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

Our site doesn't have any 5-star vacation rentals in Chianti Region. However, you will still find a few top-rated properties where the only thing on your agenda will be to unpack and enjoy yourself. Discover what's available by checking out our vacation rentals in Chianti Region .

5 Stars Hotels in Chianti Region: Compare Hotel Prices & Find the Cheapest Chianti Region, Tuscany 5 Stars Hotels

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

An aerial view of a historic estate with multiple buildings, a swimming pool, and terraced vineyards.

2. COMO Castello Del Nero

Tavarnelle Val di Pesa

Nawaf

NT$26,156 total

includes taxes & fees

Nov 10 - Nov 11

A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

3. Chapter Chianti, a Member of Design Hotels

Cavriglia

Michael

NT$9,822 total

includes taxes & fees

Nov 3 - Nov 4

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

4. LHP Certaldo Resort

Certaldo

Danilo

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

An aerial view of a rustic village with stone buildings, a central courtyard with string lights, and a swimming pool.

6. Borgo Vescine

Radda in Chianti

Natalie

NT$16,792 total

includes taxes & fees

Nov 1 - Nov 2

A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.

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

NT$2,250

NT$2,475 total

Nov 8 - Nov 9

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

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

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

Top Chianti Region Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"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."

COMO Castello Del Nero

10/10 Excellent

"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."

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Chianti Region?

There are a variety of pricing options for 5-star hotels in Chianti Region on Expedia. The amount you pay will depend on your travel dates, length of stay and other factors. Compare all of the available properties for your preferred dates and use our pricing and other filters to lock in the perfect high-end stay.

Search for the lowest price per night from NT$2,475

What makes a hotel 5 stars in Chianti Region?

Exceptional guest service is the hallmark of every 5-star hotel in Chianti Region. From the moment you arrive, staff are at your beck and call, whether offering luggage assistance and storage or providing a nightly turn-down service. In addition, hotels have to feature upscale amenities to qualify for a 5-star rating. These can include luxury toiletries, an on-site spa, swimming pools, gastronomic kitchens and knowledgeable concierge.

Are there any 5-star all-inclusive resorts in Chianti Region?

Use our filters to find an upscale escape in Chianti Region where everything you need is included in the price. From there, narrow down your results for hotels that have 5 stars and are listed as "All inclusive." The main thing on the itinerary at these stays? Pure indulgence and relaxation.

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Our top choices for Chianti Region 5-star hotels