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

Compare and book 5 Star hotels in Chianti Region, Tuscany

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Chianti Region 5 Star Hotels

Tonight
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 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 resort with a swimming pool, terraced gardens, and a view of rolling hills.
A garden with tall cypress trees, a variety of shrubs, and a stone pathway.
An outdoor dining area with a long table set for a meal, surrounded by chairs, and string lights overhead.

1. COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa
United States
Lauren
£616
includes taxes & fees
11 Nov - 12 Nov
COMO Castello Del Nero
A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.
A modern living room with a white sofa, armchairs, and a coffee table.
A compact living space with a wooden ceiling, a white sofa, a small table, a potted plant, and a cabinet with circular designs.
A rustic outdoor setting with a stone building, round tables, and outdoor seating.

2. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United States
Andon
£229
includes taxes & fees
12 Oct - 13 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 sunlit patio with a glass roof, stone walls, and outdoor seating.
An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.

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

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
Canada
Sonja
£283
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 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.

4. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
United States
Paul
£296
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 courtyard with a stone bridge over a small water feature, surrounded by greenery and a building with arched windows.
A courtyard with a lawn, seating area, and a weeping willow tree.
A large, multi-story building with a symmetrical facade, multiple windows, and a central entrance.

5. LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
Canada
Arash
£97
includes taxes & fees
19 Oct - 20 Oct
LHP Certaldo Resort
A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.
An indoor dining area with wooden tables and chairs, hanging baskets, and large windows offering a view of the outdoors.
An aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.
A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.

6. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
Natalie
£353
includes taxes & fees
5 Nov - 6 Nov
Borgo Vescine
An outdoor dining area with wicker chairs and tables, white tablecloths, and umbrellas, overlooking a scenic landscape.
A dining area with stone walls, wooden beams, and round tables set for a meal.
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.

7. Villa Le Calvane

Villa Le Calvane
Montespertoli
United States
Ilya
£501
includes taxes & fees
19 Oct - 20 Oct
Villa Le Calvane
Save an average of 15% on thousands of hotels when you're signed in

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
£63
20 Oct - 21 Oct
includes taxes & fees
Hotel Toscana Ambassador
Park Hotel Chianti

Park Hotel Chianti

Via Michelangelo, 5 Barberino Tavarnelle FI
£60
6 Nov - 7 Nov
includes taxes & fees
9/10 Wonderful! (277 reviews)
Park Hotel Chianti
Villa I Barronci Resort & Spa

Villa I Barronci Resort & Spa

Via Sorripa 10 San Casciano in Val di Pesa FI
£66
11 Nov - 12 Nov
includes taxes & fees
9.2/10 Wonderful! (475 reviews)
Villa I Barronci Resort & Spa
Still don't see what you're looking for?
See all properties in Chianti Region.
You can also use these popular filters to refine your search.
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 2 hours 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 9 days 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 1 month ago
COMO Castello Del Nero

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 £60
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.

Explore a world of travel with Expedia