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.
Aurum Firenze
Historic Centre of Florence
CA $1,249
per person
Oct 17 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Florence (FLR)
7.4/10 Good! (1,008 reviews)
Room very small, no chairs inside, ants everywhere, including the breakfast area.
Quadruple room has a double bed and a single bed, apparently this was the biggest room in the hotel. We book for 4 people ( 2 adults and 2 children 12 and 16 and they had to squeeze in a single bed.
Reviewed on Aug 12, 2026
Hotel La Scaletta Al Ponte Vecchio
Historic Centre of Florence
CA $2,695
per person
Oct 10 - Oct 16
found 14 hours ago
Roundtrip flight included
Montreal (YMQ) to Florence (FLR)
9/10 Wonderful! (1,006 reviews)
We had a wonderful stay at La Scaletta in Florence! The hotel was extremely clean, and the staff was always friendly, welcoming, and very helpful throughout our stay.
The location is fantastic, just steps from the Ponte Vecchio, with so many great shops, restaurants, and beautiful sights within easy walking distance.
One of the things we loved most was the combination of history and modern comfort. Staying in such a beautiful historic building, surrounded by gorgeous frescoes and architectural details, made the experience feel very special, while the rooms still had a fresh, modern vibe.
The terrace bar was another highlight and a wonderful place to relax and enjoy Florence. Beautiful hotel, excellent location, and great service. We would definitely recommend La Scaletta and would happily stay here again!
Reviewed on Aug 12, 2026
Eden Rock Resort
CA $2,498
per person
Oct 10 - Oct 16
found 1 day ago
Roundtrip flight included
Montreal (YUL) 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
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 $117
CA $151 total
Aug 27 - Aug 28
includes taxes & fees
Plus Florence - Hostel
Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
CA $105
CA $128 total
Aug 28 - Aug 29
includes taxes & fees
Hotel Paris
Via Banchi 2 Florence FI
Fully refundable
CA $189
CA $227 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"It’s good was a little old but it was great and good location close to everything"
Reviewed on Aug 16, 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.
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.
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.
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.
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.
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 $29
per adult
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
Frequently asked questions
How much does a Castellina in Chianti vacation package cost?
Offering great value package deals from CA $1,249 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.
