Chianti Region 5 Stars Hotels

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Check availability on Chianti Region 5 Star Hotels

Tonight
Dec 29 - Dec 30
Tomorrow
Dec 30 - Dec 31
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Chianti Region 5-star hotels

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

COMO Castello Del Nero

COMO Castello Del Nero
5.0 star property
Barberino Tavarnelle
9.6 out of 10, Exceptional, (133)
"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
The price is ₩1,084,504
₩1,206,532 total
includes taxes & fees
Jan 5 - Jan 6, 2026
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

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

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

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

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
The price is ₩73,585 per night from Jan 4 to Jan 5
₩73,585
₩80,950 total
Jan 4 - Jan 5, 2026
includes taxes & 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 3 months ago
Castello di Spaltenna- Small Luxury Hotels of the World

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 ₩80,950

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.