
Chianti Region Luxury Holidays
Book a Luxury Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to £750 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPackages with flights are ATOL protected
Top flight + Luxury hotel deals in Chianti Region

Villa Pitiana
Reviewed on 22 Jun 2024

COMO Castello Del Nero
Reviewed on 25 Oct 2025

Castello di Spaltenna- Small Luxury Hotels of the World
Reviewed on 14 Oct 2025

Villa Scacciapensieri Boutique Hotel
Reviewed on 2 May 2026

Relais Castel Bigozzi
Reviewed on 18 Mar 2026
5* Luxury holidays in Chianti Region

Castello di Spaltenna- Small Luxury Hotels of the World
Reviewed on 14 Oct 2025

COMO Castello Del Nero
Reviewed on 25 Oct 2025

Borgo San Felice Resort
Reviewed on 25 Aug 2025
3 Night Luxury holidays in Chianti Region

Villa Casagrande Resort & SPA
Reviewed on 20 Apr 2026

Hotel Palazzo San Lorenzo & SPA
Reviewed on 20 Mar 2026

Grand Hotel Continental Siena – Starhotels Collezione
Reviewed on 14 Apr 2026
4 Night Luxury holidays in Chianti Region

Villa Casagrande Resort & SPA
Reviewed on 20 Apr 2026

Villa Pitiana
Reviewed on 22 Jun 2024

Hotel Palazzo San niccolò & Spa
Reviewed on 30 Sept 2025
All you need to know about luxury holidays in Chianti Region
What can I expect from a luxury Chianti Region holiday?
Luxury on holiday is all about relaxing and feeling good. Whether you choose a sumptuous spa, Michelin-starred restaurant or super-king bed is your call. Use our amenities filters to find the things that tick all your boxes.
How can I find all-inclusive luxury holidays in Chianti Region?
Tick the all-inclusive and 5-star filters to find the crème de la crème of Chianti Region holidays. With everything included in the package price, you can drink and dine to your heart’s content, without worrying about that bill at the end.
Can I book a cheap luxury holiday to Chianti Region?
A luxury holiday doesn’t have to break the bank. Travel out of peak season, choose a hotel or resort a little way out or go for a last-minute getaway and you’ll find some cracking deals. Sort by price to find luxury holidays to Chianti Region starting at £262. Prices and availability are subject to change. Additional terms may apply.
Are there luxury spa holidays in Chianti Region?
For sunset massages on the shoreline and view-filled saunas, use our spa filter to find your ideal Chianti Region spa hotel. Book a whole weekend soaking away your stresses, or hop into the spa after the beach, some golf or a local advent-ahhhh.
What should I look for when booking a luxury family holiday in Chianti Region?
Luxury isn’t just for adults. Those little touches designed for little people make a family holiday genuinely stress free … which is the greatest luxury of all. Look for spacious suites, pools toddlers can splash in, and breakfast buffets with waffles, pancakes and Nutella galore.
Can I book luxury last-minute holidays to Chianti Region?
You can wangle a top-notch luxury holiday in Chianti Region for a fraction of the normal price by booking last minute. Just enter your dates and see what’s available – if you’re flexible ... even better!
Can I book a luxury holiday in Chianti Region with free cancellation and/or flexible dates?
If you’re splashing out on a luxury holiday, make sure your money is safe by booking with free cancellation. Just use the fully refundable filter and make sure you read all the terms and conditions.
Why should I book my luxury travel to Chianti Region with Expedia?
Nobody does luxury quite like Expedia. With so many gorgeous properties in Chianti Region to choose from, as well as access to first-class flight deals and hire cars with horsepower, there’s no better place to book.
Top Luxury Chianti Region Hotels

COMO Castello Del Nero
Amazing stay. Would be back again.
Reviewed on 11 Apr 2026

Castel Monastero - The Leading Hotels of the World
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 4 Oct 2025

Grand Hotel Continental Siena – Starhotels Collezione
This hotel had everything and more. We made use of the terrace with a lovely, extensive breakfast served to us by room service. The whole hotel is like a museum. It really is a beautiful space. The staff were all extremely helpful and friendly. Couldn’t have asked for a better experience.
Reviewed on 1 May 2026
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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. Flight-inclusive packages are ATOL protected.










