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.
Eurostars Florence Boutique
Historic Centre of Florence
CA $1,676
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
8.6/10 Excellent! (503 reviews)
The bed was comfortable but low to the floor. The shower was very slippery and could have used a shower mat. The breakfast was great. The staff were very nice and helpful.
Reviewed on Oct 10, 2026
The Moon Boutique Hotel & Spa
Historic Centre of Florence
CA $2,077
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.6/10 Exceptional! (605 reviews)
Everything was wonderful about our stay at The Moon Hotel and Spa. The room was beautiful and clean, the staff were friendly and helpful and it was a great location for sightseeing in Florence. We especially appreciated the very generous breakfast that was always served efficiently and with a smile. We would definitely stay again.
Reviewed on Oct 23, 2026
Bernini Palace
Historic Centre of Florence
CA $2,132
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.8/10 Exceptional! (1,006 reviews)
Had a fantastic stay at Bernini Palace. Our room was extremely comfortable and beautifully appointed. The public spaces are beautiful. Service was excellent. Breakfast in the beautiful breakfast room was divine. The location of the hotel was central and a stone's throw from Piazza della Signoria. I would absolutely stay here again!
Reviewed on Oct 23, 2026
Plaza Hotel Lucchesi
Historic Centre of Florence
CA $1,924
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Florence (FLR)
9.4/10 Exceptional! (1,002 reviews)
Hotel was wonderful. Stayed in the superior room which had a beautiful view over the city. Staff were incredibly helpful and the rooftop bar was fantastic.
Reviewed on Oct 21, 2026
Ready to book your vacation to Castellina in Chianti?
Castellina in Chianti Hotel Deals
Plus Florence - Hostel
Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
CA $72
CA $92 total
Nov 24 - Nov 25
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"It was a good budget hotel / motel - private room - good location Excellent value for money within walking distance of most attractions and the main railway station"
Reviewed on Oct 23, 2026
Hotel Paris
Via Banchi 2 Florence FI
Fully refundable
CA $160
CA $195 total
Nov 23 - Nov 24
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"The hotel is housed in a beautiful building, greater than 500 years old. It is very clean and well maintained, but some of the room amenities leave a little to be desired. The bathtub is very small and has a glass partition which covers just half the space. It takes a little maneuvering to stand ..."
Reviewed on Oct 22, 2026
Hotel Albani Firenze
Via Fiume 12 Florence FI
Fully refundableReserve now, pay when you stay
CA $162
CA $200 total
Nov 22 - Nov 23
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"Breakfast"
Reviewed on Oct 23, 2026
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 relaxing area.
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 walkable area, or enjoy its local tours.
Lilliano Estate Winery
You can enjoy a tasting or tour at Lilliano Estate Winery during your travels to Lilliano.
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.
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
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
CA $31
per adult
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
CA $78
per adult
78% of travellers recommend
SMALL-GROUP Wine Safari: Tuscany Wine Tasting Tour from Florence
CA $206
per adult
100% of travellers recommend
Frequently asked questions
How much does a Castellina in Chianti vacation package cost?
Offering great value package deals from CA $1,676 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.
