Castellina in Chianti Vacations from $860
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Your Castellina in Chianti Vacation
An easy way to experience this city is with a tailor-made Castellina in Chianti vacation package. Base yourself in the neighborhood of Badia Coltibuono, which is good for families, nature and walking or go someplace else — our package deals are all about you. If sightseeing is on the cards during your trip to Castellina in Chianti, look around well-known attractions like Isole e Olena Winery, Il Molino di Grace Winery and Castello di Radda Winery. Check out Expedia's wide range of travel options and begin planning your ultimate vacation to Castellina in Chianti now.
The Latest Castellina in Chianti vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Duomo Firenze
Historic Centre of Florence
$1,025
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.2/10 Wonderful! (1,004 reviews)
The room was tiny and everyone could hear every conversation in other rooms. The AC didn’t work and it was so hot in the room that we had to open the windows and then woke up covered in bug bites. Staff knocked on our door one night at 11pm to tell us someone complained about us being loud. We weren’t watching tv or anything, just laughing. The staff were kind of passive aggressive as well with every interaction. Wouldn’t go back.
Reviewed on Sep 29, 2026
Hotel Ginori al DUOMO
Historic Centre of Florence
$957
per person
Nov 17 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
8.8/10 Excellent! (62 reviews)
Fantastic stay, thank you for the upgrade, spacious, cool rooms. Great location, walk to the station and across the road is a convenience store and great restaurants and gelato in the same street
Reviewed on Sep 4, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
$946
per person
Dec 14 - Dec 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (592 reviews)
We totally loved our stay at this hotel. It’s an easy walk to all the main attractions. The spa is a major plus that we took advantage of. Really clean hotel. Really friendly staff. I would definitely recommend this property.
Reviewed on Sep 28, 2026
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See all available trips from Columbus to Castellina in Chianti
View all tripsStay 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.
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.
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 relaxing area.
Lilliano Estate Winery
You can enjoy a tasting or tour at Lilliano Estate Winery during your travels to Lilliano.
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.
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.
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, San Gimignano, Monteriggioni & Chianti from Florence
$75
per adult
88% of travellers recommend
From Siena: Chianti and Castles Tour with Wine Tastings
$98
per adult
90% of travellers recommend
Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting
$54
per adult
88% of travellers recommend
Castellina in Chianti Hotel Deals
Plus Florence - Hostel
Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
$119 nightly
$140 total
Oct 26 - Oct 27
Total with taxes and fees
The Social Hub Florence Belfiore
Viale Belfiore, 55 Florence FI
Fully refundableReserve now, pay when you stay
$136 nightly
$166 total
Oct 25 - Oct 26
Total with taxes and fees
9.4/10 Exceptional! (756 reviews)
"It's easy to reach on the tram, has good food, and is close to the center.I had a really good stay. The accommodations were comfortable, and everything went smoothly. I'd definitely recommend this place!"
Reviewed on Sep 27, 2026
Hotel Paris
Via Banchi 2 Florence FI
$197 nightly
$231 total
Oct 29 - Oct 30
Total with taxes and fees
9/10 Wonderful! (1,025 reviews)
"Very clean and staff was very helpful and friendly. Older hotel but very well maintained in a great location."
Reviewed on Sep 29, 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 Castellina in Chianti Vacation Packages
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 | 50ºF |
Max Temp Summer | 85ºF |
Top Sights | Siena Cathedral, Tenuta Torciano Winery and Monteriggioni Castle |
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Frequently asked questions
How much does a Castellina in Chianti vacation package cost?
You can grab a vacation package to this top destination from $860 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?
November, December and January are great times to look for cheap Castellina in Chianti vacation packages. Traveling in less busy months means you'll typically find better prices on accommodations and flights.
How many days is enough for Castellina in Chianti?
With about 3 days, you'll have plenty of time to enjoy popular neighborhoods like San Leonino and Villa during your Castellina in Chianti vacation. Be sure to also add Archaeological Museum of Chianti and City Hall Castellina In Chianti to your must-do list. Looking for more adventures? Consider venturing outside of Castellina in Chianti on day trips and tours.
Is it worth booking a vacation package to Castellina in Chianti?
Castellina in Chianti has all the ingredients you need for a memorable trip — dining, nature and walking trails are just the start. Whether you want to visit sights such as Walls of Monteriggioni and Archaeological Museum of Chianti, or venture off the beaten track, you'll have plenty to 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 plan to do in Castellina in Chianti and your preferred season will help you decide when to get away.
- Set your budget: Factor in costs such as flights, food and transportation when working out how much to put aside for your trip to Castellina in Chianti. Then, choose a property that works with your budget, whether that's an economical stay or a lavish retreat.
- Use Expedia's trip planning tool to explore Castellina in Chianti: Research every part of your trip to Castellina in Chianti with this comprehensive planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings.
- Decide your trip length: Consider how much time you'd like to spend discovering Castellina in Chianti. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
- Combine your airfare and accommodations: After you've settled on your trip dates and duration, book the perfect Castellina in Chianti vacation package for you.
- Add on experiences and excursions: Have a look at our travel guide to find some awesome things to do in Castellina in Chianti. Book tickets or make reservations as soon as you can to save time and skip the hassle of looking for activities when you arrive.
Does Expedia offer Book Now, Pay Later Castellina in Chianti vacation packages?
Your Castellina in Chianti break should be a relaxing escape from your busy life, not a reason for money worries. So to give you a little more flexibility, we've partnered with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
