Chianti Region Holidays

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Top Flight + Hotel Deals in Chianti Region

Price found within the past 48 hours. Click for updated prices.
The Moon Boutique Hotel & Spa

The Moon Boutique Hotel & Spa

4 out of 5
Historic Centre of Florence
per person
9 Oct - 14 Oct
found 9 hours 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

Aurum Firenze

Aurum Firenze

4 out of 5
Historic Centre of Florence
per person
9 Oct - 16 Oct
found 10 hours ago
Return direct flight included
Luxembourg (LUX) to Florence (FLR)
7.6/10 Good! (1,000 reviews)
Very small rooms and bathrooms. Breakfast and breakfast staff were awesome and on the top floor. Hotel room small and nothing special. Great location and quiet…but good luck getting out of a car with luggage.

Reviewed on 4 Aug 2025

LHP River Club

LHP River Club

5 out of 5
Santa Croce
Save 100% on your flight
per person
7 Sept - 14 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
10/10 Exceptional! (1 review)
Eurostars Florence Boutique

Eurostars Florence Boutique

4 out of 5
Historic Centre of Florence
Save 100% on your flight
per person
7 Sept - 14 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.6/10 Excellent! (468 reviews)
Great little hotel. Everything is within walking distance. The view from the terrace was amazing.

Reviewed on 6 Aug 2025

Villa Tolomei Hotel & Resort

Villa Tolomei Hotel & Resort

5 out of 5
Oltrarno
Save 100% on your flight
per person
7 Sept - 14 Sept
found 1 day ago
Return direct flight included
Dublin (DUB) to Florence (FLR)
8.8/10 Excellent! (387 reviews)
Great place to stay near Florence, it’s quite and relaxing. The pool is great.

Reviewed on 31 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
9.4/10 Exceptional! (240 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

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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 €65 per night from 20 Aug to 21 Aug
€65
20 Aug - 21 Aug
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
The price is €176 per night from 28 Aug to 29 Aug
€176
28 Aug - 29 Aug
includes taxes & fees
9.4/10 Exceptional! (437 reviews)
Adults don’t want baby food!
"Great afternoon by the pool. Evening meal menu was odd. I think the chef was trying too hard to be different. The vegetarian chick pea dish was merely a bowl of cooked onions with some vegetable mush- my wife called it baby food. The chicken with truffles was tasty although came with flabby chicken ..."

Reviewed on 28 Jul 2025

Hotel Borgo di Cortefreda Relais
See all 5,177 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

4/5(18 reviews)

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

Pisa, Siena and San Gimignano day trip from Florence

Pisa, Siena and San Gimignano day trip from Florence

€65
per adult
86% of travellers recommend
Pisa, Siena and San Gimignano day trip from Florence
Skip-the-Line Duomo: Priority-Access 30-Minute Guided Tour

Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour

€21
per adult
78% of travellers recommend
Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour
Florence: Timed Entry Ticket to Michelangelo's David & eBook

Florence: Timed Entry Ticket to Michelangelo's David & eBook

€35
per adult
96% of travellers recommend
Florence: Timed Entry Ticket to Michelangelo's David & eBook
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 €538. 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.