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

5 Star Hotels in Gaiole in Chianti, Tuscany

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Our top choices for Gaiole in Chianti 5-star hotels

2 bars/lounges

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, (616 reviews)
"Loved the location Restaurant was outstanding!! "
Canada
Julie
The price is €340
includes taxes & fees
10 Aug - 11 Aug
Grand Hotel Continental Siena – Starhotels Collezione
Garden

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
5.0 star property
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (215 reviews)
"Absolutely wonderful stay. The onsite restaurant was amazing and the staff was very attentive and helpful. There are nice wineries and restaurants nearby too and the concierge made very helpful recommendations and reservations for us. Use the hotel name (and not just the address) since the Apple Maps and Google Maps gets confused otherwise."
United States
Sachin
The price is €481
includes taxes & fees
2 Aug - 3 Aug
Borgo Scopeto Wine & Country Relais
Exterior

Borgo San Felice Resort

Borgo San Felice Resort
5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (85 reviews)
"Absolutely wonderful!"
Canada
Cynthia
The price is €701
includes taxes & fees
9 Aug - 10 Aug
Borgo San Felice Resort
Indoor pool, outdoor pool, pool loungers

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, (277 reviews)
"Very nice calm and relaxing stay"
United States
Rama
The price is €388
includes taxes & fees
9 Aug - 10 Aug
Castello di Spaltenna- Small Luxury Hotels of the World
Exterior

Hotel Le Fontanelle

Hotel Le Fontanelle
5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (108 reviews)
"Beautiful place and wonderful staff. Would recommend!"
United States
Malcolm
The price is €344
includes taxes & fees
16 Aug - 17 Aug
Hotel Le Fontanelle
2 restaurants; breakfast, lunch and dinner served

COMO Castello Del Nero

COMO Castello Del Nero
5.0 star property
Barberino Tavarnelle
9.6 out of 10, Exceptional, (141 reviews)
"Beautiful hotel, great staff."
United States
Vicente
The price is €799
includes taxes & fees
1 Aug - 2 Aug
COMO Castello Del Nero
Yoga

The Club House

The Club House
5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (20 reviews)
"Beautiful property excellent staff great spa loved everything about it!!"
United States
Natalyn
The price is €417
includes taxes & fees
2 Aug - 3 Aug
The Club House
Restaurant

Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
5.0 star property
Cavriglia
The price is €294
includes taxes & fees
25 Jul - 26 Jul
Chapter Chianti, a Member of Design Hotels
2 restaurants; breakfast served

Borgo Vescine

Borgo Vescine
5.0 star property
Radda in Chianti
9.4 out of 10, Exceptional, (251 reviews)
"Great place with incredibly helpful staff"
United States
David
The price is €505
includes taxes & fees
28 Jul - 29 Jul
Borgo Vescine
Aerial view

Villa La Massa

Villa La Massa
5.0 star property
Bagno a Ripoli
9.6 out of 10, Exceptional, (115 reviews)
"Our stay at Villa La Massa was amazing! The best customer service all around. Will definitely be coming back!"
United States
Erika
The price is €773
includes taxes & fees
24 Jul - 25 Jul
Villa La Massa
Garden

Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
5.0 star property
Radda in Chianti
10.0 out of 10, Exceptional, (40 reviews)
"I cannot say enough good things about Pieve Aldina. This property was beautiful and well maintained. Definitely worth the drive into Tuscany for a peaceful retreat. The staff were excellent and always at your service. Our room was rustic and cozy but the bathroom was spacious and luxurious. I truly enjoyed my stay and wish I had booked a few extra days!"
United States
Peyton
The price is €349
includes taxes & fees
30 Jul - 31 Jul
Pieve Aldina - Relais & Châteaux
Outdoor banquet area

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, (81 reviews)
"Amazing and incredible. Highly recommend!"
United States
Steven
The price is €2,037
includes taxes & fees
28 Jul - 29 Jul
Castello di Casole, A Belmond Hotel, Tuscany
Front of property

LHP Certaldo Resort

LHP Certaldo Resort
5.0 star property
Certaldo
9.2 out of 10, Wonderful, (536 reviews)
"nice property"
United States
Robert
The price is €145
includes taxes & fees
30 Jul - 31 Jul
LHP Certaldo Resort
Frette Italian sheets, premium bedding, down duvets, Select Comfort beds

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
5.0 star property
Siena
10.0 out of 10, Exceptional, (207 reviews)
"This is the hotel of dreams. I will remember this place for a very long time. Stunning spot, amazingly friendly staff. We ate in the restaurant (tasting menu) which was out of this world. Breakfast lovely Loved the pool Amazing amazing place."
United Kingdom
Lizzy
The price is €465
includes taxes & fees
17 Jul - 18 Jul
Hotel Certosa Di Maggiano
2 indoor pools, seasonal outdoor pool

Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
5.0 star property
Castelnuovo Berardenga
8.8 out of 10, Excellent, (144 reviews)
"Had two wonderful nights at the Castel Monastero (wish we had more). Will definitely go back"
Canada
John
The price is €615
includes taxes & fees
9 Aug - 10 Aug
Castel Monastero - The Leading Hotels of the World
Exterior

La Bagnaia Golf Resort

La Bagnaia Golf Resort
5.0 star property
Murlo
8.4 out of 10, Very good, (116 reviews)
"This properties has the nicest view set in a medival village and the staff is great. I would stay there again and take more time to enjoy the hotel."
Canada
Eric
La Bagnaia Golf Resort
Aerial view

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
Luxury Villa, 6 Bedrooms, Kitchen, Valley View | Terrace/patio

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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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
The price is €114 per night from 28 Jul to 29 Jul
€114
28 Jul - 29 Jul
includes taxes & fees
7.6/10 Good! (1,004 reviews)
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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, amazing views. Fabulous staff. They made our stay in Siena extra special."
Seth 2-night trip
Posted 12 hours ago
Grand Hotel Continental Siena – Starhotels Collezione

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 €114

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.