Castellina in Chianti Vacations from ￥268,804

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The Latest Castellina in Chianti Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Miceli - Civico 50

Hotel Miceli - Civico 50

3 out of 5
Historic Centre of Florence
per person
Sep 17 - Sep 24
just found
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9/10 Wonderful! (183 reviews)
There was no staff on-site when we arrived, but we had been in touch with the hotel via WhatsApp all day, and they were super helpful and friendly! Entering the building was very easy, but the 3-person elevator was just a little squished. The room was as expected - the only downside was that the shower was only cold water (after running it for a few minutes) and the sink in the bathroom was only hot water! The room was warm when we entered, but we turned the air conditioning up and it was perfect by the time we arrived back for bed. All-in-all, it was a good stay overnight!

Reviewed on Jun 22, 2025

Hotel Villa Liana

Hotel Villa Liana

3 out of 5
Historic Centre of Florence
per person
Sep 17 - Sep 24
just found
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
8.6/10 Excellent! (326 reviews)
Beautiful room. Excellent service and amazing breakfast. Close to the sites.

Reviewed on Jul 3, 2025

FH55 Grand Hotel Mediterraneo

FH55 Grand Hotel Mediterraneo

4 out of 5
Santa Croce
per person
Sep 17 - Sep 24
just found
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
8/10 Very Good! (884 reviews)
Everyone working here was great. Very polite and helpful. Great air conditioned rooms . Breakfast was included . Evening dinner here was also very good.

Reviewed on Jun 29, 2025

c-hotels Joy

c-hotels Joy

4 out of 5
Historic Centre of Florence
per person
Sep 17 - Sep 24
just found
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9/10 Wonderful! (1,000 reviews)
Liked my stay here very much. Very clean and modern. Staff was great. The owner welcomed me with open arms and showed me my room. Very convenient and close to the train and other areas. If you’re looking for a place. Stay here !!

Reviewed on Jun 30, 2025

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World

The James Suite Hotel Firenze 1564 - Small Luxury Hotels of the World

5 out of 5
Historic Centre of Florence
per person
Sep 17 - Sep 24
just found
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
No reviews

Find the Best Castellina in Chianti Vacation Packages

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
The price is ￥11,740 per night from Jul 31 to Aug 1
￥11,740
￥15,321 total
Jul 31 - Aug 1
includes taxes & 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
The price is ￥15,268 per night from Aug 3 to Aug 4
￥15,268
￥19,192 total
Aug 3 - Aug 4
includes taxes & 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
The price is ￥19,014 per night from Jul 29 to Jul 30
￥19,014
￥23,312 total
Jul 29 - Jul 30
includes taxes & fees
8.2/10 Very Good! (1,000 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.

What to do in Castellina in Chianti

Vintage Fiat 500 Tuscany Drive with Winery Lunch

Vintage Fiat 500 Tuscany Drive with Winery Lunch

￥25,338
per adult
90% of travellers recommend
Vintage Fiat 500 Tuscany Drive with Winery Lunch
Safari Chianti Experience on a quad with picnic

Safari Chianti Experience on a quad with picnic

￥21,865
per adult
Safari Chianti Experience on a quad with picnic
Chianti Wild Safari Adventure through Tuscan Vineyards

Chianti Wild Safari Adventure through Tuscan Vineyards

￥18,475
per adult
Chianti Wild Safari Adventure through Tuscan Vineyards
See all activities in Castellina in Chianti

Frequently asked questions

How much does a Castellina in Chianti vacation package cost?
You can grab a vacation package to this top destination from ￥268,804 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?
The off-season is the best time to travel to Castellina in Chianti if you're trying to save. Another tip for finding cheap Castellina in Chianti vacation packages? Try to avoid visiting during public holidays and any major events.
How many days is enough for Castellina in Chianti?
Dedicate around 3 days for your Castellina in Chianti vacation if you want to enjoy all that makes this place special. Wander around popular areas, including San Leonino and Villa. Then head to the top sights like Castellina Fortress and Archaeological Museum of Chianti. With a good itinerary, you can keep busy with room for some downtime too. Want to go beyond Castellina in Chianti? Consider squeezing in a day trip or two.
Is it worth booking a vacation package to Castellina in Chianti?
Castellina in Chianti has everything you need for the perfect trip --- hiking, views and walking trails are just the start. Whether you'd like to visit sights such as Walls of Monteriggioni and Castellina Fortress, or take the road less traveled, you'll find plenty to see and 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'd like to do in Castellina in Chianti and your favorite season will help you decide when to get away.
  2. Budget wisely: On top of the cost of your accommodations, you should consider other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that may arise during your trip to Castellina in Chianti.
  3. Decide how long to go for: Now that you know more about Castellina in Chianti, you can figure out the right length of your break. Pull together a rough itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customized Castellina in Chianti vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.