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Hotels in Gaiole in Chianti

October 2026
November 2026

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This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Where to stay in Gaiole in Chianti?

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.

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

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
$373
$421 total
includes taxes & fees
Oct 27 - Oct 28
Castello di Spaltenna- Small Luxury Hotels of the World
A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.
A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.
A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.
A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

2. Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
$85
$103 total
includes taxes & fees
Oct 25 - Oct 26
Ultimo Mulino Wellness Country Hotel
A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.
A stone building with a wooden door, outdoor seating, and a pergola with vines.
A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.
A stone building with a window and a light fixture.

3. Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
$74
$86 total
includes taxes & fees
Oct 18 - Oct 19
Agriturismo San Sano
A traditional stone building with a garden featuring geometric hedges and potted plants.
A formal garden with geometric hedges, a stone building with green shutters, and a staircase leading to a covered area.
A breakfast setting with a table set for two, including plates of fruit, a cup of coffee, a glass of juice, and a bottle of wine.
A spacious room with a high arched ceiling, frescoed walls, a white sofa, and a wooden cabinet.

4. Badia a Coltibuono

Badia a Coltibuono
Gaiole in Chianti
$166
$192 total
includes taxes & fees
Oct 27 - Oct 28
Badia a Coltibuono
A stone building with a yellow sign reading "b&b erioico".
An aerial view of a town with a central square, surrounding buildings, and vineyards.
A modern dining area with a wooden table, glass vases, and a staircase with glass railings.
A hotel room with neatly folded towels on the bed, a wooden headboard, and a green pendant light.

5. L' Eroico

L' Eroico
Gaiole in Chianti
$153
$178 total
includes taxes & fees
Oct 10 - Oct 11
L' Eroico
A swimming pool with a view of a historic building surrounded by olive trees.
An aerial view of a castle with a courtyard, surrounded by vineyards and dense trees.
A stone building with a circular tower, a gravel pathway, and a metal archway leading to a wooden door.
A formal dining room with a long table set for a meal, ornate ceiling, and classical architecture.

6. Castello di Meleto

Castello di Meleto
Gaiole in Chianti
$156
$181 total
includes taxes & fees
Sep 29 - Sep 30
Castello di Meleto
A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.
An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.
A stone archway leading to a window with a view of tall trees and a distant landscape.
A stone building with a tower, surrounded by people dining at tables with candles.

7. Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
$144
$167 total
includes taxes & fees
Oct 29 - Oct 30
Castello di Tornano Wine Resort
A pool with a statue in the center, surrounded by trees and hills.
A spacious bedroom with a large bed, a wooden chair, and a view of the outdoors through an open door.
A breakfast buffet with various meats, cheeses, and bread, set against a stone wall backdrop.

8. Borgo Casa al Vento

Borgo Casa al Vento
Gaiole in Chianti
$181
$208 total
includes taxes & fees
Oct 5 - Oct 6
Borgo Casa al Vento
A terrace with stone arches, green plants, and a table set for dining with a scenic mountain view.
A stone building with a balcony, potted plants, and a view of distant hills.
A rectangular swimming pool with a view of mountains in the background.
A stone house with a tiled roof, surrounded by greenery and a gravel path.

9. Podere L'Aquila

Podere L'Aquila
Gaiole in Chianti
$168
$466 total
includes taxes & fees
Oct 5 - Oct 6
Podere L'Aquila
A stone building with a tiled roof, surrounded by greenery and a clear sky.
A bedroom with a bed, bedside table, lamp, and a television on a stand.
A spacious room with wooden beams, large windows, and a cozy seating area with a patterned rug.
A group of people seated around a wooden table in a room with wooden cabinets and a wine rack in the background.

10. Brolio Agriroom

Brolio Agriroom
Gaiole in Chianti
$130
$152 total
includes taxes & fees
Sep 30 - Oct 1
Brolio Agriroom
A swimming pool with a colorful inflatable ring and a water fountain.
A neatly made bed with a purple pillow, two bedside tables with lamps, and a wooden door.
A stone bench with a rustic design, surrounded by lush greenery and trees.
A pathway leading to a swimming pool surrounded by dense greenery and trees.

