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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Our top choices for Chianti Region hotels

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.

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

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

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

1. La Certosa di Pontignano

Castelnuovo Berardenga

Malena

Rp2.373.430

Rp2.774.828 total

includes taxes & fees

30 Sept - 1 Oct

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

A bathroom with a bathtub, a window with a view of a vineyard, and a small table with a bottle and glasses.

2. Tenuta CorteDomina

Radda in Chianti

Dustin

Rp4.480.749

Rp5.010.851 total

includes taxes & fees

30 Sept - 1 Oct

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

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

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.

3. Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

Juan Antonio

Rp2.496.617

Rp2.869.319 total

includes taxes & fees

8 Oct - 9 Oct

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.

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

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

4. Villa Castiglione

Impruneta

Lee

Rp2.338.901

Rp2.634.312 total

includes taxes & fees

14 Sept - 15 Sept

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

5. Villa Le Barone

Greve in Chianti

Aditi

Rp4.322.099

Rp4.877.350 total

includes taxes & fees

13 Sept - 14 Sept

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

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 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.

6. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

Rp2.078.867

Rp2.348.223 total

includes taxes & fees

21 Sept - 22 Sept

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

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

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

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

7. Hotel Il Castello

Certaldo Alto

Thomas

Rp2.392.105

Rp2.733.850 total

includes taxes & fees

14 Sept - 15 Sept

A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.

A modern interior with a bar area, seating, and a staircase.

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

A vineyard landscape with rows of grapevines and a person holding a glass.

8. Locanda le Piazze

Castellina in Chianti

Mark

Rp6.711.336

Rp7.505.511 total

includes taxes & fees

24 Sept - 25 Sept

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

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.

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

9. Palagina la Dimora

Figline e Incisa Valdarno

Tarek

Rp2.006.690

Rp2.248.373 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 cozy room with a large window, a wooden table, a red chair, a bookshelf, and a cactus plant.

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

10. Le Cetinelle B&B

Greve in Chianti

Sebastian

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

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

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

A garden with neatly trimmed hedges, a gravel path, and a stone barrel.

11. Castello Vicchiomaggio

Greve in Chianti

Maryse

Rp3.115.569

Rp3.427.125 total

includes taxes & fees

29 Sept - 30 Sept

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

12. Hotel Villa Campomaggio

Radda in Chianti

Krishna

Rp4.144.231

Rp4.681.716 total

includes taxes & fees

29 Sept - 30 Sept

An outdoor patio area with a brick archway, potted plants, and wicker furniture.

A swimming pool with steps leading into it, surrounded by lounge chairs and a stone wall with greenery.

A room with a large window, a radiator, and a television on a stand.

A dining area with a fireplace, wooden beams, and a tiled floor.

13. Hotel Tenuta Il Burchio

Figline e Incisa Valdarno

Rp1.491.594

Rp1.671.514 total

includes taxes & fees

20 Sept - 21 Sept

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 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.

14. Belvedere di San Leonino

Castellina in Chianti

Seong Won

Rp2.028.744

Rp2.354.598 total

includes taxes & fees

21 Sept - 22 Sept

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

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

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

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

15. Borgo di Pietrafitta Relais

Castellina in Chianti

Alejandro

Rp2.665.892

Rp3.014.508 total

includes taxes & fees

4 Oct - 5 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 table set for two with wine glasses and a bottle, overlooking a scenic landscape.

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

16. 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

Rp4.435.018

Rp4.960.609 total

includes taxes & fees

3 Oct - 4 Oct

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

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

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

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

17. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Maria

Rp3.322.112

Rp3.736.350 total

includes taxes & fees

6 Oct - 7 Oct

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

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

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

A spacious living room with a high ceiling, large windows with diamond-patterned blinds, a sofa set, a coffee table, and a painting on the wall.

18. Borgo Del Cabreo

Greve in Chianti

joseph

Rp5.033.502

Rp5.618.879 total

includes taxes & fees

9 Sept - 10 Sept

A spacious living area with a large window, a sofa, a green armchair, and a patterned armchair.

A stone building with a tower, a glass structure, and outdoor seating.

A bedroom with a bed, bedside tables, a rug, and a view of the outdoors.

A swimming pool with clear water, surrounded by lounge chairs and trees.

19. Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

Ivis

Rp3.841.960

Rp4.308.286 total

includes taxes & fees

5 Oct - 6 Oct

A buffet with various food items and utensils.

A hotel room with a large bed, bedside tables, a nightstand, a vase with flowers, a tray with pastries, a teapot, and a glass of orange juice.

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".

20. Hotel Il Viandante

Terranuova Bracciolini

Michelle

Rp1.752.435

Rp2.337.815 total

includes taxes & fees

7 Oct - 8 Oct

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.

A stone pathway leading to a terrace with potted plants and flowers, overlooking a hillside with houses.

A stone building with a garden, outdoor seating, and a large tree.

Relais Villa Olmo

Impruneta

"Delightful location, comfortable bed, excellent food."

Residence

A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

A stone building with a wooden door and a balcony with flower planters.

An outdoor dining area with tables and chairs, a pergola structure, and potted plants.

A buffet setup with various baked goods and pastries, including a bundt cake, arranged on a wooden table with a stone wall background.

Riserva di Fizzano Residence

Castellina in Chianti

"Great place to stay in Tuscany! Very nice breakfast also!"

