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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 $1,389, price is now $1,008 per person
$1,008
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.4/10 Good! (1,012 reviews)
The location was the biggest reason I chose this hotel; it's very close to the train station, making it convenient for a day trip to Siena and Pisa. All the viewpoints are within walking distance, so after lunch I could walk back to rest before continuing my sightseeing. I will definitely choose this hotel again next time!

Reviewed on Jun 11, 2026

Hotel La Scaletta Al Ponte Vecchio

Hotel La Scaletta Al Ponte Vecchio

4 out of 5
Historic Centre of Florence
Price was $1,616, price is now $1,149 per person
$1,149
per person
Aug 20 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
8.8/10 Excellent! (1,000 reviews)
I highly recommend this hotel. It was an older building (as expected in Italy), but very well maintained, and the room was gorgeous. The bathroom was very modern, the space was clean, and the staff was very helpful.

Reviewed on Jun 6, 2026

Hotel degli Orafi

Hotel degli Orafi

4 out of 5
Historic Centre of Florence
Price was $1,892, price is now $1,349 per person
$1,349
per person
Aug 20 - Aug 26
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
9.6/10 Exceptional! (1,001 reviews)
Excellent hotel, clean and well maintained, great location, superb breakfast buffet, reasonably priced.

Reviewed on Jun 11, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was $1,431, price is now $1,023 per person
$1,023
per person
Jul 30 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Florence (FLR)
7.6/10 Good! (1,006 reviews)
The hotel was conveniently located, and the service was good. Overall, it was a pleasant stay. However, I hope the hotel improves its Wi-Fi coverage, as the connection can become unstable when multiple guests are accessing the network.

Reviewed on Jun 5, 2026

Donati Luxury Tower Suites

Donati Luxury Tower Suites

5 out of 5
Historic Centre of Florence
Price was $2,281, price is now $1,680 per person
$1,680
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
9.8/10 Exceptional! (66 reviews)
Agradable estancia. Excelente servicio. La habitación la mantenían siempre limpia. Todo queda cerca del área. Muy recomendable

Reviewed on May 23, 2026

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Discover the most popular places to visit in Castellina in Chianti

Buondonno Winery

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

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

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

What to do in Castellina in Chianti

Tuscany Hiking Tour from Siena Including Wine Tasting

Tuscany Hiking Tour from Siena Including Wine Tasting

$70
per adult
100% of travellers recommend
Tuscany Hiking Tour from Siena Including Wine Tasting
Florence Day Trip: Medieval Villages & Cooking Class

Florence Day Trip: Medieval Villages & Cooking Class

$162
per adult
86% of travellers recommend
Florence Day Trip: Medieval Villages & Cooking Class
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

$76
per adult
86% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
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
$130 nightly
The price is $159 total per night from Jul 5 to Jul 6
$159 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (1,407 reviews)
"The floor was a bit beaten up but the room was clean. It was modern and had a bit of a hipster vibe. Not enough elevators. Staff was helpful. Their app for laundry didn’t work. A little pricey for what it was all told."

Reviewed on Jun 11, 2026

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
$128 nightly
The price is $157 total per night from Jul 3 to Jul 4
$157 total
Jul 3 - Jul 4
Total with taxes and fees
9.4/10 Exceptional! (569 reviews)
"The hotel is clean, busy, kinda has the vibe of Millenials and Gen Z mix. The rooftop pool is nice to sit at, the water is very cool. A quick dip and most people are out! The bar at night is nice with the skyline. The 1 set of elevators takes hotel staff to explain as they lock out the room floors ..."

Reviewed on Jun 10, 2026

The Social Hub Florence Belfiore
Hotel Paris

Hotel Paris

3 out of 5
Via Banchi 2 Florence FI
Fully refundable
$221 nightly
The price is $257 total per night from Jul 12 to Jul 13
$257 total
Jul 12 - Jul 13
Total with taxes and fees
8.8/10 Excellent! (1,015 reviews)
"We had a stop over in Florence and truly enjoyed our stay! From start to finish the staff was extremely helpful and the room was exceptionally bigger than we anticipated. Location was perfect! The hotel was close to all the major sights. Would highly recommend this hotel!"

Reviewed on Jun 8, 2026

Hotel Paris
See all 15,403 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 $1,008 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.