Castellina in Chianti Vacations from $1,002

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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 $1,518, price is now $1,002 per person
$1,002
per person
Jan 13 - Jan 17
found 22 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
7.4/10 Good! (1,016 reviews)

The Place Firenze

The Place Firenze

5 out of 5
Historic Centre of Florence
Price was $3,176, price is now $2,229 per person
$2,229
per person
Jan 3 - Jan 8
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (203 reviews)

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Price was $2,952, price is now $2,186 per person
$2,186
per person
Jan 16 - Jan 22
found 23 hours ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (82 reviews)
Great location. Historical building. Rooms were stunning. Lovely breakfast box delivered daily. Nice staff. The only negative is the roof is €250 per 2 hour booking, which I didn't expect, and would have been a reason for booking. Hence 4/5.

Reviewed on Oct 19, 2026

Hotel Berchielli

Hotel Berchielli

4 out of 5
Historic Centre of Florence
Price was $1,371, price is now $1,029 per person
$1,029
per person
Jan 18 - Jan 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.4/10 Exceptional! (1,001 reviews)

Portrait Firenze - Lungarno Collection

Portrait Firenze - Lungarno Collection

5 out of 5
Historic Centre of Florence
Price was $3,408, price is now $2,669 per person
$2,669
per person
Jan 3 - Jan 8
found 12 hours ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
9.8/10 Exceptional! (320 reviews)

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Stay 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.
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What to do in Castellina in Chianti

Siena: Cathedral Complex Pass with Audio Guide

Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)

$22
per adult
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
Chianti Wine and Food Safari

SMALL-GROUP Wine Safari: Tuscany Wine Tasting Tour from Florence

$146
per adult
100% of travellers recommend
SMALL-GROUP Wine Safari: Tuscany Wine Tasting Tour from Florence
Pasta-making class at a Cesarina's home with tasting - Siena

Pasta-making class at a Cesarina's home with tasting - Siena

$201
per adult
Pasta-making class at a Cesarina's home with tasting - Siena
See all activities in Castellina in Chianti

Castellina in Chianti Hotel Deals

Plus Florence - Hostel

Plus Florence - Hostel

Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
$46 nightly
The price is $60 total per night from Dec 9 to Dec 10
$60 total
Dec 9 - Dec 10
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
"A experiência toda foi ruim, mas o pior foi ter os equipamentos do quarto com defeito e a janela não ter proteção maior contra o som da rua, pois o barulho dos carros e trem atrapalha muito."

Reviewed on Nov 8, 2026

Plus Florence - Hostel
Hotel Paris

Hotel Paris

3 out of 5
Via Banchi 2 Florence FI
Fully refundableReserve now, pay when you stay
$114 nightly
The price is $139 total per night from Nov 17 to Nov 18
$139 total
Nov 17 - Nov 18
Total with taxes and fees
Hotel Paris
Hotel Albani Firenze

Hotel Albani Firenze

4 out of 5
Via Fiume 12 Florence FI
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $131 total per night from Dec 9 to Dec 10
$131 total
Dec 9 - Dec 10
Total with taxes and fees
9.2/10 Wonderful! (1,005 reviews)
"STAFF VERY HELPFUL. EVERY THING WAS GREAT"

Reviewed on Nov 6, 2026

Hotel Albani Firenze
See all 15,514 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 $1,002 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.