11. Agriturismo Crocino in Chianti

Agriturismo Crocino in Chianti
Gaiole in Chianti
$155
$180 total
includes taxes & fees
Sep 29 - Sep 30
Agriturismo Crocino in Chianti
A terrace with outdoor seating, tables, and umbrellas, overlooking a scenic landscape.
A restaurant with brick arches, wooden tables, and chairs.
A villa with a swimming pool, surrounded by lush greenery and vineyards.
A spa area with a staircase leading to a bathroom, a reception desk, and a row of massage chairs.

12. Borgo Le Noci Chianti Retreat & Pool

Borgo Le Noci Chianti Retreat & Pool
Gaiole in Chianti
$126
$148 total
includes taxes & fees
Oct 26 - Oct 27
Borgo Le Noci Chianti Retreat & Pool
A stone building with a garden in front.
A woman sitting by a pool with lounge chairs and umbrellas in the background.
A stone building with a bell tower, arched windows, and a gravel driveway.
A courtyard with stone walls, potted plants, and a metal fence.

13. Borgo Argenina

Borgo Argenina
Gaiole in Chianti
$263
$298 total
includes taxes & fees
Oct 5 - Oct 6
Borgo Argenina
A couple dining at an outdoor table with a view of the countryside.
A narrow street with buildings on either side, a flag, and a bench.
A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.
A spacious room with high arched ceilings, a wooden dining table, chairs, and a bookshelf.

14. Palazzo Leopoldo Dimora Storica & Spa

Palazzo Leopoldo Dimora Storica & Spa
Radda in Chianti
$182
$207 total
includes taxes & fees
Oct 29 - Oct 30
Palazzo Leopoldo Dimora Storica & Spa
A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.
An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.
A reception area with a wooden ceiling, a reception desk, and seating.
A modern living room with a white sofa, armchairs, and a coffee table.

15. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
$273
$308 total
includes taxes & fees
Oct 6 - Oct 7
Chapter Chianti, a Member of Design Hotels
A spa area with a stone ceiling, a pool, and two sun loungers.
A spa area with multiple white massage chairs arranged in a row, a brick ceiling, and a staircase in the background.
A buffet area with various fruits and a bar with bottles.
A luxurious room with ornate ceiling artwork, plush seating, and elegant lighting fixtures.

16. Hotel Palazzo San niccolò & Spa

Hotel Palazzo San niccolò & Spa
Radda in Chianti
$152
$175 total
includes taxes & fees
Oct 26 - Oct 27
Hotel Palazzo San niccolò & Spa
An outdoor dining area with a pool, potted plants, and umbrellas.
A restaurant with a table set for two, overlooking a scenic landscape.
An outdoor dining area with a table set for two, overlooking a pool and vineyard.
A villa with a swimming pool, outdoor seating, and a garden.

17. Relais Vignale & Spa

Relais Vignale & Spa
Radda in Chianti
$163
$215 total
includes taxes & fees
Oct 26 - Oct 27
Relais Vignale & Spa
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.
A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.
A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.
An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

18. La Certosa di Pontignano

La Certosa di Pontignano
Castelnuovo Berardenga
$98
$117 total
includes taxes & fees
Oct 19 - Oct 20
La Certosa di Pontignano
A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.
A courtyard with a stone building, wooden pergola, and raised garden beds with various plants.
An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.
A landscaped garden with a swimming pool, a vineyard in the background, and a stone pathway.

19. Hotel Villa Campomaggio

Hotel Villa Campomaggio
Radda in Chianti
$187
$212 total
includes taxes & fees
Oct 18 - Oct 19
Hotel Villa Campomaggio
A stone building with arched windows, a grassy courtyard, and outdoor seating.
An aerial view of a residential property with multiple buildings, a swimming pool, and landscaped gardens.
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.

20. Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti
$365
$411 total
includes taxes & fees
Oct 22 - Oct 23
Pieve Aldina - Relais & Châteaux
View all properties

Check out pet-friendly hotels in Gaiole in Chianti

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.
A stone building with a wooden door, outdoor seating, and a pergola with vines.
A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.
A stone building with a window and a light fixture.

Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
$74
$86 total
includes taxes & fees
Oct 18 - Oct 19
Agriturismo San Sano
A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.
A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.
A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.
A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
$85
$103 total
includes taxes & fees
Oct 25 - Oct 26
Ultimo Mulino Wellness Country Hotel
A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.
An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.
A stone archway leading to a window with a view of tall trees and a distant landscape.
A stone building with a tower, surrounded by people dining at tables with candles.

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
$144
$167 total
includes taxes & fees
Oct 29 - Oct 30
Castello di Tornano Wine Resort
A stone building with a yellow sign reading "b&b erioico".
An aerial view of a town with a central square, surrounding buildings, and vineyards.
A modern dining area with a wooden table, glass vases, and a staircase with glass railings.
A hotel room with neatly folded towels on the bed, a wooden headboard, and a green pendant light.

L' Eroico

L' Eroico
Gaiole in Chianti
$153
$178 total
includes taxes & fees
Oct 10 - Oct 11
L' Eroico
A traditional stone building with a garden featuring geometric hedges and potted plants.
A formal garden with geometric hedges, a stone building with green shutters, and a staircase leading to a covered area.
A breakfast setting with a table set for two, including plates of fruit, a cup of coffee, a glass of juice, and a bottle of wine.
A spacious room with a high arched ceiling, frescoed walls, a white sofa, and a wooden cabinet.

Badia a Coltibuono

Badia a Coltibuono
Gaiole in Chianti
$166
$192 total
includes taxes & fees
Oct 27 - Oct 28
Badia a Coltibuono
A pool with a statue in the center, surrounded by trees and hills.
A spacious bedroom with a large bed, a wooden chair, and a view of the outdoors through an open door.
A breakfast buffet with various meats, cheeses, and bread, set against a stone wall backdrop.

Borgo Casa al Vento

Borgo Casa al Vento
Gaiole in Chianti
$181
$208 total
includes taxes & fees
Oct 5 - Oct 6
Borgo Casa al Vento
A terrace with stone arches, green plants, and a table set for dining with a scenic mountain view.
A stone building with a balcony, potted plants, and a view of distant hills.
A rectangular swimming pool with a view of mountains in the background.
A stone house with a tiled roof, surrounded by greenery and a gravel path.

Podere L'Aquila

Podere L'Aquila
Gaiole in Chianti
$168
$466 total
includes taxes & fees
Oct 5 - Oct 6
Podere L'Aquila
A swimming pool with a view of a historic building surrounded by olive trees.
An aerial view of a castle with a courtyard, surrounded by vineyards and dense trees.
A stone building with a circular tower, a gravel pathway, and a metal archway leading to a wooden door.
A formal dining room with a long table set for a meal, ornate ceiling, and classical architecture.

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
$156
$181 total
includes taxes & fees
Sep 29 - Sep 30
Castello di Meleto
A swimming pool with a colorful inflatable ring and a water fountain.
A neatly made bed with a purple pillow, two bedside tables with lamps, and a wooden door.
A stone bench with a rustic design, surrounded by lush greenery and trees.
A pathway leading to a swimming pool surrounded by dense greenery and trees.

Agriturismo Crocino in Chianti

Agriturismo Crocino in Chianti
Gaiole in Chianti
$155
$180 total
includes taxes & fees
Sep 29 - Sep 30
Agriturismo Crocino in Chianti
A stone building with a garden in front.
A woman sitting by a pool with lounge chairs and umbrellas in the background.
A stone building with a bell tower, arched windows, and a gravel driveway.
A courtyard with stone walls, potted plants, and a metal fence.

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
$263
$298 total
includes taxes & fees
Oct 5 - Oct 6
Borgo Argenina
View all properties

You may also like hotels with pools in Gaiole in Chianti

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.
A stone building with a wooden door, outdoor seating, and a pergola with vines.
A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.
A stone building with a window and a light fixture.

Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti
$74
$86 total
includes taxes & fees
Oct 18 - Oct 19
Agriturismo San Sano
A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.
A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.
A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.
A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
$85
$103 total
includes taxes & fees
Oct 25 - Oct 26
Ultimo Mulino Wellness Country Hotel
A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.
An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.
A stone archway leading to a window with a view of tall trees and a distant landscape.
A stone building with a tower, surrounded by people dining at tables with candles.

