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

Our site doesn't offer any 5-star holiday rentals in Chianti Region. However, you can still find some top-rated stays where the only thing on your itinerary will be to unpack and enjoy yourself. Discover what's available by checking out our holiday rentals in Chianti Region .

The 10 Best 5 Star Hotels in Chianti Region - 2026 Updated Prices

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Our top choices for Chianti Region 5-star hotels

Indoor pool, outdoor pool, pool loungers

Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

Christopher

includes taxes & fees

28 Jun - 29 Jun

2 restaurants; breakfast, lunch, and dinner served

COMO Castello Del Nero

Barberino Tavarnelle

Maryam

includes taxes & fees

31 May - 1 Jun

Pieve Aldina - Relais & Châteaux

Radda in Chianti

Lara

includes taxes & fees

4 Jun - 5 Jun

Borgo Vescine

Radda in Chianti

David

includes taxes & fees

7 Jun - 8 Jun

Villa Le Calvane

Montespertoli

Abdulhadi

includes taxes & fees

25 Jun - 26 Jun

LHP Certaldo Resort

Certaldo

Rob

includes taxes & fees

29 May - 30 May

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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

£56

4 Jun - 5 Jun

includes taxes & fees

8.2/10 Very Good! (340 reviews)

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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

Top Chianti Region Hotel Reviews

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a gorgeous hotel and such a relaxing experience from start to finish. The food was superb, the service was excellent, and the overall atmosphere was unforgettable. The room was comfortable and had an antique feel but considering this is an old castle, it completely made sense and added to the charm. What a wonderful stay it was."

Borgo Vescine

10/10 Excellent

"Loved absolutely everything. Property is beautiful. Food is incredible and reasonably priced. The wine is delicious. The service is excellent and the people are SO friendly. There is so much history to the location but it's also luxurious. The surrounding area has so much to do and see. Perfection, book it now"

Find out more about Chianti Region

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 according to what time of year you travel and how long you plan to be away, among a number of factors. Use our price per night filter and other search tools to find the best rate on a luxurious getaway.

Search for the lowest price per night from £56

What makes a hotel 5 stars in Chianti Region?

Flawless guest service is the hallmark of every 5-star hotel in Chianti Region. From the moment you arrive, staff attend to your every whim, whether offering luggage assistance and storage or providing a turn-down service. What's more, hotels must offer superior amenities to meet the standard for a 5-star rating. These can include deluxe baths, saunas or spas, swimming pools, gastronomic kitchens and knowledgeable concierge.

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

Use our convenient filters to find a luxury getaway in Chianti Region where everything you need is included in the price. After your initial search, narrow down your results for properties that have a 5-star rating and are listed as "All inclusive." The first 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