Find 5 Star Hotels in Chianti Region from $56

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Dec 7 - Dec 8
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Dec 8 - Dec 9
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Dec 12 - Dec 14
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Dec 19 - Dec 21

Compare Chianti Region 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

2 restaurants, breakfast, lunch, dinner served; international cuisine
COMO Castello Del Nero

COMO Castello Del Nero

5.0 star property
Barberino Tavarnelle
9.6 out of 10, Exceptional, (132)
"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). "
United States
Matthew
$835 nightly
The price is $928
Dec 14 - Dec 15
Total with taxes and fees
COMO Castello Del Nero
Front of property - evening/night
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5.0 star property
Gaiole in Chianti
9.6 out of 10, Exceptional, (261)
"The breakfast was fresh with lots of options and a outdoor setting on the property. The property is beautiful, pool area and spa so peaceful. Excellent service in all areas of hotel! "
Canada
Catherine
Castello di Spaltenna- Small Luxury Hotels of the World
Seasonal outdoor pool
Pieve Aldina - Fontenille Collection

Pieve Aldina - Fontenille Collection

5.0 star property
Radda in Chianti
10.0 out of 10, Exceptional, (32)
"Gorgeous design, high quality, delicious food and wine, friendly and helpful staff. "
United States
Lara
Pieve Aldina - Fontenille Collection
2 restaurants, breakfast served
Borgo Vescine

Borgo Vescine

5.0 star property
Radda in Chianti
9.4 out of 10, Exceptional, (244)
"This was a beautiful location. The room was spacious and loved the patio for coffee in the mornings. It was very private. We enjoyed the pool and restaurants were great. Breakfast was amazing. We did the picnic and dinner in the Olive Garden and loved getting to know others at our table. The chefs food choices were so wonderful. We would definitely stay again. "
United States
Sherie
Borgo Vescine
3 outdoor pools, pool umbrellas, sun loungers
Villa Le Calvane

Villa Le Calvane

5.0 star property
Montespertoli
9.6 out of 10, Exceptional, (82)
"We had a wonderful time! The pool is amazing with an incredible view. The staff went out of their way to make our stay fantastic, especially our server Leonardo. The breakfast was great with eggs to order and everything freshly prepared. Highly recommend!"
United States
Stephanie
Villa Le Calvane
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Chianti Region.
Hotel Ristorante Alcide

Hotel Ristorante Alcide

Viale Marconi, 67/A Poggibonsi SI
$50 nightly
The price is $56 total per night from Jan 4 to Jan 5
$56 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8/10 Very Good! (460 reviews)
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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.

Learn more about Chianti Region

Take a sightseeing trip of Tuscany's renowned wine region and visit its vineyards, wineries, ancient churches, castles and hilltop villages.

See all hotels in Chianti Region
Chianti Region which includes farmland

Top Chianti Region Hotel Reviews

COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent
"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). "
Matthew 4-night trip
Posted 2 months ago
COMO Castello Del Nero
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"The breakfast was fresh with lots of options and a outdoor setting on the property. The property is beautiful, pool area and spa so peaceful. Excellent service in all areas of hotel! "
Catherine 2-night trip
Posted 2 months ago
Castello di Spaltenna- Small Luxury Hotels of the World

Find out more about Chianti Region

Ready to experience the next standard in luxury? We know you're thinking about it. Add even more luxury on your next trip to Chianti Region by treating yourself to the best of the best when it comes to accommodation. It's an ideal combination. There's no reason to delay a getaway to Chianti Region any longer. You'll join the multitudes of vacationers who have made Chianti Region so fashionable in the last year. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Don't wait any longer. Book one of Expedia's luxurious 5-star hotels in Chianti Region and get ready to enjoy the getaway of a lifetime.

5-Star Hotels in Chianti Region

You'll have a wonderful time at one of these 5-star hotels. High-end restaurants, concierges, and in-room massages are all at the ready. We have a huge number of hotels in the area, and all of them provide amazing amenities. You'll also enjoy a high standard of care and meticulous guest relations, so get ready to kick back and indulge. How do you want to relax? A body scrub that will leave you feeling great? 24-hour room service, so you can order that chocolate soufflé© in the wee hours of the morning? A deep-tissue massage to help your cares fall away?

Ready for experiences outside your hotel room? We hear you. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. Whatever you plan to do, the 5-star hotels in Chianti Region are the perfect place to relax after an exciting day. Ready to learn more? Then check out our listings and pick the perfect accommodation for your needs.

Your Getaway Starts Today

Numerous visitors make Chianti Region the place to vacation. Why not join their ranks? If you've been dreaming about a vacation set here, then go ahead and book it. Don't put off your dream vacation any longer -- a surge in interest means these great hotel rooms will go quickly. Opt for one of the 5-star hotels in Chianti Region today and soothe yourself in total tranquility tomorrow.

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chianti Region?
How much you pay for a 5-star hotel in Chianti Region can vary based on the time of year you travel and how long you plan to stay, among a number of factors. Use our price per night filter and other search tools to find the best deal on a high-end stay.

  • Search for the lowest price per night from $56

What makes a hotel 5 stars in Chianti Region?
In Chianti Region, a hotel must offer a certain amount of upscale features to earn a 5-star rating. These may include saunas and spas, on-site gyms, gourmet restaurants, complimentary luxury toiletries, premium bedding and more. What also sets 5-star hotels apart is their guest-centric service. You can expect things like in-room massages, concierge services and nightly turn-down services. Some may even offer extra touches like welcome gifts.
Are there any 5-star all-inclusive resorts in Chianti Region?
Use our convenient filters to find a luxurious getaway in Chianti Region where most of what you need is included. From there, narrow your results for hotels that have a 5-star rating and are deemed "All inclusive." The main thing on the to-do list at these stays? Pure relaxation and indulgence.

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