Castellina in Chianti Vacations from $951
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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.
Aurum Firenze
Historic Centre of Florence
$951
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,003 reviews)
The shower in our room was ridiculously small. I am only 5'7 and 178 and had a very hard time just getting in and out . I actually scraped my side getting in yesterday. The floor in the room was dirty and the breakfast was just ok. The breakyvire was spectacular however. there is no way they can advertise this as a 4 star hotel.
The restaurant Bondi directly across the street is absolutely phenomenal .
Reviewed on Sep 15, 2026
Grand Hotel Cavour
Historic Centre of Florence
$1,262
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.2/10 Wonderful! (1,004 reviews)
Lovely hotel and great position in Florence. Staff were friendly and helpful. Breakfast was lovely plenty of choice. Wouldn’t hesitate to stay there again. Perfect for the usual sightseeing !
Reviewed on Sep 15, 2026
Hotel Duomo Firenze
Historic Centre of Florence
$1,183
per person
Nov 21 - Nov 27
found 1 day ago
Roundtrip flight included
New York (JFK) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
I have to say I was super impressed with all the staff at Hotel Duomo. I had a very rough start to vacation and they were so nice and understanding about me not getting there for the first two days of my booking. Its in the perfect location. Right next to the Duomo and right in downtown Florence City Center. I would definitely stay here again and will recommend it to anyone who asks! Thank you to all the staff for making my trip much smoother once I finally got to Florence!
Reviewed on Sep 16, 2026
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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.
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.
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.
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
From Siena: Chianti and Castles Tour with Wine Tastings
$99
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
$61
per adult
88% of travellers recommend
Tuscany Day Trip to Siena & San Gimignano with Optional Wine Tasting
$54
per adult
90% 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
$108 nightly
$128 total
Sep 21 - Sep 22
Total with taxes and fees
8.6/10 Excellent! (1,010 reviews)
"The indoor pool was undergoing maintenance and the outdoor pool closed at 7, not the 10pm advertised in the hostel’s messages after checking in. The restaurant advertises itself online as being flexible for gluten free/ vegetarian/ vegan. When sitting down and asking, nothing was completely gluten ..."
Reviewed on Sep 16, 2026
The Social Hub Florence Belfiore
Viale Belfiore, 55 Florence FI
Fully refundableReserve now, pay when you stay
$178 nightly
$213 total
Oct 9 - Oct 10
Total with taxes and fees
9.4/10 Exceptional! (728 reviews)
"Staff entered room without permission to change the towel and clean bedsheets; I don’t think it’s a secure rooms if you left something outside of locker! sink jammed throughout the stay in bathroom! Room doesn’t have even a microwave not sure it’s a Europe thing or what! Also swimming pool is not ..."
Reviewed on Sep 16, 2026
The Social Hub Florence Lavagnini
Viale Spartaco Lavagnini 70 72 Florence FI
Fully refundableReserve now, pay when you stay
$214 nightly
$252 total
Oct 16 - Oct 17
Total with taxes and 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.
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 $951 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.
