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

Aurum Firenze

4 out of 5
Historic Centre of Florence
Price was CA $2,260, price is now CA $1,471 per person
CA $1,471
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Florence (FLR)
7.4/10 Good! (1,014 reviews)
Honest review. The pros, the hotel location is great, near the station and all the attractions, the staff were super helpful and friendly, our room was on the small side but the bed was comfy and the bathroom nice. The breakfast was OK. The main con for us and I will qualify it by saying that we were at the hotel during a heat was that the aircon in our room wasn't great, only touched the edges of reducing the temperature and was noisy. There was also some noise from within the hotel. Overall a good hotel though and we enjoyed our stay.

Reviewed on Jun 30, 2026

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Price was CA $2,610, price is now CA $1,517 per person
CA $1,517
per person
Aug 31 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
7.6/10 Good! (1,004 reviews)
Highly recommended

Reviewed on Jun 30, 2026

Precise Tale Poggio Alla Sala

Precise Tale Poggio Alla Sala

5 out of 5
Price was CA $7,058, price is now CA $4,536 per person
CA $4,536
per person
Sep 6 - Sep 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.6/10 Exceptional! (147 reviews)
It’s a beautiful property, but be aware that it is secluded and that the restaurant menu is quite limited and after a couple of days, we were happy to go elsewhere. The waiting staff was attentive and nice, front desk not as much (maybe the la guard barrier?)

Reviewed on Jun 19, 2026

Hotel San Luca

Hotel San Luca

4 out of 5
Cortona Old Town
Price was CA $2,056, price is now CA $1,501 per person
CA $1,501
per person
Sep 15 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (429 reviews)
Wonderful hotel with great view for Tuscany, good breakfast, perfect location to visit Cortona

Reviewed on Jun 30, 2026

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Price was CA $2,780, price is now CA $2,034 per person
CA $2,034
per person
Aug 31 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Florence (FLR)
9.6/10 Exceptional! (568 reviews)
Very nice and friendly staff, good breakfast, nice and clean hotel

Reviewed on Jun 18, 2026

Ready to book your vacation to Castellina in Chianti?

 

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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 CA $152 per night from Jul 5 to Jul 6
CA $152
CA $190 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (1,432 reviews)
"Le personnel a été très accueillant, belle hôtel propre et le lit était confortable."

Reviewed on Jun 30, 2026

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 CA $179 per night from Jul 5 to Jul 6
CA $179
CA $219 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (602 reviews)
"The staff were super friendly and helpful and having a place to do laundry for free was amazing."

Reviewed on Jun 27, 2026

The Social Hub Florence Belfiore
Plus Florence - Hostel

Plus Florence - Hostel

Via Santa Caterina D'Alessandria, 15 Florence FI
Fully refundableReserve now, pay when you stay
The price is CA $124 per night from Jul 2 to Jul 3
CA $124
CA $149 total
Jul 2 - Jul 3
includes taxes & fees
8.6/10 Excellent! (1,003 reviews)
"Plus Florence was awesome! The atmosphere is really fun and there are lots of people to meet and hang out with! The room was clean and the ac worked wonderfully! I would definitely go back next time I’m in Florence."

Reviewed on Jun 27, 2026

Plus Florence - Hostel
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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.
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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.
See properties

What to do in Castellina in Chianti

Chianti Half Day Wine Tour from Florence

Chianti Half Day Wine Tour from Florence

CA $36
per adult
88% of travellers recommend
Chianti Half Day Wine Tour from Florence
Tuscany in 1 day: Pisa, San Gimignano and Siena with Lunch

Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch

CA $79
per adult
78% of travellers recommend
Tuscany in 1 day from Florence: Pisa, San Gimignano & Siena with Lunch
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

CA $127
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
See all activities in Castellina in Chianti

Frequently asked questions

How much does a Castellina in Chianti vacation package cost?
Offering great value package deals from CA $1,471 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?

  1. Pick your dates: The things you want to do in Castellina in Chianti and your preferred season will help you decide when to go.
  2. 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.
  3. 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.
  4. 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.

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