Hotels in Gaiole in Chianti

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Nov 15 - Nov 16
Tomorrow
Nov 16 - Nov 17
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Nov 20 - Nov 22
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Nov 27 - Nov 29

Where to stay in Gaiole in Chianti?

A swimming pool with a view of a historic building surrounded by olive trees.

1. Castello di Meleto

Castello di Meleto
Gaiole in Chianti
8.8 out of 10, Excellent, (106 reviews)
Experience authentic Tuscan charm at this farm stay featuring its own winery and restaurant. Take a refreshing dip in the seasonal pool, stroll through lush gardens, or enjoy local wines on the terrace. Free WiFi and parking make exploring nearby Meleto Castle effortless.
The price is $146
$170 total
includes taxes & fees
Nov 16 - Nov 17
Castello di Meleto
A stone building with a yellow sign reading "b&b erioico".

2. L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
Charming affittacamere surrounded by Chianti's rolling hills, offering complimentary WiFi and buffet breakfast each morning. The garden and terrace provide peaceful spots to savor local wines after visiting nearby Medieval Tower of Barbischio and town stadium.
The price is $127
$148 total
includes taxes & fees
Nov 16 - Nov 17
L' Eroico
A pool with a statue in the center, surrounded by trees and hills.

3. Borgo Casa al Vento

Borgo Casa al Vento
Gaiole in Chianti
8.6 out of 10, Excellent, (39 reviews)
Set amid Chianti vineyards, this charming farm stay offers rustic luxury with 2 outdoor pools and a full-service spa. Sample local cuisine at the restaurant after tennis or rooftop relaxation. Nearby Cantalici Winery beckons, with Florence just 70 minutes away.
The price is $146
$170 total
includes taxes & fees
Nov 16 - Nov 17
Borgo Casa al Vento
A stone building with a tiled roof, surrounded by greenery and a clear sky.

4. Brolio Agriroom

Brolio Agriroom
Gaiole in Chianti
8.8 out of 10, Excellent, (11 reviews)
Savor authentic Tuscany at this B&B with winery, restaurant, and bar in Gaiole in Chianti. Enjoy complimentary breakfast, WiFi, and parking while exploring nearby Castle of Brolio and San Felice Winery.
The price is $97
$116 total
includes taxes & fees
Nov 19 - Nov 20
Brolio Agriroom
A stone pathway leading to a stone building with a chimney, surrounded by lush greenery and lavender fields.

5. Agriturismo Vinci Banchelli

Agriturismo Vinci Banchelli
Gaiole in Chianti
The price is $165
$191 total
includes taxes & fees
Nov 16 - Nov 17
Agriturismo Vinci Banchelli
A swimming pool with a colorful inflatable ring and a water fountain.

6. Agriturismo Crocino in Chianti

Agriturismo Crocino in Chianti
Gaiole in Chianti
9.0 out of 10, Wonderful, (2 reviews)
Immerse yourself in Chianti's beauty at this countryside farm stay featuring an attached winery for tasting local vintages. After swimming in the outdoor pool or relaxing in the hot tub, enjoy meals at the restaurant while Meleto Castle waits nearby to explore.
The price is $90
$108 total
includes taxes & fees
Nov 16 - Nov 17
Agriturismo Crocino in Chianti
A traditional stone building with a garden featuring geometric hedges and potted plants.

7. Badia a Coltibuono

Badia a Coltibuono
Gaiole in Chianti
9.6 out of 10, Exceptional, (50 reviews)
Immerse yourself in the Chianti countryside at this charming farm stay. Just moments from the historic Badia a Coltibuono and local stadium, this retreat offers a refreshing seasonal outdoor pool and restaurant. Free parking makes exploring the region effortless.
Badia a Coltibuono
A spa area with stone walls, a white massage chair, and a potted plant.

8. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (308 reviews)
Relax on the rooftop terrace overlooking the Chianti countryside at this historic hotel with indoor and outdoor pools. After a spa treatment, savor local cuisine at La Perla del Palazzo restaurant or visit nearby wineries.
The price is $105
$122 total
includes taxes & fees
Dec 1 - Dec 2
Palazzo Leopoldo Dimora Storica & Spa
A spa area with a stone ceiling, a pool, and two sun loungers.

9. Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
4.0 star property
Radda in Chianti
9.2 out of 10, Wonderful, (198 reviews)
Escape to Radda in Chianti, where this spa hotel offers rejuvenating hot stone treatments and facials near Castello di Radda Winery. Enjoy 2 restaurants, a poolside bar, and fitness center after exploring Volpaia.
The price is $87
$103 total
includes taxes & fees
Dec 8 - Dec 9
Hotel Palazzo San niccolò & Spa
A building with a stone facade, a central arched doorway, and a window with a decorative frame.

