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

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Our top choices for Gaiole in Chianti 5-star hotels

1. Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione
5.0 star property
Siena City Centre
9.2 out of 10, Wonderful, (647 reviews)
"Great stay!"
United States
Darold Paul
The price is AED 1,005
AED 1,130 total
includes taxes & fees
8 Dec - 9 Dec
Grand Hotel Continental Siena – Starhotels Collezione

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

Castello di Spaltenna- Small Luxury Hotels of the World
5.0 star property
Gaiole in Chianti
9.6 out of 10, Exceptional, (295 reviews)
"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."
United States
Michelle
Castello di Spaltenna- Small Luxury Hotels of the World

3. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
5.0 star property
Siena
10.0 out of 10, Exceptional, (222 reviews)
"Everything was amazing! Staff was incredibly helpful."
United States
Tulsi
The price is AED 916
AED 1,032 total
includes taxes & fees
9 Dec - 10 Dec
Hotel Certosa Di Maggiano

4. COMO Castello Del Nero

COMO Castello Del Nero
5.0 star property
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (146 reviews)
"Everything perfectly"
United Arab Emirates
Nawaf
The price is AED 2,646
AED 2,943 total
includes taxes & fees
14 Nov - 15 Nov
COMO Castello Del Nero

5. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
5.0 star property
Cavriglia
8.4 out of 10, Very good, (23 reviews)
"Imcredible hotel and location. Perfect for a slow life getaway. Room is big and staff is kind. Food was delicious"
Canada
Carolina
The price is AED 982
AED 1,105 total
includes taxes & fees
9 Nov - 10 Nov
Chapter Chianti, a Member of Design Hotels

6. Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany
5.0 star property
Casole d'Elsa
9.6 out of 10, Exceptional, (85 reviews)
"A high end exclusive stay!"
United States
sarah
The price is AED 3,315
AED 3,655 total
includes taxes & fees
18 Nov - 19 Nov
Castello di Casole, A Belmond Hotel, Tuscany

7. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
5.0 star property
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (233 reviews)
"A peaceful luxurious stay with amazing amenities, 6 star service & and amazing dinner restaurant."
United States
Scott
Borgo Scopeto Wine & Country Relais

8. Villa La Massa

Villa La Massa
5.0 star property
Bagno a Ripoli
9.6 out of 10, Exceptional, (119 reviews)
"Had an incredible stay, staff were lovely and so helpful. The Villa was beautiful. We didn't want to leave!"
United Kingdom
Emma
The price is AED 2,553
AED 2,840 total
includes taxes & fees
9 Nov - 10 Nov
Villa La Massa

9. Borgo San Felice Resort

Borgo San Felice Resort
5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (98 reviews)
"Absolutely wonderful!"
Canada
Cynthia
Borgo San Felice Resort

10. LHP Certaldo Resort

LHP Certaldo Resort
5.0 star property
Certaldo
9.2 out of 10, Wonderful, (552 reviews)
"Hotel was clean and staff was very helpful."
United States
Oscar
LHP Certaldo Resort

11. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
5.0 star property
Radda in Chianti
9.8 out of 10, Exceptional, (48 reviews)
"An amazing staff and property! Hated to leave!!"
United States
Paul
Pieve Aldina - Relais & Châteaux

12. Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
5.0 star property
Castelnuovo Berardenga
9.0 out of 10, Wonderful, (148 reviews)
"The staff were excellent throughout — very friendly, attentive and always happy to help. Our room was lovely, comfortable and beautifully presented. Overall, we had a very enjoyable stay."
United Kingdom
G
The price is AED 1,789
AED 2,009 total
includes taxes & fees
15 Nov - 16 Nov
Castel Monastero - The Leading Hotels of the World

13. Hotel Le Fontanelle

Hotel Le Fontanelle
5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (128 reviews)
"We absolutely loved our stay at Le Fontanelle. The staff was incredibly kind, attentive, and on par for a hotel of this level. We highly recommend this hotel!"
United States
Cristina
Hotel Le Fontanelle

14. The Club House

The Club House
5.0 star property
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (24 reviews)
"Beautiful property excellent staff great spa loved everything about it!!"
United States
Natalyn
The price is AED 1,650
AED 1,856 total
includes taxes & fees
15 Nov - 16 Nov
The Club House

15. Borgo Vescine

Borgo Vescine
5.0 star property
Radda in Chianti
9.6 out of 10, Exceptional, (250 reviews)
"The staff was amazing and incredibly kind."
United States
Natalie
The price is AED 1,603
AED 1,796 total
includes taxes & fees
9 Nov - 10 Nov
Borgo Vescine

16. Podere Cavalbianco

Podere Cavalbianco
5.0 star property
Monte San Savino
10.0 out of 10, Exceptional, (5 reviews)
"Everything was perfect. The breakfast is excellent, the location and the appartment/rooms are amazing. Couldn’t expect more"
United States
Edith
Podere Cavalbianco

17. Agriturismo San Fabiano

Agriturismo San Fabiano
5.0 star property
Monteroni d'Arbia
10.0 out of 10, Exceptional, (1 review)
"I can't imagine a better home-like experience than what we experienced here. Our hosts were charming and, more importantly, gave us a great window into what living in Tuscany is all about. We can't wait to go back! And for a much longer stay..."
United States
James
Agriturismo San Fabiano
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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.

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

Top Gaiole in Chianti Hotel Reviews

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 435

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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