Townhouse

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

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

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

"Beautiful property"

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 restaurant with tables set for dining, large windows offering a view of the landscape, and a wooden ceiling structure.

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

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

Villa di Sotto

Castelnuovo Berardenga

"Great spot"

Holiday Home

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

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

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

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

Borgo Argiano

Castelnuovo Berardenga

"Amazing staff, clean room, amazing pool!"

Aparthotel

A stone building with a garden in front.

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

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

Villa il Fedino

San Casciano in Val di Pesa

Residence

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

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

A grassy area with a stone wall and a wooden fence.

A swimming pool with a white fence and a lifebuoy, surrounded by trees and a sunset.

Chianti Village Morrocco

Tavarnelle Val di Pesa

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

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"

Residence

A hillside villa with a swimming pool, terraced gardens, and a church tower.

A kitchen with wooden cabinets, a brick archway, and a vase with sunflowers.

A swimming pool with a view of rolling hills in the background.

A stone building with arched windows and a patio area with outdoor seating.

Borgo Sicelle

Castellina in Chianti

"Beautiful stay if you want to live the real Tuscany feeling. Hotel staff was extremely friendly, helpful and the overall property is extremely neat, always keeping the Italian style. "

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.

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

An arched entrance to a building with a tiled floor and a staircase leading inside.

Palazzo Pacini

Colle di Val d'Elsa

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

Residence

A breakfast buffet with various food items and beverages.

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

A nighttime swimming pool with lounge chairs and tall trees.

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".

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

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

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."

Camping

An outdoor seating area with a sofa, tables, and chairs, surrounded by a wooden deck and a canopy.

A spacious tented living area with a sofa, coffee table, and dining setup.

A wooden cabin with a ladder, a small porch, and a table with chairs.

A swimming pool with a stone wall and a building with outdoor seating and string lights.

Glamping Village Orlando in Chianti

Cavriglia

"Had an amazing stay and wished we'd had longer there"

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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

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!"

hu Firenze Certosa camping in town

8/10 Good

"We spent 3 nights here, due to being a family of 6 we had x2 bungalows. The rooms themselves are a little tired, broken shower doors, dusty and some appliances not working, but the location is phenomenal. I would not recommend to anyone with mobility issues as it is on a steep hill. The staff are very helpful and incredibly friendly. There is a busy motorway nearby, the noise is a constant humm but didn’t disturb our stay. The restaurant on site is really good, very reasonably priced and the food was fresh and a gave a nice flavour of the Italian cuisine: Only 20 mins from Florence (about €30 by taxi) but remote that there isn’t much that is walkable from the site. 100% I would recommend as a stop over, few nights or a great hub to explore the Tuscan area!"

Villa Le Barone

10/10 Excellent

"We had a wonderful stay here! The room was very clean and comfortable, and the staff was incredibly helpful, friendly, and welcoming. The location was perfect, and we especially loved the self-service beverage area — such a thoughtful and convenient touch. The owner was super friendly and took the time to come over and talk with us. He was a perfect gentleman and made us feel genuinely welcome. Our only regret is that we could stay for just one night\! We truly enjoyed our time here and would definitely come back again. Highly recommended."

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!"

Hotel Villa Campomaggio

10/10 Excellent

"Beautiful hotel room and location, definitely recommend!"

Belvedere di San Leonino

10/10 Excellent

"Staff is great. Room clean. Property beautiful and dinner was delicious"

Villa Sabolini

10/10 Excellent

"We couldn’t rate Villa Sabolini more highly - we had such an excellent time. It is a beautiful property and the perfect place to relax and enjoy Tuscany. The staff were so helpful and friendly too."

More cheap stays in Chianti Region

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

Rp1.061.230

Rp1.198.113 total

9 Sept - 10 Sept

includes taxes & fees

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

Rp2.338.901

Rp2.634.312 total

14 Sept - 15 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 Rp1.198.113

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. La Certosa di Pontignano

2. Tenuta CorteDomina

3. Villa I Barronci Resort & Spa

4. Villa Castiglione

5. Villa Le Barone

6. Moody smart & comfy Hotel

7. Hotel Il Castello

8. Locanda le Piazze

9. Palagina la Dimora

10. Le Cetinelle B&B

11. Castello Vicchiomaggio

12. Hotel Villa Campomaggio

13. Hotel Tenuta Il Burchio

14. Belvedere di San Leonino

15. Borgo di Pietrafitta Relais

16. Villa il Fedino

17. Hotel Palazzo San Lorenzo & SPA

18. Borgo Del Cabreo

19. Salvadonica - Borgo del Chianti

20. Hotel Il Viandante

Holiday Rentals in Chianti Region

Relais Villa Olmo

Riserva di Fizzano Residence

Villa Curina Resort

Villa di Sotto

Borgo Argiano

Borgo Argenina

Villa il Fedino

Chianti Village Morrocco

Villa San Filippo

Borgo Sicelle

Palazzo Pacini

Residence Poggio del Golf

Antica Pieve B&B

Relais Badia a Passignano

Glamping Village Orlando in Chianti

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

Chapter Chianti, a Member of Design Hotels

Villa Il Palagio

hu Firenze Certosa camping in town

Villa Le Barone

Castello Vicchiomaggio

Fattoria di Vegi

Hotel Villa Campomaggio

Belvedere di San Leonino

Villa Sabolini

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

Explore a world of travel with Expedia

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