Gaiole in Chianti Holiday Rentals, Tuscany: Private House Rentals

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

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Our top choices for Gaiole in Chianti hotels

A swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

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.

A sunlit patio with a glass roof, stone walls, and outdoor seating.

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

Gaiole in Chianti

Sonja

8.571.916 ₫

9.720.018 ₫ total

includes taxes & fees

30 Oct - 31 Oct

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

A formal dining room with a long table set for a meal, ornate ceiling, and classical architecture.

A stone building with a circular tower, a gravel pathway, and a metal archway leading to a wooden door.

An aerial view of a castle with a courtyard, surrounded by vineyards and dense trees.

2. Castello di Meleto

Gaiole in Chianti

Vinesh

3.433.830 ₫

4.010.035 ₫ total

includes taxes & fees

10 Oct - 11 Oct

A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.

A cozy seating area with two chairs and a table, a stone wall, and a clock on a pedestal.

An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.

3. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

Ariel

2.594.143 ₫

3.086.380 ₫ total

includes taxes & fees

21 Oct - 22 Oct

A stone building with a tiled roof, surrounded by a well-maintained garden and a view of rolling hills.

A stone building with a tiled roof, surrounded by a well-maintained garden with potted plants and a pathway.

A stone building with a tiled roof, a stone pathway, and a well-maintained lawn.

A dining area with a table set for a meal, a fireplace, and a wooden ceiling.

4. Cavarchino B&B

Gaiole in Chianti

Victor

3.863.055 ₫

4.481.888 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

A stone archway leading to a window with a view of tall trees and a distant landscape.

A historic stone building with a large arched window and a small balcony.

A stone building with a tower, surrounded by people dining at tables with candles.

5. Castello di Tornano Wine Resort

Gaiole in Chianti

Lisa

3.949.587 ₫

4.577.368 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A stone building with a yellow sign reading "b&b erioico".

A modern dining area with a wooden table, glass vases, and a staircase with glass railings.

A stone building with a wooden door and shutters, a sign reading "b.v. eroico", and a number "19" on the wall.

An aerial view of a town with a central square, surrounding buildings, and vineyards.

6. L' Eroico

Gaiole in Chianti

Angela

3.526.144 ₫

4.111.402 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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 view of a garden with neatly trimmed hedges and a central water feature.

7. Badia a Coltibuono

Gaiole in Chianti

Thomas

3.944.997 ₫

4.572.318 ₫ total

includes taxes & fees

22 Oct - 23 Oct

A pool with a statue in the center, surrounded by trees and hills.

A breakfast buffet with various meats, cheeses, and bread, set against a stone wall backdrop.

A spacious bedroom with a large bed, a wooden chair, and a view of the outdoors through an open door.

8. Borgo Casa al Vento

Gaiole in Chianti

Courtney

4.368.422 ₫

5.037.908 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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 pool surrounded by lush greenery and vineyards, with a stone building in the background.

A rustic interior with a stone fireplace, wooden beams, and a staircase leading to an upper level.

9. Agriturismo San Sano

Gaiole in Chianti

Glen

1.889.429 ₫

2.194.783 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A stone building with a garden in front.

A view through a window with a metal grid, featuring a stone building, greenery, and a clear sky.

A stone building with a bell tower, arched windows, and a gravel driveway.

A courtyard with stone walls, potted plants, and a metal fence.

10. Borgo Argenina

Gaiole in Chianti

Tatevik

4.423.614 ₫

5.098.797 ₫ total

includes taxes & fees

15 Oct - 16 Oct

A stone building with a tiled roof, surrounded by greenery and a clear sky.

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.

A bedroom with a bed, bedside table, lamp, and a television on a stand.

11. Brolio Agriroom

Gaiole in Chianti

Arturo

3.312.006 ₫

3.875.850 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A swimming pool with a colorful inflatable ring and a water fountain.

A stone bench with a rustic design, surrounded by lush greenery and trees.

A neatly made bed with a purple pillow, two bedside tables with lamps, and a wooden door.

A rustic villa with a gravel driveway, surrounded by olive trees and a clear blue sky.

12. Agriturismo Crocino in Chianti

Gaiole in Chianti

Cornelia

3.965.524 ₫

4.594.720 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A terrace with outdoor seating, tables, and umbrellas, overlooking a scenic landscape.

