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

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

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.

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

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

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

2. La Certosa di Pontignano

Castelnuovo Berardenga

Roberto

Rp1.715.875

Rp2.049.760 total

includes taxes & fees

19 Oct - 20 Oct

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

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

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.

3. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

Rp2.008.176

Rp2.269.848 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

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

4. Villa Le Barone

Greve in Chianti

Aditi

Rp4.011.926

Rp4.534.827 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

A stone house with a tiled roof, surrounded by greenery and a gravel path.

5. Podere L'Aquila

Gaiole in Chianti

Heather

Rp2.987.314

Rp8.296.343 total

includes taxes & fees

5 Oct - 6 Oct

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

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

A hotel room with 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.

6. Hotel Valdarno

Montevarchi

Emmanuel

Rp2.157.471

Rp2.373.299 total

includes taxes & fees

14 Oct - 15 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 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.

7. 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 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 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.

8. Villa Castiglione

Impruneta

Lee

Rp2.975.549

Rp3.334.519 total

includes taxes & fees

29 Sept - 30 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 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 stone building with a courtyard, a covered seating area, and a small bell tower.

9. Borgo di Pietrafitta Relais

Castellina in Chianti

Alejandro

Rp1.593.153

Rp1.833.526 total

includes taxes & fees

25 Oct - 26 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 landscaped garden with a swimming pool, a vineyard in the background, and a stone pathway.

10. 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 room with a TV mounted on the wall displaying a SmartTV interface, a small desk with a chair, and a bottle of champagne on the table.

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.

11. Hotel Toscana

Figline e Incisa Valdarno

Anonymous traveller

Rp2.333.763

Rp2.597.847 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 restaurant interior with wooden beams, a bar area, and tables with wine bottles.

12. Hotel Bellavista Impruneta

Impruneta

Caitlin

Rp1.477.306

Rp1.706.922 total

includes taxes & fees

8 Oct - 9 Oct

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

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

A pool with clear blue water, surrounded by white lounge chairs and umbrellas, with a view of distant mountains.

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.

13. Agriturismo Antico Borgo Poggitazzi

Terranuova Bracciolini

Michael

Rp1.888.294

Rp2.178.567 total

includes taxes & fees

26 Sept - 27 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 spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.

14. Locanda le Piazze

Castellina in Chianti

Tara

Rp6.220.563

Rp6.965.449 total

includes taxes & fees

18 Oct - 19 Oct

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

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

A pool area with a view of a hilly landscape.

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.

15. Borgo Del Cabreo

Greve in Chianti

Brian

Rp5.626.139

Rp6.269.972 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

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

16. Locanda Il Gallo

Greve in Chianti

Santina

Rp2.024.773

Rp2.288.105 total

includes taxes & fees

29 Sept - 30 Sept

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

An indoor dining area with stone walls, tables set with tablecloths and chairs, and hanging pendant lights.

A stone building with a wooden door and an arched window.

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

17. Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa

Sergey

Rp2.374.959

Rp2.734.163 total

includes taxes & fees

24 Oct - 25 Oct

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 reception area with a stone counter, a sign for SPA VILLA CASAGRANDE, and a staircase leading to a glass door.

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

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

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

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

19. 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

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

A clear swimming pool with lounge chairs and umbrellas, surrounded by trees and a building in the background.

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.

20. Villa San Lucchese

Poggibonsi

Simona

Rp2.240.078

Rp2.586.915 total

includes taxes & fees

2 Oct - 3 Oct

View all properties

Holiday Rentals in Chianti Region

Townhouse

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

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

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.

Villa Curina Resort

Castelnuovo Berardenga

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

Aparthotel

A stone building with a garden in front.

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

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

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."

Townhouse

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

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

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

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

Villa di Sotto

Castelnuovo Berardenga

"Great spot"

Holiday Home

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

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

A villa with a swimming pool surrounded by olive trees and a vineyard 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!"

Residence

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

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

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

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!"

Residence

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

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

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

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

Villa San Filippo

Barberino Val d'Elsa

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

Residence

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

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

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

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

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 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.

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.

Terre di Baccio

Greve in Chianti

"The stay was great, and the staff were wonderful. "

Townhouse

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

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

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.

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

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

A dining area with tables set for meals, a bar area with shelves of bottles, and a wooden cabinet.

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

A buffet with various food items, including cheeses, meats, and condiments.

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 stone building with a swimming pool and outdoor seating.

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.

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.

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

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

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

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

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

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."

Fattoria di Vegi

10/10 Excellent

"All aspects were superb and I highly recommend Vegi to friends, family and others. Beautiful locale and facility aesthetics, very well appointed, and excellent service."

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

Rp2.975.549

Rp3.334.519 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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Castello di Pratelli

Via Di Pratelli 1/a Figline e Incisa Valdarno FI

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9.2/10 Wonderful! (5 reviews)

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)

Quercia Al Poggio

Strada Di Quercia Al Poggio 4 Barberino Tavarnelle FI

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Tenuta La Pieve Casale Presciano

Via di Migliari Pergine Valdarno AR

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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 Rp1.706.922

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. Moody smart & comfy Hotel

4. Villa Le Barone

5. Podere L'Aquila

6. Hotel Valdarno

7. Villa I Barronci Resort & Spa

8. Villa Castiglione

9. Borgo di Pietrafitta Relais

10. Hotel Villa Campomaggio

11. Hotel Toscana

12. Hotel Bellavista Impruneta

13. Agriturismo Antico Borgo Poggitazzi

14. Locanda le Piazze

15. Borgo Del Cabreo

16. Locanda Il Gallo

17. Hotel Borgo di Cortefreda Relais

18. Villa Casagrande Resort & SPA

19. Hotel Palazzo San Lorenzo & SPA

20. Villa San Lucchese

Holiday Rentals in Chianti Region

Villa Curina Resort

Borgo Argenina

Villa di Sotto

Borgo Argiano

Riserva di Fizzano Residence

Villa San Filippo

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

Castello Vicchiomaggio

Villa Il Palagio

Fattoria di Vegi

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

Castello di Pratelli

Agriturismo Il Caggio di Sotto

Quercia Al Poggio

Tenuta La Pieve Casale Presciano

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