10. Dievole Wine Resort

Dievole Wine Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (219 reviews)
Escape to Chianti's wine country at this elegant resort featuring 2 outdoor pools and an onsite winery. After tasting local vintages, enjoy meals at the restaurant or drinks on the terrace. Near Chianti Sculpture Park with free breakfast, WiFi, and parking.
The price is $277
$313 total
includes taxes & fees
Nov 16 - Nov 17
Dievole Wine Resort
A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

11. La Certosa di Pontignano - Place of Charme

La Certosa di Pontignano - Place of Charme
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (582 reviews)
The price is $57
$72 total
includes taxes & fees
Dec 2 - Dec 3
La Certosa di Pontignano - Place of Charme
A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

12. Belvedere di San Leonino

Belvedere di San Leonino
4.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (214 reviews)
Surrounded by Chianti countryside, this serene hotel with winery charms visitors with Italian cuisine at Il Cortile restaurant. Cool off in the outdoor pool, unwind in the hot tub, or sample local vintages at the bar after exploring nearby attractions.
The price is $105
$122 total
includes taxes & fees
Nov 27 - Nov 28
Belvedere di San Leonino
A narrow stone pathway leading to a rustic building with a wooden door and a window.

13. Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (236 reviews)
Nestled in Castellina in Chianti, this B&B offers an attached winery and Italian cuisine at Osteria di Fonterutoli restaurant. Mazzei Winery sits nearby, with Walls of Monteriggioni just a short drive from this charming retreat.
The price is $147
$166 total
includes taxes & fees
Nov 16 - Nov 17
Castello di Fonterutoli Wine Resort
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

14. Hotel Casafrassi

Hotel Casafrassi
4.0 star property
Castellina in Chianti
8.2 out of 10, Very good, (249 reviews)
Surrounded by beautiful countryside scenery, this Castellina in Chianti hotel offers Italian dining at Osteria di Casafrassi and a winery on-site. Enjoy free breakfast near Mazzei Winery, just 9 minutes from Monteriggioni Badesse Station.
The price is $59
$72 total
includes taxes & fees
Nov 16 - Nov 17
Hotel Casafrassi
A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

15. The Club House

The Club House
5.0 star property
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (24 reviews)
Escape to this luxurious Castelnuovo Berardenga retreat featuring 2 restaurants and a welcoming bar. Enjoy complimentary breakfast, WiFi, and parking while indulging in spa services like deep-tissue massages near Chianti Sculpture Park.
The price is $449
$505 total
includes taxes & fees
Nov 21 - Nov 22
The Club House
A covered outdoor seating area with a wooden door, wicker chairs, and potted plants.

16. Borgo Vescine

Borgo Vescine
5.0 star property
Radda in Chianti
9.6 out of 10, Exceptional, (250 reviews)
Immerse yourself in Chianti's rolling landscapes from this luxurious retreat with an outdoor pool and poolside bar. Just minutes from Castellina Fortress, enjoy 2 restaurants and free breakfast after exploring nearby archaeological treasures.
The price is $455
$509 total
includes taxes & fees
Nov 16 - Nov 17
Borgo Vescine
A spacious lobby with a reception desk, seating area, and a large vase.

17. Hotel Valdarno

Hotel Valdarno
4.0 star property
Montevarchi
8.8 out of 10, Excellent, (221 reviews)
Just steps from Montevarchi-Terranuova Station, this cozy hotel offers free breakfast and WiFi. Enjoy drinks at the bar after visiting nearby Il Cassero, or maintain your workout routine in the 24-hour fitness center.
The price is $117
$129 total
includes taxes & fees
Nov 16 - Nov 17
Hotel Valdarno
A stone building with an arched entrance, a wooden door, and a small balcony with a railing.

18. Albergo Il Colombaio

Albergo Il Colombaio
3.0 star property
Castellina in Chianti
8.4 out of 10, Very good, (66 reviews)
Immerse yourself in Chianti's charm at this tranquil retreat offering a refreshing outdoor pool and convenient bar. Located minutes from Casa Vinicola Luigi Cecchi and Castellina Fortress, enjoy daily housekeeping and free breakfast after exploring nearby vineyards.
The price is $150
$169 total
includes taxes & fees
Nov 16 - Nov 17
Albergo Il Colombaio
A modern hotel lobby with a high ceiling and a glass roof, featuring wooden paneling, comfortable seating, and a large wall mural.

