Castellina in Chianti Vacations from $965
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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
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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 when you spend time at Castellina Fortress. Discover the countryside and wineries in this quaint 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 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.
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 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
$59
per adult
88% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
$158
per adult
86% of travellers recommend
Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting
$56
per adult
90% of travellers recommend
Castellina in Chianti Hotel Deals
The Social Hub Florence Lavagnini
Viale Spartaco Lavagnini 70 72 Florence FI
Fully refundableReserve now, pay when you stay
$84 nightly
$109 total
Aug 31 - Sep 1
Total with taxes and fees
9/10 Wonderful! (1,548 reviews)
"Nice clean room, friendly staff. Good location for the city… 20min walk to everything."
Reviewed on Aug 24, 2026
Plus Florence - Hostel
Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
$68 nightly
$84 total
Aug 27 - Aug 28
Total with taxes and fees
8.6/10 Excellent! (1,015 reviews)
"The best hostel in Florence."
Reviewed on Aug 24, 2026
Hotel Paris
Via Banchi 2 Florence FI
Fully refundableReserve now, pay when you stay
$149 nightly
$178 total
Aug 30 - Aug 31
Total with taxes and fees
9/10 Wonderful! (1,016 reviews)
"A so enjoyed the historic element of the hotel. The rooms were well appointed the breakfast area with the fresco ceiling was amazing as was the terrace. The front staff were excellent would stay here again without question!"
Reviewed on Aug 24, 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 $965 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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- Visit Vagliagli
- Visit Radda in Chianti
- Castello di Monsanto
- The Rock of Staggia
- Castello di Radda Winery
- Borgo di Vescine - Tenute di Castelvecchi
- San Lucchese Convent
- Casa Vinicola Luigi Cecchi
- Chianti Observatory
- Visit Panzano in Chianti
- Visit San Donato in Poggio
- Visit Castellina in Chianti
- Visit Colle Petroso
- Casa Emma
- Magione Castle
- Sentierelsa Trail
- Fountain of Fate
- Visit Fonterutoli
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- Meleto Castle
- Casa Sola - Chianti Winery
- Church of Santa Maria Assunta
- Visit Cignan Bianco
- Il Molino di Grace Winery
- Monteriggioni Castle
- Visit Cavallari
- Pieve di San Leolino
- Isole e Olena Winery
- Castello di Albola
- Visit Cignano
- Castello della Paneretta
- Monsanto Vacations
- City Hall Castellina In Chianti
- Buondonno Winery
- Church of San Lorenzo
- Visit Monsanto
- Visit Chianti Region
- Poggio al Sole
- Visit Lucarelli
- Fattoria di Montecchio
- Car rental Vagliagli
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- First-Car Rental Cars in Radda in Chianti
- Fox Rental Cars Rental Cars in Castellina in Chianti
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.