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.

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.

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

Gaiole in Chianti

Sonja

8.614.756 ₫

9.768.597 ₫ total

includes taxes & fees

30 Oct - 31 Oct

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.

An outdoor café with tables and chairs, surrounded by stone walls and greenery.

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

2. Castello di Meleto

Gaiole in Chianti

Vinesh

3.876.114 ₫

4.497.711 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

A pool with a view of a mountainous landscape and a village in the background.

3. Cavarchino B&B

Gaiole in Chianti

Victor

3.879.890 ₫

4.501.420 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

4. Castello di Tornano Wine Resort

Gaiole in Chianti

Lisa

3.688.007 ₫

4.290.792 ₫ total

includes taxes & fees

29 Oct - 30 Oct

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

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.

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

5. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

Ariel

2.428.633 ₫

2.905.154 ₫ total

includes taxes & fees

22 Oct - 23 Oct

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

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.

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

6. L' Eroico

Gaiole in Chianti

Angela

3.369.150 ₫

3.940.050 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A traditional stone building with a garden featuring geometric hedges and potted plants.

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.

A formal garden with geometric hedges, a stone building with green shutters, and a staircase leading to a covered area.

7. Badia a Coltibuono

Gaiole in Chianti

Thomas

4.261.717 ₫

4.921.547 ₫ total

includes taxes & fees

27 Oct - 28 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-walled room with a sofa, a coat rack, and a window with curtains.

A stone house with a tiled roof, surrounded by greenery and a gravel path.

8. Podere L'Aquila

Gaiole in Chianti

Heather

4.301.350 ₫

11.945.674 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

9. Borgo Casa al Vento

Gaiole in Chianti

Courtney

4.236.678 ₫

4.894.331 ₫ total

includes taxes & fees

3 Nov - 4 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 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.

10. Agriturismo San Sano

Gaiole in Chianti

Glen

1.898.871 ₫

2.205.751 ₫ 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 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.

11. Borgo Argenina

Gaiole in Chianti

Tatevik

5.203.516 ₫

5.957.852 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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

A group of people seated around a wooden table in a room with wooden cabinets and a wine rack in the background.

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.

12. Brolio Agriroom

Gaiole in Chianti

Arturo

3.326.440 ₫

3.892.742 ₫ total

includes taxes & fees

8 Oct - 9 Oct

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

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

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.

13. Agriturismo Crocino in Chianti

Gaiole in Chianti

Cornelia

3.982.806 ₫

4.614.744 ₫ total

includes taxes & fees

7 Oct - 8 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 villa with a swimming pool, surrounded by lush greenery and vineyards.

14. Borgo Le Noci Chianti Retreat & Pool

Gaiole in Chianti

Sofia

3.319.076 ₫

3.884.642 ₫ total

includes taxes & fees

18 Oct - 19 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 compact living space with a wooden ceiling, a white sofa, a small table, a potted plant, and a cabinet with circular designs.

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

15. Chapter Chianti, a Member of Design Hotels

Cavriglia

Samay

7.009.738 ₫

7.885.955 ₫ total

includes taxes & fees

7 Oct - 8 Oct

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

A restaurant with a table set for two, overlooking a scenic landscape.

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

A villa with a swimming pool, outdoor seating, and a garden.

16. Relais Vignale & Spa

Radda in Chianti

Ali

4.191.164 ₫

5.508.199 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.

17. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

3.039.679 ₫

3.519.136 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

18. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

7.633.773 ₫

8.631.135 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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 room with a large window overlooking a landscape with trees and hills. There are two upholstered sofas with a patterned rug in the center.

A pool area with lounge chairs and a service person attending to a guest.

19. Borgo San Felice Resort

Castelnuovo Berardenga

Cynthia

19.781.268 ₫

22.051.467 ₫ total

includes taxes & fees

11 Oct - 12 Oct

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

A swimming pool with lounge chairs and umbrellas, surrounded by stone buildings and trees.

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

A historic estate with a central courtyard, surrounded by lush gardens and vineyards.

20. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

10.319.583 ₫

11.644.023 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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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

"Once you get to the property the staff were all wonderful but the communication prior to arrival was none no answers to any of my questions through Expedia. The city bus is across the street takes you into Florence for 2 euros but make sure you validate your ticket front of bus to avoid a hefty fine. I loved that we could cook breakfast before heading out and there is a grocery store onsite."

