Castellina in Chianti Holidays from AU$869
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Your Castellina in Chianti Holiday
Get ready to experience Castellina in Chianti your way with a custom Castellina in Chianti holiday package! Uncovering the treasures of this lively city is easier with a base in a neighbourhood such as Badesse, which is great for history, among plenty of other things. A trip to Castellina in Chianti is a terrific opportunity to go sightseeing. Make sure you visit renowned attractions like Castello di Radda Winery, Borgo di Vescine - Tenute di Castelvecchi and Buondonno Winery. Expedia can help you escape the everyday. Tailor your holiday to Castellina in Chianti to suit your travel style, whatever that may be.
The Latest Castellina in Chianti Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Floren Hotel
Historic Centre of Florence
AU$1,881
per person
14 Nov - 21 Nov
found 9 hours ago
Return direct flight included
Vienna (VIE) to Florence (FLR)
9.4/10 Exceptional! (267 reviews)
Fantastic location in the heart of Florence. They room was big, clean and the bed comfortable. Breakfast was great too.
Reviewed on 8 Oct 2026
The Hoxton, Florence
Historic Centre of Florence
AU$1,168
per person
14 Nov - 21 Nov
found 9 hours ago
Return direct flight included
Vienna (VIE) to Florence (FLR)
9.4/10 Exceptional! (358 reviews)
We stayed at the Hoxton before we headed out to Tuscany for our wedding weekend. The staff was very accommodating and helpful, and the property itself was beautiful with a great location, it was a little bit more on the outskirts of the city center, which we are used to staying in when we travel to Florence, but we liked how quiet and secluded it was and the design of the property was really well done. We enjoyed the coffee bar downstairs and the Photo Booth in the lobby and the outdoor courtyard/bar area was a great meeting point for us and friends who were getting into town for wedding festivities.
We would recommend staying at the Hoxton and look forward to future stays in other cities and hopefully Florence again.
Reviewed on 13 Oct 2026
Palazzo Lorenzo Hotel Boutique & Spa
San Lorenzo
AU$1,061
per person
14 Nov - 21 Nov
found 9 hours ago
Return direct flight included
Vienna (VIE) to Florence (FLR)
9.4/10 Exceptional! (622 reviews)
This is a good hotel in a nice part of the city which is a 20 minute walk from the centre. The room was mid sized and clean. Had a few little niggles like noisy air conditioning, loose toilet seat and a flickering light but nothing major. Staff were very helpful. Good choice at breakfast. Nice outside seating and bar. The spa is for your personal use hence needing to book. It was lovely but a little bit tired and needing a little spruce up. Overall good hotel which we would recommend and use again.
Reviewed on 2 Oct 2026
Castellina in Chianti Holiday
Castellina in Chianti Essential Information
Language | Italian |
|---|---|
Currency | Euros |
Local Welcome | Ciao |
Local Goodbye | Ciao |
Closest Airport | Peretola Airport (FLR) |
Population | 1,350 |
Max Temp Winter | 10ºC |
Max Temp Summer | 29ºC |
Top Sights | Siena Cathedral, Antinori nel Chianti Classico and Tenuta Torciano Winery |
Our pick of the best Castellina in Chianti Hotel Deals
Plus Florence - Hostel
Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
AU$97
8 Nov - 9 Nov
includes taxes & fees
The Social Hub Florence Belfiore
Viale Belfiore, 55 Florence FI
Fully refundableReserve now, pay when you stay
AU$129
8 Nov - 9 Nov
includes taxes & fees
9.4/10 Exceptional! (786 reviews)
"Great space to regroup after jumping around in multiple places. Truly is a one-stop-shop with everything you need right there. Easy to walk to main attractions"
Reviewed on 14 Oct 2026
Hotel Paris
Via Banchi 2 Florence FI
Fully refundableReserve now, pay when you stay
AU$209
14 Nov - 15 Nov
includes taxes & fees
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.
Castellina Fortress
9.4/10 (3 reviews)
Learn about the local history of Castellina in Chianti with a stop at Castellina Fortress. Discover the countryside and wineries in this relaxing area.
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 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.
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 travels to Castellina in Chianti. Discover the beautiful countryside in this walkable 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 trip to Castellina in Chianti. Discover the beautiful countryside and wineries in this walkable 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
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
AU$79
per adult
78% of travellers recommend
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
AU$30
per adult
Chianti Half Day Wine Tour from Florence
AU$40
per adult
88% of travellers recommend
Frequently asked questions
How much does a Castellina in Chianti holiday package cost?
You can grab a holiday package to this top destination from AU$869 on Expedia. But how much your holiday 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 holiday 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 holiday 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 holiday 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 holiday.
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 holiday as a package?
Expedia holiday 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 personalised Castellina in Chianti holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Castellina in Chianti?
If you're planning a spontaneous Castellina in Chianti holiday, 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 favourite season will help you decide when to get away.
- Budget wisely: On top of the cost of your accommodation, 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 customised Castellina in Chianti holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
