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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Farm

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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 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.

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

Rp4.688.451

Rp5.238.834 total

includes taxes & fees

11 Oct - 12 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 interior corridor with arches, columns, and a brick wall.

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

2. La Certosa di Pontignano

Castelnuovo Berardenga

Leslie

Rp1.786.982

Rp2.128.824 total

includes taxes & fees

16 Oct - 17 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.

3. Moody smart & comfy Hotel

Terranuova Bracciolini

Rocco

Rp2.018.073

Rp2.281.034 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 rectangular swimming pool with a view of mountains in the background.

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

4. Podere L'Aquila

Gaiole in Chianti

Heather

Rp3.002.036

Rp8.337.228 total

includes taxes & fees

8 Oct - 9 Oct

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

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

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

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

5. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

Rp2.190.601

Rp2.450.447 total

includes taxes & fees

26 Oct - 27 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 pathway lined with wooden fences and benches, leading to a covered seating area with tables and chairs.

6. Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

Juan Antonio

Rp1.638.483

Rp1.924.689 total

includes taxes & fees

26 Oct - 27 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 dining area with a stone wall, wooden beams, and a table set for four with wine glasses and plates.

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

7. Borgo di Pietrafitta Relais

Castellina in Chianti

Alejandro

Rp1.612.234

Rp1.854.995 total

includes taxes & fees

20 Oct - 21 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 modern hotel lobby with a curved reception desk, seating area, and a bar.

8. Hotel Valdarno

Montevarchi

Emmanuel

Rp2.168.103

Rp2.384.995 total

includes taxes & fees

5 Oct - 6 Oct

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

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

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

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

9. Castello Vicchiomaggio

Greve in Chianti

Maryse

Rp2.877.161

Rp3.164.877 total

includes taxes & fees

27 Sept - 28 Sept

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 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.

10. Villa Le Barone

Greve in Chianti

Aditi

Rp4.537.532

Rp5.113.644 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

11. Hotel Bellavista Impruneta

Impruneta

Caitlin

Rp1.471.024

Rp1.699.665 total

includes taxes & fees

8 Oct - 9 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 bar area with wooden bar stools, a counter with bottles, and a tiled floor.

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

12. Hotel La Vecchia Cartiera

Colle di Val d'Elsa

Sheila

Rp1.417.654

Rp1.620.574 total

includes taxes & fees

27 Sept - 28 Sept

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

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.

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

13. Hotel Villa Campomaggio

Radda in Chianti

Dario

Rp3.344.449

Rp3.801.252 total

includes taxes & fees

18 Oct - 19 Oct

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

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.

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

14. Locanda le Piazze

Castellina in Chianti

Tara

Rp6.194.115

Rp6.935.833 total

includes taxes & fees

16 Oct - 17 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.

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

15. Villa Castiglione

Impruneta

Lee

Rp2.463.253

Rp2.770.733 total

includes taxes & fees

27 Sept - 28 Sept

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

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

16. Villa San Lucchese

Poggibonsi

James

Rp2.230.554

Rp2.575.916 total

includes taxes & fees

2 Oct - 3 Oct

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

17. Locanda Il Gallo

Greve in Chianti

Santina

Rp2.034.751

Rp2.299.380 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

A rustic room with exposed brick walls, a piano, and a dining table set with white tableware.

18. Hotel Il Castello

Certaldo Alto

Kenneth

Rp2.377.840

Rp2.717.547 total

includes taxes & fees

27 Sept - 28 Sept

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.

19. Terre di Baccio

Greve in Chianti

Gage

Rp9.861.871

Rp10.929.596 total

includes taxes & fees

27 Sept - 28 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 building with the sign "Toscana Ambassador Hotel".

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

20. Hotel Toscana Ambassador

Poggibonsi

Jennifer

Rp1.260.878

Rp1.509.273 total

includes taxes & fees

7 Oct - 8 Oct

View all properties

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 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.

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.

A pool area with a view of vineyards and hills.

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!"

Aparthotel

A stone building with a garden in front.

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

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

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

Borgo Argenina

Gaiole in Chianti

"What an amazing place. We enjoyed it so much."

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

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

Villa San Filippo

Barberino Val d'Elsa

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

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

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.

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.

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

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

Borgo Argiano

Castelnuovo Berardenga

"Amazing staff, clean room, amazing pool!"

Residence

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

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

A 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

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 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.

A hammock suspended between trees in a garden with a view of a hilly 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 dining area with tables set for meals, a bar area with shelves of bottles, and a wooden cabinet.

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."

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 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.

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."

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 sign reading "CAMERE" against a clear blue sky.

A bedroom with a large bed, a smaller bed, and a window with curtains.

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 swimming pool with a stone wall and a metal fixture on the right.

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

Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

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

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

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"

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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

Rp2.463.253

Rp2.770.733 total

27 Sept - 28 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 Rp1.844.091

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. Podere L'Aquila

5. Villa Casagrande Resort & SPA

6. Villa I Barronci Resort & Spa

7. Borgo di Pietrafitta Relais

8. Hotel Valdarno

9. Castello Vicchiomaggio

10. Villa Le Barone

11. Hotel Bellavista Impruneta

12. Hotel La Vecchia Cartiera

13. Hotel Villa Campomaggio

14. Locanda le Piazze

15. Villa Castiglione

16. Villa San Lucchese

17. Locanda Il Gallo

18. Hotel Il Castello

19. Terre di Baccio

20. Hotel Toscana Ambassador

Holiday Rentals in Chianti Region

Villa Curina Resort

Riserva di Fizzano Residence

Borgo Argenina

Villa San Filippo

Villa di Sotto

Borgo Argiano

Chianti Village Morrocco

Villa il Fedino

B&B La Fonte del Machiavelli

Relais Badia a Passignano

Antico Borgo il Cardino

La Locanda di Pietracupa

Relais Villa Belpoggio - Residenza d'Epoca

Rocca di Castagnoli

Villa Cassia di Baccano

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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