Hotels in Gaiole in Chianti

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Nov 4 - Nov 5
Tomorrow
Nov 5 - Nov 6
This weekend
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

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, (105 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 $117
$137 total
includes taxes & fees
Nov 7 - Nov 8
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 $129
$151 total
includes taxes & fees
Nov 6 - Nov 7
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 $158
$183 total
includes taxes & fees
Nov 8 - Nov 9
Borgo Casa al Vento
A pool surrounded by lush greenery and vineyards, with a stone building in the background.

4. Agriturismo San Sano

Agriturismo San Sano
3.0 star property
Gaiole in Chianti
9.8 out of 10, Exceptional, (116 reviews)
Immerse yourself in Tuscan charm at this family-friendly hotel featuring its own winery. Enjoy complimentary breakfast before exploring nearby Chianti Sculpture Park and Meleto Castle. Return for a refreshing dip in the seasonal pool or unwind at the bar.
The price is $73
$84 total
includes taxes & fees
Nov 5 - Nov 6
Agriturismo San Sano
A traditional stone building with a garden featuring geometric hedges and potted plants.

5. 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.
The price is $163
$189 total
includes taxes & fees
Nov 5 - Nov 6
Badia a Coltibuono
A stone building with a tiled roof, surrounded by greenery and a clear sky.

6. 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 $99
$118 total
includes taxes & fees
Nov 6 - Nov 7
Brolio Agriroom
A swimming pool with a colorful inflatable ring and a water fountain.

7. 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 $92
$110 total
includes taxes & fees
Nov 14 - Nov 15
Agriturismo Crocino in Chianti
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, (305 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 $104
$121 total
includes taxes & fees
Nov 23 - Nov 24
Palazzo Leopoldo Dimora Storica & Spa
A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

9. 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 $272
$308 total
includes taxes & fees
Nov 16 - Nov 17
Dievole Wine Resort
A spa area with a stone ceiling, a pool, and two sun loungers.

10. 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 $96
$113 total
includes taxes & fees
Dec 1 - Dec 2
Hotel Palazzo San niccolò & Spa
A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

11. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
5.0 star property
Cavriglia
8.4 out of 10, Very good, (23 reviews)
The price is $269
$302 total
includes taxes & fees
Nov 5 - Nov 6
Chapter Chianti, a Member of Design Hotels
A rustic stone wall with a window, a potted plant, a bust sculpture, and a table with a magazine.

12. Tenuta CorteDomina

Tenuta CorteDomina
Radda in Chianti
9.8 out of 10, Exceptional, (148 reviews)
Immerse in Chianti country at this farm stay featuring a winery where you can savor local vintages. Near Castello di Radda Winery and Volpaia, this retreat offers international cuisine, garden spaces, and complimentary breakfast that guests consistently praise.
The price is $214
$240 total
includes taxes & fees
Nov 5 - Nov 6
Tenuta CorteDomina
A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

13. Hotel Villa Campomaggio

Hotel Villa Campomaggio
4.0 star property
Radda in Chianti
9.4 out of 10, Exceptional, (196 reviews)
Surrounded by vineyards, this countryside hotel offers a full-service spa, outdoor pool, and local cuisine at La Gabbia Tuscany Lounge. After wine tasting at nearby Borgo di Vescine, unwind in the sauna or bar.
The price is $165
$188 total
includes taxes & fees
Nov 5 - Nov 6
Hotel Villa Campomaggio
An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

14. La Certosa di Pontignano - Place of Charme

La Certosa di Pontignano - Place of Charme
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (580 reviews)
The price is $73
$90 total
includes taxes & fees
Nov 9 - Nov 10
La Certosa di Pontignano - Place of Charme
A stone building with a tiled roof, green shutters, and a small staircase leading to a door.

15. Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
9.4 out of 10, Exceptional, (234 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 $168
$190 total
includes taxes & fees
Nov 8 - Nov 9
Castello di Fonterutoli Wine Resort
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.

