Are there any 5-star vacation rentals in Chianti Region?

Although there aren't any 5-star vacation rentals in Chianti Region on our site, we have a range of retreats that promise a fabulous getaway. Discover one that matches your needs by searching our vacation rentals in Chianti Region .

The Best 5 Star Hotels in Chianti Region from SAR 215

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

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Our top choices for Chianti Region 5-star hotels

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

1. Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

Michelle

A stately building with a bell tower, surrounded by well-manicured hedges and tall trees.

2. COMO Castello Del Nero

Tavarnelle Val di Pesa

Nawaf

SAR 2,975 total

includes taxes & fees

22 Nov - 23 Nov

A rustic outdoor setting with a stone building, round tables, and outdoor seating.

3. Chapter Chianti, a Member of Design Hotels

Cavriglia

Carolina

A large building with a swimming pool, surrounded by greenery and outdoor lighting.

4. LHP Certaldo Resort

Certaldo

Oscar

A courtyard with a fountain, surrounded by neatly trimmed hedges and trees, viewed through an arched doorway.

5. Pieve Aldina - Relais & Châteaux

Radda in Chianti

Paul

A covered outdoor seating area with a wooden door, wicker chairs, and potted plants.

6. Borgo Vescine

Radda in Chianti

Natalie

SAR 1,797 total

includes taxes & fees

27 Nov - 28 Nov

A spacious living room with a large window offering a view of the countryside. There are two armchairs, a sofa, and a coffee table with a vase of flowers.

7. Villa Le Calvane

Montespertoli

Ilya

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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 Toscana Ambassador

Via Salceto, 11 Poggibonsi SI

SAR 228

SAR 251 total

19 Nov - 20 Nov

includes taxes & fees

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Pool Spa Hot tub Breakfast included Waterpark

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

Discover the relaxing area of Chianti Region—wineries, pristine countryside, and sights from Borgo di Vescine - Tenute di Castelvecchi to Castello di Albola.

See all hotels in Chianti Region

Terraced vineyards on a hillside, a small village, and rolling green hills.

Top Chianti Region Hotel Reviews

Borgo Vescine

10/10 Excellent

"There are no words to describe our experience at this incredibly beautiful and wonderful charming several century old village resort in Chianti. It was everything you imagined Italy to be in wine country. Probably one of my favorite places I have ever stayed at, and I’ve stayed at hundreds of of places around the world. The staff was wonderful, the accommodations were just super cool. It was once a village dating back over 100+ years. It was truly remarkable that the owner discovered it and restored it, creating a truly wonderful experience and beautiful Tuscany. We definitely will stay here every time we go to Tuscany in the future. This is a must-stay place!"

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 SAR 215

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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Our top choices for Chianti Region 5-star hotels