
Chianti Region Luxury Vacations
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Top Luxury vacation packages in Chianti Region

Villa Casagrande Resort & SPA
Reviewed on Jul 4, 2025

Palazzo Leopoldo Dimora Storica & Spa
Reviewed on Sep 25, 2025

Grand Hotel Continental Siena – Starhotels Collezione
Reviewed on Nov 6, 2025

Hotel Palazzo San Lorenzo & SPA
Reviewed on Nov 8, 2025
5* Luxury vacations in Chianti Region

Grand Hotel Continental Siena – Starhotels Collezione
Reviewed on Nov 6, 2025
4 Night Luxury vacations in Chianti Region

Villa Casagrande Resort & SPA
Reviewed on Jul 4, 2025

Palazzo Leopoldo Dimora Storica & Spa
Reviewed on Sep 25, 2025

Hotel Chiusarelli
Reviewed on Nov 23, 2025
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 $355. 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.
Top Luxury Chianti Region Hotels

COMO Castello Del Nero
Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car).
Reviewed on Oct 25, 2025

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 Oct 4, 2025

Grand Hotel Continental Siena – Starhotels Collezione
The Grand Hotel Continental in Siena is a rare gem,elegant, inviting, and steeped in history. From the beautifully preserved interiors to the warm, attentive staff, every detail makes you feel genuinely cared for. Its central location is unbeatable, placing Siena’s most charming sights just steps ...
Reviewed on Nov 20, 2025



