16. Hotel Casafrassi

Hotel Casafrassi
4.0 star property
Castellina in Chianti
8.2 out of 10, Very good, (248 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 $70
$84 total
includes taxes & fees
Nov 14 - Nov 15
Hotel Casafrassi
A stone house with a tiled roof, large glass doors, and a stone pathway leading to it.

17. The Club House

The Club House
5.0 star property
Castelnuovo Berardenga
10.0 out of 10, Exceptional, (23 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 $357
$404 total
includes taxes & fees
Nov 15 - Nov 16
The Club House
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

18. Belvedere di San Leonino

Belvedere di San Leonino
4.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (211 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 $107
$124 total
includes taxes & fees
Nov 12 - Nov 13
Belvedere di San Leonino
A historic estate with a central courtyard, surrounded by lush gardens and vineyards.

19. Borgo Scopeto Wine & Country Relais

Borgo Scopeto Wine & Country Relais
5.0 star property
Castelnuovo Berardenga
9.4 out of 10, Exceptional, (233 reviews)
The price is $364
$411 total
includes taxes & fees
Nov 5 - Nov 6
Borgo Scopeto Wine & Country Relais
An aerial view of a rustic village with stone buildings, a central courtyard with string lights, and a swimming pool.

20. 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 $462
$517 total
includes taxes & fees
Nov 5 - Nov 6
Borgo Vescine
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.
View all properties

Get last-minute hotel deals in Gaiole in Chianti and save more

Sign in to unlock great savings.
Showing deals for:Nov 6 - Nov 8
A stone building with a yellow sign reading "b&b erioico".
L' Eroico

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
$14 off
The price is $129
per night
$302 total
includes taxes & fees
L' Eroico
Showing deals for:Nov 13 - Nov 15
A stone building with a yellow sign reading "b&b erioico".
L' Eroico

L' Eroico

L' Eroico
Gaiole in Chianti
10.0 out of 10, Exceptional, (15 reviews)
$14 off
The price is $129
per night
$302 total
includes taxes & fees
L' Eroico

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, (105)
The price is $117
$137 total
includes taxes & fees
Nov 7 - Nov 8
Castello di Meleto
View all properties

You may also like hotels with pools 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, (105)
The price is $117
$137 total
includes taxes & fees
Nov 7 - Nov 8
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.
View all properties

Go beyond your typical stay in Gaiole in Chianti

pet friendly image
Pet friendly
Pet friendly
Pool image
Pool
Pool

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.
14°
weather_sun
November, no crowd data, average high temperature 14 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
7°
10°
weather_sun
December, no crowd data, average high temperature 10 degrees Celsius, average low temperature 3 degrees Celsius. Sunny most days.
3°
9°
weather_partly_sunny
January, no crowd data, average high temperature 9 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
2°
11°
weather_partly_sunny
February, no crowd data, average high temperature 11 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
2°
14°
weather_sun
March, no crowd data, average high temperature 14 degrees Celsius, average low temperature 4 degrees Celsius. Sunny most days.
4°
18°
weather_sun
April, no crowd data, average high temperature 18 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
7°
21°
weather_sun
May, no crowd data, average high temperature 21 degrees Celsius, average low temperature 10 degrees Celsius. Sunny most days.
10°
27°
weather_sun
June, no crowd data, average high temperature 27 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
31°
weather_sun
July, no crowd data, average high temperature 31 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
31°
weather_sun
August, no crowd data, average high temperature 31 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
26°
weather_sun
September, no crowd data, average high temperature 26 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
20°
weather_sun
October, no crowd data, average high temperature 20 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
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.
See properties

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 building with a yellow sign reading "b&b erioico".
L' Eroico

L' Eroico

L' Eroico
Gaiole in Chianti

10/10 Exceptional

Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area.
United States
Angela
Reviewed June 15, 2026
L' Eroico

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.