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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Farm

Hot tub

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

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

Sonja

Rp5.916.892

Rp6.709.386 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.

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

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

2. Relais Vignale & Spa

Radda in Chianti

Ali

Rp3.089.121

Rp4.013.168 total

includes taxes & fees

19 Oct - 20 Oct

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

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.

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

3. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

Rp4.881.526

Rp5.530.387 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.

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

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.

4. Hotel Villa Campomaggio

Radda in Chianti

Dario

Rp2.958.501

Rp3.374.883 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.

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

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

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

5. Chapter Chianti, a Member of Design Hotels

Cavriglia

Andon

Rp4.808.872

Rp5.409.981 total

includes taxes & fees

13 Oct - 14 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 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.

6. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

Rp9.810.099

Rp10.991.479 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.

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

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

7. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

Rp6.584.525

Rp7.443.863 total

includes taxes & fees

5 Nov - 6 Nov

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

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

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

8. Castello La Leccia

Castellina in Chianti

Eva

Rp3.587.328

Rp4.026.209 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 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.

9. Tenuta CorteDomina

Radda in Chianti

Edgar

Rp2.203.353

Rp2.504.042 total

includes taxes & fees

8 Nov - 9 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 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.

10. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

Rp1.976.030

Rp2.294.165 total

includes taxes & fees

1 Nov - 2 Nov

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

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

11. Castello Vicchiomaggio

Greve in Chianti

Mary Margaret

Rp3.275.533

Rp3.603.086 total

includes taxes & fees

27 Oct - 28 Oct

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

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.

12. COMO Castello Del Nero

Tavarnelle Val di Pesa

Lauren

Rp14.076.802

Rp15.645.191 total

includes taxes & fees

30 Oct - 31 Oct

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 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.

13. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

Sergey

Rp2.352.008

Rp2.707.741 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 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

Rp1.961.518

Rp2.277.892 total

includes taxes & fees

10 Oct - 11 Oct

A spacious room with a wooden floor, a striped chair, a table with a decorative item, and a staircase with glass railings.

A pool area with a view of a hilly landscape.

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

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

15. Borgo Del Cabreo

Greve in Chianti

Brian

Rp3.934.532

Rp4.408.134 total

includes taxes & fees

11 Oct - 12 Oct

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

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

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

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

16. Villa Le Barone

Greve in Chianti

Tereza

Rp4.458.317

Rp5.024.371 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

17. Castello di Tornano Wine Resort

Gaiole in Chianti

Lisa

Rp2.726.261

Rp3.159.596 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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 spa area with wooden benches and a glass partition, a modern bathroom with a large sink, and a corridor leading to another room.

18. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Maria

Rp2.070.950

Rp2.358.399 total

includes taxes & fees

8 Nov - 9 Nov

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.

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

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

19. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

Rp1.828.908

Rp2.051.975 total

includes taxes & fees

8 Nov - 9 Nov

A historic stone building with multiple windows and a courtyard.

An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.

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

A stone building with outdoor seating and a garden with roses.

20. Borgo San Felice Resort

Castelnuovo Berardenga

Cynthia

Rp13.605.451

Rp15.166.882 total

includes taxes & fees

11 Oct - 12 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 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 swimming pool with a clear blue water surface, surrounded by a brick deck and a grassy area with trees.

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.

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.

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."

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 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 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.

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

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."

Residence

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

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.

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

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 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

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

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

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

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"

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

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

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

A modern kitchen with stone countertops, built-in shelves, and a large window.

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

Villa Cassia di Baccano

Loro Ciuffenna

"The staff were great and the villa was amazing"

Townhouse

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

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

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

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

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

Agriturismo La Ferrozzola

Castellina in Chianti

"Very nice agriturismo. "

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

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

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.

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.

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

"Lovely location in the hills. Really nice pool and bar."

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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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

"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."

Villa I Barronci Resort & Spa

8/10 Good

"Beautiful views, good location, nice restaurants nearby, friendly staff, lovely breakfast. The heated pool is a nice touch but was always busy, even now, out of season. Sadly, the place felt a little bit run down in the outdoor areas, broken / rotten outdoor furniture and a lot of rubbish dumped around the car park. Beware the huge ants if you plan to stay in the ‘treehouse’; which we felt would benefit from a little renovation, redecoration and sealing better against insects."

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."

Hotel Villa Campomaggio

10/10 Excellent

"Great hotel"

More cheap stays in Chianti Region

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

Rp1.158.747

Rp1.334.887 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

Get rates

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 Rp1.282.366

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. Borgo Scopeto Wine & Country Relais

8. Castello La Leccia

9. Tenuta CorteDomina

10. Palazzo Leopoldo Dimora Storica & Spa

11. Castello Vicchiomaggio

12. COMO Castello Del Nero

13. Hotel Borgo di Cortefreda Relais - Place of Charme

14. Belvedere di San Leonino

15. Borgo Del Cabreo

16. Villa Le Barone

17. Castello di Tornano Wine Resort

18. Hotel Palazzo San Lorenzo & SPA

19. Villa Casagrande Resort & SPA

20. Borgo San Felice Resort

Holiday Rentals in Chianti Region

Relais Villa Olmo - Place of Charme

Terre di Baccio

Casa Vacanze Squarcialupi

Chianti Village Morrocco

Palazzo Pacini

Rocca di Castagnoli

La Locanda di Pietracupa

L' Eroico

Villa Cassia di Baccano

B&B La Fonte del Machiavelli

Agriturismo La Ferrozzola

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

Meleto Castle

Piazza Matteotti

Learn more about Chianti Region

Top Chianti Region Hotel Reviews

Castello Vicchiomaggio

Villa I Barronci Resort & Spa

Fattoria di Vegi

Borgo Vescine

Hotel Toscana Ambassador

Relais Vignale & Spa

Villa Le Barone

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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