Skip to main content
A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

Chianti Region Luxury Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Top Luxury holiday packages in Chianti Region

Price found within the past 48 hours. Click for updated prices.
  • View from property
    14 Sept - 17 Sept

    Villa I Barronci Resort & Spa + Flight

    San Casciano in Val di Pesa
    3 nights
    4.0 star property
    9.2/10 - 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, 2026
    Return • London (LON) - Florence (FLR)
    LTN - FCO • Direct FCO - LTN • Direct
    Save 100% on your flight
    £332
    £261
    per traveller
    found 13 hours ago
    Villa I Barronci Resort & Spa
  • Front of property
    14 Sept - 19 Sept

    LHP Certaldo Resort + Flight

    Certaldo
    5 nights
    5.0 star property
    9.2/10 - Wonderful (538 reviews)
    "Amazing hotel with nice staff and super helpful ."
    Reviewed July 26, 2026
    Return • London (LON) - Florence (FLR)
    LGW - FLR • Direct FLR - LGW • Direct
    Save 100% on your flight
    £658
    £464
    per traveller
    found 2 days ago
    LHP Certaldo Resort
  • Garden
    21 Sept - 24 Sept

    Borgo Scopeto Wine & Country Relais + Flight

    Castelnuovo Berardenga
    3 nights
    5.0 star property
    9.4/10 - 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, 2026
    Return • Manchester (MAN) - Florence (FLR)
    MAN - CIA • Direct CIA - MAN • Direct
    Save 100% on your flight
    £1,136
    £802
    per traveller
    found 1 day ago
    Borgo Scopeto Wine & Country Relais
  • 2 outdoor pools, pool loungers
    24 Oct - 28 Oct

    Villa Le Barone + Flight

    Greve in Chianti
    4 nights
    4.0 star property
    9.4/10 - 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, 2026
    Return • London (LGW) - Florence (FLR)
    LGW - FCO • Direct FCO - LGW • 2 stops
    £684
    £562
    per traveller
    found 2 days ago
    Villa Le Barone
  • Exterior
    23 Oct - 28 Oct

    Locanda le Piazze + Flight

    Castellina in Chianti
    5 nights
    4.0 star property
    9.8/10 - Exceptional (200 reviews)
    "We arrived early and expected to wait until check in at 4pm however we were met by a delightful young man at recent that came to our car to collect our luggage and then proceed to take us to our accommodation. The accommodation was spotless and roomy we had lots of wardrobe space and room to move around. The pool was well set out into the grounds and there was plenty of sun loungers, bathing towels were provided. Breakfast was plentiful and lots of selection. The staff were always friendly..."
    Reviewed August 1, 2026
    Return • London (LGW) - Florence (FLR)
    LGW - FCO • Direct FCO - LGW • 2 stops
    £818
    £684
    per traveller
    found 2 days ago
    Locanda le Piazze

Discover the most popular places to visit in Chianti Region

A spiral staircase with a person standing on it.

Antinori nel Chianti Classico

9.4/10 (16 reviews)
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.

What to do in Chianti Region

City Sightseeing Florence Hop-on Hop-off

City Sightseeing Florence Hop-on Hop-off Bus Tour

£21
per adult
76% of travellers recommend
City Sightseeing Florence Hop-on Hop-off Bus Tour
See all activities in Chianti Region

Top Luxury Chianti Region Hotels

2 restaurants; breakfast served

Borgo Vescine

Borgo Vescine
5.0 star property
4 mi from Chianti Region
9.6 out of 10, Exceptional, (237 reviews)
"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."
The price is £433
includes taxes & fees
8 Aug - 9 Aug
Borgo Vescine
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.
See all properties in Chianti Region

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 £261. 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.