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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Our top choices for Chianti Region hotels

A rustic stone interior with a dining area, two armchairs, a table with a lamp, and a view through an arched doorway.

A wine cellar with wooden racks of wine bottles, a table with wine glasses, and a stone wall.

A swimming pool with lounge chairs and a pergola, surrounded by a landscaped garden and a view of a forested hillside.

A stone building with a courtyard, a tall tree, and a view of the countryside.

1. Castello di Volpaia

Radda in Chianti

Stenley

Rp4.269.376

Rp4.777.805 total

includes taxes & fees

7 Oct - 8 Oct

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

A corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

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

A restaurant setting with wooden chairs, a white tablecloth, and a waiter attending to a table.

2. La Certosa di Pontignano

Castelnuovo Berardenga

Malena

Rp2.417.657

Rp2.822.949 total

includes taxes & fees

30 Sept - 1 Oct

A poolside area with outdoor seating and umbrellas, overlooking a scenic landscape.

A table with breakfast items, a clear view of the countryside, and a white umbrella.

A woman sitting on a chair in a room with a staircase, a wall-mounted light, and a tiled floor.

A pathway lined with wooden fences and benches, leading to a covered seating area with tables and chairs.

3. Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

Juan Antonio

Rp2.590.295

Rp2.971.561 total

includes taxes & fees

14 Sept - 15 Sept

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

A white vehicle parked in front of a building with a stone facade and arched windows, surrounded by gravel and greenery.

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.

4. Tenuta CorteDomina

Radda in Chianti

Dustin

Rp4.451.433

Rp4.978.067 total

includes taxes & fees

30 Sept - 1 Oct

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

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

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.

5. Villa Le Barone

Greve in Chianti

Aditi

Rp4.149.489

Rp4.687.006 total

includes taxes & fees

11 Oct - 12 Oct

A person pouring a liquid from a bottle into a glass.

A glass table with a sandwich and a drink, a yellow sofa, and a fireplace with flames.

A modern interior with a yellow sofa, blue armchair, and a dining area with chairs and a table.

A modern interior with a blue chair, a yellow chair, and a brown sofa. There is a glass door leading to an outdoor area with chairs and plants.

6. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

Rp2.066.953

Rp2.334.767 total

includes taxes & fees

20 Sept - 21 Sept

A resort with a pool area, umbrellas, and a stage for events.

A hallway with a tiled floor, a reception desk with a gold and white color scheme, and a framed abstract painting on the wall.

A wine cellar with wooden shelves, a dining table set for six, and a brick ceiling.

A courtyard with a building featuring a tower, surrounded by trees and potted plants.

7. Villa Castiglione

Impruneta

Lee

Rp2.349.713

Rp2.645.802 total

includes taxes & fees

27 Sept - 28 Sept

A narrow cobblestone street lined with traditional brick buildings, outdoor seating with wicker chairs and tables, and hanging lanterns.

A staircase with a wooden handrail and black balusters, leading to an upper floor.

A rustic room with exposed brick walls, a piano, and a dining table set with white tableware.

A rustic room with a stone ceiling, a bench, white tables, and a window with red curtains.

8. Hotel Il Castello

Certaldo Alto

Thomas

Rp2.376.454

Rp2.715.963 total

includes taxes & fees

13 Sept - 14 Sept

A restaurant with wooden tables set for dining, red cushioned seating, and a warm ambiance.

A bedroom with a bed, a small cabinet, and a stone wall.

A building with multiple windows, a door with a light fixture, and a small porch area.

A vineyard with rows of grapevines, a few buildings, and rolling hills in the background.

9. Locanda Il Gallo

Greve in Chianti

Santina

Rp2.033.565

Rp2.298.039 total

includes taxes & fees

13 Sept - 14 Sept

A well-maintained garden with geometric hedges and a pathway leading to a building with multiple windows and outdoor seating.

A stone building with a large wooden door and arched entrance, flanked by potted plants.

A room with a large window offering a view of a vineyard and distant hills.

A cozy living room with a wooden ceiling, a television, a sofa, and a view of greenery outside.

10. Palagina la Dimora

Figline e Incisa Valdarno

Tarek

Rp1.993.560

Rp2.233.661 total

includes taxes & fees

14 Sept - 15 Sept

A spacious lobby with a reception desk, seating area, and a large vase.

A patio with a round table and chairs, potted plants, and a view of the building's interior.

A hotel room with two beds, a desk with a computer, a chair, and a tray of breakfast items.

