Chianti Region Holiday Rentals, Tuscany: Private House Rentals

A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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Farm

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Family friendly

Waterpark

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Our top choices for Chianti Region 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 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.

An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.

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

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

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.

An outdoor dining area with a table set for two, overlooking a pool and vineyard.

2. Relais Vignale & Spa

Radda in Chianti

Ali

4.239.319 ₫

5.561.169 ₫ total

includes taxes & fees

8 Oct - 9 Oct

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

3. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

7.633.773 ₫

8.631.135 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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.

A landscaped garden with a swimming pool, a vineyard in the background, and a stone pathway.

A spa area with stone flooring, wooden chairs, a table with amenities, and a view of a garden through a glass door.

4. Hotel Villa Campomaggio

Radda in Chianti

Dario

4.107.291 ₫

4.693.509 ₫ total

includes taxes & fees

7 Oct - 8 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 rustic outdoor setting with a stone building, round tables, and outdoor seating.

A compact living space with a wooden ceiling, a white sofa, a small table, a potted plant, and a cabinet with circular designs.

5. Chapter Chianti, a Member of Design Hotels

Cavriglia

Andon

7.019.561 ₫

7.897.006 ₫ total

includes taxes & fees

6 Oct - 7 Oct

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

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.

6. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

14.319.905 ₫

16.044.377 ₫ total

includes taxes & fees

14 Oct - 15 Oct

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

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

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.

7. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

3.039.679 ₫

3.519.136 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A rustic outdoor dining area with a stone wall, wooden benches, and a table set for two.

A building with a brick facade, arched entrance, and multiple windows covered in green ivy.

A bathroom with a bathtub, a window with a view of a vineyard, and a small table with a bottle and glasses.

A table set with wine glasses and a candle, viewed through a window with string lights.

8. Tenuta CorteDomina

Radda in Chianti

Edgar

6.142.116 ₫

6.873.321 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A person sitting by a swimming pool with a stone building in the background.

A person relaxing on a sun lounger by a pool with a table beside them holding a drink and a bowl.

An indoor dining area with stone walls, tables set with tablecloths and chairs, and hanging pendant lights.

A stone building with a wooden door and an arched window.

9. Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa

Sergey

3.424.429 ₫

3.942.361 ₫ total

includes taxes & fees

24 Oct - 25 Oct

A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

A person relaxing in a hot tub with a view of a building and trees in the background.

A rustic stone building with a garden in front.

A poolside area with lounge chairs and a view of the night sky.

10. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

2.863.250 ₫

3.325.064 ₫ total

includes taxes & fees

6 Oct - 7 Oct

A narrow stone pathway leading to a rustic building with a wooden door and a window.

A stone building with wooden shutters, a bench, and hanging purple flowers.

A cozy living room with a striped sofa, a wooden coffee table, and a bookshelf.

A cozy living room with a fireplace, wooden beams, and comfortable seating.

11. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Saion

5.240.740 ₫

5.881.807 ₫ total

includes taxes & fees

4 Nov - 5 Nov

A spacious interior with high arched ceilings, stone walls, and a central round mirror reflecting the room. Tables and chairs are arranged for dining or socializing.

An outdoor dining area with tables and chairs, a chef preparing food, and a scenic view in the background.

A garden with tall cypress trees, a variety of shrubs, and a stone pathway.

A resort with a swimming pool, terraced gardens, and a view of rolling hills.

12. COMO Castello Del Nero

Tavarnelle Val di Pesa

Lauren

20.495.257 ₫

22.778.768 ₫ total

includes taxes & fees

30 Oct - 31 Oct

A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.

A modern interior with a bar area, seating, and a staircase.

A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.

A vineyard landscape with rows of grapevines and a person holding a glass.

13. Locanda le Piazze

Castellina in Chianti

Colleen

9.572.129 ₫

10.704.831 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

A dining area with a table set for two, featuring wine bottles and bread.

A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a tray of items, and a window with curtains.

A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.

14. Castello La Leccia

Castellina in Chianti

Eva

6.142.116 ₫

6.873.321 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A wicker chair, a lantern, and a vase of flowers on a balcony with a mountain view.

A rustic stone building with a tiled roof, surrounded by lush greenery and white flowers.

A pool area with a view of a hilly landscape.

A bedroom with a large bed, a bedside table, and a chair.