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."

Radisson Blu Hotel, Florence

10/10 Excellent

"Great hotel and knowledgeable staff. We had a front desk person, which is from the Philippines and recommended great restaurant and helped us on our extended stay."

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 I Barronci Resort & Spa

8/10 Good

"Under renovation so it could have been better"

Fattoria di Vegi

10/10 Excellent

"Booked this as a last minute decision to shorten our time in Milan (and fine a place close to Florence on our way to Montepulciano) We only stayed one night, but wish it had been longer. If you are looking for informal luxury, you will find it at this idyllic Tuscan Estate. They are still expanding their amenities to include a gym, tennis court, and Spa (planned for a 2027 open) what they DO offer is a quiet, thoughtful experience. The room was perfection and the restaurant on the property - delicious. There were a few artists there taking advantage of the atelier, or painting on the property. The estate is located an hour’s drive outside of Florence and is well worth the trip if you are looking for a place to relax. We hope to return with more time to enjoy it."

Hotel Athena

10/10 Excellent

"The hotel is wonderful! The staff is extremely friendly and helpful. The location is great…jut a short walk to shopping, restaurants, and the cathedral. Our room was very clean and the beds were comfortable. The view from the terrace is stunning."

Hotel Casolare Le Terre Rosse

10/10 Excellent

"Absolutely stunning property with amazing staff. Tons of wineries close by and touring thru San Gimignano was fascinating. Definitely 5/5."

More cheap stays in Gaiole in Chianti

Cannon d'Oro

Via Montanini 28 Siena SI

1.493.552 ₫

1.788.943 ₫ total

28 Oct - 29 Oct

includes taxes & fees

7.8/10 Good! (258 reviews)

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

1.776.827 ₫

2.042.255 ₫ total

2 Nov - 3 Nov

includes taxes & fees

8.6/10 Excellent! (276 reviews)

Torre del Fuggisole

Via di Fieravecchia 7 Siena SI

2.407.869 ₫

2.736.401 ₫ total

3 Nov - 4 Nov

includes taxes & fees

10/10 Exceptional! (50 reviews)

Albergo Centrale

Via Cecco Angiolieri 26 Siena SI

2.476.788 ₫

2.812.212 ₫ total

3 Nov - 4 Nov

includes taxes & fees

8.8/10 Excellent! (108 reviews)

Piccolo Hotel Etruria

Via delle Donzelle, 3 Siena SI

2.867.620 ₫

3.300.418 ₫ total

6 Oct - 7 Oct

includes taxes & fees

7.8/10 Good! (445 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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Book Hotels in Gaiole in Chianti on Expedia.it

Find hotels in Gaiole in Chianti from 1.788.943 ₫

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

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Our top choices for Gaiole in Chianti hotels

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

2. Castello di Meleto

3. Cavarchino B&B

4. Castello di Tornano Wine Resort

5. Ultimo Mulino Wellness Country Hotel

6. L' Eroico

7. Badia a Coltibuono

8. Podere L'Aquila

9. Borgo Casa al Vento

10. Agriturismo San Sano

11. Borgo Argenina

12. Brolio Agriroom

13. Agriturismo Crocino in Chianti

14. Borgo Le Noci Chianti Retreat & Pool

15. Chapter Chianti, a Member of Design Hotels

16. Relais Vignale & Spa

17. Palazzo Leopoldo Dimora Storica & Spa

18. Dievole Wine Resort

19. Borgo San Felice Resort

20. Borgo Scopeto Wine & Country Relais

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

Castello di Spaltenna- Small Luxury Hotels of the World

Radisson Blu Hotel, Florence

Hotel Mulino di Firenze, WorldHotels Crafted

Poderi Arcangelo

Villa I Barronci Resort & Spa

Fattoria di Vegi

Hotel Athena

Hotel Casolare Le Terre Rosse

More cheap stays in Gaiole in Chianti

Cannon d'Oro

Villa Castiglione

Torre del Fuggisole

Albergo Centrale

Piccolo Hotel Etruria

Porta Pispini Residence

Hotels in Gaiole in Chianti with star rating

Frequently asked questions

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