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 stone building with a garden, tall trees, and a clear blue sky.

A restaurant with stone walls and a high ceiling, featuring tables set for dining.

A room with a large window offering a view of a hilly landscape. There is a sofa with patterned upholstery and a lamp on a side table.

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

Gaiole in Chianti

Rama

10.823.802 ₫

12.206.843 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

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

2. Castello di Meleto

Gaiole in Chianti

Vinesh

5.872.282 ₫

6.700.039 ₫ total

includes taxes & fees

15 Sept - 16 Sept

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

A hotel room with neatly folded towels on the bed, a wooden headboard, and a green pendant light.

3. L' Eroico

Gaiole in Chianti

Angela

4.253.153 ₫

4.919.118 ₫ total

includes taxes & fees

20 Sept - 21 Sept

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

A stone pathway flanked by wooden barrels with red bands, leading to a distant view of a hill.

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

4. Borgo Casa al Vento

Gaiole in Chianti

Courtney

5.047.828 ₫

5.793.140 ₫ total

includes taxes & fees

16 Sept - 17 Sept

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.

An outdoor patio with wooden tables and benches, stone buildings in the background, and a clear view of the surrounding landscape.

5. Brolio Agriroom

Gaiole in Chianti

Arturo

3.424.258 ₫

4.007.213 ₫ total

includes taxes & fees

23 Sept - 24 Sept

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

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

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

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

6. Borgo Le Noci Chianti Retreat & Pool

Gaiole in Chianti

Sofia

4.659.883 ₫

5.366.401 ₫ total

includes taxes & fees

30 Sept - 1 Oct

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

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

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.

7. Castello di Tornano Wine Resort

Gaiole in Chianti

Austin

5.473.980 ₫

6.261.907 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A terrace with stone arches, green plants, and a table set for dining with a scenic mountain view.

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.

A stone-walled room with a sofa, a coat rack, and a window with curtains.

8. Podere L'Aquila

Gaiole in Chianti

4.427.837 ₫

12.296.952 ₫ total

includes taxes & fees

15 Sept - 16 Sept

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

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.

9. Badia a Coltibuono

Gaiole in Chianti

Thomas

4.387.088 ₫

5.066.325 ₫ total

includes taxes & fees

14 Oct - 15 Oct

A stone staircase leading to a door, surrounded by stone walls and a potted plant with green leaves and purple flowers.

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

A stone building with a window and a light fixture.

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

10. Agriturismo San Sano

Gaiole in Chianti

Ernesto

2.234.815 ₫

2.578.470 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A stone building with a garden in front.

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

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

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

11. Borgo Argenina

Gaiole in Chianti

Tatevik

4.570.050 ₫

5.267.584 ₫ total

includes taxes & fees

16 Sept - 17 Sept

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

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

12. Agriturismo Crocino in Chianti

Gaiole in Chianti

Cornelia

4.099.925 ₫

4.750.447 ₫ total

includes taxes & fees

15 Sept - 16 Sept

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.

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

A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

13. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

"Ultimo Mulino Hotel was amazing! The property is so peaceful and beautiful. We had breakfast both mornings and ate at their on site restaurant both evenings. The food was delicious and the staff was incredible. Leno was our server both nights- she was amazing and so helpful making suggestions on food and wines. We also enjoyed the spa for the wellness package and a couples massage for our honeymoon. We highly recommend this to everyone! It was so relaxing and worth the cost."

Hannah

3.792.239 ₫

4.411.992 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

A bar area with a high ceiling, wooden beams, and a bar counter with stools.

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.

14. Chapter Chianti, a Member of Design Hotels

Cavriglia

Samay

7.215.868 ₫

8.117.852 ₫ total

includes taxes & fees

6 Oct - 7 Oct

A room with a staircase, a blue sofa with red cushions, a round table with a tray, and a red ottoman.

A building facade with a dark entrance door, two potted plants, and signage for 'TOGETHER Florence' and 'Pizzeria.'

A bed with pillows, a bedside lamp, and a candle.

A breakfast bar with a variety of food items and condiments, a coffee machine, and a seating area with a table set for two.

15. JOIVY Together Florence Secret Nest

Oltrarno

Christos

3.394.738 ₫

4.095.005 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A table with breakfast items and a wicker chair, overlooking a scenic landscape.

A dining area with checkered flooring, tables set with white tablecloths, and wicker chairs.

A bar area with a counter, bottles, and glasses.

A hotel room with a bed, a desk, a chair, a window with curtains, a lamp, and a view of the landscape.

16. Palazzo Ravizza

Siena Historical Center

XUESHENG

7.106.428 ₫

7.967.522 ₫ total

includes taxes & fees

20 Sept - 21 Sept

A lobby with a marble floor, a chandelier, a reception desk, and large green plants.

A modern hotel room with a large bed, a desk, and a chair. There is a painting on the wall and a lamp on the side table.

A dining area with brick ceiling arches, tables set with white tablecloths, and framed pictures on the walls.

A balcony with two chairs and a table, overlooking a building with a tiled roof and shutters.

17. Hotel Chiusarelli

Siena City Centre

sharon

4.892.577 ₫

5.532.166 ₫ total

includes taxes & fees

22 Sept - 23 Sept

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 corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

An interior corridor with arches, columns, and a brick wall.

An aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

18. La Certosa di Pontignano

Castelnuovo Berardenga

Malena

3.558.325 ₫

4.154.837 ₫ total

includes taxes & fees

30 Sept - 1 Oct

A table set for two with a wine glass, a bowl of nuts, and a glass of water.