19. Four Points by Sheraton Siena

Four Points by Sheraton Siena
4.0 star property
Scacciapensieri
8.8 out of 10, Excellent, (609 reviews)
Step into the vibrant heart of Siena at this business-friendly hotel with free breakfast, parking, and WiFi. The seasonal outdoor pool offers a refreshing escape after exploring nearby Palasport Mens Sana and Siena Stadium, while IL PALIO serves Italian cuisine all day.
The price is $127
$143 total
includes taxes & fees
Dec 4 - Dec 5
Four Points by Sheraton Siena
A pathway lined with trees and a large pot in the center.

20. Villa Montarioso

Villa Montarioso
Montarioso
8.8 out of 10, Excellent, (144 reviews)
Escape to a tranquil guesthouse near Monteriggioni with free WiFi, parking, and daily buffet breakfast. Discover nearby hiking and biking trails, then relax in the garden or terrace after visiting Casalvento's Wines, just moments away.
The price is $76
$89 total
includes taxes & fees
Nov 21 - Nov 22
Villa Montarioso
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.
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Check out pet-friendly hotels in Gaiole in Chianti

A swimming pool with a view of a historic building surrounded by olive trees.
Castello di Meleto

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
8.8 out of 10, Excellent, (106)
The price is $146
$170 total
includes taxes & fees
Nov 16 - Nov 17
Castello di Meleto
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.
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Go beyond your typical stay in Gaiole in Chianti

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When is the best time to visit Gaiole in Chianti?

Our prices for hotels in Gaiole in Chianti are cheapest in January

Price trends for hotels in Gaiole in Chianti

Pricing is based on two traveler single night rates
View properties in November
Currently viewing crowd sizes and weather for November.

November

High 14°C / low 7°C. Sunny most days.
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November, no crowd data, average high temperature 14 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
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December, no crowd data, average high temperature 10 degrees Celsius, average low temperature 3 degrees Celsius. Sunny most days.
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January, no crowd data, average high temperature 9 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
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February, no crowd data, average high temperature 11 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
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March, no crowd data, average high temperature 14 degrees Celsius, average low temperature 4 degrees Celsius. Sunny most days.
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April, no crowd data, average high temperature 18 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
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May, no crowd data, average high temperature 21 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
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June, no crowd data, average high temperature 27 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 31 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 31 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 26 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
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October, no crowd data, average high temperature 20 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
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Monthly weather averages (˚C)

Top landmarks in Gaiole in Chianti

Castle of Brolio

9.2/10 (44 reviews)
If you're planning a bit of sightseeing during your trip, head to Castle of Brolio— just one of the landmarks located 4 mi (6.5 km) from central Gaiole in Chianti.
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Learn more about Gaiole in Chianti

Gaiole in Chianti is well-known for its wineries and castle while attractions include Meleto Castle and Badia a Coltibuono. The city has something for everyone including sights like Cantalici Winery and Castle of Brolio within a rural setting.

See all hotels in Gaiole in Chianti
A stone castle with battlements overlooking a lush valley with vineyards.

Check out reviews of Gaiole in Chianti hotels guests love

A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.
The Club House

The Club House

The Club House
Castelnuovo Berardenga

10/10 Exceptional

Wonderful hotel. Privacy was awesome Clean sauna, amazing food Entrance to hotel was not easy. Bumpy roads, get early to hotel before dark
United States
debbie
Reviewed May 10, 2026
The Club House

Frequently Asked Questions

What hotels do travelers like in Gaiole in Chianti?

Guests like Castello di Spaltenna- Small Luxury Hotels of the World, Castello di Tornano Wine Resort and La Certosa di Pontignano.

Where can I get free parking with my stay in Gaiole in Chianti?

L' Eroico offers the perk of free parking.

Can I book a refundable hotel in Gaiole in Chianti?

If you want the flexibility to change your plans to Gaiole in Chianti, most properties provide refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.

Where can I stay in Gaiole in Chianti if I want a vacation rental instead of a traditional hotel?

If you're looking for a good alternative to a hotel, browse our selection of 18 vacation homes. You can also book one of 50 apartments or 90 villas.

What will the weather in Gaiole in Chianti be like during my trip?

August and July are typically the warmest months in Gaiole in Chianti when the average temp is 72°F. January and February are the coldest months when the average temperature is 44°F. November and October are the months with the most rain.

Why should I book my Gaiole in Chianti hotel with Hotels.com?

There are lots of reasons to book your Gaiole in Chianti trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.