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

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

Rp5.904.986

Rp6.695.886 total

includes taxes & fees

30 Oct - 31 Oct

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

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.

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

2. Relais Vignale & Spa

Radda in Chianti

Ali

Rp3.090.848

Rp4.015.411 total

includes taxes & fees

22 Oct - 23 Oct

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

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

3. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

Rp4.871.704

Rp5.519.260 total

includes taxes & fees

9 Nov - 10 Nov

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

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.

An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.

4. Chapter Chianti, a Member of Design Hotels

Cavriglia

Andon

Rp4.811.559

Rp5.413.004 total

includes taxes & fees

11 Oct - 12 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.

An aerial view of a property with a swimming pool, a sun terrace, and a vineyard in the background.

5. Hotel Villa Campomaggio

Radda in Chianti

Dario

Rp2.952.547

Rp3.368.091 total

includes taxes & fees

3 Nov - 4 Nov

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

An arched brick corridor leading to a dining area with tables set for a meal.

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.

6. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

Rp6.906.208

Rp7.797.311 total

includes taxes & fees

6 Nov - 7 Nov

A modern bedroom with a wooden ceiling, a large window, a bed, and a bathroom with a large sink and toiletries.

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

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

7. Castello La Leccia

Castellina in Chianti

Eva

Rp3.179.502

Rp3.577.807 total

includes taxes & fees

17 Oct - 18 Oct

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

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

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.

8. Tenuta CorteDomina

Radda in Chianti

Edgar

Rp2.198.919

Rp2.499.004 total

includes taxes & fees

8 Nov - 9 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 a long table set for a meal, surrounded by chairs, and string lights overhead.

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

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

9. COMO Castello Del Nero

Tavarnelle Val di Pesa

Lauren

Rp13.532.510

Rp15.046.146 total

includes taxes & fees

9 Nov - 10 Nov

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

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

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

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

10. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

Sergey

Rp2.539.191

Rp2.913.399 total

includes taxes & fees

9 Nov - 10 Nov

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

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

11. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

Rp1.972.054

Rp2.289.548 total

includes taxes & fees

1 Nov - 2 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 bedroom with a large bed, a bedside table, and a chair.

A spacious living room with a high ceiling, large windows with diamond-patterned blinds, a sofa set, a coffee table, and a painting on the wall.

12. Borgo Del Cabreo

Greve in Chianti

Brian

Rp3.944.668

Rp4.419.489 total

includes taxes & fees

11 Oct - 12 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 stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

A rustic stone building with a garden in front.

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

13. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

Rp1.986.386

Rp2.305.557 total

includes taxes & fees

15 Oct - 16 Oct

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

A bedroom with a large arched window, a bed, a hanging light fixture, and a view of a green landscape.

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

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

14. Castello Vicchiomaggio

Greve in Chianti

Mary Margaret

Rp3.268.942

Rp3.595.836 total

includes taxes & fees

27 Oct - 28 Oct

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

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.

A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.

15. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

Rp9.815.581

Rp10.997.621 total

includes taxes & fees

21 Oct - 22 Oct

A stone building with a circular window and a door, surrounded by purple flowers.

A terrace with wicker furniture, a pool, and a vineyard view.

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

A stone building with a tiled pathway leading to a large planter.

16. La pietra del cabreo

Greve in Chianti

Jorge Aaron

Rp4.264.791

Rp4.771.463 total

includes taxes & fees

13 Oct - 14 Oct

A clear swimming pool with a view of a lush green landscape and distant hills.

A courtyard with outdoor seating, a gravel path, and a building covered in ivy.

A garden with pink roses, a lawn, and a white umbrella.

A restaurant with multiple tables set for dining, featuring wooden beams and a chandelier.

17. Villa Le Barone

Greve in Chianti

Tereza

Rp4.460.808

Rp5.027.178 total

includes taxes & fees

25 Oct - 26 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.

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.

18. Castello di Tornano Wine Resort

Gaiole in Chianti

Lisa

Rp2.720.776

Rp3.153.239 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

19. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

Rp1.932.843

Rp2.166.204 total

includes taxes & fees

8 Nov - 9 Nov

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.

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

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

20. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Leslie

Rp1.697.715

Rp2.027.871 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 swimming pool with a clear blue water surface, surrounded by a brick deck and a grassy area with trees.

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

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

Relais Villa Olmo - Place of Charme

Impruneta

"Very friendly and clean."

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.

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

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."

Apartment

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

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

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.

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

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

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

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

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 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.