A hotel room with a large bed, two armchairs, a small table with a tray of breakfast items, a television, and curtains.

11. Hotel Valdarno

Montevarchi

Emmanuel

Rp2.166.840

Rp2.383.605 total

includes taxes & fees

13 Sept - 14 Sept

A balcony with a table set for two, two wine glasses, and a bottle of wine.

A rectangular swimming pool with a stone deck and a wooden deck border, surrounded by grass and trees.

A stone building with a sloped roof, multiple windows, and a staircase leading to an upper level.

A cozy room with a large window, a wooden table, a red chair, a bookshelf, and a cactus plant.

12. Le Cetinelle B&B

Greve in Chianti

Sebastian

A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.

A cozy living room with a stone fireplace, striped sofas, and a coffee table.

A dining area with a stone wall, wooden beams, and a striped sofa.

A stone building with a courtyard, a covered seating area, and a small bell tower.

13. Borgo di Pietrafitta Relais

Castellina in Chianti

Alejandro

Rp2.648.450

Rp2.994.786 total

includes taxes & fees

4 Oct - 5 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 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.

14. Belvedere di San Leonino

Castellina in Chianti

Seong Won

Rp2.244.560

Rp2.591.584 total

includes taxes & fees

7 Oct - 8 Oct

A buffet with various food items and utensils.

A hotel entrance with a sign reading "HOTEL il Viandante".

A covered outdoor seating area with wicker furniture and a potted plant.

A modern lobby with a reception desk, two seating areas with orange chairs, and a marble floor.

15. Hotel Il Viandante

Terranuova Bracciolini

Michelle

Rp1.696.454

Rp2.274.660 total

includes taxes & fees

20 Sept - 21 Sept

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

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.

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

16. Hotel Villa Campomaggio

Radda in Chianti

Krishna

Rp3.593.290

Rp4.075.187 total

includes taxes & fees

12 Oct - 13 Oct

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

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

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

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

17. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Maria

Rp3.300.377

Rp3.711.906 total

includes taxes & fees

7 Oct - 8 Oct

A cobblestone street lined with historic stone buildings, some with ivy, and large terracotta pots with flowers.

An outdoor patio with stone flooring, a table with chairs, and potted plants.

A lobby with a marble reception desk, a vase with pampas grass, and a view of the garden through a large window.

18. Hotel Borgo San Luigi

Monteriggioni

Raman

Rp3.176.465

Rp3.637.107 total

includes taxes & fees

13 Sept - 14 Sept

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

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

A bedroom with a four-poster bed, a sofa, a dining table with chairs, and a large painting on the wall.

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

19. Villa il Fedino

San Casciano in Val di Pesa

"This is an excellent property. Very historic, rustic and with great views across the Tuscan landscapes. Lorenzo and his mother were super duper hosts who took great care of us. The property dates back to 1380 and the rooms are decorated with choicest artifacts that adds greatly to the experience. The location is fantastic too with the local market and restaurants in easy walking reach. The breakfast service is fabulous with many choices and Lorenzo himself is great chef as well! Highly recommend...

Nilesh

Rp4.417.969

Rp4.941.539 total

includes taxes & fees

11 Oct - 12 Oct

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

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.

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

20. Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa

Sergey

Rp2.482.005

Rp2.852.773 total

includes taxes & fees

7 Oct - 8 Oct

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Holiday Rentals in Chianti Region

Townhouse

A villa with a swimming pool, outdoor seating, and a tennis court.

A pool area with lounge chairs and umbrellas, a stone planter with flowers, and a building with balconies in the background.

A hotel room with a bed, a nightstand, a lamp, and a view of a landscape through a window.

A lobby with a stone archway, a reception desk, and a seating area with a sofa and armchairs.

Villa Curina Resort

Castelnuovo Berardenga

"Unique property good value staff was great. Nice location to other areas"

Residence

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

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.

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

Chianti Village Morrocco

Tavarnelle Val di Pesa

"Front desk was very helpful and very comfortable room. "

Townhouse

Villa il Fedino

San Casciano in Val di Pesa

Aparthotel

A stone building with a garden in front.

A courtyard with stone walls, potted plants, and a metal fence.

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

A woman sitting by a pool with lounge chairs and umbrellas in the background.

Borgo Argenina

Gaiole in Chianti

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

Townhouse

A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

A group of people toasting with wine glasses at a table with a view of the countryside.

A stone-walled sauna with a wooden interior and a hot tub in the foreground.