15. Borgo Del Cabreo

Greve in Chianti

Brian

8.112.273 ₫

9.040.610 ₫ total

includes taxes & fees

11 Oct - 12 Oct

An indoor courtyard with stone flooring, arched columns, and tables set up for dining.

A modern spa area with a wooden sauna, a glass-enclosed shower, and a marble-floored pool.

A historic building with a stone facade, arched entrance, and a wooden balcony.

A modern reception area with a stone counter, a sign for SPA VILLA CASAGRANDE, and a staircase leading to a glass door.

16. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

2.902.434 ₫

3.251.174 ₫ total

includes taxes & fees

4 Nov - 5 Nov

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

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

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

An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.

17. Castello di Tornano Wine Resort

Gaiole in Chianti

Lisa

3.969.237 ₫

4.600.145 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A spa room with a stone ceiling, a window with frosted glass, a bed with pillows, and a wall-mounted artwork.

A garden with a gravel path leading to a white metal table and chairs, surrounded by red roses and a large terracotta pot.

A bedroom with a bed, bedside tables, a sofa, a window with curtains, and a wall with a painting.

A rectangular pool with clear water, surrounded by white lounge chairs and a grassy area.

18. Palazzo Squarcialupi

Castellina in Chianti

yvette

5.233.668 ₫

5.932.407 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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.

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

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.

19. La Certosa di Pontignano

Castelnuovo Berardenga

Leslie

2.519.863 ₫

3.005.834 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A pool with a view of a lush valley and distant buildings.

A courtyard with stone buildings, arched doorways, and potted plants.

A terraced vineyard with stone walls and a stone pathway leading to a seating area with metal chairs and tables.

A garden with neatly trimmed hedges, a gravel path, and a stone barrel.

20. Castello Vicchiomaggio

Greve in Chianti

Maryse

4.714.799 ₫

5.186.279 ₫ total

includes taxes & fees

9 Oct - 10 Oct

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Holiday Rentals in Chianti Region

Residence

A spacious indoor area with arched windows, wooden furniture, and hanging plants.

A stone building with a garden, outdoor seating, and a large tree.

A stone pathway leading to a terrace with potted plants and flowers, overlooking a hillside with houses.

A swimming pool with a clear blue water surface, surrounded by a brick deck and a grassy area with trees.

Relais Villa Olmo

Impruneta

"Very friendly and clean."

Apartment

A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

A modern two-story residential building with a stone facade, a well-maintained garden with hedges and grass, and a clear sky.

A modern kitchen with dark wooden cabinets, a dining table with chairs, and a vase of flowers on the table.

A bedroom with a bed, bedside tables, a chair, and a window with curtains.

Casa Vacanze Squarcialupi

Castellina in Chianti

"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "

Aparthotel

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

Borgo Argenina

Gaiole in Chianti

"What an amazing place. We enjoyed it so much."

Residence

A table with breakfast items and a view of rolling hills.

A large, modern building with a blue roof, surrounded by lush green fields and trees.

A grassy area with a stone wall and a wooden fence.

A swimming pool with a white fence and a lifebuoy, surrounded by trees and a sunset.

Chianti Village Morrocco

Tavarnelle Val di Pesa

"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."

Townhouse

A stone building with a tiled roof, multiple windows, and a prominent tower.

A clear blue swimming pool with lounge chairs and umbrellas, surrounded by trees and a clear sky.

A terrace with stone walls, two wooden chairs with cushions, and a table.

A rustic interior with a wooden dining table, a fireplace, a sofa, and a staircase.

Rocca di Castagnoli

Gaiole in Chianti

"It was wonderful to stay in a castle in Tuscany no less Every person we met was attentive and kind We were staying near friends and didn’t hang around the grounds much or use the pool but everything seemed well kept It’s really a place to retreat to eat at and sleep at which served our purpose well "

Townhouse

An arched entrance with a lantern above, flanked by two potted plants.

A hammock suspended between trees in a garden with a view of a hilly landscape.

A table set for two with wine glasses and a bottle, overlooking a scenic landscape.

A bedroom with a four-poster bed, a sofa, a dining table with chairs, and a large painting on the wall.

Villa il Fedino

San Casciano in Val di Pesa

"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."

Aparthotel

A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

A kitchen with wooden cabinets, a dining table with chairs, a chandelier, and a view of the outdoors through a glass door.

