Castiglione del Bosco Vacations from $972
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Your Castiglione del Bosco Vacation
Take the guesswork out of travel planning with a Castiglione del Bosco vacation package. A great neighborhood 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 vacation is just clicks away. Search flights, accommodations and more on Expedia for an adventure that's tailored just for you.
The Latest Castiglione del Bosco vacation packages
Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa
Historic Centre of Florence
$972
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
The Moon Hotel exceeded my expectations and is highly recommended.
The restaurant services and breakfast offerings were excellent
Management and particularly Ivan was absolutely outstanding.
Reviewed on Sep 9, 2026
Grand Hotel Cavour
Historic Centre of Florence
$1,049
per person
Nov 18 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,004 reviews)
I absolutely loved my stay at this hotel in the center of Florence! The rooms, breakfast, and rooftop bar were all fantastic. Thank you to the staff for your wonderful service and professionalism.
Reviewed on Sep 12, 2026
Aurum Firenze
Historic Centre of Florence
$1,291
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
Rooms were clean....modern design unlike other older Tuscany hotels. Air conditioning good. Ok breakfast. Location close to train station and not far from attractions...everything with in 15 minute walk. Safe area. Staff not rude, just inattentive.
Reviewed on Sep 12, 2026
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View all tripsStay 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
$53
per adult
From Rome: Bagnoregio & Orvieto Day Trip with Tuscany Wine Tasting & Lunch
$98
per adult
98% of travellers recommend
Montepulciano Wine Tasting in the Tuscan Countryside
$29
per adult
Castiglione del Bosco Hotel Deals
Castiglion del Bosco, A Rosewood Hotel
Localita Castiglion del Bosco Montalcino SI
$2,373 nightly
$2,622 total
Oct 8 - Oct 9
Total with taxes and fees
10/10 Exceptional! (80 reviews)
"Best hotel ever."
Reviewed on Jul 27, 2026
Hotel Athena
P Mascagni 55 Siena SI
Fully refundableReserve now, pay when you stay
$281 nightly
$314 total
Sep 30 - Oct 1
Total with taxes and fees
9.2/10 Wonderful! (1,000 reviews)
"We had a wonderful stay at Hotel Athena in Siena. The service was exceptional, the staff were warm, welcoming and genuinely helpful throughout our visit. The location was fantastic for exploring Siena, with everything within walking distance, while the hotel itself provided a comfortable and relaxing ..."
Reviewed on Sep 11, 2026
Castello di Velona Resort Thermal SPA & Winery
Località Velona Montalcino SI
Fully refundableReserve now, pay when you stay
$764 nightly
$852 total
Sep 27 - Sep 28
Total with taxes and fees
9/10 Wonderful! (370 reviews)
"Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, ..."
Reviewed on Sep 9, 2026
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.
Find the Best Castiglione del Bosco Vacation Packages
Castiglione del Bosco Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Max Temp Winter | 50ºF |
Max Temp Summer | 85ºF |
Top Sights | Castello Banfi, Tenuta Greppo Franco Biondi Santi and Capanna of Cencioni |
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Frequently asked questions
How much does a Castiglione del Bosco vacation package cost?
Offering excellent value package deals from $972 on Expedia, you'll be thrilled with how little a vacation 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?
February, March and November are great times to search for cheap Castiglione del Bosco vacation packages. Traveling in quieter months means you can typically find lower prices on flights and accommodations.
How many days is enough for Castiglione del Bosco?
Generally, a handful of days is enough to visit the top attractions during your Castiglione del Bosco vacation. But if you want to have time to relax or go on day trips, think about extending your itinerary.
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 vacation package well in advance.
Is it cheaper to book a Castiglione del Bosco vacation as a package?
You can enjoy significant savings on your Castiglione del Bosco retreat by booking a personalized vacation 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 vacation 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?
- Choose when to go: Check your calendar and pack your bags. Your preferred season and the type of activities available will also help you decide when to escape to Castiglione del Bosco.
- Plan your budget wisely: In addition to the cost of your stay, you'll need to consider other expenses. These include flights, transportation and food. Also, set aside some extra funds for unexpected costs that could arise during your trip to Castiglione del Bosco.
- Organize your Castiglione del Bosco getaway with Expedia's trip planning tool: Look for and book accommodations and things to do all in one place. You can also collaborate with friends and family to plan an unforgettable trip to Castiglione del Bosco together.
- Decide how long to go away for: Now that you know more about Castiglione del Bosco, you can work out the right length of your break. Pull together a draft itinerary and allocate enough time to get through everything on your must-do list.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Castiglione del Bosco vacation package.
- Book activities and experiences in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on Castiglione del Bosco's highlights. Find all the fun things to do in Castiglione del Bosco with our dedicated activity guide.
Does Expedia offer Book Now, Pay Later Castiglione del Bosco vacation packages?
Set off on your perfect escape to Castiglione del Bosco with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or hold off until the next payday — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to budget for your trip and snap up travel deals while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
