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

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Check availability on Gaiole in Chianti 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 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 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.
A grand entrance with a revolving door, potted plants, and a classic stone facade.
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
£276
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.
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
£604
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.
An outdoor dining area with a long table set for a meal, surrounded by chairs, and string lights overhead.

3. COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa
United States
Lauren
£631
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.
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 modern living room with a white sofa, armchairs, and a coffee table.

4. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United States
Andon
£229
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 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
£283
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 arched brick corridor leading to a dining area with tables set for a meal.
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
£329
includes taxes & fees
6 Nov - 7 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.
A dining area with round tables, chairs, chandeliers, and large windows with curtains.
A covered outdoor seating area with a pool in the background.

7. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tulsi
£221
includes taxes & fees
9 Nov - 10 Nov
Hotel Certosa Di Maggiano
A hotel with a pool, outdoor seating, and a mountainous backdrop.
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.
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
£821
includes taxes & fees
6 Nov - 7 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 view from a window overlooking a river, with a table in the foreground featuring a vase and a bowl.
A poolside area with lounge chairs and umbrellas, a stone building, and a large orange house with a tiled roof.

9. Villa La Massa

Villa La Massa
Bagno a Ripoli
United Kingdom
Katie
£451
includes taxes & fees
25 Oct - 26 Oct
Villa La Massa
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.

10. 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 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.

11. LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
Canada
Arash
£116
includes taxes & fees
31 Oct - 1 Nov
LHP Certaldo Resort
A swimming pool with lounge chairs and a person in a patterned dress.
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".
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
£431
includes taxes & fees
9 Nov - 10 Nov
Castel Monastero - The Leading Hotels of the World
A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.
A bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.
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.

13. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
Natalie
£361
includes taxes & fees
8 Nov - 9 Nov
Borgo Vescine
A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.
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.
A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.
A restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.

14. Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
United States
Cristina
£396
includes taxes & fees
29 Oct - 30 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.
A large indoor swimming pool with clear water, surrounded by modern architecture and a glass railing.
An arched stone structure with a view of a landscaped garden and a building with outdoor seating.

15. The Club House

The Club House
Castelnuovo Berardenga
United States
Natalyn
£264
includes taxes & fees
6 Nov - 7 Nov
The Club House
A stone villa with a swimming pool, outdoor seating, and a scenic sunset view.
An arched stone corridor leading to a room with a billiards table, a lamp, and a view of the outdoors.
A cozy living room with a fireplace, a clock, and a sofa.
A large, historic building with multiple wings and a courtyard.

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 swimming pool with lounge chairs and umbrellas, surrounded by a stone building with multiple windows.
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.

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.
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9 Nov - 10 Nov
includes taxes & fees
Italiana Hotels Florence
Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

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£101
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (181 reviews)
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Hotel Executive

Hotel Executive

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£57
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 4 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 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

Find out more about Gaiole in Chianti

Frequently asked questions

What are the best 5-star hotels in Gaiole in Chianti?
Get ready for 5-star opulence at Castello di Spaltenna, Pieve Aldina or Borgo San Felice Resort. These are some of the most popular escapes in Gaiole in Chianti according to Expedia guest reviews. Choose one and enjoy a taste of the good life!
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 can vary depending on when you decide to travel and how long you plan to be away, among several factors. Use our price per night filter and other search tools to score the best deal on a luxurious stay.
  • Search for the lowest price per night from £57
What makes a hotel 5 stars in Gaiole in Chianti?
From fine dining restaurants and all-day gyms to swimming pools and the finest bedding, the 5-star experience in Gaiole in Chianti is all about comfort and indulgence. But it calls for more than just top-notch perks to receive a 5-star rating. Accommodation must also provide extraordinary guest-centric services like in-room massage treatments, dry cleaning and laundry and concierge services.

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