Chianti Region Holidays

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Chianti Region Holiday

Our pick of the best Chianti Region Hotel Deals

Hotel Ristorante Alcide

Hotel Ristorante Alcide

4 out of 5
Viale Marconi, 67/A Poggibonsi SI
Fully refundable
The price is NZ$143 per night from 26 Apr to 27 Apr
NZ$143
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (481 reviews)
I highly recommended

Reviewed on 14 Oct 2025

Hotel Ristorante Alcide
Borgo Vescine

Borgo Vescine

5 out of 5
Località Vescine Radda in Chianti SI
Fully refundableReserve now, pay when you stay
The price is NZ$972 per night from 13 Apr to 14 Apr
NZ$972
13 Apr - 14 Apr
includes taxes & fees
9.4/10 Exceptional! (244 reviews)
You are paying for the view!!!! This hotel was not worth the money spent in my opinion. The hotel staff was not very accommodating, though the restaurant staff was lovely. We had to bring our luggage up to our room and back down during check in and check out — no one even offered and trust me it ...

Reviewed on 5 Oct 2025

Borgo Vescine
Relais Villa Olmo

Relais Villa Olmo

Via Imprunetana Per Tavarnuzze 19 Impruneta FI
Fully refundableReserve now, pay when you stay
The price is NZ$349 per night from 27 Apr to 28 Apr
NZ$349
27 Apr - 28 Apr
includes taxes & fees
9.4/10 Exceptional! (231 reviews)
The room was spotless and cleaned daily, the staff was very kind and helpful, the breakfast was amazing and fresh every morning! We have the best experience.

Reviewed on 2 Apr 2026

Relais Villa Olmo
See all 4,764 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

A woman on a spiral stairway, part of the modern architecture at Antinori Winery Nel Chianti Classico, San Casciano in Val di Pesa, Tuscany, Italy.

Antinori nel Chianti Classico

You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Visit the churches and wineries in this walkable area.

Antinori nel Chianti Classico
Night view of the architecture of the small town of Florence, Shanghai

The Mall Luxury Outlet

4/5(8 reviews)

During your visit to Leccio, 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 quaint area.

Tenuta Torciano Winery

What to do in Chianti Region

Small-Group Wine Tasting Experience in the Tuscan Countryside

Small-Group Wine Tasting Experience in the Tuscan Countryside

NZ$176
per adult
98% of travellers recommend
Small-Group Wine Tasting Experience in the Tuscan Countryside
Siena, San Gimignano, Monteriggioni & Chianti from Florence

Siena, San Gimignano, Monteriggioni & Chianti from Florence

NZ$90
per adult
86% of travellers recommend
Siena, San Gimignano, Monteriggioni & Chianti from Florence
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine

NZ$157
per adult
88% of travellers recommend
Florence: San Gimignano, Siena, Monteriggioni, Chianti & Lunch with Wine
See all activities in Chianti Region

Frequently asked questions

Can I cancel my flight booking to Chianti Region due to COVID-19?
Our Customer Service Portal is your one-stop shop for almost every travel question, including about flight changes related to COVID-19. For more peace of mind, we suggest looking over the terms and conditions of your preferred airline before reserving a seat.
What's the best way to find cheap flights to Chianti Region that have flexible change policies?
It's as easy as can be with Expedia. Step 1: Type in your travel dates and click the "Search" button. Second step: Check the "No change fee" box below the "Flexible change policies" filter to the left of your screen. Step 3. Reserve your flexible and cheap flight to Chianti Region.
What are some of the general tips for travellers to Chianti Region during the COVID-19 outbreak?
COVID-19 has changed how the world works in countless ways, including how we're able to travel safely. These tips will help you understand these new challenges and prepare you for your trip to Chianti Region:
  • Look into if any restrictions apply to both your destination and origin. You may not be able to travel depending on local circumstances, so make sure you check before you book.
  • Wear a face mask even during airport screening. A TSA employee will require you to adjust your mask for ID purposes.
  • Avoid handing your boarding pass directly to a TSA officer. Rather, position the pass on the reader and then hold it up for inspection.
  • TSA is now allowing passengers to take one container of hand sanitizer, up to 12 oz (350 ml) in size, in carry-on bags. This will need to be removed from your bag to be screened.
  • To reduce handling during the screening process, place items such as your phone, keys and wallet into your carry-on rather than into the bins.
  • If you're taking food through the security checkpoint, place it in a clear plastic bag and then into a screening bin. This lessens the likelihood that a TSA agent will need to touch your carry-on bag or food container for closer inspection.

Which airlines fly to Chianti Region?
Alitalia offers flights into or near Chianti Region, including 121 that fly into Peretola Airport (FLR) each month. Select your travel dates and then book your seat early for the biggest bargain.
How can I find cheap tickets to Chianti Region?
To nab a terrific deal to Chianti Region, book well in advance. Also think about using Expedia's handy "flexible dates" link at the top of your search results. This will list prices for similar time frames. In the last seven days, was the best price for a flight to Chianti Region.
How much is a flight to Chianti Region?
One-way flights from () sold for as little as in the last seven days. During this time, the cost of a return air ticket to Chianti Region ranged between and . If you find a fantastic deal, book quickly — these prices don't stick around.
What are the most popular airports to fly into in Chianti Region?
Peretola Airport (FLR) is the main entryway for those headed to Chianti Region. Roughly 1323 flights a month land at this airport.
When is the cheapest time to fly to Chianti Region?
Fly out on a Tuesday to better your chances of securing the cheapest airfare to Chianti Region. Mondays are usually the next most affordable day to depart. Saturday is typically the priciest day to fly anywhere.
How much is a plane ticket to Chianti Region?
In the last seven days, tickets to Chianti Region varied between and . Prices usually rise as your travel date nears, so book a great deal today.
Which airlines with flights to Chianti Region employ COVID-19 cleanliness policies?
As passengers and cabin crew begin travelling again, many airlines have introduced social distancing and other vital measures to reduce the impact of COVID-19. Here are some good examples:
  • Ryanair - this airline is known for cleaning with disinfectant and providing passenger masks.
  • Vueling - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Air Dolomiti - this airline is known for cleaning with disinfectant and conducting passenger temperature checks.

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