Chianti Region Luxury Vacations

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Flight and Luxury hotel deals in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

CA $1,169
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (463 reviews)
Under renovation so it could have been better

Reviewed on Sep 30, 2026

Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa

CA $1,673
per person
Nov 8 - Nov 15
found 20 hours ago
Roundtrip flight included
Vancouver (YVR) to Florence (FLR)
9.2/10 Wonderful! (300 reviews)
Amazing historical hotel in a beautiful town, 10 out of 10.

Reviewed on Sep 28, 2026

Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa

CA $1,366
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.2/10 Wonderful! (196 reviews)
Great stay!

Reviewed on Sep 4, 2026

Hotel Palazzo San Lorenzo & SPA

Hotel Palazzo San Lorenzo & SPA

CA $1,361
per person
Dec 6 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Florence (FLR)
9.4/10 Exceptional! (467 reviews)
On the previous rating and comments that we were requested, there were enough space, so si wanted to add that the hotel was very generous with the mini bar. The breakfast service was more present during the 2nd morning, but you can tell that some staff were not trained for this line of work. From how to hand a spoon to a guest to clear plates during the meal (you pretty much had to do it by yourself). The check-out process went well with a couple of gift to apologize for the short coming. When we checked in in the next hotel, we noticed that a large sum of foreign currency, that had been placed in the safety box was missing. Another enveloppe was ripper open but no bills ot not many of those smaller bills were taken as I guess the person did not want a too bulge in their pocket. Nobody explained anything when we were accompanied to the room or at the front desk and, apparently, did not read properly the instructions that indicated to press a red button inside the box, before entering your own code, so the code used previously must still have been the one that enabled the opening of the safe. On the check-out morning, we requested the help of the front desk to open the box, We never thought that something would be missing as that had never happened to us during any stay in the many years of frequent travel. I guess that we should have read the instructions but this large loss of money will be hard to forget.

Reviewed on Sep 27, 2026

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

Siena City Centre
CA $2,938
per person
Nov 8 - Nov 15
found 20 hours ago
Roundtrip flight included
Vancouver (YVR) to Florence (FLR)
9.2/10 Wonderful! (631 reviews)
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5* Luxury holidays in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

Siena City Centre
CA $2,938
per person
Nov 8 - Nov 15
found 20 hours ago
Roundtrip flight included
Vancouver (YVR) to Florence (FLR)
9.2/10 Wonderful! (631 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Chianti Region
View all trips

4 Night Luxury holidays in Chianti Region

Price found within the past 48 hours. Click for updated prices.
Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

CA $1,072
per person
Nov 2 - Nov 6
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Florence (FLR)
9.2/10 Wonderful! (463 reviews)
Under renovation so it could have been better

Reviewed on Sep 30, 2026

Don't see what you're looking for?
See all available trips from Columbus to Chianti Region
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Plan the perfect luxury Chianti Region vacation with Expedia

What are some benefits when booking luxury Chianti Region vacations?

When you book a luxury Chianti Region vacation, you get to enjoy some of the best amenities and special features available. Luxury vacation options often feature spa facilities right in your accommodation, along with room service and an on-site restaurant. The quality of the bedding and even the water pressure tends to be better, so it's the perfect solution for travellers looking to put their feet up and relax.

How can I find all-inclusive luxury vacations in Chianti Region?

If you're looking for something luxurious in Chianti Region, all you have to do is take advantage of our search filters. You can implement a filter to only show 5-star accommodations as well as some amenities you may be interested in, like spa facilities and hot tubs. When you opt for an all-inclusive package, you can enjoy luxury alongside a potential discount for booking your accommodation and flight together.

Can I book a cheap luxury vacation?

While luxury vacations tend to be on the more costly end of the spectrum, ranging from CA $1,072, there are a few methods you can try to lower the price as much as possible. When booking a flight and accommodation together, you can enjoy savings of up to 8. After implementing filters for luxury features, you can also sort by price to list the cheapest luxury packages first.

Are there luxury spa vacations?

Yes, luxury spa vacations are available and quite popular in Chianti Region. When you book one of these experiences, it's easier than ever to relax, unwind and recharge in between excursions. Either way, you can easily find spa vacations by implementing the spa filter in your search.

What should I look for in a luxury family vacation in Chianti Region?

When booking something for the whole family, it's important to consider exactly what kind of experience your family will want.Luxury packages make it easy to keep everyone happy with creature comforts. Kids especially enjoy features like pools, a delicious breakfast and plenty of space. Suites tend to offer your family members a bit more privacy and comfort compared to simple rooms throughout Chianti Region.

Can I book last-minute luxury vacations?

Yes, last-minute bookings are often available in Chianti Region. All you have to do is enter your travel dates to see what's available. Sometimes, you'll even find additional discounts for booking last-minute, as accommodations are desperate to fill their last remaining spaces.

What can help me find the best luxury vacation deals in Chianti Region?

You can use a few strategies to find the best deals on luxury vacation packages. Consider travelling during the off-season to take advantage of the typically lower overall prices. Additionally, staying in the less popular parts of Chianti Region or travelling to more obscure destinations altogether can often lead to lower prices.

Can I book a luxury vacation that is fully refundable?

Yes, fully refundable reservations are sometimes available on luxury vacation packages in Chianti Region. You can implement a filter for it specifically or check out the policy section on any one of your search results. It should clearly state what's necessary to qualify for a fully refundable booking.

Why should I book my luxury vacation with Expedia?

When you book with Expedia, you can enjoy a one-stop shop for all your travel planning needs. We offer accommodations as well as flights, and you may even be able to enjoy discounts by booking them together. Of course, Expedia Rewards members will find even more discounts and earn points that can be put toward discounts on future bookings.

Luxury Hotels in Chianti Region

COMO Castello Del Nero

COMO Castello Del Nero

Strada Spicciano 7 Barberino Tavarnelle FI
  • 10 min drive from Antinori nel Chianti Classico
Book a stay at this luxury hotel in Barberino Tavarnelle. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Castello di Barberino Val d'Elsa ...
9.6/10 Exceptional! (145 reviews)
"The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back."

Reviewed on Sep 11, 2026

COMO Castello Del Nero
Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World

Monastero D'Ombrone Castelnuovo Berardenga SI
  • 1 hour drive from Antinori nel Chianti Classico
Book a stay at this luxury hotel in Castelnuovo Berardenga. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Berardenga Riding Centre and ...
9/10 Wonderful! (147 reviews)
"Beautiful hotel, staff amazing, tranquil surroundings, and incredible food. The perfect stay in Tuscany!"

Reviewed on Sep 7, 2026

Castel Monastero - The Leading Hotels of the World
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

Banchi Di Sopra 85 Siena SI
  • 53 min drive from Antinori nel Chianti Classico
Book a stay at this luxury hotel in Siena. Enjoy free WiFi, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular ...
Grand Hotel Continental Siena – Starhotels Collezione
See all 4,895 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.

Things to do

City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

CA $47
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
Florence Accademia Gallery Tour with Entrance Ticket Included

Florence Accademia Gallery Tour with Entrance Ticket Included

CA $77
per adult
94% of travellers recommend
Florence Accademia Gallery Tour with Entrance Ticket Included
Florence: Pasta Cooking Class with Unlimited Wine

Florence: Pasta Cooking Class with Unlimited Wine

CA $29
per adult
94% of travellers recommend
Florence: Pasta Cooking Class with Unlimited Wine
See all activities in Chianti Region

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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.