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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Go beyond your typical stay in Chianti Region

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Pool

Villa

Spa

Apartment

Apart hotel

Farm

Hot tub

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.

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

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

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

Gaiole in Chianti

Michelle

Rp5.903.993

Rp6.694.760 total

includes taxes & fees

30 Oct - 31 Oct

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

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.

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

2. Relais Vignale & Spa

Radda in Chianti

Ali

Rp2.905.318

Rp3.811.225 total

includes taxes & fees

16 Oct - 17 Oct

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

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

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.

3. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

Rp4.870.885

Rp5.518.332 total

includes taxes & fees

9 Nov - 10 Nov

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

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

4. Hotel Villa Campomaggio

Radda in Chianti

Dario

Rp2.952.051

Rp3.367.525 total

includes taxes & fees

3 Nov - 4 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.

5. Chapter Chianti, a Member of Design Hotels

Cavriglia

Andon

Rp4.796.519

Rp5.396.084 total

includes taxes & fees

18 Oct - 19 Oct

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

Rp6.821.423

Rp7.704.014 total

includes taxes & fees

3 Nov - 4 Nov

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

A courtyard with stone buildings, outdoor tables set for dining, and a gravel ground.

7. Castello La Leccia

Castellina in Chianti

Eva

Rp3.578.113

Rp4.015.867 total

includes taxes & fees

4 Nov - 5 Nov

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 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.

8. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

Rp2.083.198

Rp2.411.787 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.

9. Tenuta CorteDomina

Radda in Chianti

Edgar

Rp3.185.300

Rp3.584.008 total

includes taxes & fees

12 Nov - 13 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.

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

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

10. COMO Castello Del Nero

Tavarnelle Val di Pesa

Lauren

Rp12.956.225

Rp14.412.205 total

includes taxes & fees

8 Nov - 9 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 person relaxing on a sun lounger by a pool with a table beside them holding a drink and a bowl.

11. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

Sergey

Rp2.494.483

Rp2.864.201 total

includes taxes & fees

14 Nov - 15 Nov

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

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

12. Locanda le Piazze

Castellina in Chianti

Colleen

Rp6.540.708

Rp7.314.692 total

includes taxes & fees

22 Oct - 23 Oct

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

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.

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

13. Castello Vicchiomaggio

Greve in Chianti

Mary Margaret

Rp3.952.796

Rp4.348.075 total

includes taxes & fees

29 Oct - 30 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 person relaxing in a hot tub with a view of a building and trees in the background.

14. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

Rp1.941.461

Rp2.255.877 total

includes taxes & fees

16 Oct - 17 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 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.

15. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

Rp9.784.899

Rp10.963.244 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 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.

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

16. Borgo Del Cabreo

Greve in Chianti

Brian

Rp4.264.074

Rp4.770.660 total

includes taxes & fees

16 Oct - 17 Oct

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

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

A bar area with a fireplace, bar stools, a table with bottles, and a shelf with glasses.

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

17. Villa Le Barone

Greve in Chianti

Tereza

Rp4.442.837

Rp5.007.390 total

includes taxes & fees

31 Oct - 1 Nov

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

An indoor swimming pool with clear glass walls, wooden beams, and large windows.

18. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

Rp1.932.518

Rp2.165.840 total

includes taxes & fees

8 Nov - 9 Nov

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

A bottle of wine and two glasses on a windowsill with a vineyard view.

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.

19. La pietra del cabreo

Greve in Chianti

Jorge Aaron

Rp4.264.074

Rp4.770.660 total

includes taxes & fees

15 Oct - 16 Oct

A person sitting in a hot tub with a waterfall feature in the background.

A hotel room with a large bed, a desk, and a chair, a view of a city through the window, and a ceiling light.

A dining area with tables and chairs, a chandelier, and wall-mounted lighting.

A tiled shower area with a square light fixture above the showerhead.

20. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Maria

Rp2.066.436

Rp2.353.259 total

includes taxes & fees

8 Nov - 9 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.

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."

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."

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

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

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 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

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

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

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 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 "

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

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 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.

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

La Locanda di Pietracupa

Tavarnelle Val di Pesa

"Great place, wonderful restaurant"

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

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

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.

A dining area with tables set for meals, a bar area with shelves of bottles, and a wooden cabinet.

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

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

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

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. "

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.

An interior space with a wooden bench, a potted plant, and two framed pictures on the wall.

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

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...

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.

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

An outdoor dining area with wooden tables and chairs, string lights, and a view of greenery.

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.

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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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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

Salvadonica - Borgo del Chianti

8/10 Good

"Lit un peut moins confortable"

Villa I Barronci Resort & Spa

10/10 Excellent

"Great spot and friendly staff."

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."

Villa Le Barone

10/10 Excellent

"Charming place in Tuscany! Everything was absolutely perfect. We highly suggest to dine at the villa, it was exceptional. Breakfast was delicious as well."

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."

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

Rp1.156.220

Rp1.331.976 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

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 Rp1.331.976

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. Borgo Scopeto Wine & Country Relais

7. Castello La Leccia

8. Palazzo Leopoldo Dimora Storica & Spa

9. Tenuta CorteDomina

10. COMO Castello Del Nero

11. Hotel Borgo di Cortefreda Relais - Place of Charme

12. Locanda le Piazze

13. Castello Vicchiomaggio

14. Belvedere di San Leonino

15. Hotel Le Fontanelle

16. Borgo Del Cabreo

17. Villa Le Barone

18. Villa Casagrande Resort & SPA

19. La pietra del cabreo

20. Hotel Palazzo San Lorenzo & SPA

Holiday Rentals in Chianti Region

Relais Villa Olmo - Place of Charme

Borgo Argenina

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

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

Salvadonica - Borgo del Chianti

Villa I Barronci Resort & Spa

Fattoria di Vegi

Borgo Vescine

Hotel Toscana Ambassador

Relais Vignale & Spa

Villa Le Barone

Hu Norcenni Girasole Village

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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