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

5 Star Hotels in Chianti Region, Tuscany

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Check availability on Chianti Region 5 Star Hotels

Tonight
10 Oct - 11 Oct
Tomorrow
11 Oct - 12 Oct
Next weekend
16 Oct - 18 Oct
In two weeks
23 Oct - 25 Oct

Our top choices for Chianti Region 5-star hotels

A spacious interior with high arched ceilings, stone walls, and a central round mirror reflecting the room. Tables and chairs are arranged for dining or socializing.
A garden with tall cypress trees, a variety of shrubs, and a stone pathway.
An outdoor dining area with tables and chairs, a chef preparing food, and a scenic view in the background.
A resort with a swimming pool, terraced gardens, and a view of rolling hills.

1. COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa
United States
Lauren
€751
includes taxes & fees
9 Nov - 10 Nov
COMO Castello Del Nero
A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.
An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.
A rustic outdoor setting with a stone building, round tables, and outdoor seating.
A compact living space with a wooden ceiling, a white sofa, a small table, a potted plant, and a cabinet with circular designs.

2. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United States
Andon
€270
includes taxes & fees
11 Oct - 12 Oct
Chapter Chianti, a Member of Design Hotels
A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.
A restaurant with stone walls and a high ceiling, featuring tables set for dining.
A stone building with a garden, tall trees, and a clear blue sky.
A sunlit patio with a glass roof, stone walls, and outdoor seating.

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

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
Canada
Sonja
€334
includes taxes & fees
30 Oct - 31 Oct
Castello di Spaltenna- Small Luxury Hotels of the World
A stone building with arched windows, a grassy courtyard, and outdoor seating.
A bedroom with a wooden ceiling, a stone wall, a bed, a desk, a chair, a sofa, and a window with curtains.
A person relaxing in a clear pool surrounded by natural scenery.
A cozy living room with a sofa, a dining table with chairs, a hanging lamp, and a mirror on the wall.

4. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
United States
Paul
€349
includes taxes & fees
22 Oct - 23 Oct
Pieve Aldina - Relais & Châteaux
A large building with a swimming pool, surrounded by greenery and outdoor lighting.
A large, multi-story building with a symmetrical facade, multiple windows, and a central entrance.
A dining area with tables and chairs, a kitchen in the background, and a patterned wall.
A courtyard with a lawn, seating area, and a weeping willow tree.

5. LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
Canada
Arash
€135
includes taxes & fees
11 Oct - 12 Oct
LHP Certaldo Resort
A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.
An aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.
An indoor dining area with wooden tables and chairs, hanging baskets, and large windows offering a view of the outdoors.
A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.

6. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
Natalie
€467
includes taxes & fees
4 Nov - 5 Nov
Borgo Vescine
An outdoor dining area with wicker chairs and tables, white tablecloths, and umbrellas, overlooking a scenic landscape.
A bar area with a dark bar counter, red chairs, and a fireplace.
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.
A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.

7. Villa Le Calvane

Villa Le Calvane
Montespertoli
United States
Ilya
€613
includes taxes & fees
18 Oct - 19 Oct
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 Toscana Ambassador

Hotel Toscana Ambassador

Via Salceto, 11 Poggibonsi SI
€74
20 Oct - 21 Oct
includes taxes & fees
Hotel Toscana Ambassador
Park Hotel Chianti

Park Hotel Chianti

Via Michelangelo, 5 Barberino Tavarnelle FI
€71
6 Nov - 7 Nov
includes taxes & fees
9/10 Wonderful! (277 reviews)
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Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI
€82
9 Nov - 10 Nov
includes taxes & fees
9.2/10 Wonderful! (475 reviews)
Villa I Barronci Resort & Spa
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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
Terraced vineyards on a hillside, a small village, and rolling green hills.

Top Chianti Region Hotel Reviews

Borgo Vescine

Borgo Vescine

10/10 Excellent
"The staff was amazing and incredibly kind."
Natalie 2-night trip
Posted 8 days ago
Borgo Vescine
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."
Sonja 3-night trip
Posted 8 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
COMO Castello Del Nero

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."
Lauren 3-night trip
Posted 1 month ago
COMO Castello Del Nero

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 €71
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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