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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Hot tub

Farm

Family friendly

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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.

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

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.

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

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

Gaiole in Chianti

Sonja

Rp5.927.928

Rp6.721.901 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.

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

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

2. Relais Vignale & Spa

Radda in Chianti

Ali

Rp2.917.096

Rp3.826.674 total

includes taxes & fees

16 Oct - 17 Oct

A stone pillar with carvings, a glass door leading outside, and a person sitting on a lounge chair.

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

A courtyard with a stone building, wooden pergola, and raised garden beds with various plants.

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

3. Hotel Villa Campomaggio

Radda in Chianti

Dario

Rp2.826.317

Rp3.229.705 total

includes taxes & fees

7 Oct - 8 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 cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

4. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

Rp5.252.900

Rp5.939.198 total

includes taxes & fees

28 Oct - 29 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 modern living room with a white sofa, armchairs, and a coffee table.

5. Chapter Chianti, a Member of Design Hotels

Cavriglia

Andon

Rp4.830.253

Rp5.434.035 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 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.

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.

6. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

Rp9.853.717

Rp11.040.350 total

includes taxes & fees

14 Oct - 15 Oct

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

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

7. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

Rp2.091.644

Rp2.421.565 total

includes taxes & fees

2 Nov - 3 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.

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.

An outdoor dining area with a long table set for a meal, surrounded by chairs, and string lights overhead.

8. COMO Castello Del Nero

Tavarnelle Val di Pesa

Lauren

Rp14.103.059

Rp15.674.373 total

includes taxes & fees

30 Oct - 31 Oct

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.

9. Tenuta CorteDomina

Radda in Chianti

Edgar

Rp4.226.472

Rp4.729.623 total

includes taxes & fees

1 Nov - 2 Nov

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

A sunset scene with a person holding a child, benches, and umbrellas in a park setting.

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

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

10. Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa

Sergey

Rp2.356.395

Rp2.712.790 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 rustic stone building with a garden in front.

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

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

11. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

Rp1.970.240

Rp2.288.020 total

includes taxes & fees

6 Oct - 7 Oct

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

A spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.

12. Locanda le Piazze

Castellina in Chianti

Colleen

Rp6.586.709

Rp7.366.136 total

includes taxes & fees

12 Oct - 13 Oct

An aerial view of a village with traditional stone buildings, narrow streets, and a central square with a fountain.

A well-lit outdoor garden area with stone planters, a paved walkway, and a building with large windows.

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

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

13. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Saion

Rp3.545.808

Rp3.980.934 total

includes taxes & fees

26 Oct - 27 Oct

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

A pool area with a view of a hilly landscape.

14. Borgo Del Cabreo

Greve in Chianti

Brian

Rp5.582.163

Rp6.220.964 total

includes taxes & fees

11 Oct - 12 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.

15. Castello La Leccia

Castellina in Chianti

Eva

Rp4.226.472

Rp4.729.623 total

includes taxes & fees

2 Nov - 3 Nov

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.

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

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

16. Castello di Tornano Wine Resort

Gaiole in Chianti

Lisa

Rp2.731.284

Rp3.165.421 total

includes taxes & fees

25 Oct - 26 Oct

A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.

An aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.

A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.

A bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.

17. Borgo Vescine

Radda in Chianti

Natalie

Rp8.398.054

Rp9.398.867 total

includes taxes & fees

4 Nov - 5 Nov

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

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

18. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

Rp6.596.806

Rp7.457.748 total

includes taxes & fees

5 Nov - 6 Nov

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

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

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

A historic building with a courtyard, stone arches, and a tiled roof.

19. Palazzo Squarcialupi

Castellina in Chianti

yvette

Rp3.601.356

Rp4.082.168 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.

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.

20. La Certosa di Pontignano

Castelnuovo Berardenga

Leslie

Rp1.733.951

Rp2.068.354 total

includes taxes & fees

2 Nov - 3 Nov

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Holiday Rentals in Chianti Region

Residence

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

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

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

An outdoor dining area with tables set for a meal, large windows, and a stone wall in the background.

Relais Villa Olmo

Impruneta

"Very friendly and clean."

Aparthotel

A stone building with a garden in front.

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.

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

Borgo Argenina

Gaiole in Chianti

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

Apartment

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

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

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

A dining area with a wooden table and chairs, a white sofa with cushions, and a staircase with a metal railing.