A restaurant with brick arches, wooden tables, and chairs.

A clear blue pool with a stone deck, surrounded by lounge chairs and a scenic mountain view.

A spa area with a staircase leading to a bathroom, a reception desk, and a row of massage chairs.

13. Borgo Le Noci Chianti Retreat & Pool

Gaiole in Chianti

Sofia

3.558.651 ₫

4.147.338 ₫ total

includes taxes & fees

22 Oct - 23 Oct

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 modern living room with a white sofa, armchairs, and a coffee table.

A rustic outdoor setting with a stone building, round tables, and outdoor seating.

14. Chapter Chianti, a Member of Design Hotels

Cavriglia

Andon

6.979.323 ₫

7.851.738 ₫ total

includes taxes & fees

11 Oct - 12 Oct

An outdoor dining area with a pool, potted plants, and umbrellas.

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.

A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.

15. Relais Vignale & Spa

Radda in Chianti

Ali

4.486.798 ₫

5.828.930 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A couple dining at an outdoor table with a view of the countryside.

A room with a view of a valley, a stone shelf with flowers, a wooden bench, and a fireplace.

A narrow street with buildings on either side, a flag, and a bench.

A spacious room with high arched ceilings, a wooden dining table, chairs, and a bookshelf.

16. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

2.862.714 ₫

3.323.601 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

A room with a view of a forest through a window, a table with a lamp, and a chair.

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

17. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

7.066.564 ₫

8.005.864 ₫ total

includes taxes & fees

9 Nov - 10 Nov

A historic stone building with multiple windows and a courtyard.

A stone building with outdoor seating and a garden with roses.

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.

18. Borgo San Felice Resort

Castelnuovo Berardenga

Cynthia

19.710.480 ₫

21.972.555 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A large building with multiple rooms, surrounded by a field of lavender.

An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.

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.

19. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

9.531.849 ₫

10.775.839 ₫ total

includes taxes & fees

5 Nov - 6 Nov

A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.

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.

A table set for breakfast with various dishes, drinks, and a newspaper.

20. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

14.237.818 ₫

15.952.405 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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Stay near popular Gaiole in Chianti attractions

Castle of Brolio

9.2/10 (44 reviews)

This ancestral seat of the Ricasoli family since 1141 stands as Italy's oldest winery, pivotal in Chianti Classico's development. Stroll through formal gardens before sampling estate wines in historic cellars.

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Meleto Castle

8.6/10 (10 reviews)

This 11th-century Tuscan fortress houses an unexpected 18th-century theatre among its medieval walls. Tour the historic wine cellars and conclude with a tasting of the estate's renowned Chianti Classico wines.

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Badia a Coltibuono

9.6/10 (12 reviews)

This 11th-century abbey turned winery showcases Tuscan history through frescoed rooms and gardens. Sample organic Chianti Classico wines and savour traditional cuisine made with estate-grown ingredients.

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Cantalici Winery

10.0/10 (1 review)

This 16th-century Tuscan estate crafts organic Chianti Classico using traditional methods. Tour the historic cellars before savouring wine and olive oil tastings with the Cantalici brothers.

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Gaiole in Chianti Stadium

This local sports venue serves as the athletic heart of Gaiole in Chianti. Visitors can catch regional football matches while experiencing authentic Italian community spirit.

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Medieval Tower of Barbischio

8.0/10 (1 review)

This medieval watchtower once guarded Chianti's rolling hills as part of Florence's defensive network. Explore the ancient walls and savour panoramic countryside views from its strategic hilltop position.

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Castello di Meleto Cantina

This 11th-century castle invites you to explore noble rooms, ancient cellars, and an 18th-century theatre. Conclude your visit with a guided tasting of their renowned Chianti Classico wines in the atmospheric enoteca.

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Church of San Sigismondo

This 1930s stone church houses a remarkable 1699 marble altar featuring the Madonna del Rosario. Visit in morning light to appreciate its medieval-inspired artworks and tranquil atmosphere.

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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

Top Gaiole in Chianti Hotel Reviews

Hu Firenze Camping In Town

10/10 Excellent

"Très agréable, offrant les avantages du camping et de la ville"

Villa Olmi Firenze

10/10 Excellent

"Wow! What a beautiful property with lush gardens. The staff was very helpful from check-in, breakfast and checkout."

