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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Spa

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Hot tub

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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 narrow street with stone buildings, a wrought iron gate, and a street lamp.

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

1. Castello di Volpaia

Radda in Chianti

Stenley

Rp4.483.766

Rp5.013.855 total

includes taxes & fees

14 Oct - 15 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.

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

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

2. La Certosa di Pontignano

Castelnuovo Berardenga

Malena

Rp2.316.538

Rp2.711.616 total

includes taxes & fees

15 Oct - 16 Oct

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

A bedroom with a large bed, a view of a green landscape through a sliding door, and a potted plant on the windowsill.

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

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

3. Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

Juan Antonio

Rp2.002.318

Rp2.325.117 total

includes taxes & fees

15 Oct - 16 Oct

A building with ivy-covered walls and a vintage car parked in front.

A building with a brick facade, arched entrance, and multiple windows covered in green ivy.

A bedroom with a stone wall, a bathtub, a bottle of wine, and a robe hanging on a rack.

A buffet table with various desserts including pastries, a fruit salad, and a pie.

4. Tenuta CorteDomina

Radda in Chianti

Dustin

Rp4.463.523

Rp4.991.587 total

includes taxes & fees

30 Sept - 1 Oct

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

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

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

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

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

A modern building with a glass facade, a car parked in front, and a well-lit entrance area.

6. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

Rp2.072.566

Rp2.341.107 total

includes taxes & fees

20 Sept - 21 Sept

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

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.

An aerial view of a church with a bell tower, surrounded by olive groves and a hilly landscape.

7. Villa Castiglione

Impruneta

Lee

Rp2.356.094

Rp2.652.988 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 living room with a sofa, armchairs, a coffee table, and a painting on the wall.

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.

8. Hotel Il Castello

Certaldo Alto

Thomas

Rp2.382.908

Rp2.723.339 total

includes taxes & fees

17 Sept - 18 Sept

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

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

A bar area with a large ELEKTRA grill, shelves of liquor bottles, and a menu board.

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

9. Locanda Il Gallo

Greve in Chianti

Santina

Rp2.039.088

Rp2.304.280 total

includes taxes & fees

17 Sept - 18 Sept

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

A restaurant with tables set for dining, large umbrellas, and a view of the landscape.

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

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

10. Palagina la Dimora

Figline e Incisa Valdarno

Tarek

Rp2.479.498

Rp2.768.304 total

includes taxes & fees

29 Sept - 30 Sept

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

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

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

A modern hotel lobby with a curved reception desk, seating area, and a bar.

11. Hotel Valdarno

Montevarchi

Emmanuel

Rp2.172.725

Rp2.390.079 total

includes taxes & fees

16 Sept - 17 Sept

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

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

A breakfast table with a bowl of fruit, a pitcher of orange juice, and a cup of coffee.

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

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

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

A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and lush greenery, overlooking a valley.

13. Borgo di Pietrafitta Relais

Castellina in Chianti

Alejandro

Rp1.604.417

Rp1.846.489 total

includes taxes & fees

14 Oct - 15 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 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.

A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

14. Belvedere di San Leonino

Castellina in Chianti

Seong Won

Rp2.244.560

Rp2.591.584 total

includes taxes & fees

23 Sept - 24 Sept

A buffet with various food items and utensils.

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.

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

15. Hotel Il Viandante

Terranuova Bracciolini

Michelle

Rp1.745.699

Rp2.328.830 total

includes taxes & fees

7 Oct - 8 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.

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

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

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

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.

17. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Maria

Rp3.309.340

Rp3.721.986 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.

18. Hotel Borgo San Luigi

Monteriggioni

Raman

Rp4.633.077

Rp5.239.381 total

includes taxes & fees

15 Oct - 16 Oct

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

4 Oct - 5 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 lobby with a stone archway, a reception desk, and a seating area with a sofa and armchairs.

An aerial view of a property with a swimming pool, tennis court, and vineyard.

Villa Curina Resort

Castelnuovo Berardenga

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

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 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.

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

Villa di Sotto

Castelnuovo Berardenga

"Great spot"

Aparthotel

A stone building with a garden in front.

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

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

A stone building with a bell tower, arched windows, and a gravel driveway.

Borgo Argenina

Gaiole in Chianti

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

Residence

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

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

A 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.

Chianti Village Morrocco

Tavarnelle Val di Pesa

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

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.

An outdoor patio with wicker furniture, stone walls, and a view of the landscape.

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

Borgo Argiano

Castelnuovo Berardenga

"Amazing staff, clean room, amazing pool!"

Residence

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

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

A stone building with a balcony, a stone wall, and a pathway leading to a fountain.

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"

Townhouse

Villa il Fedino

San Casciano in Val di Pesa

Residence

An outdoor dining area with a table and chairs, surrounded by greenery and trees, overlooking a scenic landscape.

A room with a large window, a cabinet, and a person sitting by the window.

A poolside area with lounge chairs and umbrellas, a clear sky, and a view of the landscape.

A dining area with a table, chairs, a television, and a view of the outdoors.

Castello Del Nero - Podere San Filippo

Tavarnelle Val di Pesa

"The hotel and property was soo beautiful!"

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

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

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

"The beautiful place, very comfortable, the incredible attention, the breakfast felt like in Homewith a lot of love We hope to return one day"

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 stone archway, a wooden dresser, and a chandelier.

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

Relais Villa Belvedere

Figline e Incisa Valdarno

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

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 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.

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 bedroom with a large bed, a smaller bed, and a window with curtains.

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

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

La Locanda di Pietracupa

Tavarnelle Val di Pesa

"Great place, wonderful restaurant"

Villa

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

A gravel path leading through a vineyard with stone pillars and a potted plant at the entrance.

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

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."

Townhouse

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

A room with two beds, a desk with a chair, a television, and a window with curtains.

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

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

Antico Borgo il Cardino

San Gimignano

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

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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

hu Firenze Certosa camping in town

10/10 Excellent

"Old stains were found on the matrass. Some ants around the fridge. It would be better to install a TV. Everything else was fine."

Relais Vignale & Spa

10/10 Excellent

"Very nice property"

Fattoria di Vegi

10/10 Excellent

"Incredible magical place. Couldn’t recommend it more…"

Castello Vicchiomaggio

10/10 Excellent

"Clean, comfortable, upgraded, true a/c, and beautiful"

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."

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."

More cheap stays in Chianti Region

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

Rp1.057.150

Rp1.193.507 total

15 Sept - 16 Sept

includes taxes & fees

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

Rp2.356.094

Rp2.652.988 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 Rp1.193.507

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

Villa di Sotto

Borgo Argenina

Chianti Village Morrocco

Borgo Argiano

Villa San Filippo

Villa il Fedino

Castello Del Nero - Podere San Filippo

Villa Cassia di Baccano

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

Relais Villa Belvedere

Rocca di Castagnoli

La Locanda di Pietracupa

Relais Badia a Passignano

Antico Borgo il Cardino

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

hu Firenze Certosa camping in town

Relais Vignale & Spa

Fattoria di Vegi

Castello Vicchiomaggio

Salvadonica - Borgo del Chianti

Borgo Vescine

Villa Le Barone

Hotel Villa Campomaggio

Chapter Chianti, a Member of Design Hotels

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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