A bedroom with a stone archway, a wooden dresser, and a chandelier.

A buffet with various food items, including cheeses, meats, and condiments.

Relais Villa Belvedere

Figline e Incisa Valdarno

"True Tuscan style, beautiful views and a lovely breakfast."

Townhouse

A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

A swimming pool surrounded by stone walls and lush greenery, with a view of distant hills.

A rustic stone building with ivy-covered walls, outdoor seating, and gravel ground.

A garden with potted plants and a wrought iron gate.

I Parigi Corbinelli

Florence

"Beautiful setting, stunning views, incredible pool and gardens and so easy to jump on the bus into the city."

Townhouse

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

L' Eroico

Gaiole in Chianti

"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."

Residence

An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

A dining area with wooden chairs and tables, a chandelier, and potted plants.

A view through a window of a stone staircase leading to a building with arched windows and a tower, overlooking a hilly landscape.

A bedroom with a large bed, a sofa, a television, and a painting on the wall.

Palazzo Pacini

Colle di Val d'Elsa

"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "

Townhouse

A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

A living room with a blue sofa, a coffee table, and a potted plant.

An outdoor dining area with a stone wall backdrop, metal chairs, and a table set with white tablecloths, plates, and glassware.

A stone archway with a barrel at its base, surrounded by greenery and flowering plants.

Terre di Baccio

Greve in Chianti

"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."

Holiday Home

A stone building with multiple windows and a chimney.

A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, set against a stone building with a garden.

A rustic interior with exposed wooden beams, a wooden dining table with wine bottles, a sofa, and a staircase leading to an upper level.

A stone building with a gravel driveway leading to a table set for dining, surrounded by greenery and a vineyard in the background.

Agriturismo La Ferrozzola

Castellina in Chianti

"Very nice agriturismo. "

Holiday Home

A hallway leading to an outdoor patio with a table and chairs, framed artwork on the walls, and a rustic ceiling.

A swimming pool with a clear view of a mountainous landscape and greenery in the background.

A view from a window overlooking a vineyard with rolling hills and a clear sky.

A stone building with a tiled roof, a covered patio with outdoor seating, and a garden with potted plants.

Casale di Villore

Poggibonsi

"Fantastic property. Can’t wait to return next year. "

Aparthotel

A stone building with a tiled roof, a chimney, and a circular window.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

A dining area with a table and chairs, a large vase with flowers, and a view through an open archway.

A stone house with a red-tiled roof, surrounded by a well-maintained garden with various flowering plants and shrubs.

Podere il Pino

Poggibonsi

"Beautiful place to stay. Great for kids and has an amazing view. "

Townhouse

A dining area with a table set for two, featuring a view of greenery through a window.

A bedroom with a large bed, a smaller bed, and a window with curtains.

A table with a bottle of Chianti wine, two wine glasses, a book, a magazine, and a bouquet of lilacs.

A sign reading "CAMERE" against a clear blue sky.

La Locanda di Pietracupa

Tavarnelle Val di Pesa

"Great place, wonderful restaurant"

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Stay near popular Chianti Region attractions

A spiral staircase with a person standing on it.

Antinori nel Chianti Classico

9.4/10 (16 reviews)

You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Visit the churches and wineries in this walkable area.

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A grand, illuminated building with arched windows and a central fountain.

The Mall Luxury Outlet

8.8/10 (355 reviews)

During your visit to Leccio, you can enjoy retail therapy at The Mall Luxury Outlet. Discover the acclaimed art galleries and stunning cathedral in this walkable area.

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Tenuta Torciano Winery

9.2/10 (40 reviews)

You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this quaint area.

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Verrazzano Castle

9.8/10 (10 reviews)

You can find out about the history of Greve in Chianti when you stop by Verrazzano Castle. Discover the area's countryside and wineries.

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Castello di Albola

9.0/10 (9 reviews)

You can enjoy a tasting or tour at Castello di Albola during your travels to Radda in Chianti. Discover the beautiful countryside in this quaint area or enjoy its local tours.

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Castle of Brolio

9.2/10 (44 reviews)

You can find out about the history of Gaiole in Chianti with a visit to Castle of Brolio. Discover the beautiful countryside and wineries in this walkable area.

