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

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Check availability on Chianti Region 5 Star Hotels

Tonight
Oct 23 - Oct 24
Tomorrow
Oct 24 - Oct 25
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

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.
An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.
A sunlit patio with a glass roof, stone walls, and outdoor seating.
A stone building with a garden, tall trees, and a clear blue sky.

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

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
United States
Michelle
￥52,316
￥59,323 total
includes taxes & fees
Oct 30 - Oct 31
Castello di Spaltenna- Small Luxury Hotels of the World
An aerial view of a historic estate with multiple buildings, a swimming pool, and terraced vineyards.
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.
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.

2. COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa
United States
Lauren
￥113,659
￥126,432 total
includes taxes & fees
Nov 15 - Nov 16
COMO Castello Del Nero
A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.
A rustic outdoor setting with a stone building, round tables, and outdoor seating.
An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.
A modern living room with a white sofa, armchairs, and a coffee table.

3. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
Canada
Michael
￥42,203
￥47,478 total
includes taxes & fees
Nov 2 - Nov 3
Chapter Chianti, a Member of Design Hotels
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 courtyard with a stone bridge over a small water feature, surrounded by greenery and a building with arched windows.
A dining area with tables and chairs, a kitchen in the background, and a patterned wall.

4. LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
Canada
Danilo
￥22,395
￥25,701 total
includes taxes & fees
Oct 29 - Oct 30
LHP Certaldo Resort
A stone building with arched windows, a grassy courtyard, and outdoor seating.
A cozy living room with a sofa, a dining table with chairs, a hanging lamp, and a mirror on the wall.
A person relaxing in a clear pool surrounded by natural scenery.
An aerial view of a residential property with multiple buildings, a swimming pool, and landscaped gardens.

5. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
United States
Paul
￥55,110
￥62,043 total
includes taxes & fees
Nov 1 - Nov 2
Pieve Aldina - Relais & Châteaux
An aerial view of a rustic village with stone buildings, a central courtyard with string lights, and a swimming pool.
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 villa with a swimming pool surrounded by lush greenery and vineyards.

6. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
Natalie
￥65,920
￥73,933 total
includes taxes & fees
Oct 30 - Oct 31
Borgo Vescine
A poolside area with lounge chairs and umbrellas, overlooking a scenic landscape.
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 dining area with stone walls, wooden beams, and round tables set for a meal.

7. Villa Le Calvane

Villa Le Calvane
Montespertoli
United States
Ilya
￥113,676
￥126,286 total
includes taxes & fees
Oct 24 - Oct 25
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

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￥10,107
￥11,118 total
Nov 22 - Nov 23
includes taxes & fees
Hotel Toscana Ambassador
Hotel Borgo San Luigi

Hotel Borgo San Luigi

STRADA DELLA CERRETA,7 Monteriggioni SI
￥17,655
￥20,664 total
Nov 15 - Nov 16
includes taxes & fees
9.2/10 Wonderful! (451 reviews)
Hotel Borgo San Luigi
Park Hotel Chianti

Park Hotel Chianti

Via Michelangelo, 5 Barberino Tavarnelle FI
￥10,322
￥12,409 total
Nov 22 - Nov 23
includes taxes & fees
Park Hotel Chianti
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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

Castello di Spaltenna- Small Luxury Hotels of the World

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."
Michelle 3-night trip
Posted 11 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
Borgo Vescine

Borgo Vescine

10/10 Excellent
"The staff was amazing and incredibly kind."
Natalie 2-night trip
Posted 3 weeks ago
Borgo Vescine
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 2 months 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 ￥11,118
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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