Castiglione del Bosco Holidays from £288

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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.
Hotel Miceli - Civico 50

Hotel Miceli - Civico 50

3 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £513, price is now £288 per person
£288
per person
5 Oct - 8 Oct
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9/10 Wonderful! (197 reviews)
The young lady that checked us in was so friendly and helpful!!!

Reviewed on 13 Aug 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was £878, price is now £338 per person
£338
per person
18 Oct - 22 Oct
found 1 day ago
Return flight included
London (LGW) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
The hotel is located a 25 min walk away from the heart of Florence so very easy to access the main attractions within the city. The hotel itself is immaculate and the staff are extremely helpful with dealing with any questions you may have. Being able to access the spa everyday for 1 and 30 minutes is an excellent perk as the facilities are well worth a visit, you are also able to book massages for an extra fee. The breakfast also gives a variety of options to start each day and the room itself is spacious, with the shower particularly being very comfortable.

Reviewed on 13 Aug 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was £1,198, price is now £561 per person
£561
per person
7 Oct - 11 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.8/10 Good! (1,005 reviews)
Our stay was lovely, very comfortable, small but good choice of breakfast. Beds were comfy and room was clean when we arrived and cleaned everyday. I would only suggest maybe for a shower curtains as when we had a shower the bathroom floor would be all wet, but easily to clean. And just a note on how to use the phone if we need to call reception but overall the hotel facilities and the staff were brilliant if i could give more then 5 stars i would.

Reviewed on 19 Aug 2025

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
Price was £792, price is now £419 per person
£419
per person
8 Oct - 11 Oct
found 1 day ago
Return direct flight included
Birmingham (BHX) to Florence (FLR)
7.8/10 Good! (1,005 reviews)
Great location. Few minutes away from train station. Not so quiet. You could hear people from outside even the windows closed. If you are staying for a few days, it’s a great location.

Reviewed on 14 Aug 2025

Hotel Bencista

Hotel Bencista

3 out of 5
Save 100% on your flight
Price was £966, price is now £538 per person
£538
per person
21 Sept - 28 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Florence (FLR)
7.4/10 Good! (13 reviews)

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
The price is £1,672 per night from 31 Aug to 1 Sept
£1,672
31 Aug - 1 Sept
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 refundable
The price is £143 per night from 31 Aug to 1 Sept
£143
31 Aug - 1 Sept
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"Older, more traditional style but excellent hotel. The staff are amazing, super kind and helpful. We were really impressed, and would definately stay here again."

Reviewed on 14 Aug 2025

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 £103 per night from 24 Aug to 25 Aug
£103
24 Aug - 25 Aug
includes taxes & fees
9.2/10 Wonderful! (687 reviews)
Just beautiful
"The building, the views, the staff, the food, everything was just incredible. It was so quiet we felt like we were the only people there until we went for breakfast and realised there were others in the hotel. The view from the our room at the back of the hotel over the Tuscan hills will live with ..."

Reviewed on 9 Aug 2025

Palazzo Ravizza
See all 3,263 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

small town in Italy

Brunello di Montalcino Small Group Wine Tour from Siena

£138
per adult
98% of travellers recommend
Brunello di Montalcino Small Group Wine Tour from Siena
Cooking Tuscan Pasta Class and Brunello Tasting with Lunch

Cooking Tuscan Pasta Class and Brunello Tasting with Lunch

£146
per adult
Cooking Tuscan Pasta Class and Brunello Tasting with Lunch
Classic Wine Tasting in Montalcino

Classic Wine Tasting in Montalcino

£26
per adult
Classic Wine Tasting in 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 £288. 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.