Find 5 Star Hotels in Gaiole in Chianti from $56

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Check availability on Gaiole in Chianti 5 Star Hotels

Tonight
Dec 7 - Dec 8
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Dec 8 - Dec 9
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Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Compare Gaiole in Chianti 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Ballroom
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, (573)
"Great hotel / room, city center, friendly staff. "
United States
Nebojsa
$243 nightly
The price is $275
Dec 22 - Dec 23
Total with taxes and fees
Grand Hotel Continental Siena – Starhotels Collezione
Villa (Thesan) | Terrace/patio
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, (79)
"Top-notch hotel. Everything, from the grounds, to the breakfast, to the pool, to the spa + gym, is perfect."
United States
Michael
Castello di Casole, A Belmond Hotel, Tuscany
2 restaurants, breakfast, lunch, dinner served; international cuisine
COMO Castello Del Nero

COMO Castello Del Nero

5.0 star property
Barberino Tavarnelle
9.6 out of 10, Exceptional, (132)
"Wonderful stay. 5-stars across the board if you’re looking for disconnecting and relaxing in the rolling hills of the Tuscan countryside. Easy day/dinner trips to Florence or Siena (rental car). "
United States
Matthew
$835 nightly
The price is $928
Dec 14 - Dec 15
Total with taxes and fees
COMO Castello Del Nero
2 outdoor pools, pool umbrellas, sun loungers
Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais

5.0 star property
Castelnuovo Berardenga
9.2 out of 10, Wonderful, (192)
"Best in the world!"
United States
ALFREDO
Borgo Scopeto Wine & Country Relais
Front of property - evening/night
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, (261)
"The breakfast was fresh with lots of options and a outdoor setting on the property. The property is beautiful, pool area and spa so peaceful. Excellent service in all areas of hotel! "
Canada
Catherine
Castello di Spaltenna- Small Luxury Hotels of the World
Seasonal outdoor pool
Pieve Aldina - Fontenille Collection

Pieve Aldina - Fontenille Collection

5.0 star property
Radda in Chianti
10.0 out of 10, Exceptional, (32)
"Gorgeous design, high quality, delicious food and wine, friendly and helpful staff. "
United States
Lara
Pieve Aldina - Fontenille Collection
2 restaurants, breakfast served
Borgo Vescine

Borgo Vescine

5.0 star property
Radda in Chianti
9.4 out of 10, Exceptional, (244)
"This was a beautiful location. The room was spacious and loved the patio for coffee in the mornings. It was very private. We enjoyed the pool and restaurants were great. Breakfast was amazing. We did the picnic and dinner in the Olive Garden and loved getting to know others at our table. The chefs food choices were so wonderful. We would definitely stay again. "
United States
Sherie
Borgo Vescine
2 restaurants, breakfast served
The Club House

The Club House

5.0 star property
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (7)
"Unbelievable stay. All amenities are included. The staff is very welcoming. Having traveled extensively, this luxury resort is among the most impressive run hotels. The grounds, food, and staff all A+"
United States
Robert
The Club House
Exterior
Hotel Le Fontanelle

Hotel Le Fontanelle

5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (95)
"We had a perfect stay at this hotel! 100% recommend. "
Netherlands
Andreea
Hotel Le Fontanelle
2 restaurants, lunch, dinner served; local cuisine
Borgo San Felice Resort

Borgo San Felice Resort

5.0 star property
Castelnuovo Berardenga
9.8 out of 10, Exceptional, (79)
"One of our favorite places we’ve ever stayed at. 100% recommend. Hopefully we can visit again. "
United States
Maria D
Borgo San Felice Resort
Couples treatment rooms, Turkish bath, body treatments, body wraps
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)
"Had two wonderful nights at the Castel Monastero (wish we had more). Will definitely go back"
Canada
John
$565 nightly
The price is $634
Dec 20 - Dec 21
Total with taxes and fees
Castel Monastero - The Leading Hotels of the World
Aerial view
Villa La Massa

Villa La Massa

5.0 star property
Bagno a Ripoli
9.4 out of 10, Exceptional, (108)
"We stayed here for one night and it was a lovely stay! Very comfortable, nice restaurant and great service! "
United Kingdom
Elisabeth
Villa La Massa
Outdoor dining
La Bagnaia Golf & Spa Resort Siena, Curio

La Bagnaia Golf & Spa Resort Siena, Curio

5.0 star property
Murlo
8.4 out of 10, Very Good, (116)
"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 & Spa Resort Siena, Curio
Luxury Apartment, 5 Bedrooms, Air conditioning, Hill View | Living area | 60-inch Smart TV with cable channels
Podere Cavalbianco

Podere Cavalbianco

5.0 star property
Monte San Savino
10.0 out of 10, Exceptional, (4)
"Everything was perfect. The breakfast is excellent, the location and the appartment/rooms are amazing. Couldn’t expect more"
United States
Edith
Podere Cavalbianco
Front of property
Agriturismo San Fabiano

Agriturismo San Fabiano

5.0 star property
Monteroni d'Arbia
10.0 out of 10, Exceptional, (1)
"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.
Hotel Athena

Hotel Athena

P Mascagni 55 Siena SI
$91 nightly
The price is $104 total per night from Dec 15 to Dec 16
$104 total
Dec 15 - Dec 16
Total with taxes and fees
9.2/10 Wonderful! (1,007 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
View over the hills from the Brolio Castle

Top Gaiole in Chianti Hotel Reviews

Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent
"The Grand Hotel Continental in Siena is a rare gem,elegant, inviting, and steeped in history. From the beautifully preserved interiors to the warm, attentive staff, every detail makes you feel genuinely cared for. Its central location is unbeatable, placing Siena’s most charming sights just steps away. A perfect blend of luxury and authentic Tuscan character, this hotel transforms a stay in Siena into something truly unforgettable. The foods were yummy took! "
Betty 4-night trip
Posted 2 weeks 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
"The breakfast was fresh with lots of options and a outdoor setting on the property. The property is beautiful, pool area and spa so peaceful. Excellent service in all areas of hotel! "
Catherine 2-night trip
Posted 2 months ago
Castello di Spaltenna- Small Luxury Hotels of the World

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 $56

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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