Castiglione del Bosco Holidays

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Top Flight + Hotel Deals in Castiglione del Bosco

Price found within the past 48 hours. Click for updated prices.
Hotiday Room Collection - Rapallo

Hotiday Room Collection - Rapallo

4 out of 5
Save 100% on your flight
per person
21 Sept - 24 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Pisa (PSA)
No reviews
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
14 Sept - 17 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
7.6/10 Good! (1,012 reviews)
The hotel is situated on busy street, it is walking distance from Santa Maria train station, the room was clean but small and the breakfast was average.

Reviewed on 25 Jul 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
14 Sept - 17 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) 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

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Save 100% on your flight
per person
14 Sept - 17 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.8/10 Excellent! (382 reviews)
It is such a beautiful property and our apartment was clean and comfortable. Ate at the lovely restaurant one nigh and had take out the second. The breakfast was fantastic, so delicious with many options. The staff were so friendly and helpful.

Reviewed on 21 Jul 2025

Grand Hotel Torre Fara

Grand Hotel Torre Fara

4 out of 5
Save 100% on your flight
per person
3 Sept - 10 Sept
found 24 hours ago
Return direct flight included
Dublin (DUB) to Pisa (PSA)
9.6/10 Exceptional! (116 reviews)
The staff is incredibly kind and efficient. The location is stunning, the hotel amenities very comfortable. We would def recommend it.

Reviewed on 6 Jul 2025

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 €1,630 per night from 5 Aug to 6 Aug
€1,630
5 Aug - 6 Aug
includes taxes & fees
10/10 Exceptional! (64 reviews)
"Peaceful, Relaxing Stay in Tuscany We had a great experience here. The setting is quiet and secluded—felt like a true escape from everyday life. The golf was excellent, the food was consistently good, and the service was friendly and professional. It is remote, which adds to the charm, but just a ..."

Reviewed on 21 Jun 2025

Rosewood Castiglion del Bosco
Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundable
The price is €130 per night from 30 Jul to 31 Jul
€130
30 Jul - 31 Jul
includes taxes & fees
9.2/10 Wonderful! (1,010 reviews)
"Great place to stay nearby attraction and walking distance"

Reviewed on 26 Jul 2025

Hotel Athena
NH Siena

NH Siena

4 out of 5
Piazza La Lizza 1, Siena, SI
Fully refundableReserve now, pay when you stay
The price is €118 per night from 3 Aug to 4 Aug
€118
3 Aug - 4 Aug
includes taxes & fees
8/10 Very Good! (996 reviews)
"We just need a mirror in the room to see your entire body please urgent . Other than these is the perfect hotel to stay in Lake Como area"

Reviewed on 21 Jul 2025

NH Siena
See all 3,250 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.

Popular places to visit

San Giovanni d'Asso Station

You can take time to visit San Giovanni d'Asso Station during your travels to San Giovanni d'Asso. Discover the area's countryside and spas.

San Giovanni d'Asso Station

What to do in Castiglione del Bosco

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano

€229
per adult
100% of travellers recommend
Val d'Orcia Brunello Wine Tour with Montalcino and Montepulciano
Brunello di Montalcino small-group Wine Tour

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

€180
per adult
100% of travellers recommend
Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena
small town in Italy

Brunello di Montalcino Small Group Wine Tour from Siena

€160
per adult
98% of travellers recommend
Brunello di Montalcino Small Group Wine Tour from Siena
See all activities in Castiglione del Bosco

Frequently asked questions

How much does a Castiglione del Bosco holiday package cost?
Offering excellent value package deals from €364 on Expedia, you'll be thrilled with how little a holiday to Castiglione del Bosco costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Castiglione del Bosco?
To score cheap Castiglione del Bosco holiday packages, plan your getaway outside of busy periods such as school holidays. You'll typically find better availability and lower prices when it's less busy.
How many days is enough for Castiglione del Bosco?
Typically, a handful of days is enough to visit the main sights during your Castiglione del Bosco holiday. However, if you prefer to have some time to kick back or take day trips, think about extending your trip.
How to find the best Castiglione del Bosco package deals?
Use Expedia's filters to find some of the best Castiglione del Bosco package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Castiglione del Bosco package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
Is it cheaper to book a Castiglione del Bosco holiday as a package?
You can enjoy significant savings on your Castiglione del Bosco retreat by booking a personalised holiday package. Check the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Castiglione del Bosco?
If you're considering an impromptu Castiglione del Bosco getaway, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Castiglione del Bosco?

  1. Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Castiglione del Bosco.
  2. Set a budget: Consider expenses like flights, food and transportation when working out how much to put aside for your trip to Castiglione del Bosco. Then, pick a property that matches your budget, whether that's a low-cost stay or a high-end retreat.
  3. Decide how long to go away for: Now that you're up to speed on Castiglione del Bosco, you can work out the right length of your holiday. Create a rough itinerary and allocate enough time to cover everything you want to see.
  4. Combine your accommodation and airfare: Once you've settled on your dates and duration, book the right Castiglione del Bosco holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.