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti
$144
$167 total
includes taxes & fees
Oct 29 - Oct 30
Castello di Tornano Wine Resort
A traditional stone building with a garden featuring geometric hedges and potted plants.
A formal garden with geometric hedges, a stone building with green shutters, and a staircase leading to a covered area.
A breakfast setting with a table set for two, including plates of fruit, a cup of coffee, a glass of juice, and a bottle of wine.
A spacious room with a high arched ceiling, frescoed walls, a white sofa, and a wooden cabinet.

Badia a Coltibuono

Badia a Coltibuono
Gaiole in Chianti
$166
$192 total
includes taxes & fees
Oct 27 - Oct 28
Badia a Coltibuono
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.

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
$373
$421 total
includes taxes & fees
Oct 27 - Oct 28
Castello di Spaltenna- Small Luxury Hotels of the World
A pool with a statue in the center, surrounded by trees and hills.
A spacious bedroom with a large bed, a wooden chair, and a view of the outdoors through an open door.
A breakfast buffet with various meats, cheeses, and bread, set against a stone wall backdrop.

Borgo Casa al Vento

Borgo Casa al Vento
Gaiole in Chianti
$181
$208 total
includes taxes & fees
Oct 5 - Oct 6
Borgo Casa al Vento
A terrace with stone arches, green plants, and a table set for dining with a scenic mountain view.
A stone building with a balcony, potted plants, and a view of distant hills.
A rectangular swimming pool with a view of mountains in the background.
A stone house with a tiled roof, surrounded by greenery and a gravel path.

Podere L'Aquila

Podere L'Aquila
Gaiole in Chianti
$168
$466 total
includes taxes & fees
Oct 5 - Oct 6
Podere L'Aquila
A swimming pool with a view of a historic building surrounded by olive trees.
An aerial view of a castle with a courtyard, surrounded by vineyards and dense trees.
A stone building with a circular tower, a gravel pathway, and a metal archway leading to a wooden door.
A formal dining room with a long table set for a meal, ornate ceiling, and classical architecture.

Castello di Meleto

Castello di Meleto
Gaiole in Chianti
$156
$181 total
includes taxes & fees
Sep 29 - Sep 30
Castello di Meleto
A swimming pool with a colorful inflatable ring and a water fountain.
A neatly made bed with a purple pillow, two bedside tables with lamps, and a wooden door.
A stone bench with a rustic design, surrounded by lush greenery and trees.
A pathway leading to a swimming pool surrounded by dense greenery and trees.

Agriturismo Crocino in Chianti

Agriturismo Crocino in Chianti
Gaiole in Chianti
$155
$180 total
includes taxes & fees
Sep 29 - Sep 30
Agriturismo Crocino in Chianti
A stone building with a garden in front.
A woman sitting by a pool with lounge chairs and umbrellas in the background.
A stone building with a bell tower, arched windows, and a gravel driveway.
A courtyard with stone walls, potted plants, and a metal fence.

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
$263
$298 total
includes taxes & fees
Oct 5 - Oct 6
Borgo Argenina
View all properties

You can also stay at hotels with a spa in Gaiole in Chianti

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.

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
$373
$421 total
includes taxes & fees
Oct 27 - Oct 28
Castello di Spaltenna- Small Luxury Hotels of the World
A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.
A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.
A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.
A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti
$85
$103 total
includes taxes & fees
Oct 25 - Oct 26
Ultimo Mulino Wellness Country Hotel
A pool with a statue in the center, surrounded by trees and hills.
A spacious bedroom with a large bed, a wooden chair, and a view of the outdoors through an open door.
A breakfast buffet with various meats, cheeses, and bread, set against a stone wall backdrop.

Borgo Casa al Vento

Borgo Casa al Vento
Gaiole in Chianti
$181
$208 total
includes taxes & fees
Oct 5 - Oct 6
Borgo Casa al Vento
A stone building with a garden in front.
A woman sitting by a pool with lounge chairs and umbrellas in the background.
A stone building with a bell tower, arched windows, and a gravel driveway.
A courtyard with stone walls, potted plants, and a metal fence.

