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

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Check availability on Gaiole in Chianti 5 Star Hotels

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Aug 23 - Aug 24
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Aug 24 - Aug 25
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Aug 28 - Aug 30
In two weeks
Sep 4 - Sep 6

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 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.
A grand entrance with a revolving door, potted plants, and a classic stone facade.

1. Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione
Siena City Centre
United States
Suresh
$446 nightly
$502 total
Aug 25 - Aug 26
Total with taxes and fees
Grand Hotel Continental Siena – Starhotels Collezione
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 outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.
An arched brick corridor leading to a dining area with tables set for a meal.

2. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
United States
Qingwen
$511 nightly
$573 total
Aug 26 - Aug 27
Total with taxes and fees
Borgo Scopeto Wine & Country Relais
A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.
A stone building with a garden, tall trees, and a clear blue sky.
A restaurant with stone walls and a high ceiling, featuring tables set for dining.
A room with a large window offering a view of a hilly landscape. There is a sofa with patterned upholstery and a lamp on a side table.

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

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
United States
Rama
$401 nightly
$453 total
Aug 24 - Aug 25
Total with taxes and fees
Castello di Spaltenna- Small Luxury Hotels of the World
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 room with a large window overlooking a landscape with trees and hills. There are two upholstered sofas with a patterned rug in the center.
An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.

4. Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga
Canada
Cynthia
$718 nightly
$801 total
Aug 24 - Aug 25
Total with taxes and fees
Borgo San Felice Resort
A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.
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.
A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.
A restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.

5. Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
Canada
Briana
$535 nightly
$600 total
Sep 2 - Sep 3
Total with taxes and fees
Hotel Le Fontanelle
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.
A garden with tall cypress trees, a variety of shrubs, and a stone pathway.
An outdoor dining area with tables and chairs, a chef preparing food, and a scenic view in the background.
An outdoor dining area with a long table set for a meal, surrounded by chairs, and string lights overhead.

6. COMO Castello Del Nero

COMO Castello Del Nero
Barberino Tavarnelle
United States
Vicente
$812 nightly
$903 total
Aug 31 - Sep 1
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 modern interior with a fireplace, two plush armchairs, and a large abstract sculpture.
An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.
A modern living room with a white sofa, armchairs, and a coffee table.

7. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
United Kingdom
Samay
$397 nightly
$444 total
Aug 24 - Aug 25
Total with taxes and fees
Chapter Chianti, a Member of Design Hotels
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.

8. Villa La Massa

Villa La Massa
Bagno a Ripoli
United Kingdom
Katie
$781 nightly
$868 total
Sep 1 - Sep 2
Total with taxes and fees
Villa La Massa
A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.
A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.
A bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.
An aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.

9. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
Gabrielle
$716 nightly
$797 total
Aug 24 - Aug 25
Total with taxes and fees
Borgo Vescine
A large building with a swimming pool, surrounded by greenery and outdoor lighting.
A courtyard with a stone bridge over a small water feature, surrounded by greenery and a building with arched windows.
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.

10. LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
Canada
Arash
$152 nightly
$174 total
Sep 1 - Sep 2
Total with taxes and fees
LHP Certaldo Resort
A hotel with a pool, outdoor seating, and a mountainous backdrop.
A bedroom with a stone archway, a bed, a chair, a table, and a window with curtains.
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.

11. Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany
Casole d'Elsa
United States
sarah
$1,810 nightly
$1,993 total
Aug 24 - Aug 25
Total with taxes and fees
Castello di Casole, A Belmond Hotel, Tuscany
A stone building with arched windows, a grassy courtyard, and outdoor seating.
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.
A cozy living room with a sofa, a dining table with chairs, a hanging lamp, and a mirror on the wall.

12. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
Italy
Matteo
$628 nightly
$700 total
Sep 2 - Sep 3
Total with taxes and fees
Pieve Aldina - Relais & Châteaux
A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.
A large indoor swimming pool with clear water, surrounded by modern architecture and a glass railing.
A spacious living area with a high arched ceiling, a sofa set, and a glass coffee table.
An indoor dining area with brick arches, tables set for dining, and a view of the outdoors.

13. The Club House

The Club House
Castelnuovo Berardenga
United States
Karla
$794 nightly
$885 total
Sep 8 - Sep 9
Total with taxes and fees
The Club House
A bed with white bedding and a decorative headboard with a floral pattern.
A covered outdoor seating area with benches and tables, a pathway, and a view of a garden and pool.
A courtyard with a stone building featuring a bell tower, outdoor seating, and greenery.
An aerial view of a historic building with a central tower, surrounded by lush greenery and a swimming pool.

14. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tomas
$496 nightly
$557 total
Aug 25 - Aug 26
Total with taxes and fees
Hotel Certosa Di Maggiano
A swimming pool with lounge chairs and a person in a patterned dress.
A stone staircase with candles and a sign reading "CANTINA".
A person performing a yoga pose in a grassy area with a historic building in the background.
A restaurant with brick walls, wooden tables, and hanging lanterns.

15. Castel Monastero - The Leading Hotels of the World

Castel Monastero - The Leading Hotels of the World
Castelnuovo Berardenga
United Kingdom
G
$566 nightly
$635 total
Sep 23 - Sep 24
Total with taxes and fees
Castel Monastero - The Leading Hotels of the World
A stone villa with a swimming pool, outdoor seating, and a scenic sunset view.
A cozy living room with a fireplace, a clock, and a sofa.
An arched stone corridor leading to a room with a billiards table, a lamp, and a view of the outdoors.
A large, historic building with multiple wings and a courtyard.

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 cozy living area with wicker sofas, a coffee table, and a brick wall.
A restaurant with brick arches, wooden tables, and a piano.
A view of a countryside landscape with rolling hills, a swimming pool, and a building with a tiled roof.

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
$85 nightly
$110 total
Aug 30 - Aug 31
Total with taxes and fees
Italiana Hotels Florence
Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

Via Giovanni Agnelli 33 Florence FI
$93 nightly
$119 total
Aug 30 - Aug 31
Total with taxes and fees
Radisson Blu Hotel, Florence
Hotel Athena

Hotel Athena

P Mascagni 55 Siena SI
$173 nightly
$197 total
Aug 24 - Aug 25
Total with taxes and fees
9.2/10 Wonderful! (1,011 reviews)
Hotel Athena
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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
"Everything was absolutely perfect, this is our newest favorite hotel in sienna and we will definitely come back"
Tyler 1-night trip
Posted 5 days 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
"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"
Ashley 2-night trip
Posted 3 weeks 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 $110
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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