Chianti Region Holiday Rentals, Tuscany: Private House Rentals

A vineyard with rows of grapevines, a house surrounded by trees, and a road with vehicles.

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Go beyond your typical stay in Chianti Region

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

1. Tenuta CorteDomina

Radda in Chianti

Dustin

Rp4.690.386

Rp5.240.997 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 aerial view of a historic building complex with a central courtyard, surrounded by vineyards and greenery.

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.

2. La Certosa di Pontignano

Castelnuovo Berardenga

Leslie

Rp1.786.982

Rp2.128.824 total

includes taxes & fees

16 Oct - 17 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 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.

3. Hotel Valdarno

Montevarchi

Emmanuel

Rp2.168.998

Rp2.385.979 total

includes taxes & fees

5 Oct - 6 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.

4. Podere L'Aquila

Gaiole in Chianti

Heather

Rp3.003.275

Rp8.340.669 total

includes taxes & fees

5 Oct - 6 Oct

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

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

A modern 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.

5. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

Rp2.018.905

Rp2.281.975 total

includes taxes & fees

2 Oct - 3 Oct

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.

6. Hotel Bellavista Impruneta

Impruneta

Kimberly

Rp1.471.632

Rp1.700.367 total

includes taxes & fees

28 Sept - 29 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.

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

7. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

Rp2.190.601

Rp2.450.447 total

includes taxes & fees

26 Oct - 27 Oct

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

A terraced vineyard with stone walls and a stone pathway leading to a seating area with metal chairs and tables.

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

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

8. Castello Vicchiomaggio

Greve in Chianti

Maryse

Rp3.088.749

Rp3.397.624 total

includes taxes & fees

27 Oct - 28 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 table with breakfast items, a clear view of the countryside, and a white umbrella.

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

9. Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

Juan Antonio

Rp1.530.030

Rp1.805.391 total

includes taxes & fees

28 Oct - 29 Oct

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

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

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.

10. Villa Le Barone

Greve in Chianti

Aditi

Rp4.537.532

Rp5.113.644 total

includes taxes & fees

25 Oct - 26 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 stone building with a courtyard, a covered seating area, and a small bell tower.

11. Borgo di Pietrafitta Relais

Castellina in Chianti

Alejandro

Rp1.612.900

Rp1.855.762 total

includes taxes & fees

20 Oct - 21 Oct

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

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.

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

12. Terre di Baccio

Greve in Chianti

Gage

Rp10.353.147

Rp11.470.033 total

includes taxes & fees

28 Sept - 29 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 spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.

13. Locanda le Piazze

Castellina in Chianti

Tara

Rp6.196.671

Rp6.938.696 total

includes taxes & fees

16 Oct - 17 Oct

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

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.

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

14. Villa San Lucchese

Poggibonsi

James

Rp2.231.474

Rp2.576.980 total

includes taxes & fees

2 Oct - 3 Oct

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

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.

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

15. Hotel La Vecchia Cartiera

Colle di Val d'Elsa

Sheila

Rp1.468.295

Rp1.676.303 total

includes taxes & fees

28 Sept - 29 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 living room with a sofa, armchairs, a coffee table, and a painting on the wall.

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

16. Hotel Il Castello

Certaldo Alto

Kenneth

Rp2.378.821

Rp2.718.668 total

includes taxes & fees

30 Sept - 1 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.

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

A hallway with a tiled floor, a reception desk with a gold and white color scheme, and a framed abstract painting on the wall.

17. Villa Castiglione

Impruneta

Lee

Rp2.964.120

Rp3.321.711 total

includes taxes & fees

29 Sept - 30 Sept

A staircase with a modern design, featuring a combination of stone steps and a carpeted landing.

A modern bar area with a curved counter, a coffee machine, and a variety of bottles and glasses on shelves.

A hotel room with a bed, a TV, a desk, and a mirror.

A modern kitchen with a built-in microwave, sink, and stove. There is a dining area with a table and chairs, and a window with blinds.

18. Delta Hotel

Montevarchi

weixing

Rp2.335.924

Rp2.569.516 total

includes taxes & fees

28 Sept - 29 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 spa area with stone flooring, wooden chairs, a table with amenities, and a view of a garden through a glass door.

