

Reviewed on 2 Aug 2025

Palazzo Ravizza
See all 3,265 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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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

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
Olive Oil Tours and Tasting at Frantoio di Montalcino

Olive Oil Tours and Tasting at Frantoio di Montalcino

£44
per adult
Olive Oil Tours and Tasting at Frantoio di Montalcino
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 £632. 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.