Chianti Region Vacations from ￥280,194

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The Latest Chianti Region Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Caravaggio

Hotel Caravaggio

3 out of 5
Historic Centre of Florence
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
8.8/10 Excellent! (1,004 reviews)
Wonderful stay - thank you!

Reviewed on Jul 7, 2025

Grand Hotel Cavour

Grand Hotel Cavour

4 out of 5
Historic Centre of Florence
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.2/10 Wonderful! (1,003 reviews)
Everyone is so helpful and kind. Wonderful hotel with wonderful people!

Reviewed on Jul 6, 2025

Hotel Miceli - Civico 50

Hotel Miceli - Civico 50

3 out of 5
Historic Centre of Florence
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9/10 Wonderful! (183 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

Residenza Florentia

Residenza Florentia

1 out of 5
Historic Centre of Florence
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
8.6/10 Excellent! (40 reviews)
Location, accommodations, and communication. Simple but comfortable. A basic facilities, and nice AC, elevator, and luggage storage.

Reviewed on Jun 12, 2025

Il Perseo

Il Perseo

3 out of 5
Historic Centre of Florence
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Florence (FLR)
9.4/10 Exceptional! (1,001 reviews)
The staff were wonderful! The hotel is in a great location. The rooms and hallways are tired. The bathroom door was cracked at the bottom and didn’t shut properly and the shower leaked. This, along with the mediocre toiletries make it a budget hotel and we will likely stay elsewhere next time.

Reviewed on Jul 6, 2025

Find the Best Chianti Region Vacation Packages

Chianti Region Hotel Deals

Castello di Spaltenna- Small Luxury Hotels of the World
Castello di Spaltenna- Small Luxury Hotels of the World
5 out of 5
Via Spaltenna 13, Gaiole in Chianti, SI
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (230 reviews)
"We stayed here as a family of six, including our two 3-year-olds, and it was by far our favorite place during our time in Italy! The kids absolutely loved swimming in the pools and running around the beautiful property. It felt peaceful, safe, and perfect. The breakfast was lovely each morning—fresh, ..."

Reviewed on Jun 28, 2025

Get rates
Castello di Spaltenna- Small Luxury Hotels of the World
Hotel Borgo di Cortefreda Relais
Hotel Borgo di Cortefreda Relais
4 out of 5
Via Roma 191, Barberino Tavarnelle, FI
Fully refundableReserve now, pay when you stay
The price is ￥30,720 per night from Jul 13 to Jul 14
￥30,720
￥34,813 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (427 reviews)
"We were a group of 10 who just returned from a 4 night stay at this beautiful hotel. It exceeded our groups expectations. It is quaint, in a beautiful setting. The staff was excellent, accommodating any request that was made. Restaurant is very good, included breakfast was great, many choices. We ..."

Reviewed on Jun 29, 2025

Hotel Borgo di Cortefreda Relais
Hotel Ristorante Alcide
Hotel Ristorante Alcide
4 out of 5
Viale Marconi, 67/A, Poggibonsi, SI
Fully refundableReserve now, pay when you stay
The price is ￥7,705 per night from Jul 13 to Jul 14
￥7,705
￥9,503 total
Jul 13 - Jul 14
includes taxes & fees
8/10 Very Good! (448 reviews)
"Room was nice and spacious. Air conditioner barely kept up with the heat. Had mosquitoes in the room the second night and don’t know how it got in the room. Overall all it’s a decent place to stay."

Reviewed on May 28, 2025

Hotel Ristorante Alcide
See all 5,181 properties in Chianti Region
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.

Discover the most popular places to visit in Chianti Region

Montegufoni Castle

4/5(2 reviews)

Find out about the history of Montegufoni with a stop at Montegufoni Castle. Visit the stunning cathedral and notable monuments in this walkable area.

Montegufoni Castle

What to do in Chianti Region

Having fun while tasting Chianti

Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence

￥14,492
per adult
100% of travellers recommend
Tuscany Wine Tour : 2 Wineries & San Gimignano from Florence
VIP Tour: Wine Tasting & Dinner in the Vineyards of Chianti

VIP Tour: Wine Tasting & Dinner in the Vineyards of Chianti

￥20,340
per adult
92% of travellers recommend
VIP Tour: Wine Tasting & Dinner in the Vineyards of Chianti
Chianti Colours and Flavours from Florence

Chianti Wineries Tour with 7 Wine Tastings from Florence

￥14,465
per adult
Chianti Wineries Tour with 7 Wine Tastings from Florence
See all activities in Chianti Region

Frequently asked questions

How much does a Chianti Region vacation package cost?
Live it up in Chianti Region from as low as ￥280,194. Choose from a wonderful selection of flights, hotels and rental cars to suit your travel style. You can pick up even more discounts when you add a couple of tours or experiences to your package.
How do I get a cheap travel package to Chianti Region?
Find flights that suit your busy schedule, add a hotel to your booking and watch how much you save with a Chianti Region vacation package. It's that easy! From flights and hotels to rental cars and activities, Expedia is your gateway to cheap travel. And with over 550 air carriers and 1,000,000 properties around the world to pick from, you won't be short of choice.
Where should I stay in Chianti Region?
Val dElsa is in the top spot on many Chianti Region must-see lists. Collegiate Church of Santa Maria Assunta is one reason why.
What are the top hotels in Chianti Region?
When it comes to hotels in Val dElsa, Grand Hotel Baglioni and Hotel Spadai are among the favorites. If you're spending time in Greve in Chianti, Hotel Pendini and The Market Urban Hotel will make you feel at home.
How far in advance should I book my Chianti Region vacation?
While prices change from time to time, we generally suggest booking your flight as soon as possible. Many international airfares can be compared on Expedia up to a year in advance. If circumstances have left you booking late, you may still get lucky. Low prices to Chianti Region sometimes emerge only weeks before departure.
What does an Expedia Chianti Region travel package include?
Much of that is up to you. You can pick from a variety of Chianti Region packages, such as a hotel, rental car and flight. You can also book a flight with a hotel, or a flight with a rental car. Once you've made your booking, you can add the fun stuff like experiences and tours. Whatever your perfect Chianti Region vacation looks like, get set to save!
What should I know before booking a Chianti Region travel package?
When you book your flights, hotels and car rentals together, you'll pick up fantastic discounts. Whether you're organizing a mountain getaway in a cabin or would rather stay in a fancy hotel in the city, Expedia will help make it happen.
Can I choose my airline with a Chianti Region Expedia vacation package?
Yes --- that's one of the best things about an Expedia package. You can mix and match your flights, hotels and more. We have more than 550 partner airlines across the globe, so you have loads of choice when creating your Chianti Region adventure.
If I'm not able to travel, can I cancel my Chianti Region vacation package?
Your situation can change in a flash, so yes. You may be able to cancel or amend your Chianti Region vacation package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still make the necessary changes, but your airline, hotel or car rental company may charge additional fees. Need more information? Look up our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.