A hallway with a wooden floor, a painting on the wall, and a vase with flowers on a table.

A bathroom with a large bathtub, wooden flooring, and a chandelier.

A room with two yellow sofas, a wooden floor, a large painting, a chandelier, and a patterned rug.

19. Relais degli Angeli

Siena City Centre

Colin

7.153.421 ₫

7.989.027 ₫ total

includes taxes & fees

28 Sept - 29 Sept

An outdoor patio with tables and chairs, surrounded by potted plants and a red building.

A swimming pool with a clear view of the water, a metal structure on the right, and a landscaped area with chairs and plants in the background.

A courtyard with brick buildings, a stone wall, and a view of the surrounding town.

A rustic interior with a fireplace, wooden beams, and a metal rack holding various tools.

20. Borgo Grondaie

Siena

Simon

4.126.774 ₫

4.689.782 ₫ total

includes taxes & fees

5 Oct - 6 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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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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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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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

Hotel Chiusarelli

10/10 Excellent

"Excellent location. Easy parking and helpful staff."

Fattoria di Vegi

10/10 Excellent

"Incredible magical place. Couldn’t recommend it more…"

Grand Hotel Continental Siena – Starhotels Collezione

10/10 Excellent

"Excellent location. Even though a walking only area, easy walk. Great service and breakfast was delicious. My only complaint is the included breakfast was only for 1 person."

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Lovely hotel, great location, good pool, friendly staff, good food"

Hotel Athena

10/10 Excellent

"We had a wonderful stay at Hotel Athena in Siena. The service was exceptional, the staff were warm, welcoming and genuinely helpful throughout our visit. The location was fantastic for exploring Siena, with everything within walking distance, while the hotel itself provided a comfortable and relaxing place to come back to after a day of exploring. We also loved the beautiful views from the terrace which was the perfect spot to unwind with a drink and take in the scenery. Sunset was especially beautiful and I would recommend calling the terrace staff themselves to reserve your seat. They are VERY busy up there so please exercise patience and kindness to the server and bartender as they work so hard to get your orders to you as quickly as possible. Self parking our car was a huge bonus as we rented a vehicle to explore Tuscany. A lovely hotel, a great location and wonderful service. We would happily stay here again when visiting Siena!"

NH Siena

10/10 Excellent

"Superior room not great, Very small with leaking shower and other issues. Upgraded to suite on 5th floor which was excellent. Very spacious, huge bathroom with bath and walk in shower. Great views and comfortable bed."

Villa Pitiana

10/10 Excellent

"We spent our honeymoon here and it was absolutely beautiful"

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"The staff were very friendly and helpful. The bar service is the best."

Villa Olmi Firenze

10/10 Excellent

"Amazing stay a perfect escape from Florence"

More cheap stays in Gaiole in Chianti

Cannon d'Oro

Via Montanini 28 Siena SI

2.495.217 ₫

2.895.070 ₫ total

24 Sept - 25 Sept

includes taxes & fees

7.8/10 Good! (258 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

3.279.940 ₫

3.758.265 ₫ total

14 Sept - 15 Sept

includes taxes & fees

7.8/10 Good! (435 reviews)

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

3.467.717 ₫

3.904.687 ₫ total

27 Sept - 28 Sept

includes taxes & fees

8.6/10 Excellent! (276 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

4.095.825 ₫

4.655.738 ₫ total

4 Oct - 5 Oct

includes taxes & fees

8.8/10 Excellent! (106 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

4.605.036 ₫

5.215.871 ₫ total

11 Oct - 12 Oct

includes taxes & fees

10/10 Exceptional! (49 reviews)

Porta Pispini Residence

Via Baldassarre Peruzzi 33 Siena SI

Get rates

9.4/10 Exceptional! (23 reviews)

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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Book Hotels in Gaiole in Chianti on Expedia.it

Find hotels in Gaiole in Chianti from 2.578.470 ₫

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. L' Eroico

4. Borgo Casa al Vento

5. Brolio Agriroom

6. Borgo Le Noci Chianti Retreat & Pool

7. Castello di Tornano Wine Resort

8. Podere L'Aquila

9. Badia a Coltibuono

10. Agriturismo San Sano

11. Borgo Argenina

12. Agriturismo Crocino in Chianti

13. Ultimo Mulino Wellness Country Hotel

14. Chapter Chianti, a Member of Design Hotels

15. JOIVY Together Florence Secret Nest

16. Palazzo Ravizza

17. Hotel Chiusarelli

18. La Certosa di Pontignano

19. Relais degli Angeli

20. Borgo Grondaie

Stay near popular Gaiole in Chianti attractions

Castle of Brolio

Meleto Castle

Badia a Coltibuono

Cantalici Winery

Gaiole in Chianti Stadium

Castello di Meleto Cantina

Medieval Tower of Barbischio

Church of San Sigismondo

Learn more about Gaiole in Chianti

Top Gaiole in Chianti Hotel Reviews

Hotel Chiusarelli

Fattoria di Vegi

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Casolare Le Terre Rosse

Hotel Athena

NH Siena

Villa Pitiana

Villa Scacciapensieri Boutique Hotel

Villa Olmi Firenze

More cheap stays in Gaiole in Chianti

Cannon d'Oro

Piccolo Hotel Etruria

Villa Castiglione

Albergo Centrale

Torre del Fuggisole

Porta Pispini Residence

Hotels in Gaiole in Chianti with star rating

Frequently asked questions

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