Chianti Region Luxury Holidays
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Top Luxury holiday packages in Chianti Region
- LHP Certaldo Resort
14 Sept - 17 SeptLHP Certaldo Resort + Flight
Certaldo3 nights5.0 star property9.2/10 - Wonderful (538 reviews)"Amazing hotel with nice staff and super helpful ."Reviewed July 26, 2026Return • Manchester (MAN) - Florence (FLR)MAN - CIA • Direct CIA - MAN • Direct - Borgo Scopeto Wine & Country Relais
21 Sept - 24 SeptBorgo Scopeto Wine & Country Relais + Flight
Castelnuovo Berardenga3 nights5.0 star property9.4/10 - Exceptional (219 reviews)"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while..."Reviewed August 5, 2026Return • Manchester (MAN) - Florence (FLR)MAN - CIA • Direct CIA - MAN • Direct - Villa I Barronci Resort & Spa
14 Sept - 17 SeptVilla I Barronci Resort & Spa + Flight
San Casciano in Val di Pesa3 nights4.0 star property9.2/10 - Wonderful (449 reviews)"This was a fabulous stay. The property is beautiful, the grounds were fun to walk and the swimming pool was lovely. Breakfast every morning was delicious. Hotel was very quiet during the week but was noticeably busier starting Friday (I think local people come just for the weekend). Our room was spacious and very clean. Bed was very comfortable. There is a bar near the pool that serves drinks in the afternoon and dinner nightly on the terrace. The nearby town was so cute and had a coop as well..."Reviewed August 1, 2026Return • London (LON) - Florence (FLR)LTN - FCO • Direct FCO - LTN • Direct - Villa Le Calvane
19 Oct - 22 OctVilla Le Calvane + Flight
Montespertoli3 nights5.0 star property9.8/10 - 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 August 3, 2026Return • London (LHR) - Florence (FLR)LHR - FLR • 1 stop FLR - LHR • 1 stop - Villa Le Barone
12 Oct - 16 OctVilla Le Barone + Flight
Greve in Chianti4 nights4.0 star property9.4/10 - Exceptional (147 reviews)"First let me list the things I loved about the property. The staff is wonderful. They were quick to accommodate requests, were friendly, and kind. The food on the property was delicious. The pool was outstanding, overlooking the Tuscan vineyards. All wonderful. There are drinks and snacks available in various locations on the property, using an honor system to record purchases. There's also a wine dispenser, and the staff provides each guest with a "credit card" for wine purchases. I was..."Reviewed June 16, 2026Return • Edinburgh (EDI) - Florence (FLR)EDI - CIA • Direct CIA - EDI • Direct£824£690found 9 hours agoper traveller
Discover the most popular places to visit in Chianti Region
What to do in Chianti Region
City Sightseeing Florence Hop-on Hop-off Bus Tour
Skip-the-Line Florence Duomo: Priority-Access Express Guided Tour
Siena: Cathedral Complex Pass with Audio Guide (OPA SI PASS)
Top Luxury Chianti Region Hotels
"We enjoyed our stay immensely. The staff was very accommodating, especially with our two year old. The activities we did (movie night- included; dinner in the olive grove, truffle hunting, & a cooking class- paid) were all lovely experiences. We loved the property grounds."
Castello di Spaltenna- Small Luxury Hotels of the World
Castello di Spaltenna- Small Luxury Hotels of the World"Very nice calm and relaxing stay"
Chapter Chianti, a Member of Design Hotels
Chapter Chianti, a Member of Design Hotels"Great place, clean facilities and lovely staff"
Pieve Aldina - Relais & Châteaux
Pieve Aldina - Relais & Châteaux"Todo"
"Amazing hotel with nice staff and super helpful ."
Borgo Scopeto Wine & Country Relais
Borgo Scopeto Wine & Country Relais"We spent a wonderful week at Borgo Scopeto and thoroughly enjoyed every minute. It has everything you'd hope for from a luxury Tuscan retreat: beautiful historic buildings, immaculately kept grounds, and a peaceful atmosphere full of character. The staff were warm, attentive and genuinely welcoming without ever feeling intrusive, and the food was consistently excellent. One of the biggest advantages is its location. Siena is only a short drive away - you can even see the city's campanile while...
"Absolutely wonderful!"
"Great staff!"
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 £219. 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.