View over the hills from the Brolio Castle

Find 5 Star Hotels in Gaiole in Chianti from $91

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Gaiole in Chianti 5 Star Hotels

Next weekend
Jun 26 - Jun 28
In two weeks
Jul 3 - Jul 5

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, (609 reviews)
"Loved the location Restaurant was outstanding!! "
Canada
Julie
$282 nightly
The price is $321
Jul 4 - Jul 5
Total with taxes and fees
Grand Hotel Continental Siena – Starhotels Collezione
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
$739 nightly
The price is $825
Jul 16 - Jul 17
Total with taxes and fees
Borgo San Felice Resort
Garden

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
5.0 star property
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (204 reviews)
"Amazing hotel"
United Kingdom
Bogdan
$404 nightly
The price is $456
Jun 28 - Jun 29
Total with taxes and fees
Borgo Scopeto Wine & Country Relais
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, (273 reviews)
"Beautiful historic property with incredible spa and pool."
United States
Stacy
$394 nightly
The price is $445
Jun 30 - Jul 1
Total with taxes and fees
Castello di Spaltenna- Small Luxury Hotels of the World
Aerial view

Villa La Massa

Villa La Massa
5.0 star property
Bagno a Ripoli
9.6 out of 10, Exceptional, (112 reviews)
"We stayed here for one night and it was a lovely stay! Very comfortable, nice restaurant and great service! "
United Kingdom
Elisabeth
$768 nightly
The price is $854
Jul 1 - Jul 2
Total with taxes and fees
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, (39 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
$649 nightly
The price is $723
Jun 25 - Jun 26
Total with taxes and fees
Pieve Aldina - Relais & Châteaux
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, (139 reviews)
"Beautiful hotel, great staff."
United States
Vicente
$1,184 nightly
The price is $1,312
Jul 10 - Jul 11
Total with taxes and fees
COMO Castello Del Nero
Exterior

Hotel Le Fontanelle

Hotel Le Fontanelle
5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (102 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
$330 nightly
The price is $375
Jul 5 - Jul 6
Total with taxes and fees
Hotel Le Fontanelle
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
$2,294 nightly
The price is $2,526
Jul 21 - Jul 22
Total with taxes and fees
Castello di Casole, A Belmond Hotel, Tuscany
2 restaurants, breakfast served

Borgo Vescine

Borgo Vescine
5.0 star property
Radda in Chianti
9.4 out of 10, Exceptional, (248 reviews)
"Great place with incredibly helpful staff"
United States
David
$560 nightly
The price is $625
Jun 27 - Jun 28
Total with taxes and fees
Borgo Vescine
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, (203 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
$411 nightly
The price is $464
Jul 12 - Jul 13
Total with taxes and fees
Hotel Certosa Di Maggiano
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
$557 nightly
The price is $625
Jul 17 - Jul 18
Total with taxes and fees
The Club House
Front of property

LHP Certaldo Resort

LHP Certaldo Resort
5.0 star property
Certaldo
9.2 out of 10, Wonderful, (532 reviews)
"The staff were excellent, especially Carim."
United Kingdom
Rob
$168 nightly
The price is $192
Jul 20 - Jul 21
Total with taxes and fees
LHP Certaldo Resort
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
$763 nightly
The price is $851
Jul 15 - Jul 16
Total with taxes and fees
Castel Monastero - The Leading Hotels of the World
Restaurant

Chapter Chianti

Chapter Chianti
5.0 star property
Cavriglia
$318 nightly
The price is $356
Jul 21 - Jul 22
Total with taxes and fees
Chapter Chianti
Free toiletries, hair dryer, bathrobes, slippers

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, (4 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
$106 nightly
The price is $133 total per night from Jun 23 to Jun 24
$133 total
Jun 23 - Jun 24
Total with taxes and 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
View over the hills from the Brolio Castle

Top Gaiole in Chianti Hotel Reviews

Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

10/10 Excellent
"This place was the best part of my trip! The property is absolutely stunning. The pool is beautiful. The view is breathtaking. The staff is amazing. The food at the restaurant is high quality. It is about 25-30mins from Siena and it’s higher in a hill/mountain. We loved everything about Borgo Scopeto and would definitely be back again. It is so peaceful and relaxing."
Antoneta 2-night trip
Posted 3 days ago
Borgo Scopeto Wine & Country Relais

Find out more about Gaiole in Chianti

Ready for an incredible adventure? Add even more enjoyment on your next trip to Gaiole in Chianti by treating yourself to the best of the best when it comes to lodging. It's an ideal combination. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Gaiole in Chianti so popular in the last year. There's no reason to delay a getaway to Gaiole in Chianti any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Book one of Expedia's luxurious 5-star hotels in Gaiole in Chianti and get ready to enjoy the getaway of a lifetime. You deserve an outstanding getaway.

Book the Best Gaiole in Chianti 5-Star Hotels

You'll have a fantastic time at one of these 5-star hotels. Top-notch service, delicious meals, and one-on-one attention are all ready for you. You're sure to find exactly the accommodation you need. You'll also enjoy a high standard of care and meticulous guest relations, so get ready for a wonderful adventure. What kind of amenities will make your stay a wonderful one? A concierge to help you pick out your next adventure? A deep-tissue massage to help your cares fall away? Comfortable beds, delectable chocolate desserts, and even space for your family pet in some cases...these hotels are one-of-a-kind. Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs.

You won't sleep and order room service the entire time, though. Don't worry. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Gaiole in Chianti are the perfect place to relax after an exciting day.

Make Your Escape

The results are in, and Gaiole in Chianti 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. Expedia can help you land a great deal on accommodation. It's time to indulge yourself. Select one of Expedia's Gaiole in Chianti 5-star hotels today and settle down in luxe surroundings tomorrow.

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 $91

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