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Beautiful hotel and very helpful staff. Excellent location in the heart of Siena. Disappointed with our hotel room. Not up to our expectations."

Borgo Vescine

10/10 Excellent

"The staff was amazing and incredibly kind."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

Hotel Mulino di Firenze, WorldHotels Crafted

10/10 Excellent

"From the moment we arrived to the moment we left the staff were fantastic. Lapo, at the front desk, was extremely helpful in making last minute arrangements for anything we needed. The entire staff from the porters, bar tenders, cleaning staff and managers were friendly and accommodating. The property was picturesque and absolutely stunning. We wish we would have stayed more days just to enjoy the property itself. If you're having an afternoon drink on the patio bar or enjoying a scrumptious evening meal in the restaurant you will not be disappointed."

Poderi Arcangelo

10/10 Excellent

"Beautiful property, nice and helping staff. We enjoy our stay ."

Villa Pitiana

10/10 Excellent

"Beautiful property with priceless views. The on-site restaurant also offered a nice light lunch. The pool area could have been spruced up a bit with some better furniture, but the room was beautiful. Be careful when using the shower as well as it is easy for the water to spray onto the floor. Make sure you understand where the property is located before booking as it is quite a ways outside of Florence city center. I rented a car and drove through the Tuscan hills to arrive."

More cheap stays in Gaiole in Chianti

Cannon d'Oro

Via Montanini 28 Siena SI

1.487.072 ₫

1.723.021 ₫ total

9 Nov - 10 Nov

includes taxes & fees

7.8/10 Good! (258 reviews)

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

1.677.417 ₫

1.932.400 ₫ total

9 Nov - 10 Nov

includes taxes & fees

8.6/10 Excellent! (278 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

2.004.334 ₫

2.292.009 ₫ total

4 Nov - 5 Nov

includes taxes & fees

10/10 Exceptional! (50 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

2.188.969 ₫

2.495.107 ₫ total

4 Nov - 5 Nov

includes taxes & fees

7.8/10 Good! (451 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

2.462.591 ₫

2.796.092 ₫ total

8 Nov - 9 Nov

includes taxes & fees

8.8/10 Excellent! (111 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

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Hotels in Gaiole in Chianti with star rating

Frequently asked questions

What's the seasonal weather in Gaiole in Chianti?

The hottest months are usually August and July, with an average temperature of 22°C, while the coldest months are January and February, with an average of 6°C. Average annual precipitation for Gaiole in Chianti is 935 mm.

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Find hotels in Gaiole in Chianti from 1.723.021 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Gaiole in Chianti

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Gaiole in Chianti hotels

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

2. Castello di Meleto

3. Ultimo Mulino Wellness Country Hotel

4. Cavarchino B&B

5. Castello di Tornano Wine Resort

6. L' Eroico

7. Badia a Coltibuono

8. Borgo Casa al Vento

9. Agriturismo San Sano

10. Borgo Argenina

11. Brolio Agriroom

12. Agriturismo Crocino in Chianti

13. Borgo Le Noci Chianti Retreat & Pool

14. Chapter Chianti, a Member of Design Hotels

15. Relais Vignale & Spa

16. Palazzo Leopoldo Dimora Storica & Spa

17. Dievole Wine Resort

18. Borgo San Felice Resort

19. Borgo Scopeto Wine & Country Relais

20. Hotel Le Fontanelle

Stay near popular Gaiole in Chianti attractions

Castle of Brolio

Meleto Castle

Badia a Coltibuono

Cantalici Winery

Gaiole in Chianti Stadium

Medieval Tower of Barbischio

Castello di Meleto Cantina

Church of San Sigismondo

Learn more about Gaiole in Chianti

Top Gaiole in Chianti Hotel Reviews

Hu Firenze Camping In Town

Villa Olmi Firenze

Grand Hotel Continental Siena – Starhotels Collezione

Borgo Vescine

Castello di Spaltenna- Small Luxury Hotels of the World

Hotel Mulino di Firenze, WorldHotels Crafted

Poderi Arcangelo

Villa Pitiana

More cheap stays in Gaiole in Chianti

Cannon d'Oro

Villa Castiglione

Torre del Fuggisole

Piccolo Hotel Etruria

Albergo Centrale

Porta Pispini Residence

Hotels in Gaiole in Chianti with star rating

Frequently asked questions

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