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

Pool

Pet friendly

Spa

Farm

Apartment

Apart hotel

Hot tub

Family friendly

Waterpark

Condo

Check prices for these dates

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This weekend

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Our top choices for Chianti Region hotels

Hotel

Breakfast included

Bed & breakfast

Reserve now, pay later

Pool

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

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

A table set with wine glasses and a candle, viewed through a window with string lights.

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

1. Tenuta CorteDomina

Radda in Chianti

Dustin

Rp4.962.850

Rp5.541.818 total

includes taxes & fees

26 Aug - 27 Aug

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

2. La Certosa di Pontignano

Castelnuovo Berardenga

Edyta

Rp1.453.358

Rp1.764.038 total

includes taxes & fees

8 Sept - 9 Sept

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

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

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

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

3. Hotel Villa Campomaggio

Radda in Chianti

Stacey

Rp4.227.987

Rp4.774.727 total

includes taxes & fees

24 Sept - 25 Sept

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 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.

4. Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

Lauren

Rp3.288.614

Rp3.741.499 total

includes taxes & fees

25 Sept - 26 Sept

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 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.

5. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Elizabeth Ann Brand

Rp3.576.973

Rp4.017.354 total

includes taxes & fees

28 Aug - 29 Aug

An outdoor patio with round tables and chairs, set against a backdrop of mountains and a cloudy sky.

A room with a sofa, a desk, a bunk bed, and a patterned floor.

A yellow building with stone pillars, multiple windows, and a statue in the garden.

A room with a fireplace, two armchairs, a sofa, a chandelier, and a large mirror on the wall.

6. Villa San Lucchese

Poggibonsi

Simona

Rp2.662.688

Rp3.052.980 total

includes taxes & fees

9 Sept - 10 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 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.

7. Villa Le Barone

Greve in Chianti

Aditi

Rp3.930.442

Rp4.447.510 total

includes taxes & fees

31 Aug - 1 Sept

An outdoor dining area with multiple tables and umbrellas, surrounded by greenery and hills in the background.

A resort with a large swimming pool, sun loungers, and umbrellas.

A modern bedroom with a large bed, a wooden headboard, a built-in bathtub, and a stone wall.

A dining area with a wooden table, chairs, and a decorative glass centerpiece.

8. Palagina la cascina

Figline e Incisa Valdarno

Peter

Rp1.352.508

Rp1.508.422 total

includes taxes & fees

7 Sept - 8 Sept

A rock garden with various succulents and plants.

A modern bedroom with a large bed, a nightstand, a chair, and a TV.

A modern hotel lobby with a curved reception desk, seating areas, and large windows.

A modern reception area with a wooden reception desk, a laptop, and a potted plant.

9. Hotel Toscana Ambassador

Poggibonsi

Shalayna

Rp1.217.257

Rp1.462.963 total

includes taxes & fees

31 Aug - 1 Sept

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

An outdoor courtyard with stone walls, potted plants, and a wooden door leading to an interior space.

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

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

10. Hotel Tenuta Il Burchio

Figline e Incisa Valdarno

Rp1.643.377

Rp1.838.721 total

includes taxes & fees

2 Sept - 3 Sept

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

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.

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

Rp2.198.537

Rp2.418.473 total

includes taxes & fees

27 Aug - 28 Aug

A spacious indoor area with arched windows, wooden furniture, and hanging plants.

A pool with a view of a hilly landscape, outdoor seating, and a stone wall.

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.

12. Relais Villa Olmo

Impruneta

Rupert

Rp3.119.398

Rp3.493.350 total

includes taxes & fees

26 Aug - 27 Aug

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 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.

13. Villa Castiglione

Impruneta

Lee

Rp2.019.640

Rp2.283.615 total

includes taxes & fees

30 Aug - 31 Aug

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

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

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

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

14. Moody smart & comfy Hotel

Terranuova Bracciolini

Maurizio

Rp2.096.438

Rp2.368.072 total

includes taxes & fees

14 Sept - 15 Sept

A kitchen counter with various food items and kitchenware.

A dining area with a brick fireplace, a table set with plates and bowls, and a bookshelf with books and decorative items.

15. Residenza Il Colle

Impruneta

ANTONIO

Rp2.567.302

Rp2.886.044 total

includes taxes & fees

25 Sept - 26 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 stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

A rustic stone building with a garden in front.

A person relaxing in a hot tub with a view of a building and trees in the background.

