Chianti Region Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 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

Top Flight + Hotel Deals in Chianti Region

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

Aurum Firenze

4 out of 5
Historic Centre of Florence
per person
9 Oct - 16 Oct
found 1 day ago
Return direct flight included
Luxembourg (LUX) to Florence (FLR)
7.6/10 Good! (1,007 reviews)
Hotel is well located but in a very busy street, HORRIBLE BREAKFAST SERVICE, but with a nice view

Reviewed on 6 Aug 2025

The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
per person
9 Oct - 16 Oct
found 1 day ago
Return direct flight included
Luxembourg (LUX) 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 6 Jun 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
per person
9 Oct - 16 Oct
found 1 day ago
Return direct flight included
Luxembourg (LUX) to Florence (FLR)
10/10 Exceptional! (1 review)
Hotel Balestri

Hotel Balestri

4 out of 5
Historic Centre of Florence
per person
9 Oct - 16 Oct
found 1 day ago
Return direct flight included
Luxembourg (LUX) to Florence (FLR)
9.2/10 Wonderful! (967 reviews)
The hotel was wonderful! The staff were friendly and helpful. The room was clean and comfortable. We were lucky to have a balcony overlooking the Arno River. It was spectacular at night! The bar and restaurant made dining easy and the food / service was excellent! I highly recommend this hotel to visitors!

Reviewed on 8 Aug 2025

Palazzo Lorenzo Hotel Boutique & Spa

Palazzo Lorenzo Hotel Boutique & Spa

4 out of 5
San Lorenzo
per person
9 Oct - 16 Oct
found 1 day ago
Return direct flight included
Luxembourg (LUX) to Florence (FLR)
9.4/10 Exceptional! (569 reviews)
We stayed at Palazzo Lorenzo for 3 nights in July. I can’t fault this hotel. It’s quaint and very quiet mainly due to its location being on the outskirts of the city (15 mins walk) The T2 tram is nearby which brings you direct to the airport. Hotel staff were at hand if needed and breakfast had an extensive buffet choice no matter what your dietary requirements were. I would definitely recommend this hotel.

Reviewed on 28 Jul 2025

Top hotels in Chianti Region

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! (241 reviews)
"This is truly my favorite place in the world—peaceful, beautiful, and filled with the kindest staff. I’m so glad we found it. I didn’t want to leave and joked with my family that I might just run away and stay forever. The location and scenery are absolutely stunning. We enjoyed fantastic meals during ..."

Reviewed on 16 Jul 2025

Get rates
Castello di Spaltenna- Small Luxury Hotels of the World
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 €57 per night from 31 Aug to 1 Sept
€57
31 Aug - 1 Sept
includes taxes & fees
8/10 Very Good! (450 reviews)
Good Value for the cost !
"The hotel was good value for the price. The room was clean. The hotel is in a good, safe area. The A/C was able to keep up with the 98F temps outside. Check in was easy. The breakfast was very good. Parking is a little tricky but not to bad. The only issues we had with our room was the safe wouldnt ..."

Reviewed on 7 Jul 2025

Hotel Ristorante Alcide
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 €176 per night from 28 Aug to 29 Aug
€176
28 Aug - 29 Aug
includes taxes & fees
9.2/10 Wonderful! (439 reviews)
"Absolutely beautiful!!! It’s a bit of a long way to get to from Florence especially if you’re taking the bus but the accommodation and food is spectacular!"

Reviewed on 7 Aug 2025

Hotel Borgo di Cortefreda Relais
See all 5,185 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.

Popular places to visit

The Mall Luxury Outlet

During your visit to Reggello, you can enjoy retail therapy at The Mall Luxury Outlet. Discover the acclaimed art galleries and stunning cathedral in this walkable area.

The Mall Luxury Outlet

Tenuta Torciano Winery

You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this relaxing area.

Tenuta Torciano Winery

Verrazzano Castle

You can find out about the history of Greve in Chianti when you stop by Verrazzano Castle. Discover the area's countryside and wineries.

Verrazzano Castle

What to do in Chianti Region

Chianti Colours and Flavours from Florence

Chianti Wineries Tour with 7 Wine Tastings from Florence

€86
per adult
Chianti Wineries Tour with 7 Wine Tastings from Florence
San Gimignano: Chianti wine tasting and lunch

San Gimignano: Chianti wine tasting and lunch

€70
per adult
San Gimignano: Chianti wine tasting and lunch
Chianti Wineries Tour with Food and Wine Tasting from Florence

Chianti Wineries Tour with Food and Wine Tasting from Florence

€86
per adult
Chianti Wineries Tour with Food and Wine Tasting from Florence
See all activities in Chianti Region

Frequently asked questions

How much does a Chianti Region holiday package cost?
Live it up in Chianti Region from as low as €700. 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 holiday 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 favourites. 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 holiday?
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 holiday 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 organising 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 holiday 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 holiday package?
Your situation can change in a flash, so yes. You may be able to cancel or amend your Chianti Region holiday 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.