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

Find 5 Star Hotels in Gaiole in Chianti from AED 378

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Check availability on Gaiole in Chianti 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 Gaiole in Chianti 5-star hotels

An interior with a grand arched ceiling, a large clock, and a central round table with chairs.
A grand entrance with a revolving door, potted plants, and a classic stone facade.
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.
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
AED 1,197
AED 1,341 total
includes taxes & fees
9 Nov - 10 Nov
Grand Hotel Continental Siena – Starhotels Collezione
A historic stone building with multiple windows and a courtyard.
A pool area with lounge chairs and a service person attending to a guest.
A stone building with outdoor seating and a garden with roses.
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
AED 2,775
AED 3,094 total
includes taxes & fees
7 Nov - 8 Nov
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.
An outdoor dining area with a long table set for a meal, surrounded by chairs, and string lights overhead.
A garden with tall cypress trees, a variety of shrubs, and a stone pathway.
A resort with a swimming pool, terraced gardens, and a view of rolling hills.

3. COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa
United States
Lauren
AED 2,693
AED 2,995 total
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 rustic outdoor setting with a stone building, round tables, and outdoor seating.
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.

4. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United States
Andon
AED 987
AED 1,111 total
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 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.
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
Canada
Sonja
AED 1,212
AED 1,374 total
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.
A swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.
An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.
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
AED 1,297
AED 1,467 total
includes taxes & fees
4 Nov - 5 Nov
Borgo Scopeto Wine & Country Relais
A hotel room with a large bed, a vanity with a mirror, and a green archway.
A courtyard with a stone building featuring a bell tower, outdoor seating, and greenery.
An arched hallway with a marble reception desk, potted plants, and a staircase in the background.
A covered outdoor seating area with a pool in the background.

7. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tulsi
AED 956
AED 1,077 total
includes taxes & fees
9 Nov - 10 Nov
Hotel Certosa Di Maggiano
A hotel with a pool, outdoor seating, and a mountainous backdrop.
A bedroom with a stone archway, a bed, a chair, a table, and a window with curtains.
An outdoor patio with a stone wall, wooden table, chairs, potted plants, and a stone fireplace.
A cozy living room with a stone wall, wooden beams, a sofa, a coffee table, and a view through open doors.

8. Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany
Casole d'Elsa
United States
sarah
AED 3,497
AED 3,855 total
includes taxes & fees
11 Nov - 12 Nov
Castello di Casole, A Belmond Hotel, Tuscany
An aerial view of a town with a large lake, surrounded by greenery and hills.
A poolside area with lounge chairs and umbrellas, a stone building, and a large orange house with a tiled roof.
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
AED 1,962
AED 2,191 total
includes taxes & fees
18 Oct - 19 Oct
Villa La Massa
A stone building with arched windows, a grassy courtyard, and outdoor seating.
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.
A bedroom with a wooden ceiling, a stone wall, a bed, a desk, a chair, a sofa, and a window with curtains.

10. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
United States
Paul
AED 1,276
AED 1,437 total
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 lawn, seating area, and a weeping willow tree.
A dining area with tables and chairs, a kitchen in the background, and a patterned wall.
A large, multi-story building with a symmetrical facade, multiple windows, and a central entrance.

11. LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
Canada
Arash
AED 408
AED 474 total
includes taxes & fees
19 Oct - 20 Oct
LHP Certaldo Resort
A swimming pool with lounge chairs and a person in a patterned dress.
A person performing a yoga pose in a grassy area with a historic building in the background.
A stone building with a swimming pool, surrounded by a well-maintained garden and a clear sky.
A stone staircase with candles and a sign reading "CANTINA".

12. Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
Castelnuovo Berardenga
United Kingdom
G
AED 1,762
AED 1,980 total
includes taxes & fees
11 Nov - 12 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 bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.
An aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.

13. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
Natalie
AED 1,528
AED 1,714 total
includes taxes & fees
6 Nov - 7 Nov
Borgo Vescine
A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.
A restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.
A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.
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
AED 1,712
AED 1,924 total
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.
A spacious living area with a high arched ceiling, a sofa set, and a glass coffee table.
An arched stone structure with a view of a landscaped garden and a building with outdoor seating.
An indoor dining area with brick arches, tables set for dining, and a view of the outdoors.

15. The Club House

The Club House
Castelnuovo Berardenga
United States
Natalyn
AED 1,220
AED 1,383 total
includes taxes & fees
2 Nov - 3 Nov
The Club House
A stone villa with a swimming pool, outdoor seating, and a scenic sunset view.
A large, historic building with multiple wings and a courtyard.
A cozy living room with a fireplace, a clock, and a sofa.
An arched stone corridor leading to a room with a billiards table, a lamp, and a view of the outdoors.

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 view of a countryside landscape with rolling hills, a swimming pool, and a building with a tiled roof.
A cozy living area with wicker sofas, a coffee table, and a brick wall.
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

Viale Europa 205 Florence FI
AED 319
AED 408 total
9 Nov - 10 Nov
includes taxes & fees
Italiana Hotels Florence
Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

Via Giovanni Agnelli 33 Florence FI
AED 393
AED 490 total
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (181 reviews)
Radisson Blu Hotel, Florence
Hotel Executive

Hotel Executive

Via Nazareno Orlandi 32 Siena SI
AED 332
AED 378 total
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
"Beautiful hotel and very helpful staff. Excellent location in the heart of Siena. Disappointed with our hotel room. Not up to our expectations."
JOHN 3-night trip
Posted 5 days ago
Grand Hotel Continental Siena – Starhotels Collezione
Borgo Vescine

Borgo Vescine

10/10 Excellent
"The staff was amazing and incredibly kind."
Natalie 2-night trip
Posted 9 days ago
Borgo Vescine

Frequently asked questions

What are the best 5-star hotels in Gaiole in Chianti?
According to Expedia guest reviews, Castello di Spaltenna, Hotel Borgo San Felice and Hotel Le Fontanelle are among the most popular 5-star hotels in Gaiole in Chianti. Featuring top-quality amenities and unmatchable service, you'll enjoy an indulgent and memorable stay.
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 travel and the length of your escape. An insider tip for landing the best deal? Use our pricing filters to check out the available accommodations for your preferred dates.
  • Search for the lowest price per night from AED 378
What makes a hotel 5 stars in Gaiole in Chianti?
From fine dining venues and 24-hour gyms to swimming pools and superior bedding, the 5-star experience in Gaiole in Chianti is all about indulgence and comfort. But it requires more than just top-notch conveniences to earn a 5-star rating. Hotels also have to provide outstanding guest-focused services like in-room massage treatments, on-site laundry and 24-hour room service.

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