Borgo Argenina

Borgo Argenina
Gaiole in Chianti
$263
$298 total
includes taxes & fees
Oct 5 - Oct 6
Borgo Argenina
A terrace with outdoor seating, tables, and umbrellas, overlooking a scenic landscape.
A restaurant with brick arches, wooden tables, and chairs.
A villa with a swimming pool, surrounded by lush greenery and vineyards.
A spa area with a staircase leading to a bathroom, a reception desk, and a row of massage chairs.

Borgo Le Noci Chianti Retreat & Pool

Borgo Le Noci Chianti Retreat & Pool
Gaiole in Chianti
$126
$148 total
includes taxes & fees
Oct 26 - Oct 27
Borgo Le Noci Chianti Retreat & Pool
View all properties

Go beyond your typical stay in Gaiole in Chianti

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Pet friendly
Pet friendly
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Pool
Pool
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Hot tub
Hot tub
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Spa
Spa
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Farm
Farm
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Castle
Castle
Family friendly image
Family friendly
Family friendly
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Apart hotel
Apart hotel
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Apart­ment
Apart­ment
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Villa
Villa
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Campsite
Campsite
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Waterpark
Waterpark
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 September

September

High 26°C / low 14°C. 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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Meleto Castle

8.6/10 (10 reviews)
If you're planning a bit of sightseeing during your trip, head to Meleto Castle— just one of the landmarks located 1.3 mi (2.1 km) from central Gaiole in Chianti. You could also start your cultural experience by heading over to the cathedral in the area.
See properties

Badia a Coltibuono

9.6/10 (12 reviews)
Travelers might want a tour of Badia a Coltibuono, just one of the places to visit in the heart of Badia Coltibuono.
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Cantalici Winery

10.0/10 (1 review)
Travelers might want a tour of Cantalici Winery, just one of the places to visit, and located 2.1 mi (3.4 km) from central Gaiole in Chianti.
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Gaiole in Chianti Stadium

Gaiole in Chianti Stadium is in the heart of Gaiole in Chianti, so why not stop by during your stay.
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Medieval Tower of Barbischio

8.0/10 (1 review)
Medieval Tower of Barbischio is just one of the landmarks located 1.1 mi (1.8 km) from central Gaiole in Chianti, so you might want to stop by for a few pics during your trip.
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Castello di Meleto Cantina

Travelers might want a tour of Castello di Meleto Cantina, just one of the places to visit, and located 1.1 mi (1.7 km) from central Gaiole in Chianti. If you enjoy your tour, head to PoggioBrandani, just a short walk away.
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Church of San Sigismondo

Church of San Sigismondo is in the heart of Gaiole in Chianti, so why not stop by during your stay.
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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 building with a yellow sign reading "b&b erioico".
An aerial view of a town with a central square, surrounding buildings, and vineyards.
A modern dining area with a wooden table, glass vases, and a staircase with glass railings.
A hotel room with neatly folded towels on the bed, a wooden headboard, and a green pendant light.

L' Eroico

L' Eroico
Gaiole in Chianti

10/10 Exceptional

United States
Angela
L' Eroico
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.

Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti

10/10 Exceptional

United States
Lucas
Castello di Spaltenna- Small Luxury Hotels of the World
A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.
A stone building with a wooden door, outdoor seating, and a pergola with vines.
A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.
A stone building with a window and a light fixture.

Agriturismo San Sano

Agriturismo San Sano
Gaiole in Chianti

10/10 Exceptional

United States
Angela
Agriturismo San Sano
A stone building with arched windows, a grassy courtyard, and outdoor seating.
An aerial view of a residential property with multiple buildings, a swimming pool, and landscaped gardens.
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.

Pieve Aldina - Relais & Châteaux

Pieve Aldina - Relais & Châteaux
Radda in Chianti

10/10 Exceptional

United States
Lara
Pieve Aldina - Relais & Châteaux
A stone building with a garden in front.
A woman sitting by a pool with lounge chairs and umbrellas in the background.
A stone building with a bell tower, arched windows, and a gravel driveway.
A courtyard with stone walls, potted plants, and a metal fence.

