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Chianti Region Luxury Vacations

Book a Hotel + Flight or Car together to unlock savings

Top Luxury vacation packages in Chianti Region

Price found within the past 48 hours. Click for updated prices.
  • Jan 12 - Jan 17

    Albergo Firenze + Flight

    Historic Centre of Florence
    4 nights
    3.0 star property
    8.8/10 - Excellent (342 reviews)
    Roundtrip • New York (JFK) - Florence (FLR)
    JFK - FLR • 1 stop FLR - JFK • 1 stop
    $1,345
    $987
    per traveler
    found 17 hours ago
    Albergo Firenze
  • Jan 12 - Jan 17

    Aurum Firenze + Flight

    Historic Centre of Florence
    4 nights
    4.0 star property
    7.4/10 - Good (1,004 reviews)
    Roundtrip • New York (JFK) - Florence (FLR)
    JFK - FLR • 1 stop FLR - JFK • 1 stop
    $1,518
    $1,003
    per traveler
    found 17 hours ago
    Aurum Firenze
  • Jan 2 - Jan 8

    The Place Firenze + Flight

    Historic Centre of Florence
    5 nights
    5.0 star property
    9.8/10 - Exceptional (203 reviews)
    Roundtrip • Boston (BOS) - Florence (FLR)
    BOS - FCO • Nonstop FCO - BOS • 1 stop
    $3,177
    $2,229
    per traveler
    found 7 hours ago
    The Place Firenze
  • Jan 15 - Jan 22

    Donati Luxury Tower Suites + Flight

    Historic Centre of Florence
    6 nights
    5.0 star property
    9.8/10 - Exceptional (82 reviews)
    "Great location. Historical building. Rooms were stunning. Lovely breakfast box delivered daily. Nice staff. The only negative is the roof is €250 per 2 hour booking, which I didn't expect, and would have been a reason for booking. Hence 4/5."
    Reviewed October 19, 2026
    Roundtrip • New York (JFK) - Florence (FLR)
    JFK - FLR • 1 stop FLR - JFK • 1 stop
    $2,952
    $2,186
    per traveler
    found 18 hours ago
    Donati Luxury Tower Suites
  • Jan 17 - Jan 23

    Hotel Berchielli + Flight

    Historic Centre of Florence
    5 nights
    4.0 star property
    9.4/10 - Exceptional (1,000 reviews)
    Roundtrip • Boston (BOS) - Florence (FLR)
    BOS - FLR • 1 stop FLR - BOS • 1 stop
    $1,372
    $1,030
    per traveler
    found 1 day ago
    Hotel Berchielli

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Top Luxury Chianti Region Hotels

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.

All you need to know about luxury vacations in Chianti Region

What can I expect from a luxury Chianti Region vacation?

Luxury means the very finest of the things you enjoy most. Indulge your every waking moment—and restful night—with a luxury Chianti Region vacation. Sip handcrafted cocktails by an infinity pool, sink into bliss at a full-service spa with a massage cabana on the beach, and chat, cheers, and laugh through exquisite breakfasts, lunches, and dinners with spectacular views. 

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

By refining your filters, the most opulent all-inclusive vacation packages will appear before your eyes. Check the 5* filter to find truly sensational stays. You barely need to lift a finger. 

Can I book a cheap Chianti Region luxury vacation?

Affordable luxury is only ever a few clicks away. Enter your travel dates and sort the grandiose getaways on offer by price to see the most fiscally friendly retreats first. Filter by budget, too, to find your perfect balance of luxury. Right now, luxury vacations start at $987. Prices and availability are subject to change. Additional terms may apply.

How can I book a luxury family vacation in Chianti Region?

Tailor your luxury family escape by checking the filters that set the whole family’s hearts a-flutter. Whether that’s wet and wild water parks, heavenly hot tubs, or the kid-quieting magic of free Wi-Fi. 

Can I book a package in Chianti Region with a luxury vacation home?

A private paradise is true luxury! Filter by property type for houses, villas, and apartments. For an amazingly affordable all-in-one luxury experience, book your accommodation, airfare, and car rental as a package.   

How can I find the best luxury vacation deals in Chianti Region?

Find absolute delight in the dropdown! Simply sort your tempting search results by deals to find that lean-budget luxury. For a budget conscious stay, consider booking a stay away from big cities or outside the peak months.

Can I book a luxury holiday in Chianti Region with free cancellation and/or flexible dates?

Freedom and flexibility are the greatest luxuries of all. Get both when you filter by payment option and book a trip with free cancellation or on a buy now, pay later plan. 

Why should I book my luxury trip to Chianti Region with Expedia?

A luxurious trip follows a stress-free booking experience. Find, build, and book the most glorious of getaways in seconds—with ATOL protection for added peace of mind.