A room with a large window overlooking a courtyard with a brick building, trees, and a clear sky.

Villa di Sotto

Castelnuovo Berardenga

"Great spot"

Residence

A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

An open dining area with a table set for breakfast, a view of the outdoors, and a rustic brick archway.

A stone wall with a metal railing, overlooking a valley with trees and distant hills.

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

Villa San Filippo

Barberino Val d'Elsa

"This place was beautiful, quiet like a picture you’d see in the movies"

Holiday Home

A bedroom with a large bed, a wooden ceiling, and a brick archway.

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

A villa with a swimming pool surrounded by olive trees and a vineyard in the background.

A villa with a swimming pool surrounded by a garden, set in a rural landscape with vineyards in the background.

Borgo Argiano

Castelnuovo Berardenga

"Amazing staff, clean room, amazing pool!"

Townhouse

An aerial view of a hotel with a swimming pool, outdoor seating area, and well-maintained gardens.

A nighttime swimming pool with a clear view of the surrounding area, including a covered seating area and distant buildings.

An outdoor dining area with stone walls and white tables and chairs.

An outdoor patio area with stone walls and arched doorways, featuring tables and chairs.

Antica Pieve B&B

Tavarnelle Val di Pesa

"Very nice stay here! Great breakfast and coffee every morning. Great location to tour around to different wineries and towns. Free parking. "

Villa

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

A bedroom with a stone wall, a bed with a white bedspread, a television mounted on the wall, and a window with curtains.

A staircase leading to a room with a stone wall, a green chair, a sofa, and a view through a large window.

A stone building with a swimming pool and outdoor seating.

Relais Badia a Passignano

Tavarnelle Val di Pesa

"A beautiful estate in a scenic Chianti location. The villa was freshly renovated and perfect for a few days of relaxation and wine tours."

Residence

A breakfast buffet with various food items and beverages.

A neatly made bed with a grey blanket and pillows, a bedside table with a lamp, a tray with a coffee pot, cups, and a book titled "L'ITALIA".

A nighttime swimming pool with lounge chairs and tall trees.

A stone staircase surrounded by lush greenery and trees, leading to a building in the distance.

Residence Poggio del Golf

Impruneta

"Pool was a welcome treat after hard days touring, kitchenette and full fridge freezer was great, air con worked well, laundry a great bonus. Nice location Would recommend to friends"

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

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

Villa Cassia di Baccano

Loro Ciuffenna

"The staff were great and the villa was amazing"

Townhouse

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

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

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

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 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.

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

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."

Townhouse

A garden with a stone pathway, wooden benches, and various potted plants.

A swimming pool with lounge chairs and blue umbrellas, surrounded by trees and a stone wall.

An aerial view of a residential area with a large house, a swimming pool, and surrounding greenery.

A patio area with outdoor furniture, a table set for dining, and a large umbrella providing shade.

Antico Borgo il Cardino

San Gimignano

"It was perfect for my one night stop before moving on to another location in Toscana."

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 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.

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 "

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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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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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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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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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Castello di Radda Winery

9.2/10 (12 reviews)

You can enjoy a tasting or tour at Castello di Radda Winery during your travels to Radda in Chianti. 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

Top Chianti Region Hotel Reviews

Salvadonica - Borgo del Chianti

10/10 Excellent

"Amazing time - staff were so friendly and the property is stunning. Do the cooking class with Chef Ivana if you go"

Borgo Vescine

10/10 Excellent

"⭐️⭐️⭐️⭐️⭐️ We genuinely did not want to leave Borgo Vescine was everything we hoped a stay in Tuscany would be. The property is absolutely stunning, incredibly peaceful, and so beautifully cared for that once we arrived, we honestly didn’t want to leave. What made the experience even more special was the staff. Everyone we encountered was warm, welcoming and genuinely delightful. The hospitality never felt forced or overly formal. We simply felt very well taken care of throughout our stay. We had dinner at the property and the restaurant was excellent, which made staying in for the evening an easy decision. Breakfast was included with our stay and was such a delicious treat each morning. Being able to wake up somewhere this beautiful, have a wonderful breakfast and then simply enjoy the property was exactly the kind of Tuscan experience we were looking for. The grounds themselves are gorgeous and meticulously maintained, with beautiful views and so many quiet little areas to sit and take everything in. Despite everything the property offers, it still feels serene, intimate and wonderfully quiet. Borgo Vescine is the kind of place that makes you reconsider whatever plans you had for the day because you would rather just stay there. One of our favorite stays in Tuscany and a property I would happily return to. Highly recommend."

hu Firenze Certosa camping in town

10/10 Excellent

"Friendly staff!"

