A stone castle with battlements overlooking a lush valley with vineyards.

5 Star Hotels in Gaiole in Chianti, Tuscany

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Check availability on Gaiole in Chianti 5 Star Hotels

Tonight
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Gaiole in Chianti 5-star hotels

An interior with a grand arched ceiling, a large clock, and a central round table with chairs.
A spacious lobby with a high ceiling, ornate columns, and a central chandelier. There are multiple seating areas with chairs and tables, and a large potted plant in the center.
A grand hallway with high ceilings, ornate columns, and a central chandelier. There are seating areas with tables and chairs, and a large potted plant in the middle.
An outdoor dining setup with a table set for two, surrounded by candles and greenery, with a historic building in the background.

1. Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione
Siena City Centre
United States
Lisa
€326
includes taxes & fees
12 Nov - 13 Nov
Grand Hotel Continental Siena – Starhotels Collezione
A historic stone building with multiple windows and a courtyard.
A stone building with outdoor seating and a garden with roses.
An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.
A room with a large window overlooking a landscape with trees and hills. There are two upholstered sofas with a patterned rug in the center.

2. Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga
Canada
Cynthia
€765
includes taxes & fees
25 Oct - 26 Oct
Borgo San Felice Resort
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.
An outdoor dining area with tables and chairs, a chef preparing food, and a scenic view in the background.
A garden with tall cypress trees, a variety of shrubs, and a stone pathway.

3. COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa
United States
Lauren
€719
includes taxes & fees
8 Nov - 9 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 modern kitchen with a large window, wooden ceiling, and a view of a forested area.
An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.

4. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United States
Andon
€270
includes taxes & fees
15 Oct - 16 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 stone building with a garden, tall trees, and a clear blue sky.
A sunlit patio with a glass roof, stone walls, and outdoor seating.
A restaurant with stone walls and a high ceiling, featuring tables set for dining.

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

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
United States
Michelle
€334
includes taxes & fees
30 Oct - 31 Oct
Castello di Spaltenna- Small Luxury Hotels of the World
A large building with multiple rooms, surrounded by a field of lavender.
An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.
An arched brick corridor leading to a dining area with tables set for a meal.
A historic estate with a central courtyard, surrounded by lush gardens and vineyards.

6. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
United States
Scott
€384
includes taxes & fees
3 Nov - 4 Nov
Borgo Scopeto Wine & Country Relais
A hotel room with a large bed, a vanity with a mirror, and a green archway.
A covered outdoor seating area with a pool in the background.
A courtyard with a stone building featuring a bell tower, outdoor seating, and greenery.
A dining area with round tables, chairs, chandeliers, and large windows with curtains.

7. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tulsi
€262
includes taxes & fees
9 Nov - 10 Nov
Hotel Certosa Di Maggiano
A hotel with a pool, outdoor seating, and a mountainous backdrop.
An aerial view of a large estate with a central building surrounded by manicured gardens, a swimming pool, and a fountain.
An outdoor patio with a stone wall, wooden table, chairs, potted plants, and a stone fireplace.
A bedroom with a stone archway, a bed, a chair, a table, and a window with curtains.

8. Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany
Casole d'Elsa
United States
sarah
€948
includes taxes & fees
12 Nov - 13 Nov
Castello di Casole, A Belmond Hotel, Tuscany
An aerial view of a town with a large lake, surrounded by greenery and hills.
An arched entrance leading to a pool area with a decorative emblem on the wall.
A table set for dining with a view of a lake and hills in the background.
A view from a window overlooking a river, with a table in the foreground featuring a vase and a bowl.

9. Villa La Massa

Villa La Massa
Bagno a Ripoli
United Kingdom
Katie
€566
includes taxes & fees
18 Oct - 19 Oct
Villa La Massa
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 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.

10. 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 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 dining area with tables and chairs, a kitchen in the background, and a patterned wall.

11. LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
Canada
Arash
€115
includes taxes & fees
19 Oct - 20 Oct
LHP Certaldo Resort
A swimming pool with lounge chairs and a person in a patterned dress.
An indoor dining area with tables set for meals, stone walls, and hanging light fixtures.
A stone staircase with candles and a sign reading "CANTINA".
A person performing a yoga pose in a grassy area with a historic building in the background.

12. Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
Castelnuovo Berardenga
United Kingdom
G
€564
includes taxes & fees
1 Nov - 2 Nov
Castel Monastero - The Leading Hotels of the World
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.
A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.
A bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.

13. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
Natalie
€467
includes taxes & fees
4 Nov - 5 Nov
Borgo Vescine
A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.
A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.
A table set for breakfast with various dishes, drinks, and a newspaper.
A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.

14. Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
United States
Cristina
€549
includes taxes & fees
21 Oct - 22 Oct
Hotel Le Fontanelle
A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.
An arched stone structure with a view of a landscaped garden and a building with outdoor seating.
A spacious living area with a high arched ceiling, a sofa set, and a glass coffee table.
A large indoor swimming pool with clear water, surrounded by modern architecture and a glass railing.

15. The Club House

The Club House
Castelnuovo Berardenga
United States
Natalyn
€361
includes taxes & fees
1 Nov - 2 Nov
The Club House
A stone villa with a swimming pool, outdoor seating, and a scenic sunset view.
A cozy living room with a fireplace, a clock, and a sofa.
A large, historic building with multiple wings and a courtyard.
An open doorway leading to a living room with a sofa, a coffee table, and a lamp.

16. Podere Cavalbianco

Podere Cavalbianco
Monte San Savino
United States
Edith
Podere Cavalbianco
A dining area with a long table set for breakfast, featuring bread, pastries, and fruit.
A cozy living area with wicker sofas, a coffee table, and a brick wall.
A restaurant with brick arches, wooden tables, and a piano.
A swimming pool with lounge chairs and umbrellas, surrounded by a stone building with multiple windows.

17. Agriturismo San Fabiano

Agriturismo San Fabiano
Monteroni d'Arbia
United States
James
Agriturismo San Fabiano
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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 Gaiole in Chianti.
Italiana Hotels Florence

Italiana Hotels Florence

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€114
1 Nov - 2 Nov
includes taxes & fees
Italiana Hotels Florence
Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

Via Giovanni Agnelli 33 Florence FI
€119
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (185 reviews)
Radisson Blu Hotel, Florence
Hotel Executive

Hotel Executive

Via Nazareno Orlandi 32 Siena SI
€92
1 Nov - 2 Nov
includes taxes & fees
8.4/10 Very good! (555 reviews)
Hotel Executive
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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 Gaiole in Chianti

Medieval stone buildings house family-run wine shops where you can taste Chianti Classico from surrounding vineyards. Join locals at Piazza Ricasoli's cafés before exploring L'Eroica cycling route that winds through nearby hilltop villages.

See all hotels in Gaiole in Chianti
A stone castle with battlements overlooking a lush valley with vineyards.

Top Gaiole in Chianti Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"Gorgeous hotel in the heart of historic Siena."
Steven 1-night trip
Posted 1 day ago
Grand Hotel Continental Siena – Starhotels Collezione
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 3 days ago
Castello di Spaltenna- Small Luxury Hotels of the World

Frequently asked questions

What are the best 5-star hotels in Gaiole in Chianti?
Castello di Spaltenna, Hotel Borgo San Felice and Hotel Le Fontanelle are some of the top 5-star hotels in Gaiole in Chianti, according to our customer reviews. These plush hotels rate highly for things such as their location, conveniences and service standards. Book your favourite and enjoy the best of everything.
How much does it cost to stay in a 5-star hotel in Gaiole in Chianti?
The amount you pay for a 5-star hotel in Gaiole in Chianti depends on factors such as when you plan to go and the length of your break. Our insider tip for landing an awesome deal? Use our pricing filters to compare all of the available hotels for your chosen dates.
  • Search for the lowest price per night from €92
What makes a hotel 5 stars in Gaiole in Chianti?
From fine dining venues and fitness centres to pools and dreamy bedding, the 5-star experience in Gaiole in Chianti is all about relaxation and luxury. But it calls for more than just top-notch perks to receive a 5-star rating. Stays must also provide remarkable services like in-room beauty treatments, on-site dry cleaning and laundry and a nightly turn-down service.