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

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Check availability on Gaiole in Chianti 5 Star Hotels

Tonight
Oct 8 - Oct 9
Tomorrow
Oct 9 - Oct 10
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Gaiole in Chianti 5-star hotels

An interior with a grand arched ceiling, a large clock, and a central round table with chairs.
An outdoor dining setup with a table set for two, surrounded by candles and greenery, with a historic building in the background.
A grand hallway with high ceilings, ornate columns, and a central chandelier. There are seating areas with tables and chairs, and a large potted plant in the middle.
A spacious lobby with a high ceiling, ornate columns, and a central chandelier. There are multiple seating areas with chairs and tables, and a large potted plant in the center.

1. Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione
Siena City Centre
United States
Lisa
$368 nightly
$412 total
Nov 1 - Nov 2
Total with taxes and fees
Grand Hotel Continental Siena – Starhotels Collezione
A historic stone building with multiple windows and a courtyard.
A pool area with lounge chairs and a service person attending to a guest.
A stone building with outdoor seating and a garden with roses.
An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.

2. Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga
Canada
Cynthia
$648 nightly
$724 total
Oct 11 - Oct 12
Total with taxes and fees
Borgo San Felice Resort
A spacious interior with high arched ceilings, stone walls, and a central round mirror reflecting the room. Tables and chairs are arranged for dining or socializing.
An outdoor dining area with a long table set for a meal, surrounded by chairs, and string lights overhead.
An outdoor dining area with tables and chairs, a chef preparing food, and a scenic view in the background.
A resort with a swimming pool, terraced gardens, and a view of rolling hills.

3. COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa
United States
Lauren
$789 nightly
$877 total
Oct 30 - Oct 31
Total with taxes and fees
COMO Castello Del Nero
A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.
A compact living space with a wooden ceiling, a white sofa, a small table, a potted plant, and a cabinet with circular designs.
An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.
A rustic outdoor setting with a stone building, round tables, and outdoor seating.

4. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United States
Andon
$269 nightly
$302 total
Oct 12 - Oct 13
Total with taxes and fees
Chapter Chianti, a Member of Design Hotels
A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.
A restaurant with stone walls and a high ceiling, featuring tables set for dining.
An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.
A swimming pool with stone walls and a stone pathway leading to a building with multiple floors and a balcony.

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

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
Canada
Sonja
$332 nightly
$376 total
Oct 30 - Oct 31
Total with taxes and fees
Castello di Spaltenna- Small Luxury Hotels of the World
A large building with multiple rooms, surrounded by a field of lavender.
A swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.
An arched brick corridor leading to a dining area with tables set for a meal.
An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.

6. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
United States
Scott
$362 nightly
$410 total
Nov 5 - Nov 6
Total with taxes and fees
Borgo Scopeto Wine & Country Relais
A hotel room with a large bed, a vanity with a mirror, and a green archway.
A courtyard with a stone building featuring a bell tower, outdoor seating, and greenery.
A dining area with round tables, chairs, chandeliers, and large windows with curtains.
A covered outdoor seating area with a pool in the background.

7. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tulsi
$316 nightly
$354 total
Nov 3 - Nov 4
Total with taxes and fees
Hotel Certosa Di Maggiano
A hotel with a pool, outdoor seating, and a mountainous backdrop.
A cozy living room with a stone wall, wooden beams, a sofa, a coffee table, and a view through open doors.
An aerial view of a large estate with a central building surrounded by manicured gardens, a swimming pool, and a fountain.
A bedroom with a stone archway, a bed, a chair, a table, and a window with curtains.

8. Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany
Casole d'Elsa
United States
sarah
$1,008 nightly
$1,111 total
Nov 1 - Nov 2
Total with taxes and fees
Castello di Casole, A Belmond Hotel, Tuscany
An aerial view of a town with a large lake, surrounded by greenery and hills.
A table set for dining with a view of a lake and hills in the background.
A poolside area with lounge chairs and umbrellas, a stone building, and a large orange house with a tiled roof.
A view from a window overlooking a river, with a table in the foreground featuring a vase and a bowl.

