Chianti Region Holiday Rentals, Tuscany: Private House Rentals

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

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Farm

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

A restaurant with stone walls and a high ceiling, featuring tables set for dining.

A swimming pool with stone walls and a stone pathway leading to a building with multiple floors and a balcony.

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

Gaiole in Chianti

Sonja

Rp5.901.688

Rp6.692.146 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 spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.

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

2. Relais Vignale & Spa

Radda in Chianti

Ali

Rp3.089.121

Rp4.013.168 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 room with a glass table, a vase with flowers, a bottle of wine, and a chair.

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

Rp5.229.648

Rp5.912.909 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 modern living room with a white sofa, armchairs, and a coffee table.

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

4. Chapter Chianti, a Member of Design Hotels

Cavriglia

Andon

Rp4.808.872

Rp5.409.981 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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

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

5. Hotel Villa Campomaggio

Radda in Chianti

Dario

Rp2.950.898

Rp3.366.210 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.

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

6. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

Rp6.567.606

Rp7.424.737 total

includes taxes & fees

5 Nov - 6 Nov

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 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.

7. Castello La Leccia

Castellina in Chianti

Eva

Rp3.587.328

Rp4.026.209 total

includes taxes & fees

8 Nov - 9 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.

8. Tenuta CorteDomina

Radda in Chianti

Edgar

Rp2.197.691

Rp2.497.608 total

includes taxes & fees

8 Nov - 9 Nov

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

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.

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

9. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

Rp1.970.953

Rp2.288.270 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

10. COMO Castello Del Nero

Tavarnelle Val di Pesa

Lauren

Rp14.119.644

Rp15.692.807 total

includes taxes & fees

30 Oct - 31 Oct

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

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.

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

11. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

Sergey

Rp2.345.964

Rp2.700.782 total

includes taxes & fees

24 Oct - 25 Oct

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

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

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

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

12. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Saion

Rp3.426.321

Rp3.849.101 total

includes taxes & fees

8 Nov - 9 Nov

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

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

A pool area with a view of a hilly landscape.

13. Borgo Del Cabreo

Greve in Chianti

Brian

Rp4.945.841

Rp5.521.024 total

includes taxes & fees

9 Oct - 10 Oct

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

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

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

A restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.

14. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

Rp9.810.099

Rp10.991.479 total

includes taxes & fees

21 Oct - 22 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.

15. Castello Vicchiomaggio

Greve in Chianti

Mary Margaret

Rp3.229.996

Rp3.552.996 total

includes taxes & fees

9 Oct - 10 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 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.

A rustic stone building with a garden in front.

16. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

Rp2.020.589

Rp2.343.546 total

includes taxes & fees

10 Oct - 11 Oct

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

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

A stone 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.

17. Castello di Tornano Wine Resort

Gaiole in Chianti

Lisa

Rp2.719.257

Rp3.151.479 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

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

18. La pietra del cabreo

Greve in Chianti

Jorge Aaron

Rp4.945.841

Rp5.521.025 total

includes taxes & fees

9 Oct - 10 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 bar area with a fireplace, bar stools, a table with bottles, and a shelf with glasses.

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

19. Villa Le Barone

Greve in Chianti

Tereza

Rp4.483.405

Rp5.052.643 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

20. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

Rp1.824.208

Rp2.046.703 total

includes taxes & fees

8 Nov - 9 Nov

View all properties

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

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

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

Terre di Baccio

Greve in Chianti

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

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 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.

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 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 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.

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

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 "

Residence

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

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

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

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

Palazzo Pacini

Colle di Val d'Elsa

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

Townhouse

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

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

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

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 yellow sign reading "b&b erioico".

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

A stone building with a wooden door and shutters, a sign reading "b.v. eroico", and a number "19" on the wall.

An aerial view of a town with a central square, surrounding buildings, and vineyards.

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 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 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"

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

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

Agriturismo La Ferrozzola

Castellina in Chianti

"Very nice agriturismo. "

Townhouse

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

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.

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

B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

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

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

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 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.

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

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."

Camping

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

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

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

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

hu Firenze Certosa camping in town

Impruneta

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

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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

"Simply amazing. A nice break in a busy trip with beautiful views and lots of space. Just book a villa, they are incredible. I also loved the wine tour and diner at the castle. Only wish they would ship wine to Canada had one of the best white wines I ever tasted there."

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!"

Villa I Barronci Resort & Spa

8/10 Good

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

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."

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."

More cheap stays in Chianti Region

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

Rp1.155.769

Rp1.331.457 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. 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. Palazzo Leopoldo Dimora Storica & Spa

10. COMO Castello Del Nero

11. Hotel Borgo di Cortefreda Relais - Place of Charme

12. Castello di Fonterutoli Wine Resort

13. Borgo Del Cabreo

14. Hotel Le Fontanelle

15. Castello Vicchiomaggio

16. Belvedere di San Leonino

17. Castello di Tornano Wine Resort

18. La pietra del cabreo

19. Villa Le Barone

20. Villa Casagrande Resort & SPA

Holiday Rentals in Chianti Region

Relais Villa Olmo - Place of Charme

Terre di Baccio

Casa Vacanze Squarcialupi

Chianti Village Morrocco

Rocca di Castagnoli

Palazzo Pacini

Villa il Fedino

L' Eroico

La Locanda di Pietracupa

Agriturismo La Ferrozzola

B&B La Fonte del Machiavelli

Rocca Palazzaccio

Villa Cassia di Baccano

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

hu Firenze Certosa camping in town

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

Fattoria di Vegi

Villa I Barronci Resort & Spa

Salvadonica - Borgo del Chianti

Borgo Vescine

Hotel Toscana Ambassador

Relais Vignale & Spa

Villa Le Barone

Hu Norcenni Girasole Village

More cheap stays in Chianti Region

Villa Castiglione

Villa Norcenni Aparthotel

Agriturismo Il Caggio di Sotto

Castello di Pratelli

Hotel Albergo Italia

Quercia Al Poggio

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