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

Find 5 Star Hotels in Gaiole in Chianti from AED 518

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Gaiole in Chianti 5 Star Hotels

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

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, (612 reviews)
"Loved the location Restaurant was outstanding!! "
Canada
Julie
The price is AED 1,144
AED 1,300 total
includes taxes & fees
4 Jul - 5 Jul
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, (207 reviews)
"Amazing hotel"
United Kingdom
Bogdan
The price is AED 1,794
AED 2,016 total
includes taxes & fees
8 Jul - 9 Jul
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 AED 2,780
AED 3,100 total
includes taxes & fees
6 Jul - 7 Jul
Borgo San Felice Resort
Indoor pool, outdoor pool, sun 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, (274 reviews)
"Beautiful historic property with incredible spa and pool."
United States
Stacy
The price is AED 1,441
AED 1,627 total
includes taxes & fees
7 Jul - 8 Jul
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, (103 reviews)
"This was one of the most beautiful properties we have ever stayed! The staff was very informative and inviting. The room was extremely clean. Breakfast was much better than advertised with one of the most beautiful views we had while in Italy. Can’t wait to come back. Highly recommend"
United States
Shawn
The price is AED 1,222
AED 1,386 total
includes taxes & fees
15 Jul - 16 Jul
Hotel Le Fontanelle
Aerial view

Villa La Massa

Villa La Massa
5.0 star property
Bagno a Ripoli
9.6 out of 10, Exceptional, (113 reviews)
"We stayed here for one night and it was a lovely stay! Very comfortable, nice restaurant and great service! "
United Kingdom
Elisabeth
The price is AED 2,845
AED 3,163 total
includes taxes & fees
2 Jul - 3 Jul
Villa La Massa
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 AED 3,014
AED 3,349 total
includes taxes & fees
1 Aug - 2 Aug
COMO Castello Del Nero
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 AED 2,491
AED 2,774 total
includes taxes & fees
1 Aug - 2 Aug
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, (80 reviews)
"Amazing hotel - friendly staff - top of hotel world "
Singapore
Bingjian
The price is AED 9,106
AED 10,025 total
includes taxes & fees
12 Jul - 13 Jul
Castello di Casole, A Belmond Hotel, Tuscany
Yoga

The Club House

The Club House
5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful property excellent staff great spa loved everything about it!!"
United States
Natalyn
The price is AED 2,132
AED 2,387 total
includes taxes & fees
9 Jul - 10 Jul
The Club House
Frette Italian sheets, premium bedding, down comforters

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
5.0 star property
Siena
10.0 out of 10, Exceptional, (204 reviews)
"Beautiful rooms, amazing breakfasts, very helpful staff and lovely outdoor spaces with great views. Perfect spot for relaxing only half an hour walk from the centre of Siena."
United Kingdom
Sophie
The price is AED 1,691
AED 1,902 total
includes taxes & fees
12 Jul - 13 Jul
Hotel Certosa Di Maggiano
2 restaurants, breakfast served

Borgo Vescine

Borgo Vescine
5.0 star property
Radda in Chianti
9.4 out of 10, Exceptional, (250 reviews)
"Great place with incredibly helpful staff"
United States
David
The price is AED 1,936
AED 2,163 total
includes taxes & fees
1 Aug - 2 Aug
Borgo Vescine
Front of property

LHP Certaldo Resort

LHP Certaldo Resort
5.0 star property
Certaldo
9.2 out of 10, Wonderful, (533 reviews)
"The staff were excellent, especially Carim."
United Kingdom
Rob
The price is AED 519
AED 596 total
includes taxes & fees
30 Jul - 31 Jul
LHP Certaldo Resort
Restaurant

Chapter Chianti

Chapter Chianti
5.0 star property
Cavriglia
The price is AED 1,184
AED 1,327 total
includes taxes & fees
1 Aug - 2 Aug
Chapter Chianti
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 AED 2,575
AED 2,875 total
includes taxes & fees
1 Aug - 2 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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 AED 417 per night from Jul 5 to Jul 6
AED 417
AED 518 total
5 Jul - 6 Jul
includes taxes & fees
7.6/10 Good! (1,000 reviews)
Still don't see what you're looking for?
See all properties in Gaiole in Chianti.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

10/10 Excellent
"Wonderful on all counts"
Rita 1-night trip
Posted 9 days ago
Borgo Scopeto Wine & Country Relais
Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"It is wonderful! Everything is nice!"
awah 2-night trip
Posted 2 weeks ago
Grand Hotel Continental Siena – Starhotels Collezione

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 518

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.

Explore a world of travel with Expedia