16. Belvedere di San Leonino

Castellina in Chianti

Jess

Rp2.044.953

Rp2.373.411 total

includes taxes & fees

21 Sept - 22 Sept

A scenic outdoor venue with multiple covered seating areas and a view of the surrounding landscape.

A spa room with a massage table, towels, and candles.

A terraced garden with a pool, outdoor seating, and a view of rolling hills.

A restaurant with white tables and chairs, wine bottles on shelves, and a chandelier.

17. Azienda agricola la camporena

Greve in Chianti

Pawel

Rp2.604.510

Rp2.947.644 total

includes taxes & fees

26 Aug - 27 Aug

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

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

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

A spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.

18. Locanda le Piazze

Castellina in Chianti

Oluwafunmilayo

Rp6.762.541

Rp7.562.775 total

includes taxes & fees

9 Sept - 10 Sept

An outdoor dining area with tables and chairs, surrounded by greenery and a stone pathway.

A view through a window of a building with a tiled roof, bare trees, and a hillside in the background.

A restaurant interior with wooden beams, a bar area, and tables with wine bottles.

A cozy room with a fireplace, a bookshelf, and a comfortable seating area with a view of the outdoors.

19. Hotel Bellavista Impruneta

Impruneta

Nancy

Rp1.417.090

Rp1.641.482 total

includes taxes & fees

26 Aug - 27 Aug

A formal garden with neatly trimmed hedges, a gravel path, and tall trees.

A dining area with tables set for two, featuring a rustic ceiling and a view of the outdoors through a door.

A bedroom with a large window, a striped armchair, a purple ottoman, and a patterned rug.

A swimming pool with lounge chairs and a view of vineyards and mountains.

20. Torre a Cona Wine Estate

Rignano sull'Arno

Danielle

Rp4.680.936

Rp5.211.042 total

includes taxes & fees

31 Aug - 1 Sept

View all properties

Holiday Rentals in Chianti Region

Residence

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

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

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

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

Villa San Filippo

Barberino Tavarnelle

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

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 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

Barberino Tavarnelle

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

Townhouse

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 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

"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...

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.

An outdoor dining area with a table set for breakfast, surrounded by dense greenery and a tall tree.

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

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"

Apartment

A swimming pool with a clear blue water surface, surrounded by a well-lit deck area with outdoor seating.

A spacious hallway with an arched ceiling, wooden beams, and a view of a dining area with tables and chairs.

A breakfast table with bowls of cereal, a glass of orange juice, and a cup.

A corridor with a tiled floor leading to a building with a white exterior and multiple windows.

Villa Il Palagio

Rignano sull'Arno

"Clean room. Staff was amazing and friendly! Breakfast was delicious. The place is super relaxing. Pool is bra. Rooms are SQUEAKY CLEAN and spacious! Would absolutely come back!"

Townhouse

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

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.

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

La Locanda di Pietracupa

Barberino Tavarnelle

"Charming and very original. Great warmth from the staff and very helpful. Enjoyed the room and restaurant at and surrounding towns."

Townhouse

A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

A room with a window featuring sheer curtains, a radiator below, and a view of a green landscape.

A covered outdoor seating area with wicker furniture and potted plants.

A bedroom with a bed, a painting, and a bathroom door.

Mariani Bed & Breakfast

Castellina in Chianti

"Very nice and quiet neighbourhood. Close to city centre. The host is very kind."

Camping

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

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

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

A restaurant interior with wooden beams, hanging plants, and a variety of seating arrangements.

Glamping Village Orlando in Chianti

Cavriglia

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

Aparthotel

A stone building with a tiled roof, a chimney, and a circular window.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

A stone staircase leading to a door, surrounded by a well-maintained garden with various plants and a clear view of the countryside.

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

Podere il Pino

Poggibonsi

"Beautiful place to stay. Great for kids and has an amazing view. "

Townhouse

A restaurant with hanging baskets of greenery, wicker furniture, and a view of the outdoors.

A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

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

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

Terre di Baccio

Greve in Chianti

"We had a wonderful experience! The staff was kind and very helpful. Our room was stunning and very spacious for a family of 5! The breakfast was amazing, and all of the activities on site were very fun - we especially enjoyed the cooking class! I would absolutely love to return here. I recommend looking into and booking on-site activities in advance so you can get the most out of your experience!"

Townhouse

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

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.

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

Antico Borgo il Cardino

San Gimignano

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

Camping

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

A modern bedroom with a bed, an air conditioning unit, a bedside lamp, a laptop, and a mirror.