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. "

Residence

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

A bedroom with a bed, a bedside table with a lamp, a chair, and a view of a balcony with wooden shutters.

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

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

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

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

A pool area with a view of a hilly landscape, surrounded by greenery and outdoor furniture.

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

Townhouse

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

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

A hotel room with a bed, two bedside lamps, a TV, a window with curtains, a wooden wardrobe, and a tray with glasses and a bottle.

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

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 "

Aparthotel

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

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

A bedroom with a view of the city at night, a window, and a radiator.

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

Relais Villa Belvedere

Figline e Incisa Valdarno

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

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.

An arched entrance to a building with a tiled floor and a staircase leading inside.

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

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

A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

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."

Townhouse

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.

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.

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."

Holiday Home

A stone building with multiple windows and a chimney.

A stone staircase leading up to a rustic stone building with a flat roof, surrounded by greenery and trees.

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

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

A stone staircase leading up a hill, surrounded by olive trees and greenery.

Casale di Villore

Poggibonsi

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

Townhouse

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

A two-story house with a patio area, potted plants, and outdoor furniture.

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

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

La Locanda di Pietracupa

Tavarnelle Val di Pesa

"Great place, wonderful restaurant"

Residence

A swimming pool with a stone fountain, surrounded by a grassy area and trees.

A stone fountain with a tiered design, surrounded by a well-maintained lawn and a stone wall.

A modern kitchen with white cabinetry, a built-in microwave, and an oven. There is a white dining table with a vase of flowers.

A modern hotel room with a large bed, a bedside table with a lamp, a wardrobe, and a view of the outside through a window.

Rocca Palazzaccio

Impruneta

"A lovely stay at this property with our 2 year old.The apartment had everything we needed and communication with the host was very good There are steep hills to access the property by car or foot so bear that in mind but we managed fine with a pram and a car its just worth noting Handy to have laundry facilities on site aswell. There is a coop just a few minutes down the road Lovely views and a clean pool which was perfect for our little one to use and toys there that he could play in the...

Townhouse

A cozy living room with a stone wall, a wine rack, and two sofas.

A spa room with a bathtub, candles, towels, and a bottle of wine.

A wooden deck with a pool, lounge chairs, and a small table with towels.

A dining area with white tables and chairs, stone walls, and large windows with curtains.

Villa Cassia di Baccano

Loro Ciuffenna

"Such a lovely experience, the perfect getaway place with perfect room, breakfast, pool, staff, lunch and dinner. we will definitely come back. 10/10 ❤️"

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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.

See properties

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

Take a sightseeing trip of Tuscany's renowned wine region and visit its vineyards, wineries, ancient churches, castles and hilltop villages.

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

"What a gorgeous place! We loved it here and can’t wait to go back!"

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."

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."

Hotel Villa Campomaggio

10/10 Excellent

"Great hotel"

More cheap stays in Chianti Region

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

Rp1.222.657

Rp1.405.301 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

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 Rp1.405.301

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. Hotel Villa Campomaggio

4. Dievole Wine Resort

5. Chapter Chianti, a Member of Design Hotels

6. Hotel Le Fontanelle

7. Palazzo Leopoldo Dimora Storica & Spa

8. COMO Castello Del Nero

9. Tenuta CorteDomina

10. Hotel Borgo di Cortefreda Relais

11. Belvedere di San Leonino

12. Locanda le Piazze

13. Castello di Fonterutoli Wine Resort

14. Borgo Del Cabreo

15. Castello La Leccia

16. Castello di Tornano Wine Resort

17. Borgo Vescine

18. Borgo Scopeto Wine & Country Relais

19. Palazzo Squarcialupi

20. La Certosa di Pontignano

Holiday Rentals in Chianti Region

Relais Villa Olmo

Borgo Argenina

Casa Vacanze Squarcialupi

Chianti Village Morrocco

Villa il Fedino

Rocca di Castagnoli

Relais Villa Belvedere

Palazzo Pacini

Terre di Baccio

L' Eroico

Agriturismo La Ferrozzola

Casale di Villore

La Locanda di Pietracupa

Rocca Palazzaccio

Villa Cassia di Baccano

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

Hotel Toscana Ambassador

Relais Vignale & Spa

Hu Norcenni Girasole Village

Hotel Villa Campomaggio

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

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