Castellina in Chianti Vacation Packages
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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.
Top Castellina in Chianti Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Villa Liana
Historic Centre of Florence
CA $1,524
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
8.8/10 Excellent! (360 reviews)
clean, spacious, well-stocked with toiletries and breakfast items too. walkable distance to all iconic sites. Grace, the breakfast host, did an incredible job, very welcoming & served with options for hot coffee drinks. All together, wonderful, memorable stay!!
Reviewed on May 23, 2026
Eden Rock Resort
CA $1,683
per person
Oct 8 - Oct 12
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.8/10 Exceptional! (109 reviews)
This was a beautiful property about 10 mins away from Florence. You get the beauty of Tuscany without having to go too far. The hotel only has 12 rooms and everyone knows you by name. We traveled with 2 kids and the rooms were very spacious. Staff are wonderful, Onsite restaurant was great. Views were breathtaking. We didn't have a car, and the hotel was able to help us with cabs easily. Service was excellent and we would highly recommend this hotel!
Reviewed on Jul 18, 2026
Grand Hotel Cavour
Historic Centre of Florence
CA $4,039
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (1,001 reviews)
Staff were very welcoming and helpful from check in to departure. We had the basic room which was very nice indeed, a decent size and nicely furnished. Rooftop bar reasonable value for a cocktail surrounded by the sights of Florence. Very central location. Aircon very good and controllable. Highly recommended.
Reviewed on Aug 19, 2026
Ready to book your vacation to Castellina in Chianti?
Castellina in Chianti Hotel Deals
The Social Hub Florence Lavagnini
Viale Spartaco Lavagnini 70 72 Florence FI
Fully refundableReserve now, pay when you stay
CA $132
CA $168 total
Aug 25 - Aug 26
includes taxes & fees
9/10 Wonderful! (1,545 reviews)
"Muy buena ubicación, la propiedad es la mejor que he estado en Italia hasta ahora, el personal tuvo mi habitación lista mucho antes de la hora del check in, el proceso de check-in fue muy rápido y placentero apenas demore 1 min. Cada vez que contacté a la propiedad, enseguida me respondían. Cuando ..."
Reviewed on Aug 22, 2026
Plus Florence - Hostel
Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
CA $86
CA $108 total
Aug 26 - Aug 27
includes taxes & fees
8.6/10 Excellent! (1,011 reviews)
"Great place to stay."
Reviewed on Aug 21, 2026
Hotel Paris
Via Banchi 2 Florence FI
Fully refundableReserve now, pay when you stay
CA $189
CA $228 total
Aug 25 - Aug 26
includes taxes & fees
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.
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.
Castellina Fortress
9.4/10 (3 reviews)
Learn about the local history of Castellina in Chianti when you spend time at Castellina Fortress. Discover the countryside and wineries in this quaint area.
Archaeological Museum of Chianti
8.0/10 (6 reviews)
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.
Walls of Monteriggioni
9.2/10 (5 reviews)
You can study the exhibits at Walls of Monteriggioni, a museum with a storied past, during your travels to Castellina in Chianti. Discover the beautiful countryside and wineries in this walkable area.
Lilliano Estate Winery
You can enjoy a tasting or tour at Lilliano Estate Winery during your travels to Lilliano.
Casa Vinicola Luigi Cecchi
9.0/10 (4 reviews)
You can enjoy a tasting or tour at Casa Vinicola Luigi Cecchi during your travels to Castellina in Chianti. Discover the beautiful countryside in this quaint area, or enjoy its local tours.
Mazzei Winery
You can enjoy a tasting or tour at Mazzei Winery during your travels to Fonterutoli. You can enjoy the restaurants while in the area.
Casina di Cornia Winery
You can enjoy a tasting or tour at Casina di Cornia Winery during your travels to Castellina in Chianti. Discover the countryside and wineries in this relaxing area.
What to do in Castellina in Chianti
Chianti Half Day Wine Tour from Florence
CA $39
per adult
88% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
CA $84
per adult
88% of travellers recommend
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
CA $79
per adult
78% of travellers recommend
Frequently asked questions
How much does a Castellina in Chianti vacation package cost?
Offering great value package deals from CA $1,524 on Expedia, you'll be pleasantly surprised at how much a vacation to Castellina in Chianti costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Castellina in Chianti?
Plan your getaway for the shoulder or low season and you're likely to find cheap Castellina in Chianti vacation packages. Keep in mind that public holidays and major events and festivals can have an impact on prices, so do your research before booking.
How many days is enough for Castellina in Chianti?
We suggest planning a Castellina in Chianti vacation for a minimum of 3 days. This will allow you plenty of time to check off key attractions such as Borgo di Vescine - Tenute di Castelvecchi and Buondonno Winery, and check out neighbourhoods like San Leonino and Villa. You could even make time for one or two day trips beyond Castellina in Chianti.
Is it worth booking a vacation package to Castellina in Chianti?
Well known for its hiking, views and walking trails, a Castellina in Chianti vacation offers something for everyone. Be sure to check out main sights like Walls of Monteriggioni and Castellina Fortress, and consider renting a set of wheels for day trips to discover even more.
How to find the best Castellina in Chianti package deals?
Bagging a cheap Castellina in Chianti package deal is a breeze with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your budget, add a couple of filters and see what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Castellina in Chianti package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Castellina in Chianti vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and hotels individually. Better still, you can tailor your Castellina in Chianti getaway to fit your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Castellina in Chianti?
If you have your Castellina in Chianti travel dates locked in, book as early as you can to grab some outstanding deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are ideal for travelling on a whim.
How to plan a trip to Castellina in Chianti?
- Pick your dates: The things you want to do in Castellina in Chianti and your preferred season will help you decide when to go.
- Plan your budget wisely: Besides the cost of your hotel, you'll need to factor in other expenses too. These include flights, transportation and food. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Castellina in Chianti.
- Decide your trip length: Think about how much time you want to spend exploring Castellina in Chianti. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
- Combine your airfare and accommodations: Once you've settled on your dates and duration, lock in the right Castellina in Chianti vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