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Meleto Castle

8.6/10 (10 reviews)

Find out about the history of Gaiole in Chianti when you take a trip to Meleto Castle. Discover the beautiful countryside in this walkable area or enjoy its local tours.

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Piazza Matteotti

9.4/10 (21 reviews)

Find out about the history of Greve in Chianti with a stop at Piazza Matteotti. Discover the beautiful countryside in this quaint area or enjoy its local tours.

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Learn more about Chianti Region

Explore the relaxing area of Chianti Region—wineries, pristine countryside and sights from Borgo di Vescine - Tenute di Castelvecchi to Castello di Albola.

See all hotels in Chianti Region

Terraced vineyards on a hillside, a small village, and rolling green hills.

Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

10/10 Excellent

"Stunning property with beautiful views and extremely friendly and helpful hosts."

Villa I Barronci Resort & Spa

8/10 Good

"We quite enjoyed the heated pool and views. Thank you for having us."

Fattoria di Vegi

10/10 Excellent

"The entire estate was perfectly curated, every aspect was completely flawless. Food and wine…. 10/10. Best place we’ve ever stayed."

Salvadonica - Borgo del Chianti

10/10 Excellent

"Property was beautiful staff was great last time with my family"

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 Toscana Ambassador

8/10 Good

"Close to train station"

Relais Vignale & Spa

10/10 Excellent

"In a convenient location."

Hu Norcenni Girasole Village

10/10 Excellent

"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."

More cheap stays in Chianti Region

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! (277 reviews)

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

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Agriturismo Il Caggio di Sotto

Loc. Il Caggio di Sotto, 26 Colle di Val d'Elsa SI

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9.6/10 Exceptional! (16 reviews)

Castello di Pratelli

Via Di Pratelli 1/a Figline e Incisa Valdarno FI

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9.2/10 Wonderful! (5 reviews)

Hotel Albergo Italia

Via Trento, 36 Poggibonsi SI

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Quercia Al Poggio

Strada Di Quercia Al Poggio 4 Barberino Tavarnelle FI

Get rates

Hotels in Chianti Region with star rating

Explore a world of travel with Expedia

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Book Hotels in Chianti Region on Expedia.it

Find hotels in Chianti Region from 2.042.255 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Chianti Region

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Chianti Region hotels

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

2. Relais Vignale & Spa

3. Dievole Wine Resort

4. Hotel Villa Campomaggio

5. Chapter Chianti, a Member of Design Hotels

6. Hotel Le Fontanelle

7. Palazzo Leopoldo Dimora Storica & Spa

8. Tenuta CorteDomina

9. Hotel Borgo di Cortefreda Relais

10. Belvedere di San Leonino

11. Castello di Fonterutoli Wine Resort

12. COMO Castello Del Nero

13. Locanda le Piazze

14. Castello La Leccia

15. Borgo Del Cabreo

16. Villa Casagrande Resort & SPA

17. Castello di Tornano Wine Resort

18. Palazzo Squarcialupi

19. La Certosa di Pontignano

20. Castello Vicchiomaggio

Holiday Rentals in Chianti Region

Relais Villa Olmo

Casa Vacanze Squarcialupi

Borgo Argenina

Chianti Village Morrocco

Rocca di Castagnoli

Villa il Fedino

Relais Villa Belvedere

I Parigi Corbinelli

L' Eroico

Palazzo Pacini

Terre di Baccio

Agriturismo La Ferrozzola

Casale di Villore

Podere il Pino

La Locanda di Pietracupa

Stay near popular Chianti Region attractions

Antinori nel Chianti Classico

The Mall Luxury Outlet

Tenuta Torciano Winery

Verrazzano Castle

Castello di Albola

Castle of Brolio

Meleto Castle

Piazza Matteotti

Learn more about Chianti Region

Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

Villa I Barronci Resort & Spa

Fattoria di Vegi

Salvadonica - Borgo del Chianti

Borgo Vescine

Castello di Spaltenna- Small Luxury Hotels of the World

Hotel Toscana Ambassador

Relais Vignale & Spa

Hu Norcenni Girasole Village

More cheap stays in Chianti Region

Villa Castiglione

Villa Norcenni Aparthotel

Agriturismo Il Caggio di Sotto

Castello di Pratelli

Hotel Albergo Italia

Quercia Al Poggio

Hotels in Chianti Region with star rating

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