9. Villa La Massa

Villa La Massa
Bagno a Ripoli
United Kingdom
Katie
$523 nightly
$584 total
Nov 8 - Nov 9
Total with taxes and fees
Villa La Massa
A stone building with arched windows, a grassy courtyard, and outdoor seating.
A cozy living room with a sofa, a dining table with chairs, a hanging lamp, and a mirror on the wall.
A bedroom with a wooden ceiling, a stone wall, a bed, a desk, a chair, a sofa, and a window with curtains.
A person relaxing in a clear pool surrounded by natural scenery.

10. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
United States
Paul
$314 nightly
$354 total
Oct 28 - Oct 29
Total with taxes and fees
Pieve Aldina - Relais & Châteaux
A large building with a swimming pool, surrounded by greenery and outdoor lighting.
A courtyard with a lawn, seating area, and a weeping willow tree.
A large, multi-story building with a symmetrical facade, multiple windows, and a central entrance.
A courtyard with a stone bridge over a small water feature, surrounded by greenery and a building with arched windows.

11. LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
Canada
Arash
$126 nightly
$146 total
Oct 18 - Oct 19
Total with taxes and fees
LHP Certaldo Resort
A swimming pool with lounge chairs and a person in a patterned dress.
A stone building with a swimming pool, surrounded by a well-maintained garden and a clear sky.
A person performing a yoga pose in a grassy area with a historic building in the background.
A stone staircase with candles and a sign reading "CANTINA".

12. Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
Castelnuovo Berardenga
United Kingdom
G
$565 nightly
$632 total
Nov 2 - Nov 3
Total with taxes and fees
Castel Monastero - The Leading Hotels of the World
A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.
An aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.
An indoor dining area with wooden tables and chairs, hanging baskets, and large windows offering a view of the outdoors.
A bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.

13. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
Natalie
$421 nightly
$472 total
Nov 5 - Nov 6
Total with taxes and fees
Borgo Vescine
A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.
A table set for breakfast with various dishes, drinks, and a newspaper.
A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.
A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.

14. Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
United States
Cristina
$483 nightly
$542 total
Oct 21 - Oct 22
Total with taxes and fees
Hotel Le Fontanelle
A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.
A spacious living area with a high arched ceiling, a sofa set, and a glass coffee table.
An arched stone structure with a view of a landscaped garden and a building with outdoor seating.
A large indoor swimming pool with clear water, surrounded by modern architecture and a glass railing.

15. The Club House

The Club House
Castelnuovo Berardenga
United States
Natalyn
$307 nightly
$349 total
Nov 8 - Nov 9
Total with taxes and fees
The Club House
A stone villa with a swimming pool, outdoor seating, and a scenic sunset view.
An open doorway leading to a living room with a sofa, a coffee table, and a lamp.
An arched stone corridor leading to a room with a billiards table, a lamp, and a view of the outdoors.
A cozy living room with a fireplace, a clock, and a sofa.

16. Podere Cavalbianco

Podere Cavalbianco
Monte San Savino
United States
Edith
Podere Cavalbianco
A dining area with a long table set for breakfast, featuring bread, pastries, and fruit.
A swimming pool with lounge chairs and umbrellas, surrounded by a stone building with multiple windows.
A cozy living area with wicker sofas, a coffee table, and a brick wall.
A restaurant with brick arches, wooden tables, and a piano.

17. Agriturismo San Fabiano

Agriturismo San Fabiano
Monteroni d'Arbia
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
$92 nightly
$117 total
Nov 2 - Nov 3
Total with taxes and fees
Italiana Hotels Florence
Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

Via Giovanni Agnelli 33 Florence FI
$107 nightly
$133 total
Nov 1 - Nov 2
Total with taxes and fees
8.8/10 Excellent! (175 reviews)
Radisson Blu Hotel, Florence
Hotel Executive

Hotel Executive

Via Nazareno Orlandi 32 Siena SI
$66 nightly
$76 total
Nov 1 - Nov 2
Total with taxes and fees
8.4/10 Very Good! (555 reviews)
Hotel Executive
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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
"Beautiful hotel and very helpful staff. Excellent location in the heart of Siena. Disappointed with our hotel room. Not up to our expectations."
JOHN 3-night trip
Posted 2 days ago
Grand Hotel Continental Siena – Starhotels Collezione
Borgo Vescine

Borgo Vescine

10/10 Excellent
"The staff was amazing and incredibly kind."
Natalie 2-night trip
Posted 6 days ago
Borgo Vescine
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."
Sonja 3-night trip
Posted 6 days 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 $76
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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