19. Hotel Villa Campomaggio

Radda in Chianti

Dario

Rp3.344.449

Rp3.801.252 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

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

20. Locanda Il Gallo

Greve in Chianti

Santina

Rp2.035.590

Rp2.300.328 total

includes taxes & fees

28 Sept - 29 Sept

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Holiday Rentals in Chianti Region

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

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

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 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.

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

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"

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.

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

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"

Holiday Home

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

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

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

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

Borgo Argiano

Castelnuovo Berardenga

"Amazing staff, clean room, amazing pool!"

Residence

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

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

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

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

A hammock suspended between trees in a garden with a view of a hilly landscape.

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

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

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.

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

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."

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

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

Antico Borgo il Cardino

San Gimignano

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

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"

Residence

A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

A two-story building with a symmetrical facade, green shutters, and a central arched entrance.

A stone building with a turret and a tree with purple flowers in front.

A room with a large arched window offering a view of a tree and landscape.

Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"

Townhouse

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

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

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.

Villa Cassia di Baccano

Loro Ciuffenna

"The staff were great and the villa was amazing"

Townhouse

A stone building with a tiled roof, multiple windows, and a prominent tower.

A terrace with stone walls, two wooden chairs with cushions, and a table.

A clear blue swimming pool with lounge chairs and umbrellas, surrounded by trees and a clear sky.

A rustic interior with a wooden dining table, a fireplace, a sofa, and a staircase.

Rocca di Castagnoli

Gaiole in Chianti

"It was wonderful to stay in a castle in Tuscany no less Every person we met was attentive and kind We were staying near friends and didn’t hang around the grounds much or use the pool but everything seemed well kept It’s really a place to retreat to eat at and sleep at which served our purpose well "

Townhouse

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

San Casciano in Val di Pesa

"Me and my girlfriend really did enjoy this property. Both host were very friendly and welcoming to us. We both did enjoy the feel at Home environment. We would definitely come back here on a future trip. Big shout out to the host for the wonderful cook meals. Great to know a bit about them as well."

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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 Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

Rp1.132.088

Rp1.275.886 total

28 Sept - 29 Sept

includes taxes & fees

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

Rp2.964.120

Rp3.321.711 total

29 Sept - 30 Sept

includes taxes & fees

8.6/10 Excellent! (276 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)

Castello di Pratelli

Via Di Pratelli 1/a Figline e Incisa Valdarno FI

Get rates

9.2/10 Wonderful! (5 reviews)

Hotel Albergo Italia

Via Trento, 36 Poggibonsi SI

Get rates

Quercia Al Poggio

Strada Di Quercia Al Poggio 4 Barberino Tavarnelle FI

Get rates

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Book Hotels in Chianti Region on Expedia.it

Find hotels in Chianti Region from Rp1.275.886

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 Valdarno

4. Podere L'Aquila

5. Moody smart & comfy Hotel

6. Hotel Bellavista Impruneta

7. Villa Casagrande Resort & SPA

8. Castello Vicchiomaggio

9. Villa I Barronci Resort & Spa

10. Villa Le Barone

11. Borgo di Pietrafitta Relais

12. Terre di Baccio

13. Locanda le Piazze

14. Villa San Lucchese

15. Hotel La Vecchia Cartiera

16. Hotel Il Castello

17. Villa Castiglione

18. Delta Hotel

19. Hotel Villa Campomaggio

20. Locanda Il Gallo

Holiday Rentals in Chianti Region

Villa Curina Resort

Riserva di Fizzano Residence

Borgo Argenina

Villa di Sotto

Villa San Filippo

Borgo Argiano

Chianti Village Morrocco

Villa il Fedino

B&B La Fonte del Machiavelli

Antico Borgo il Cardino

La Locanda di Pietracupa

Relais Villa Belpoggio - Residenza d'Epoca

Villa Cassia di Baccano

Rocca di Castagnoli

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

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 Norcenni Aparthotel

Villa Castiglione

Agriturismo Il Caggio di Sotto

Castello di Pratelli

Hotel Albergo Italia

Quercia Al Poggio

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