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

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."

Camping

A pool area with a water slide and a stage for performances.

A wooden interior with a high ceiling, a wooden door, and a view of an outdoor deck with chairs.

A wooden cabin with a deck, a dining area, and a lounge with a table and chairs.

A modern wooden cabin with a deck, surrounded by lush greenery and a clear sky.

Hu Norcenni Girasole Village

Figline e Incisa Valdarno

"We all loved this place. It is conveniently close to Florence or Sienna so you can take a day trips if you get bored but there are plenty of activities on site. We wished we have reserved more days to stay but we will do that next year."

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

"It was a wonderful stay the bed was comfortable and the view was beautiful. "

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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 stunning cathedral 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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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 cosy cafes in this walkable 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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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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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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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

La pietra del cabreo

10/10 Excellent

"Such a wonderful stay! The property is beautiful and everything is well appointed. We arrived and were upgraded to an incredible suite with sweeping views of the Tuscan hills. The pool is great, the staff is great, breakfast is great. Will definitely stay again!"

Castello Vicchiomaggio

10/10 Excellent

"Staff was incredibly friendly, rooms very clean and were cleaned every day, and the property is amazing! The restaurant had such great food with a nice atmosphere as well! Highly recommend staying here!"

Villa Casagrande Resort & SPA

10/10 Excellent

"Incredible property, steeped in history. The rooms are beautifully traditional and the staff incredibly friendly. A beautiful place to unwind for a few days in Tuscany! We would re-book in a heartbeat."

Park Hotel Chianti

10/10 Excellent

"A clean hotel, we got upgraded so no issues on room was updated and pleasant, AC could have been stronger but was ok, nice buffet breakfast with good assortment of food:) Front desk ladies were helpful in giving restaurant suggestions in the surrounding area 👌"

Belvedere di San Leonino

10/10 Excellent

"The most beautiful and breathtaking place to stay. The staff were lovely, the rooms were quiet, the views were exceptional. The breakfast was perfect. Idyllic!"

Hu Norcenni Girasole Village

10/10 Excellent

"Two large pool sites. Helpful staff. Lots of entertainment. Restaurant options and a well stocked reasonably priced food market."

Hotel Toscana Ambassador

10/10 Excellent

"Room was clean, staff was helpful and easy to park."

More cheap stays in Chianti Region

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

Rp1.458.695

Rp1.666.577 total

26 Aug - 27 Aug

includes taxes & fees

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

Rp2.019.640

Rp2.283.615 total

30 Aug - 31 Aug

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

Explore a world of travel with Expedia

More ways to book

Book Hotels in Chianti Region on Expedia.it

Find hotels in Chianti Region from Rp1.508.422

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. Tenuta CorteDomina

2. La Certosa di Pontignano

3. Hotel Villa Campomaggio

4. Villa I Barronci Resort & Spa

5. Hotel Palazzo San Lorenzo & SPA

6. Villa San Lucchese

7. Villa Le Barone

8. Palagina la cascina

9. Hotel Toscana Ambassador

10. Hotel Tenuta Il Burchio

11. Hotel Valdarno

12. Relais Villa Olmo

13. Villa Castiglione

14. Moody smart & comfy Hotel

15. Residenza Il Colle

16. Belvedere di San Leonino

17. Azienda agricola la camporena

18. Locanda le Piazze

19. Hotel Bellavista Impruneta

20. Torre a Cona Wine Estate

Holiday Rentals in Chianti Region

Villa San Filippo

Chianti Village Morrocco

Villa il Fedino

Residence Poggio del Golf

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

Villa Il Palagio

La Locanda di Pietracupa

Mariani Bed & Breakfast

Glamping Village Orlando in Chianti

Podere il Pino

Terre di Baccio

Antico Borgo il Cardino

hu Firenze Certosa camping in town

Hu Norcenni Girasole Village

B&B La Fonte del Machiavelli

Stay near popular Chianti Region attractions

Antinori nel Chianti Classico

The Mall Luxury Outlet

Tenuta Torciano Winery

Castle of Brolio

Verrazzano Castle

Castello di Albola

Castello di Radda Winery

Meleto Castle

Learn more about Chianti Region

Top Chianti Region Hotel Reviews

La pietra del cabreo

Castello Vicchiomaggio

Villa Casagrande Resort & SPA

Park Hotel Chianti

Belvedere di San Leonino

Hu Norcenni Girasole Village

Hotel Toscana Ambassador

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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