Castellina in Chianti Vacations from $748

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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 Caravaggio

Hotel Caravaggio

3 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Florence (FLR)
8.8/10 Excellent! (1,004 reviews)
Wonderful stay - thank you!

Reviewed on Jul 7, 2025

Hotel Balestri

Hotel Balestri

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Florence (FLR)
9.2/10 Wonderful! (951 reviews)
Service was top notch. We had to wait 10 minutes for our room to be ready but they were great about everything and accommodating an early morning checkout with bag breakfasts for us. Location is also great next to the river and near major attractions in the city.

Reviewed on Jul 3, 2025

Hotel Ville sull'Arno

Hotel Ville sull'Arno

5 out of 5
Campo di Marte
Save 100% on your flight
per person
Sep 9 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Florence (FLR)
9.6/10 Exceptional! (728 reviews)
Nice property. Decent room, but pay attention to room choice. My room, a suite, only had one small window overlooking the river. Some of the staff members are fantastic and others not. While marketed as a 5 star hotel, it is a mid 4 star hotel. While it has parking, it can only accommodate a few cars and street parking is rough. I had some day trips to do so parking for a rental was important. Otherwise I would have stayed in town center.

Reviewed on May 14, 2025

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Cortona Old Town
Save 100% on your flight
per person
Sep 22 - Sep 29
found 15 hours ago
Roundtrip flight included
New York (NYC) to Florence (FLR)
10/10 Exceptional! (212 reviews)
Amazing hotel, a must stay if visiting Cortona..best hotel in Tuscany

Reviewed on Jul 5, 2025

Hotel Bencista

Hotel Bencista

3 out of 5
Save 100% on your flight
per person
Aug 22 - Aug 27
found 16 hours ago
Roundtrip non-stop flight included
New York (NYC) to Florence (FLR)
7.2/10 Good! (12 reviews)
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Discover the most popular places to visit in Castellina in Chianti

Castellina in Chianti which includes farmland

Buondonno Winery

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.

Buondonno Winery

City Hall Castellina In Chianti

5/5(1 review)

City Hall Castellina In Chianti is just one of the places to see in Castellina in Chianti, so why not enjoy the other things to explore during your travels? Discover the beautiful countryside and wineries in this quaint area.

City Hall Castellina In Chianti

Casa Vinicola Luigi Cecchi

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.

Casa Vinicola Luigi Cecchi

What to do in Castellina in Chianti

Chianti Wine Tour with Tuscan Lunch Open Top Van

Chianti Wine Tour with Tuscan Lunch Open Top Van

$229
per adult
100% of travellers recommend
Chianti Wine Tour with Tuscan Lunch Open Top Van
Cooking class in Tuscany

Cooking Class in Tuscany

$288
per adult
Cooking Class in Tuscany
Cooking Class in Tuscan Farmhouse from San Gimignano

Private Cooking Class in Chianti from San Gimignano

$423
per adult
Private Cooking Class in Chianti from San Gimignano
See all activities in Castellina in Chianti

Castellina in Chianti Hotel Deals

The Social Hub Florence Lavagnini
The Social Hub Florence Lavagnini
4 out of 5
Viale Spartaco Lavagnini 70 72, Florence, FI
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $105 total per night from Jul 31 to Aug 1
$105 total
Jul 31 - Aug 1
Total includes taxes and fees
8.8/10 Excellent! (1,022 reviews)
"Great spot. Most beautiful rooftop in Florence. Rooms are spacious and comfortable. Breakfaat is delicious. Has tons on great options."

Reviewed on Jul 5, 2025

The Social Hub Florence Lavagnini
The Social Hub Florence Belfiore
The Social Hub Florence Belfiore
4 out of 5
Viale Belfiore, 55, Florence, FI
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $113 total per night from Aug 3 to Aug 4
$113 total
Aug 3 - Aug 4
Total includes taxes and fees
9.2/10 Wonderful! (184 reviews)
"Good social experience"

Reviewed on Jul 5, 2025

The Social Hub Florence Belfiore
c-hotels Ambasciatori
c-hotels Ambasciatori
4 out of 5
Via Luigi Alamanni 3, Florence, FI
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $147 total per night from Jul 27 to Jul 28
$147 total
Jul 27 - Jul 28
Total includes taxes and fees
8.2/10 Very Good! (1,008 reviews)
"Great spot to stay for the convenience of the train and walkable to sites. Extra convenient if you are dropping off a rental car and taking the train to Rome early the next day."

Reviewed on Jun 30, 2025

c-hotels Ambasciatori
See all 15,482 properties in Castellina in Chianti
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 $748 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.