Explore top 2026 5 Star Hotels in Chianti Region

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Top Chianti Region 5 Star hotels

COMO Castello Del Nero

COMO Castello Del Nero

5 out of 5
Strada Spicciano 7 Barberino Tavarnelle FI
Fully refundableReserve now, pay when you stay
$726 nightly
The price is $808 total per night from Nov 8 to Nov 9
$808 total
Nov 8 - Nov 9
Total with taxes and fees
A full-service spa, 2 restaurants, and 2 outdoor tennis courts are all featured at this smoke-free hotel. Families will appreciate the playground, kid-friendly ...
9.6/10 Exceptional! (145 reviews)
"The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back."

Reviewed on Sep 11, 2026

Opens in a new windowCOMO Castello Del Nero
Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels

5 out of 5
Loc. Fontebussi Cavriglia AR
Fully refundableReserve now, pay when you stay
$270 nightly
The price is $303 total per night from Oct 20 to Oct 21
$303 total
Oct 20 - Oct 21
Total with taxes and fees
This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Family-friendly amenities include a children's pool and in-room childcare. Relax with a ...
8.2/10 Very Good! (22 reviews)
"We thoroughly enjoyed staying at this beautiful modern farmhouse. The rooms were very spacious clean staff were friendly and helpful. This spa was lovely. My only complaint is that it is very isolated and far from the two main city Sienna and San Gimiano ( at last hour away) and the winding Road ..."

Reviewed on Oct 14, 2026

Opens in a new windowChapter Chianti, a Member of Design Hotels
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

5 out of 5
Via Spaltenna 13 Gaiole in Chianti SI
Fully refundableReserve now, pay when you stay
$331 nightly
The price is $375 total per night from Oct 30 to Oct 31
$375 total
Oct 30 - Oct 31
Total with taxes and fees
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center ...
9.6/10 Exceptional! (295 reviews)
"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."

Reviewed on Oct 11, 2026

Opens in a new windowCastello di Spaltenna- Small Luxury Hotels of the World
Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux

5 out of 5
Traversa del Chianti Radda in Chianti SI
Fully refundableReserve now, pay when you stay
$348 nightly
The price is $392 total per night from Oct 22 to Oct 23
$392 total
Oct 22 - Oct 23
Total with taxes and fees
An attached winery and a restaurant are featured at this luxury hotel. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and valet parking. ...
9.8/10 Exceptional! (46 reviews)
"An amazing staff and property! Hated to leave!!"

Reviewed on Sep 16, 2026

Opens in a new windowPieve Aldina - Relais & Châteaux
LHP Certaldo Resort

LHP Certaldo Resort

5 out of 5
via del Molino, 74 Certaldo FI
Fully refundableReserve now, pay when you stay
$128 nightly
The price is $148 total per night from Oct 29 to Oct 30
$148 total
Oct 29 - Oct 30
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, ...
Opens in a new windowLHP Certaldo Resort
Borgo Vescine

Borgo Vescine

5 out of 5
Località Vescine Radda in Chianti SI
Fully refundableReserve now, pay when you stay
$399 nightly
The price is $447 total per night from Nov 18 to Nov 19
$447 total
Nov 18 - Nov 19
Total with taxes and fees
An attached winery, 2 restaurants, and an outdoor pool are all featured at this luxury hotel. Traveling on business? Take advantage of the free WiFi in public ...
9.6/10 Exceptional! (248 reviews)
"The staff was amazing and incredibly kind."

Reviewed on Oct 2, 2026

Opens in a new windowBorgo Vescine
Villa Le Calvane

Villa Le Calvane

5 out of 5
Via Castiglioni 1,3,5 Montespertoli FI
$697 nightly
The price is $774 total per night from Oct 21 to Oct 22
$774 total
Oct 21 - Oct 22
Total with taxes and fees
An attached winery, a full-service spa, and 3 outdoor pools are all featured at this luxury hotel. Families will appreciate the children's pool, kid-friendly ...
9.8/10 Exceptional! (90 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 on Aug 3, 2026

Opens in a new windowVilla Le Calvane
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Chianti Region Resorts & 5 Star Hotels

Looking for your own little slice of heaven during your next trip? Check out all the best 5-star hotels in Chianti Region to make sure your trip is as extravagantly comfortable as you expect.

Whether you plan on staying in your room the whole time or getting out and enjoying the city, you’ll be living the life while staying at your luxury accommodation. With so many amenities at your beck and call, you might try to turn your stay into a staycation!

Many of the 5-star hotels have award-winning restaurants you can dine at, as well as plush bedding and a concierge service to take care of your every need. Most also offer pools and modern fitness centers, not to mention high-speed Wi-Fi.

For your next trip, book a hotel that can be your own little hideaway, whether you’re in town for business or leisure. Chianti Region 5-star hotels provide you with all the comforts and amenities you expect from a sophisticated hotel, with a staff that’s happy to ensure you have everything you need to feel at home.

Whether you’re a first-time guest, or you’ve stayed in 5-star hotels in Chianti Region before, you’ll have no shortage of options to choose from on your next trip when you book with Travelocity. Browse our vast selection and find great deals on luxury lodging.

Recent Chianti Region hotel reviews by fellow wanderers

Fattoria di Vegi

Fattoria di Vegi

5 out of 5
Posted 1 day ago
Travelocity Verified Review
"We loved our stay here! It was the perfect place to slow down and take in the beauty of Tuscany. We enjoyed the cooking class and wine tasting we took with the other couples staying there. Highly recommend booking this as part of your stay! We also enjoyed the amenities they offered like the art room - we set up easels in the grass, drank wine, and drew each other’s portraits which ended up being pretty funny. The food at the restaurant was good although it felt like some of the dishes could’ve been simpler. Our favorite dishes was the pasta with mushrooms and the pizzas on pizza night. The majority of the staff was friendly too. Highly recommend this location if you’re looking for a beautifully designed, relaxing location with amenities/activities. We hope to be back!"
A verified traveler stayed at Fattoria di Vegi
Fattoria di Vegi

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