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

Find 5 Star Hotels in Gaiole in Chianti from $106

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Oct 25 - Oct 26
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Oct 30 - Nov 1
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Nov 6 - Nov 8

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

1. Grand Hotel Continental Siena – Starhotels Collezione

Grand Hotel Continental Siena – Starhotels Collezione
Siena City Centre
Canada
Steven
$336 nightly
$376 total
Nov 9 - Nov 10
Total with taxes and fees
Grand Hotel Continental Siena – Starhotels Collezione
A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.
An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.
A restaurant with stone walls and a high ceiling, featuring tables set for dining.
A stone building with a garden, tall trees, and a clear blue sky.

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

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
United States
Michelle
$330 nightly
$374 total
Oct 30 - Oct 31
Total with taxes and fees
Castello di Spaltenna- Small Luxury Hotels of the World
A hotel room with a large bed, a vanity with a mirror, and a green archway.
An arched hallway with a marble reception desk, potted plants, and a staircase in the background.
A view of a courtyard with a large tree, outdoor seating, and a building in the background.
A covered outdoor seating area with a pool in the background.

3. Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena
United States
Tulsi
$254 nightly
$286 total
Nov 25 - Nov 26
Total with taxes and fees
Hotel Certosa Di Maggiano
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.
A resort with a swimming pool, terraced gardens, and a view of rolling hills.
An outdoor dining area with tables and chairs, a chef preparing food, and a scenic view in the background.

4. COMO Castello Del Nero

COMO Castello Del Nero
Tavarnelle Val di Pesa
United States
Lauren
$724 nightly
$805 total
Nov 8 - Nov 9
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 rustic outdoor setting with a stone building, round tables, and outdoor seating.
A modern living room with a white sofa, armchairs, and a coffee table.
A poolside area with lounge chairs and umbrellas.

5. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
Canada
Michael
$269 nightly
$302 total
Oct 26 - Oct 27
Total with taxes and fees
Chapter Chianti, a Member of Design Hotels
A hotel with a pool, outdoor seating, and a mountainous backdrop.
An aerial view of a large estate with a central building surrounded by manicured gardens, a swimming pool, and a fountain.
A courtyard with a pool, outdoor seating, and a building with a tiled roof.
A cozy living room with a stone wall, wooden beams, a sofa, a coffee table, and a view through open doors.

6. Castello di Casole, A Belmond Hotel, Tuscany

Castello di Casole, A Belmond Hotel, Tuscany
Casole d'Elsa
United States
sarah
$907 nightly
$1,000 total
Nov 19 - Nov 20
Total with taxes and fees
Castello di Casole, A Belmond Hotel, Tuscany
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.
A historic estate with a central courtyard, surrounded by lush gardens and vineyards.
An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.

7. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
Castelnuovo Berardenga
United States
Scott
$364 nightly
$412 total
Nov 4 - Nov 5
Total with taxes and fees
Borgo Scopeto Wine & Country Relais
An aerial view of a town with a large lake, surrounded by greenery and hills.
An arched entrance leading to a pool area with a decorative emblem on the wall.
A poolside area with lounge chairs and umbrellas, a stone building, and a large orange house with a tiled roof.
A table set for dining with a view of a lake and hills in the background.

8. Villa La Massa

Villa La Massa
Bagno a Ripoli
United Kingdom
Katie
$656 nightly
$730 total
Oct 30 - Oct 31
Total with taxes and fees
Villa La Massa
A historic stone building with multiple windows and a courtyard.
A pool area with lounge chairs and a service person attending to a guest.
An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.
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.

9. Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga
Canada
Cynthia
$787 nightly
$877 total
Oct 27 - Oct 28
Total with taxes and fees
Borgo San Felice Resort
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 courtyard with a stone bridge over a small water feature, surrounded by greenery and a building with arched windows.
A dining area with tables and chairs, a kitchen in the background, and a patterned wall.

10. LHP Certaldo Resort

LHP Certaldo Resort
Certaldo
Canada
Danilo
$118 nightly
$137 total
Oct 29 - Oct 30
Total with taxes and fees
LHP Certaldo Resort
A stone building with a tiled roof, a staircase leading to an entrance, and a garden area with a table and chairs.
A cozy living room with a sofa, a dining table with chairs, a hanging lamp, and a mirror on the wall.
A person relaxing in a clear pool surrounded by natural scenery.
A bedroom with a wooden ceiling, a stone wall, a bed, a desk, a chair, a sofa, and a window with curtains.

11. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
United States
Paul
$348 nightly
$391 total
Nov 1 - Nov 2
Total with taxes and fees
Pieve Aldina - Relais & Châteaux
A swimming pool with lounge chairs and a person in a patterned dress.
An indoor dining area with tables set for meals, stone walls, and hanging light fixtures.
A courtyard with outdoor seating, stone buildings, and trees.
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
$519 nightly
$583 total
Nov 25 - Nov 26
Total with taxes and fees
Castel Monastero - The Leading Hotels of the World
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 restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.
A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.

13. Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga
United States
Cristina
$581 nightly
$650 total
Oct 27 - Oct 28
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.
An indoor dining area with brick arches, tables set for dining, and a view of the outdoors.
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.

14. The Club House

The Club House
Castelnuovo Berardenga
United States
Natalyn
$336 nightly
$380 total
Nov 1 - Nov 2
Total with taxes and fees
The Club House
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.
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.

15. Borgo Vescine

Borgo Vescine
Radda in Chianti
United States
Natalie
$430 nightly
$482 total
Nov 1 - Nov 2
Total with taxes and fees
Borgo Vescine
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 open doorway leading to a living room with a sofa, a coffee table, and a lamp.
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 restaurant with brick arches, wooden tables, and a piano.
A cozy living area with wicker sofas, a coffee table, and a brick wall.
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
$83 nightly
$106 total
Nov 19 - Nov 20
Total with taxes and fees
Italiana Hotels Florence
Radisson Blu Hotel, Florence

Radisson Blu Hotel, Florence

Via Giovanni Agnelli 33 Florence FI
$99 nightly
$124 total
Nov 15 - Nov 16
Total with taxes and fees
Radisson Blu Hotel, Florence
Villa Olmi Firenze

Villa Olmi Firenze

Via del Crocefisso del Lume 18 Bagno a Ripoli FI
$112 nightly
$129 total
Nov 8 - Nov 9
Total with taxes and fees
Villa Olmi Firenze
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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

8/10 Good
"Excellent location. Very nice service."
mauricio 1-night trip
Posted 2 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
"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."
Michelle 3-night trip
Posted 2 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 $106
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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