Luxury Vacations in Chianti Region 2026

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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

CA $1,266

per person

Oct 22 - Oct 28

found 4 hours ago

Roundtrip flight included

Toronto (YYZ) to Florence (FLR)

9.2/10 Wonderful! (447 reviews)

Villa Pitiana

CA $1,296

per person

Oct 22 - Oct 28

found 4 hours ago

Roundtrip flight included

Toronto (YYZ) to Florence (FLR)

8.6/10 Excellent! (153 reviews)

Villa Le Calvane

CA $9,563

per person

Oct 10 - Oct 16

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Florence (FLR)

9.8/10 Exceptional! (89 reviews)

Great staff! Beautiful property. The food is amazing. The pool is beautiful. The view is unreal. We live it. We will be back. Thanks

Reviewed on Aug 3, 2026

Villa Scacciapensieri Boutique Hotel

Scacciapensieri

CA $1,459

per person

Oct 22 - Oct 28

found 4 hours ago

Roundtrip flight included

Toronto (YYZ) to Florence (FLR)

9.2/10 Wonderful! (450 reviews)

All in all a lovely property with lovely staff. Good location, easy bus ride to Siena town.

Reviewed on Aug 16, 2026

Villa Casagrande Resort & SPA

CA $1,883

per person

Oct 2 - Oct 7

found 11 hours ago

Roundtrip flight included

Vancouver (YVR) to Florence (FLR)

9.2/10 Wonderful! (402 reviews)

What a wonderful 3 night break at Villa Casagrande! My wife and I had a beautiful stay in this historic villa. There’s a little steep walk up to the pool and restaurant next to it which were perfect and where we spent most of our time relaxing and sunbathing with the view of the trees and the Tuscan mountains. The staff were incredible, so kind, quick to help and made our stay even more pleasant. We both had lovely massages and relaxed in the spa area and one evening did the historic tour and wine tasting which was exceptional. The guides and sommeliers were so knowledgeable and so lovely and the organic Chianti wines they produce are an absolute must to taste and buy. The hotel’s main restaurant was the best in Filigne (the local town) and the food was incredible. One of the nights we had a live musician who was fantastic. We had dinner twice there; mushroom tagliatelle, the lamb, the wild boar gnocchi and paccheri carbonara were to die for! It’s only 50 mins on the train to Florence which is one of our favourite cities to explore in one day and we picked this place especially because it’s only a 12 minute walk from the Filigne Valdarno station and avoids the need to hire a car. We went for the comfort room which was spacious and clean and the air con was great and important for us it had a powerful shower. We truly had a wonderful time and absolutely cannot wait to go back next year! Grazie Villa Casagrande!

Reviewed on Aug 14, 2026

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5* Luxury holidays in Chianti Region

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

Villa Le Calvane

CA $9,563

per person

Oct 10 - Oct 16

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Florence (FLR)

9.8/10 Exceptional! (89 reviews)

Great staff! Beautiful property. The food is amazing. The pool is beautiful. The view is unreal. We live it. We will be back. Thanks

Reviewed on Aug 3, 2026

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3 Night Luxury holidays in Chianti Region

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

Villa Scacciapensieri Boutique Hotel

Scacciapensieri

CA $1,841

per person

Sep 20 - Sep 22

found 1 day ago

Roundtrip flight included

Calgary (YYC) to Florence (FLR)

9.2/10 Wonderful! (450 reviews)

All in all a lovely property with lovely staff. Good location, easy bus ride to Siena town.

Reviewed on Aug 16, 2026

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4 Night Luxury holidays in Chianti Region

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

Palagina la Dimora

CA $1,081

per person

Oct 17 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Hamilton (YHM) to Florence (FLR)

9/10 Wonderful! (353 reviews)

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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 $1,081, 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 12. 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

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 Antinori nel Chianti Classico ...

9.6/10 Exceptional! (142 reviews)

"Great staff!"

Reviewed on Jun 27, 2026

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 ...

8.8/10 Excellent! (145 reviews)

"Overall great. It was a bit colder when we went. I wish they put heat lamps in outside seating areas in the evenings. I did ask and they put one but it needed time to heat up. But other than that - amazing stay!"

Reviewed on Oct 4, 2025

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 ...

See all 4,867 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.