Villa Le Barone

10/10 Excellent

"Excellent stay with wonderful , friendly staff!"

Hotel Villa Campomaggio

10/10 Excellent

"This resort is one of the most beautiful properties I have ever stayed in. Free use of the spa just was icing on the cake! Great breakfast spread and our dinner in the restaurant was delicious! We will be back!!"

Chapter Chianti, a Member of Design Hotels

8/10 Good

"The property is beautiful and newly renovated. Surrounded by olive trees and tuscan hills. The stay was very pleasant and the staff is very friendly. However, the management needs to improve two things. Firstly, the hotel is extremely understaffed. This means you wait for everything (e.g. I waited for a pool towel for 40 min). Even though the staff is very engaged they simply don’t have the manpower to attend to all guests. Secondly, the agressive in-hotel pricing policy makes for an unpleasant element. The hotel asks to be paid 20 eur for an avocado toast for breakfast, which is unacceptable. An espresso costs 5 eur or a bottle of water by the pool costs 7 eur. Comparing these prices to hotels/restaurants etc. in Tuscany makes you wonder why is this hotel so expensive."

Villa Il Palagio

10/10 Excellent

"Great loved everything thank you!"

Castello Vicchiomaggio

10/10 Excellent

"Very nice place in the heart of Chianti Pool and premises are extraordinary"

Fattoria di Vegi

10/10 Excellent

"Amazing! I wish I could have stayed forever!"

More cheap stays in Chianti Region

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

Rp1.054.287

Rp1.190.275 total

13 Sept - 14 Sept

includes taxes & fees

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

Rp2.349.713

Rp2.645.802 total

27 Sept - 28 Sept

includes taxes & fees

8.6/10 Excellent! (276 reviews)

Castello di Pratelli

Via Di Pratelli 1/a Figline e Incisa Valdarno FI

Get rates

9.2/10 Wonderful! (5 reviews)

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)

Quercia Al Poggio

Strada Di Quercia Al Poggio 4 Barberino Tavarnelle FI

Get rates

Tenuta La Pieve Casale Presciano

Via di Migliari Pergine Valdarno AR

Get rates

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Book Hotels in Chianti Region on Expedia.it

Find hotels in Chianti Region from Rp1.190.275

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 Volpaia

2. La Certosa di Pontignano

3. Villa I Barronci Resort & Spa

4. Tenuta CorteDomina

5. Villa Le Barone

6. Moody smart & comfy Hotel

7. Villa Castiglione

8. Hotel Il Castello

9. Locanda Il Gallo

10. Palagina la Dimora

11. Hotel Valdarno

12. Le Cetinelle B&B

13. Borgo di Pietrafitta Relais

14. Belvedere di San Leonino

15. Hotel Il Viandante

16. Hotel Villa Campomaggio

17. Hotel Palazzo San Lorenzo & SPA

18. Hotel Borgo San Luigi

19. Villa il Fedino

20. Hotel Borgo di Cortefreda Relais

Holiday Rentals in Chianti Region

Villa Curina Resort

Chianti Village Morrocco

Villa il Fedino

Borgo Argenina

Villa di Sotto

Villa San Filippo

Borgo Argiano

Antica Pieve B&B

Relais Badia a Passignano

Residence Poggio del Golf

Villa Cassia di Baccano

La Locanda di Pietracupa

I Parigi Corbinelli

Antico Borgo il Cardino

Rocca di Castagnoli

Stay near popular Chianti Region attractions

Antinori nel Chianti Classico

The Mall Luxury Outlet

Tenuta Torciano Winery

Verrazzano Castle

Castle of Brolio

Castello di Albola

Meleto Castle

Castello di Radda Winery

Learn more about Chianti Region

Top Chianti Region Hotel Reviews

Salvadonica - Borgo del Chianti

Borgo Vescine

hu Firenze Certosa camping in town

Villa Le Barone

Hotel Villa Campomaggio

Chapter Chianti, a Member of Design Hotels

Villa Il Palagio

Castello Vicchiomaggio

Fattoria di Vegi

More cheap stays in Chianti Region

Villa Norcenni Aparthotel

Villa Castiglione

Castello di Pratelli

Agriturismo Il Caggio di Sotto

Quercia Al Poggio

Tenuta La Pieve Casale Presciano

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