Castellina in Chianti Holidays

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Top hotels in Castellina in Chianti

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

4 out of 5
Viale Spartaco Lavagnini 70 72, Florence, FI
Fully refundable
The price is S$179 per night from 29 Aug to 30 Aug
S$179
29 Aug - 30 Aug
includes taxes & fees
8.8/10 Excellent! (1,176 reviews)
"Everything was excellent!"

Reviewed on 25 Aug, 2025

The Social Hub Florence Lavagnini
Grand Hotel Baglioni

Grand Hotel Baglioni

4 out of 5
Piazza Unita Italiana 6, Florence, FI
Fully refundableReserve now, pay when you stay
The price is S$275 per night from 28 Aug to 29 Aug
S$275
28 Aug - 29 Aug
includes taxes & fees
9/10 Wonderful! (1,009 reviews)
"Beautifully restored hotel situated very conveniently across from the train station and within easy walking distance of the main city sights. Beautiful views from the rooftop terrace, with panoramic views of Florence. One of the best buffet breakfasts we have had, including a full spread of both ..."

Reviewed on 23 Aug, 2025

Grand Hotel Baglioni
Hotel Calimala Florence

Hotel Calimala Florence

4 out of 5
Via Lamberti 5, Florence, FI
Fully refundableReserve now, pay when you stay
The price is S$534 per night from 31 Aug to 1 Sept
S$534
31 Aug - 1 Sept
includes taxes & fees
9.6/10 Exceptional! (860 reviews)
"Wonderful hotel right in the heart of Florence. Big room and gorgeous view of surrounding neighborhood."

Reviewed on 25 Aug, 2025

Hotel Calimala Florence
See all 15,475 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

S$224
per adult
90% of travellers recommend
Vintage Fiat 500 Tuscany Drive with Winery Lunch
scooter riders and passengers on city roads in Italy

Full-Day Tour of Chianti by Vespa with Lunch from Siena

S$193
per adult
Full-Day Tour of Chianti by Vespa with Lunch from Siena
Winemaker For a day: craft your dream blend and take it home

Winemaker For a day: craft your dream blend and take it home

S$88
per adult
Winemaker For a day: craft your dream blend and take it home
See all activities in Castellina in Chianti

Frequently asked questions

How much does a Castellina in Chianti holiday package cost?
You can grab a holiday package to this top destination on Expedia. But how much your holiday 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 holiday 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 holiday 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 holiday 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 holiday.
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 holiday as a package?
Expedia holiday 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 personalised Castellina in Chianti holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Castellina in Chianti?
If you're planning a spontaneous Castellina in Chianti holiday, 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 favourite season will help you decide when to get away.
  2. Budget wisely: On top of the cost of your accommodation, 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 customised Castellina in Chianti holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.