Castellina in Chianti Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
per person
Aug 25 - Aug 28
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
9.2/10 Wonderful! (1,002 reviews)
Excellent location right in the middle of everything. If thinking about using public transportation The hotel is on the C bus line these are small electric buses very difficult to get luggage on had to get a taxi

Reviewed on Jul. 15, 2025

Palazzo Firenze by Baglioni Hotels & Resorts

Palazzo Firenze by Baglioni Hotels & Resorts

5 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 19 - Sep 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (228 reviews)
Great service esp Fillippo and Daniel at the breakfast service

Reviewed on Jul. 6, 2025

Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 17 - Sep 23
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
8.6/10 Excellent! (464 reviews)
Nice hotel, very clean, a little far from main attractions, but in general I really like it

Reviewed on Jul. 14, 2025

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
per person
Sep 6 - Sep 12
found 17 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Florence (FLR)
8.8/10 Excellent! (382 reviews)
Incredible off-season stay. The breakfast each morning was incredible. So much better than any other hotel I’ve stayed at. Fresh and delicious. The staff were friendly and helpful and our room was amazing. The Villa itself is a renovated Renaissance property and all around are little reminders of its glorious past. We were too early for the pool (starts in June) but I have a feeling that’s why we got such a great deal. The views from the decks are incredible and it’s close to Florence. The roads are windy and narrow, so be careful! But one of the roads down from the Villa revealed a spectacular view of Florence. I can’t recommend this hotel enough. Would gladly return.

Reviewed on May 31, 2025

Hotel Palazzo Ognissanti

Hotel Palazzo Ognissanti

4 out of 5
Historic Centre of Florence
per person
Sep 17 - Sep 23
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Florence (FLR)
7.8/10 Good! (479 reviews)
We loved the location close to the Arno River and the city center. Had a delicious pizza around the corner and there is also a small grocery store for last minute necessities and water! The staff was very kind, and the breakfast was delicious. They offer free luggage storage which was convenient. Within walking distance from the main train station. We loved our stay and will be back!

Reviewed on Jun. 27, 2025

Ready to book your vacation to Castellina in Chianti?

 

Choose your dates

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 $108 per night from Aug 3 to Aug 4
CA $108
CA $141 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (1,042 reviews)
"Phenomenal place to stay - rooftop pool with cityscape of Florence, laundry facilities, the tram station right outside the hotel. Hosted community events / Had a fresh and modern style. We enjoyed this hotel so much, we regret not staying an extra couple of days!"

Reviewed on Jul. 13, 2025

The Social Hub Florence Lavagnini
c-hotels Ambasciatori

c-hotels Ambasciatori

4 out of 5
Via Luigi Alamanni 3, Florence, FI
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Jul 29 to Jul 30
CA $153
CA $191 total
Jul 29 - Jul 30
includes taxes & fees
8.2/10 Very Good! (1,008 reviews)
"Great staff, easy check in and close to train and major Florence attractions. Clean and modern and spacious!"

Reviewed on Jul. 11, 2025

c-hotels Ambasciatori
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 $121 per night from Aug 3 to Aug 4
CA $121
CA $156 total
Aug 3 - Aug 4
includes taxes & fees
9.2/10 Wonderful! (201 reviews)
"Love our stays. Hotel was very beautiful, comfortable and lots of area to relax or socialize. The 5th floor where the pool area is the best I had seen in all the hotels I had stayed."

Reviewed on Jul. 12, 2025

The Social Hub Florence Belfiore
See all 15,496 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Discover the most popular places to visit in Castellina in Chianti

Castellina in Chianti showing farmland

Buondonno Winery

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.

Buondonno Winery

Casa Vinicola Luigi Cecchi

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.

Casa Vinicola Luigi Cecchi

What to do in Castellina in Chianti

Vintage Fiat 500 Tuscany Drive with Winery Lunch

Vintage Fiat 500 Tuscany Drive with Winery Lunch

CA $240
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

CA $206
per adult
Full-Day Tour of Chianti by Vespa with Lunch from Siena
Chianti Wine Tour with Tuscan Lunch Open Top Van

Chianti Wine Tour with Tuscan Lunch Open Top Van

CA $270
per adult
100% of travellers recommend
Chianti Wine Tour with Tuscan Lunch Open Top Van
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 $1,443 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.

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