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

Gaiole in Chianti 5 Stars Hotels

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Check availability on Gaiole in Chianti 5 Star Hotels

Tonight
Oct 25 - Oct 26
Tomorrow
Oct 26 - Oct 27
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

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 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
Canada
Steven
NT$10,956
NT$12,271 total
includes taxes & fees
Nov 9 - Nov 10
Grand Hotel Continental Siena – Starhotels Collezione
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.
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.

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

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
United States
Michelle
NT$10,757
NT$12,198 total
includes taxes & fees
Oct 30 - Oct 31
Castello di Spaltenna- Small Luxury Hotels of the World
A hotel room with a large bed, a vanity with a mirror, and a green archway.
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.
An outdoor dining area with tables and chairs, potted plants, and a tiled floor.

3. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tulsi
NT$8,342
NT$9,395 total
includes taxes & fees
Nov 25 - Nov 26
Hotel Certosa Di Maggiano
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 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.
A resort with a swimming pool, terraced gardens, and a view of rolling hills.

4. COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa
United States
Lauren
NT$23,605
NT$26,258 total
includes taxes & fees
Nov 8 - Nov 9
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.
An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.
A poolside area with lounge chairs and umbrellas.

5. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
Canada
Michael
NT$8,765
NT$9,860 total
includes taxes & fees
Oct 26 - Oct 27
Chapter Chianti, a Member of Design Hotels
A hotel with a pool, outdoor seating, and a mountainous backdrop.
A courtyard with a pool, outdoor seating, and a building with a tiled roof.
An outdoor patio with a stone wall, wooden table, chairs, potted plants, and a stone fireplace.
An aerial view of a large estate with a central building surrounded by manicured gardens, a swimming pool, and a fountain.

6. Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany
Casole d'Elsa
United States
sarah
NT$29,581
NT$32,612 total
includes taxes & fees
Nov 19 - Nov 20
Castello di Casole, A Belmond Hotel, Tuscany
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 swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.

7. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
United States
Scott
NT$11,970
NT$13,532 total
includes taxes & fees
Nov 3 - Nov 4
Borgo Scopeto Wine & Country Relais
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.

8. Villa La Massa

Villa La Massa
Bagno a Ripoli
United Kingdom
Katie
NT$23,240
NT$25,856 total
includes taxes & fees
Oct 31 - Nov 1
Villa La Massa
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 room with a large window overlooking a landscape with trees and hills. There are two upholstered sofas with a patterned rug in the center.
An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.

9. Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga
Canada
Cynthia
NT$26,726
NT$29,763 total
includes taxes & fees
Oct 26 - Oct 27
Borgo San Felice Resort
A large building with a swimming pool, surrounded by greenery and outdoor lighting.
A dining area with tables and chairs, a kitchen in the background, and a patterned wall.
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.

10. LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
Canada
Danilo
NT$3,877
NT$4,484 total
includes taxes & fees
Oct 29 - Oct 30
LHP Certaldo Resort
A stone building with a tiled roof, a staircase leading to an entrance, and a garden area with a table and chairs.
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 cozy living room with a sofa, a dining table with chairs, a hanging lamp, and a mirror on the wall.

11. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
United States
Paul
NT$11,331
NT$12,757 total
includes taxes & fees
Oct 28 - Oct 29
Pieve Aldina - Relais & Châteaux
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 courtyard with outdoor seating, stone buildings, and trees.
A stone building with a swimming pool and a tennis court.

12. Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
Castelnuovo Berardenga
United Kingdom
G
NT$18,406
NT$20,612 total
includes taxes & fees
Nov 1 - Nov 2
Castel Monastero - The Leading Hotels of the World
A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.
A table set for breakfast with various dishes, drinks, and a newspaper.
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.

13. Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
United States
Cristina
NT$21,035
NT$23,504 total
includes taxes & fees
Oct 26 - Oct 27
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.

14. The Club House

The Club House
Castelnuovo Berardenga
United States
Natalyn
NT$11,641
NT$13,170 total
includes taxes & fees
Nov 1 - Nov 2
The Club House
A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.
An aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.
A bedroom with a bed, pillows, a lamp, and a mural of a cityscape on the wall.
A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.

15. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
Natalie
NT$15,059
NT$16,857 total
includes taxes & fees
Oct 27 - Oct 28
Borgo Vescine
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.
An open doorway leading to a living room with a sofa, a coffee table, and a lamp.
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 view of a countryside landscape with rolling hills, a swimming pool, and a building with a tiled roof.
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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NT$3,023
NT$3,837 total
Nov 19 - Nov 20
includes taxes & fees
Italiana Hotels Florence
Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

Via Giovanni Agnelli 33 Florence FI
NT$3,220
NT$4,054 total
Nov 15 - Nov 16
includes taxes & fees
Radisson Blu Hotel, Florence
Villa Olmi Firenze

Villa Olmi Firenze

Via del Crocefisso del Lume 18 Bagno a Ripoli FI
NT$4,452
NT$5,080 total
Nov 8 - Nov 9
includes taxes & fees
Villa Olmi Firenze
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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

8/10 Good
"Excellent location. Very nice service."
mauricio 1-night trip
Posted 2 days 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 2 weeks 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 favorite 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 NT$3,837
What makes a hotel 5 stars in Gaiole in Chianti?
From fine dining venues and fitness centers 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.

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