Castellina in Chianti Vacations from $698

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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

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was $959, price is now $698 per person
$698
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,007 reviews)
We were able to check-in early. It is walkable from Santa Maria Novella train station and so are the points of interest. When we arrived, the electric metal blinds was not working. Letitia gave us a sheet to temporarily give us privacy. When we came back from our tour the next day, it was already fixed. Great place to stay. Worth the money we paid for. Santa Maria Novella Basilica is close by. Worth visiting. Well recommended.

Reviewed on Oct 19, 2025

Collegio alla Querce, Auberge Collection

Collegio alla Querce, Auberge Collection

5 out of 5
Le Cure
Save 100% on your flight
Price was $2,755, price is now $1,817 per person
$1,817
per person
Dec 9 - Dec 12
found 9 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Florence (FLR)
10/10 Exceptional! (3 reviews)
Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,031, price is now $716 per person
$716
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,015 reviews)
Very central. You can walk to

Reviewed on Oct 20, 2025

Villa Cora

Villa Cora

5 out of 5
Oltrarno
Price was $1,535, price is now $1,101 per person
$1,101
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (465 reviews)
The hotel is very beautiful, and the surrounding environment is also excellent.

Reviewed on Sep 26, 2025

The St. Regis Florence

The St. Regis Florence

5 out of 5
Historic Centre of Florence
Price was $1,567, price is now $1,125 per person
$1,125
per person
Jan 8 - Jan 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (261 reviews)
Nice property in a great location.

Reviewed on Jun 29, 2025

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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

Archaeological Museum of Chianti

4/5(1 review)

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.

Archaeological Museum of Chianti

What to do in Castellina in Chianti

Medieval Centre

Skip the Line: Siena Duomo and City Walking Tour

$47
per adult
100% of travellers recommend
Skip the Line: Siena Duomo and City Walking Tour
Full-Day Tour of San Gimignano, Siena & Chianti

San Gimignano, Siena and Chianti - Small Group Tour

$138
per adult
86% of travellers recommend
San Gimignano, Siena and Chianti - Small Group Tour
Monteriggioni fortress

Tuscany Hiking Tour from Siena Including Wine Tasting

$64
per adult
Tuscany Hiking Tour from Siena Including Wine Tasting
See all activities in Castellina in Chianti

Castellina in Chianti Hotel Deals

Grand Hotel Baglioni

Grand Hotel Baglioni

4 out of 5
Piazza Unita Italiana 6, Florence, FI
Fully refundableReserve now, pay when you stay
$163 nightly
The price is $195 total per night from Nov 10 to Nov 11
$195 total
Nov 10 - Nov 11
Total with taxes and fees
9/10 Wonderful! (1,029 reviews)
"Very nice hotel, wonderful staff. Only issue was room was a bit noisy when the window was open and warm when closed. Area outside is very crowded with people and cars. Hotel did offer to change rooms."

Reviewed on Oct 19, 2025

Grand Hotel Baglioni
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
$85 nightly
The price is $110 total per night from Nov 2 to Nov 3
$110 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,264 reviews)
"I only had 36 hours in Florence, with my Daughter. We enjoyed what the hotel offered and its modern facilities. I think an extra day or two would have been even better, to try out more of what you offer. Well done."

Reviewed on Oct 20, 2025

The Social Hub Florence Lavagnini
IQ Hotel Firenze

IQ Hotel Firenze

4 out of 5
Via Camillo Cavour, 88, Florence, FI
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $154 total per night from Nov 10 to Nov 11
$154 total
Nov 10 - Nov 11
Total with taxes and fees
9.6/10 Exceptional! (1,013 reviews)
"Nice balcony Good amenities Clean Staff was very welcoming"

Reviewed on Oct 18, 2025

IQ Hotel Firenze
See all 15,407 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 $698 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.

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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.