Castellina in Chianti Vacations from ￥484,132
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The Latest Castellina in Chianti Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Palazzo Firenze by Baglioni Hotels & Resorts
Historic Centre of Florence
￥886,714
per person
Sep 17 - Sep 24
found 12 hours ago
Roundtrip flight included
Tokyo (HND) to Florence (FLR)
9.4/10 Exceptional! (239 reviews)
L’hôtel est sensationnel et le service offert par le personnel est impeccable. Merci !
Reviewed on Aug 1, 2026
Find the Best Castellina in Chianti Vacation Packages
Castellina in Chianti Hotel Deals
The Social Hub Florence Lavagnini
Viale Spartaco Lavagnini 70 72 Florence FI
Fully refundableReserve now, pay when you stay
￥14,719
￥18,772 total
Aug 29 - Aug 30
includes taxes & fees
Plus Florence - Hostel
Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
￥12,588
￥15,322 total
Aug 19 - Aug 20
includes taxes & fees
Hotel Paris
Via Banchi 2 Florence FI
Fully refundableReserve now, pay when you stay
￥22,446
￥26,903 total
Aug 27 - Aug 28
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
"They were amazing"
Reviewed on Aug 17, 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.
Stay near popular Castellina in Chianti attractions
Buondonno Winery
9.6/10 (4 reviews)
You can enjoy a tasting or tour at Buondonno Winery during your travels to Castellina in Chianti. Discover the beautiful countryside and wineries in this relaxing area.
Archaeological Museum of Chianti
8.0/10 (6 reviews)
You can browse the exhibits at Archaeological Museum of Chianti, a museum with a story of its own, during your trip to Castellina in Chianti. Discover the beautiful countryside in this walkable area, or enjoy its local tours.
Lilliano Estate Winery
You can enjoy a tasting or tour at Lilliano Estate Winery during your travels to Lilliano.
Casa Vinicola Luigi Cecchi
9.0/10 (4 reviews)
You can enjoy a tasting or tour at Casa Vinicola Luigi Cecchi during your travels to Castellina in Chianti. Discover the beautiful countryside in this quaint area, or enjoy its local tours.
Walls of Monteriggioni
9.2/10 (5 reviews)
You can study the exhibits at Walls of Monteriggioni, a museum with a storied past, during your travels to Castellina in Chianti. Discover the beautiful countryside and wineries in this walkable area.
Castellina Fortress
9.4/10 (3 reviews)
Learn about the local history of Castellina in Chianti when you spend time at Castellina Fortress. Discover the countryside and wineries in this quaint area.
Mazzei Winery
You can enjoy a tasting or tour at Mazzei Winery during your travels to Fonterutoli. You can enjoy the restaurants while in the area.
Casina di Cornia Winery
You can enjoy a tasting or tour at Casina di Cornia Winery during your travels to Castellina in Chianti. Discover the countryside and wineries in this relaxing area.
What to do in Castellina in Chianti
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
￥3,349
per adult
Siena, San Gimignano, Monteriggioni & Chianti from Florence
￥9,570
per adult
88% of travellers recommend
Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting
￥9,018
per adult
90% of travellers recommend
Frequently asked questions
How much does a Castellina in Chianti vacation package cost?
You can grab a vacation package to this top destination from ￥484,132 on Expedia. But how much your vacation to Castellina in Chianti costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Castellina in Chianti?
The off-season is the best time to travel to Castellina in Chianti if you're trying to save. Another tip for finding cheap Castellina in Chianti vacation packages? Try to avoid visiting during public holidays and any major events.
How many days is enough for Castellina in Chianti?
Dedicate around 3 days for your Castellina in Chianti vacation if you want to enjoy all that makes this place special. Wander around popular areas, including San Leonino and Villa. Then head to the top sights like Castellina Fortress and Archaeological Museum of Chianti. With a good itinerary, you can keep busy with room for some downtime too. Want to go beyond Castellina in Chianti? Consider squeezing in a day trip or two.
Is it worth booking a vacation package to Castellina in Chianti?
Castellina in Chianti has everything you need for the perfect trip — hiking, views and walking trails are just the start. Whether you'd like to visit sights such as Walls of Monteriggioni and Castellina Fortress, or take the road less traveled, you'll find plenty to see and do on your Castellina in Chianti vacation.
How to find the best Castellina in Chianti package deals?
Start your search for a Castellina in Chianti package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Castellina in Chianti package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Castellina in Chianti escape underway.
Is it cheaper to book a Castellina in Chianti vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Castellina in Chianti vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Castellina in Chianti?
If you're planning a spontaneous Castellina in Chianti vacation, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Castellina in Chianti?
- Choose your travel dates: The things you'd like to do in Castellina in Chianti and your favorite season will help you decide when to get away.
- Budget wisely: On top of the cost of your accommodations, you should consider other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that may arise during your trip to Castellina in Chianti.
- Decide how long to go for: Now that you know more about Castellina in Chianti, you can figure out the right length of your break. Pull together a rough itinerary and allocate enough time to cover everything you want to see.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customized Castellina in Chianti vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