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

Relais Villa Belvedere

Figline e Incisa Valdarno

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

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 sign reading "CAMERE" against a clear blue sky.

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

La Locanda di Pietracupa

Tavarnelle Val di Pesa

"Great place, wonderful restaurant"

Townhouse

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

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

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."

Townhouse

An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

An aerial view of a large, two-story house with a swimming pool, surrounded by lush greenery and fields.

A swimming pool surrounded by lush greenery and a forested hillside.

A stone building with arched windows and a balcony overlooking a garden with lavender plants.

B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

"Beautiful location, beautiful rooms. Host is very friendly and accommodating."

Holiday Home

A stone building with multiple windows and a chimney.

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

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.

Agriturismo La Ferrozzola

Castellina in Chianti

"Very nice agriturismo. "

Townhouse

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

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

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

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."

Residence

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

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.

A modern living room with a fireplace, a dining area, and a kitchen.

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...

Aparthotel

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

A stone staircase leading to a door, surrounded by a well-maintained garden with various plants and a clear view of the countryside.

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

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

Podere il Pino

Poggibonsi

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

Camping

A water park with a pool, slides, and a wooden deck area.

A modern bedroom with a bed, an air conditioning unit, a bedside lamp, a laptop, and a mirror.

A row of wooden cabins with white canopies, each with a wooden deck and a small porch.

An indoor dining area with tables and chairs, a bar in the background, and large green plants.

hu Firenze Certosa camping in town

Impruneta

"Friendly staff!"

Townhouse

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

San Casciano in Val di Pesa

"Me and my girlfriend really did enjoy this property. Both host were very friendly and welcoming to us. We both did enjoy the feel at Home environment. We would definitely come back here on a future trip. Big shout out to the host for the wonderful cook meals. Great to know a bit about them as well."

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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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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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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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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

Villa I Barronci Resort & Spa

10/10 Excellent

"Great spot and friendly staff."

Castello Vicchiomaggio

10/10 Excellent

"A unique stay with a picturesque view. Breakfast, lunch, and dinner were fantastic. The property was great for relaxing at but also a good launching spot for exploring some of the nearby towns and sites."

Fattoria di Vegi

10/10 Excellent

"LOVE LOVE LOVE This was the highlight of our 2.5 week Toscana trip!! You won't regret booking. The space is stunning and newly opened and staff are welcoming and wonderful!"

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"

Villa Casagrande Resort & SPA

8/10 Good

"Restaurant was great. Towels have too much use"

More cheap stays in Chianti Region

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

Rp1.156.414

Rp1.332.199 total

8 Nov - 9 Nov

includes taxes & fees

8.6/10 Excellent! (278 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

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Book Hotels in Chianti Region on Expedia.it

Find hotels in Chianti Region from Rp1.332.199

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. Chapter Chianti, a Member of Design Hotels

5. Hotel Villa Campomaggio

6. Borgo Scopeto Wine & Country Relais

7. Castello La Leccia

8. Tenuta CorteDomina

9. COMO Castello Del Nero

10. Hotel Borgo di Cortefreda Relais - Place of Charme

11. Palazzo Leopoldo Dimora Storica & Spa

12. Borgo Del Cabreo

13. Belvedere di San Leonino

14. Castello Vicchiomaggio

15. Hotel Le Fontanelle

16. La pietra del cabreo

17. Villa Le Barone

18. Castello di Tornano Wine Resort

19. Villa Casagrande Resort & SPA

20. La Certosa di Pontignano - Place of Charme

Holiday Rentals in Chianti Region

Relais Villa Olmo - Place of Charme

Terre di Baccio

Casa Vacanze Squarcialupi

Chianti Village Morrocco

Rocca di Castagnoli

Relais Villa Belvedere

La Locanda di Pietracupa

L' Eroico

B&B La Fonte del Machiavelli

Agriturismo La Ferrozzola

I Parigi Corbinelli

Rocca Palazzaccio

Podere il Pino

hu Firenze Certosa camping in town

B&B Le Dimore di Mezza Costa - Home Restaurant & Cooking Classes

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

Piazza Matteotti

Meleto Castle

Learn more about Chianti Region

Top Chianti Region Hotel Reviews

Villa I Barronci Resort & Spa

Castello Vicchiomaggio

Fattoria di Vegi

Borgo Vescine

Hotel Toscana Ambassador

Relais Vignale & Spa

Hu Norcenni Girasole Village

Hotel Villa Campomaggio

Villa Casagrande Resort & SPA

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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