Cavallari Vacations from $844

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Your Cavallari Vacation

From its highlights to its hidden gems, this city is best experienced with a Cavallari vacation package. Book a hotel in Badia Coltibuono, which is great for families, nature and walking. If your trip to Cavallari includes some sightseeing, take in famous attractions like Buondonno Winery, Casa Vinicola Luigi Cecchi and City Hall Castellina In Chianti. Don't put off your visit to this destination any longer. The perfect Cavallari vacation is only a few clicks away with Expedia.

The Latest Cavallari vacation packages

Price found within the past 48 hours. Click for updated prices.
Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
7.6/10 Good! (1,012 reviews)
I’ve had a wonderful stay at Autumn Hotel! It was very clean! The staff was amazing the room was perfect with a balcony you didn’t hear the busy noise from the street at night I will definitely book with them again! Thank you!

Reviewed on Jul 19, 2025

Hotel Miceli - Civico 50

Hotel Miceli - Civico 50

3 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 1 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Florence (FLR)
8.8/10 Excellent! (185 reviews)
There was no staff on-site when we arrived, but we had been in touch with the hotel via WhatsApp all day, and they were super helpful and friendly! Entering the building was very easy, but the 3-person elevator was just a little squished. The room was as expected - the only downside was that the shower was only cold water (after running it for a few minutes) and the sink in the bathroom was only hot water! The room was warm when we entered, but we turned the air conditioning up and it was perfect by the time we arrived back for bed. All-in-all, it was a good stay overnight!

Reviewed on Jun 22, 2025

Aurum Uffizi

Aurum Uffizi

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 3 - Oct 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Florence (FLR)
7.8/10 Good! (1,001 reviews)
Everything was perfect! Thank you!!

Reviewed on Jul 20, 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Oct 8 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Florence (FLR)
9.6/10 Exceptional! (462 reviews)
Hands down the best place we have stayed. They accommodated to go breakfasts for our tours, arranged taxis, made cappuccino when we were heading out the door. Wonderful experience

Reviewed on Jun 6, 2025

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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

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Discover the most popular places to visit in Cavallari

Castellina in Chianti which includes 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

City Hall Castellina In Chianti

5/5(1 review)

City Hall Castellina In Chianti is just one of the places to see in Castellina in Chianti, so why not enjoy the other things to explore during your travels? Discover the beautiful countryside and wineries in this quaint area.

City Hall Castellina In Chianti

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 Cavallari

Dinner in Chianti Vineyards with Wine Tasting

From Florence: Dinner in Chianti Vineyards with Wine Tasting

$128
per adult
80% of travellers recommend
From Florence: Dinner in Chianti Vineyards with Wine Tasting
Cooking class in Tuscany

Cooking Class in Tuscany

$293
per adult
Cooking Class in Tuscany
Cooking Class in Tuscan Farmhouse from San Gimignano

Private Cooking Class in Chianti from San Gimignano

$431
per adult
Private Cooking Class in Chianti from San Gimignano
See all activities in Cavallari

Cavallari Hotel Deals

Hotel Athena

Hotel Athena

4 out of 5
P Mascagni 55, Siena, SI
Fully refundable
$132 nightly
The price is $151 total per night from Jul 30 to Jul 31
$151 total
Jul 30 - Jul 31
Total includes taxes and fees
9.2/10 Wonderful! (1,000 reviews)
"The front desk that was exceptional"

Reviewed on Jul 18, 2025

Hotel Athena
NH Siena

NH Siena

4 out of 5
Piazza La Lizza 1, Siena, SI
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $137 total per night from Aug 20 to Aug 21
$137 total
Aug 20 - Aug 21
Total includes taxes and fees
8/10 Very Good! (993 reviews)
Very nice hotel
"Very nice and clean hotel. Just outside the ztl, close to historic city centre area."

Reviewed on Jul 10, 2025

NH Siena
Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo

4 out of 5
Via Di Giogoli 12, Florence, FI
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $136 total per night from Jul 27 to Jul 28
$136 total
Jul 27 - Jul 28
Total includes taxes and fees
8/10 Very Good! (203 reviews)
"Beautiful setting and very nice pool. We really liked the apartment with the Tuscan charm. The AC worked very good. We did not have a car and the taxi fares were €29-50 each way to get into town. There is a nice restaurant nearby that is walkable. We did enjoy our stay and it was very memorable."

Reviewed on Jul 1, 2025

Fattoria il Milione Agriturismo
See all 7,447 properties in Cavallari
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.

Find the Best Cavallari Vacation Packages

Cavallari Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Peretola Airport (FLR)
Top Sights
Buondonno Winery, Casa Vinicola Luigi Cecchi and Archaeological Museum of Chianti

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Frequently asked questions

How much does a Cavallari vacation package cost?
Offering excellent value package deals from $844 on Expedia, you'll be surprised at how little a vacation to Cavallari costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Cavallari?
November, December and January are great times to search for cheap Cavallari vacation packages. Traveling in quieter periods means you'll typically find better prices on flights and accommodations.
How many days is enough for Cavallari?
With a well-planned schedule, you can easily visit the main Cavallari sights in a handful of days. But if you want to explore off the beaten track or go on day trips, consider booking your Cavallari vacation for longer.
How to find the best Cavallari package deals?
Bagging a cheap Cavallari package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, apply a few filters and browse what's available. You can tweak your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Cavallari 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 often lower.
Is it cheaper to book a Cavallari vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically score a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Cavallari vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Cavallari?
If you've got your Cavallari vacation dates finalized, book early to bag some unbeatable deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are ideal for impromptu escapes.
Does Expedia offer Book Now, Pay Later Cavallari vacation packages?
Your Cavallari break should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you that extra flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.