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

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

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.

1. Tenuta CorteDomina

Radda in Chianti

Dustin

Rp4.432.187

Rp4.956.544 total

includes taxes & fees

5 Oct - 6 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 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.

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

2. La Certosa di Pontignano

Castelnuovo Berardenga

Roberto

Rp1.715.875

Rp2.049.760 total

includes taxes & fees

19 Oct - 20 Oct

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

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

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

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

3. Villa Le Barone

Greve in Chianti

Aditi

Rp4.011.926

Rp4.534.827 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

4. Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

Juan Antonio

Rp1.661.309

Rp1.949.148 total

includes taxes & fees

25 Oct - 26 Oct

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 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.

5. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

Rp2.008.176

Rp2.269.848 total

includes taxes & fees

27 Sept - 28 Sept

A terrace with stone arches, green plants, and a table set for dining with a scenic mountain view.

A stone-walled room with a sofa, a coat rack, and a window with curtains.

A stone building with a balcony, potted plants, and a view of distant hills.

A rectangular swimming pool with a view of mountains in the background.

6. Podere L'Aquila

Gaiole in Chianti

Heather

Rp2.987.314

Rp8.296.343 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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.

7. Hotel Valdarno

Montevarchi

Emmanuel

Rp2.157.471

Rp2.373.299 total

includes taxes & fees

28 Sept - 29 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.

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

8. Villa Castiglione

Impruneta

Lee

Rp2.948.368

Rp3.304.059 total

includes taxes & fees

29 Sept - 30 Sept

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

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

9. Villa San Lucchese

Poggibonsi

Simona

Rp2.219.616

Rp2.563.285 total

includes taxes & fees

25 Sept - 26 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 building with three storefronts: VINO-OLIO, RISTORO, and HOTEL BELLAVISTA.

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

10. Hotel Bellavista Impruneta

Impruneta

Caitlin

Rp1.463.811

Rp1.691.330 total

includes taxes & fees

19 Oct - 20 Oct

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

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

11. Hotel Villa Campomaggio

Radda in Chianti

Dario

Rp3.402.135

Rp3.864.015 total

includes taxes & fees

25 Oct - 26 Oct

A modern lobby with a bar area, seating, and a large window.

A hotel entrance with a covered staircase, potted plants, and a sign indicating it is a hotel and restaurant.

An outdoor patio with tables and chairs, potted plants, and a view of the cityscape.

A buffet area with various food items, condiments, and a refrigerator.

12. Hotel Toscana

Figline e Incisa Valdarno

Anonymous traveller

Rp2.312.445

Rp2.574.117 total

includes taxes & fees

25 Sept - 26 Sept

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

13. Locanda le Piazze

Castellina in Chianti

Tara

Rp6.163.740

Rp6.901.822 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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 table set for four with wine glasses and plates.

14. Borgo di Pietrafitta Relais

Castellina in Chianti

Alejandro

Rp1.593.153

Rp1.833.526 total

includes taxes & fees

20 Oct - 21 Oct

A hotel entrance with a glass facade, a brown awning, and a garden with pink flowers.

A spacious lobby with a reception desk, a staircase with a glass railing, and a wooden floor.

A hotel room with a bed, a desk, a chair, and a window with curtains.

A spacious living area with a sofa, a coffee table, and a view of buildings through large windows.

15. Hotel La Vecchia Cartiera

Colle di Val d'Elsa

Sheila

Rp1.410.702

Rp1.612.627 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

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

16. Locanda Il Gallo

Greve in Chianti

Santina

Rp2.024.773

Rp2.288.105 total

includes taxes & fees

29 Sept - 30 Sept

A stone building with a brick facade, a well-maintained lawn, and a pathway leading to the entrance.

A stone building with arched windows and a courtyard.

A rustic kitchen with wooden cabinets, a dining table set for two, and a sofa in a cozy corner.

A patio with green metal chairs and tables, a white building with large windows, and a view of a hill with greenery and a house in the distance.

17. Agriturismo Antico Borgo Poggitazzi

Terranuova Bracciolini

Michael

Rp1.888.294

Rp2.178.567 total

includes taxes & fees

26 Sept - 27 Sept

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

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

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

An indoor swimming pool with clear glass walls, wooden beams, and large windows.

18. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

Rp2.248.088

Rp2.513.466 total

includes taxes & fees

25 Oct - 26 Oct

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.

19. Hotel Il Castello

Certaldo Alto

Kenneth

Rp2.366.179

Rp2.704.220 total

includes taxes & fees

27 Sept - 28 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 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.

20. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Maria

Rp2.987.370

Rp3.367.245 total

includes taxes & fees

25 Oct - 26 Oct

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Holiday Rentals in Chianti Region

Townhouse

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

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

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.

Villa Curina Resort

Castelnuovo Berardenga

"Beautiful resort in the hills, lovely and charming room, incredibly spacious."

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 pool area with a view of vineyards and hills.

Riserva di Fizzano Residence

Castellina in Chianti

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

Aparthotel

A stone building with a garden in front.

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

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

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

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.

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

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 a garden, set in a rural landscape with vineyards in the background.

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

Borgo Argiano

Castelnuovo Berardenga

"Amazing staff, clean room, amazing pool!"

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"

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

Chianti Village Morrocco

Tavarnelle Val di Pesa

"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."

Townhouse

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

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

Terre di Baccio

Greve in Chianti

"Amazing property. Air conditioning works. Dinner and breakfast is first class. Free parking"

Townhouse

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

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

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.

Villa il Fedino

San Casciano in Val di Pesa

"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."

Townhouse

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

A swimming pool surrounded by lush greenery and a forested hillside.