Borgo Argenina

Borgo Argenina
Gaiole in Chianti

10/10 Exceptional

United States
Andrea
Borgo Argenina
A traditional stone building with a garden featuring geometric hedges and potted plants.
A formal garden with geometric hedges, a stone building with green shutters, and a staircase leading to a covered area.
A breakfast setting with a table set for two, including plates of fruit, a cup of coffee, a glass of juice, and a bottle of wine.
A spacious room with a high arched ceiling, frescoed walls, a white sofa, and a wooden cabinet.

Badia a Coltibuono

Badia a Coltibuono
Gaiole in Chianti

10/10 Exceptional

United States
Grace
Badia a Coltibuono
A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.
An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.
A stone archway leading to a window with a view of tall trees and a distant landscape.
A stone building with a tower, surrounded by people dining at tables with candles.

Castello di Tornano Wine Resort

Castello di Tornano Wine Resort
Gaiole in Chianti

10/10 Exceptional

United States
Arwen
Castello di Tornano Wine Resort
A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.
A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.
A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.
A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole in Chianti

10/10 Exceptional

United States
Lawrence
Ultimo Mulino Wellness Country Hotel
A swimming pool with a view of a historic building surrounded by olive trees.
An aerial view of a castle with a courtyard, surrounded by vineyards and dense trees.
A stone building with a circular tower, a gravel pathway, and a metal archway leading to a wooden door.
A formal dining room with a long table set for a meal, ornate ceiling, and classical architecture.

Castello di Meleto

Castello di Meleto
Gaiole in Chianti

10/10 Exceptional

United States
Jennifer
Castello di Meleto
A stone building with a tiled roof, surrounded by greenery and a clear sky.
A bedroom with a bed, bedside table, lamp, and a television on a stand.
A spacious room with wooden beams, large windows, and a cozy seating area with a patterned rug.
A group of people seated around a wooden table in a room with wooden cabinets and a wine rack in the background.

Brolio Agriroom

Brolio Agriroom
Gaiole in Chianti

10/10 Exceptional

United States
David
Brolio Agriroom
A pool with a statue in the center, surrounded by trees and hills.
A spacious bedroom with a large bed, a wooden chair, and a view of the outdoors through an open door.
A breakfast buffet with various meats, cheeses, and bread, set against a stone wall backdrop.

Borgo Casa al Vento

Borgo Casa al Vento
Gaiole in Chianti

10/10 Exceptional

United States
Jonathan
Borgo Casa al Vento
A terrace with stone arches, green plants, and a table set for dining with a scenic mountain view.
A stone building with a balcony, potted plants, and a view of distant hills.
A rectangular swimming pool with a view of mountains in the background.
A stone house with a tiled roof, surrounded by greenery and a gravel path.

Podere L'Aquila

Podere L'Aquila
Gaiole in Chianti

10/10 Exceptional

United States
Mike
Podere L'Aquila
A historic stone building with multiple windows and a courtyard.
An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.
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.

Borgo San Felice Resort

Borgo San Felice Resort
Castelnuovo Berardenga

10/10 Exceptional

United States
Yael
Borgo San Felice Resort
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 covered outdoor seating area with a pool in the background.
A courtyard with a stone building featuring a bell tower, outdoor seating, and greenery.

Hotel Certosa Di Maggiano

Hotel Certosa Di Maggiano
Siena

10/10 Exceptional

United States
Anonymous traveler
Hotel Certosa Di Maggiano
A covered outdoor seating area with white chairs and tables, overlooking a scenic landscape with mountains and trees.
A long table set for a formal event, with clear chairs and white tablecloths, under a large chandelier and surrounded by greenery.
An aerial view of a villa surrounded by lush greenery and rolling hills.
A poolside area with a swimming pool, lounge chairs, and a grassy lawn.

Il Verreno

Il Verreno
Ambra

10/10 Exceptional

United States
James
Il Verreno
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.

Hotel Le Fontanelle

Hotel Le Fontanelle
Castelnuovo Berardenga

10/10 Exceptional

United States
Anonymous traveler
Hotel Le Fontanelle
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.
A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.
A spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.
A vineyard landscape with rows of grapevines and a person holding a glass.

Locanda le Piazze

Locanda le Piazze
Castellina in Chianti

10/10 Exceptional

United States
Anonymous traveler
Locanda le Piazze

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 20 vacation homes. You can also book one of 54 apartments or 88 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.