A stone building with arched windows and a balcony overlooking a garden with lavender plants.

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

B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

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

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

A bedroom with a stone archway, a wooden dresser, and a chandelier.

Relais Villa Belvedere

Figline e Incisa Valdarno

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

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."

Townhouse

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

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.

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

Antico Borgo il Cardino

San Gimignano

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

Townhouse

A cozy living room with a stone wall, a wine rack, and two sofas.

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.

A dining area with white tables and chairs, stone walls, and large windows with curtains.

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

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

La Locanda di Pietracupa

Tavarnelle Val di Pesa

"Great place, wonderful restaurant"

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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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Piazza Matteotti

9.4/10 (21 reviews)

Find out about the history of Greve in Chianti with a stop at Piazza Matteotti. Discover the beautiful countryside in this quaint area or enjoy its local tours.

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Learn more about Chianti Region

Take a sightseeing trip of Tuscany's renowned wine region and visit its vineyards, wineries, ancient churches, castles and hilltop villages.

See all hotels in Chianti Region

Terraced vineyards on a hillside, a small village, and rolling green hills.

Top Chianti Region Hotel Reviews

Fattoria di Vegi

10/10 Excellent

"This is a newly renovated and opened property cared for by a wonderful family. Everything has been taken care of down to the last detail. The food is delicious, the rooms are well appointed and till we thoroughly enjoyed exploring the property and every interesting nook! There's lots to do including a ping pong table and a beautiful pool. My only regret was not staying longer"

Castello Vicchiomaggio

8/10 Good

"Really liked the location! Helpful staff."

Villa Il Palagio

10/10 Excellent

"The check in went great and the property is amazingly managed, a beautiful villa in the hills of Tuscany. It felt magic just walking to it, I would absolutely recommend renting a car if you want to go into Florence often."

Hotel Villa Campomaggio

10/10 Excellent

"Great hotel"

Hu Norcenni Girasole Village

10/10 Excellent

"Perfect can’t fault it. Maybe a bigger train/bus at peak times would help. Lovely restaurant, bars, ice cream. Clean swimming pools. Good, kind, friendly staff. Safe place. Clean accommodation. Peaceful environment. Must take mosquito treatment as they’re bad out here. Lovely bonus is the pump at the pools to pump donuts up. Can’t fault it. Will 100000% return."

Salvadonica - Borgo del Chianti

10/10 Excellent

"Beautiful escape weekend. I would go back again and again. The staff was amazing. Food was incredible."

Relais Vignale & Spa

10/10 Excellent

"Beautiful small medieval town with castle and narrow streets. Close to wineries but not much else to do….location is very beautiful on top of hill."

Park Hotel Chianti

10/10 Excellent

"The staff are very helpful and kind."

Palagina la Dimora

8/10 Good

"Nice property to relax. Pool is nice. Breakfast is meh but works. Room was spacious although felt outdated and lacking lighting. Some staff were very helpful while some could have been more friendly."

More cheap stays in Chianti Region

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

Rp2.948.368

Rp3.304.059 total

29 Sept - 30 Sept

includes taxes & fees

8.6/10 Excellent! (276 reviews)

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

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Agriturismo Il Caggio di Sotto

Loc. Il Caggio di Sotto, 26 Colle di Val d'Elsa SI

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9.6/10 Exceptional! (16 reviews)

Castello di Pratelli

Via Di Pratelli 1/a Figline e Incisa Valdarno FI

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9.2/10 Wonderful! (5 reviews)

Hotel Albergo Italia

Via Trento, 36 Poggibonsi SI

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Quercia Al Poggio

Strada Di Quercia Al Poggio 4 Barberino Tavarnelle FI

Get rates

Explore a world of travel with Expedia

More ways to book

Book Hotels in Chianti Region on Expedia.it

Find hotels in Chianti Region from Rp1.691.330

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. Villa Le Barone

4. Villa I Barronci Resort & Spa

5. Moody smart & comfy Hotel

6. Podere L'Aquila

7. Hotel Valdarno

8. Villa Castiglione

9. Villa San Lucchese

10. Hotel Bellavista Impruneta

11. Hotel Villa Campomaggio

12. Hotel Toscana

13. Locanda le Piazze

14. Borgo di Pietrafitta Relais

15. Hotel La Vecchia Cartiera

16. Locanda Il Gallo

17. Agriturismo Antico Borgo Poggitazzi

18. Villa Casagrande Resort & SPA

19. Hotel Il Castello

20. Hotel Palazzo San Lorenzo & SPA

Holiday Rentals in Chianti Region

Villa Curina Resort

Riserva di Fizzano Residence

Borgo Argenina

Villa San Filippo

Borgo Argiano

Villa di Sotto

Chianti Village Morrocco

Terre di Baccio

Villa il Fedino

B&B La Fonte del Machiavelli

Relais Villa Belvedere

Relais Badia a Passignano

Antico Borgo il Cardino

Villa Cassia di Baccano

La Locanda di Pietracupa

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

Piazza Matteotti

Learn more about Chianti Region

Top Chianti Region Hotel Reviews

Fattoria di Vegi

Castello Vicchiomaggio

Villa Il Palagio

Hotel Villa Campomaggio

Hu Norcenni Girasole Village

Salvadonica - Borgo del Chianti

Relais Vignale & Spa

Park Hotel Chianti

Palagina la Dimora

More cheap stays in Chianti Region

Villa Castiglione

Villa Norcenni Aparthotel

Agriturismo Il Caggio di Sotto

Castello di Pratelli

Hotel Albergo Italia

Quercia Al Poggio

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