𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chianti Region from S$97 (2026) - Fully Refundable Options

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 candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

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

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

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

1. La Certosa di Pontignano

Castelnuovo Berardenga

Leslie

S$148

includes taxes & fees

19 Oct - 20 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 dining area with a stone wall, wooden beams, and a table set for four with wine glasses and plates.

A stone building with a courtyard, a covered seating area, and a small bell tower.

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

2. Borgo di Pietrafitta Relais

Castellina in Chianti

Alejandro

S$122

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

3. Castello Vicchiomaggio

Greve in Chianti

Maryse

S$240

includes taxes & fees

27 Oct - 28 Oct

A rustic stone building with a wooden pergola, outdoor seating, and a garden with various plants.

A historic stone building with a large arched window and a small balcony.

A stone building with a tower, surrounded by people dining at tables with candles.

An aerial view of a castle with a swimming pool, surrounded by dense forest and vineyards.

4. Castello di Tornano Wine Resort

Gaiole in Chianti

Lisa

S$211

includes taxes & fees

26 Oct - 27 Oct

An outdoor dining area with a pool, potted plants, and umbrellas.

A spa area with a brick archway leading to a circular hot tub surrounded by mosaic tiles.

An outdoor dining area with a table set for two, overlooking a pool and vineyard.

A villa with a swimming pool, outdoor seating, and a garden.

5. Relais Vignale & Spa

Radda in Chianti

Ali

S$271

includes taxes & fees

26 Oct - 27 Oct

A building with a stone facade, a central arched doorway, and a window with a decorative frame.

A room with a view of a forest through a window, a table with a lamp, and a chair.

A room with a glass table, a vase with flowers, a bottle of wine, and a chair.

A narrow, tree-lined road leading to a house with a tiled roof and a stone wall on one side.

6. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

S$408

includes taxes & fees

28 Oct - 29 Oct

A spacious living area with a large window, a sofa, a green armchair, and a patterned armchair.

A bedroom with a bed, bedside tables, a rug, and a view of the outdoors.

A swimming pool with clear water, surrounded by lounge chairs and trees.

A kitchen area with a marble countertop, a stone wall, and a sign reading "Cooking Class".

7. Salvadonica - Borgo del Chianti

San Casciano in Val di Pesa

Jonathan

S$153

includes taxes & fees

3 Nov - 4 Nov

A couple dining at an outdoor table with a view of the countryside.

A spacious room with high arched ceilings, a wooden dining table, chairs, and a bookshelf.

A woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.

A narrow street with buildings on either side, a flag, and a bench.

8. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

S$173

includes taxes & fees

2 Nov - 3 Nov

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

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

9. Hotel Villa Campomaggio

Radda in Chianti

Dario

S$225

includes taxes & fees

3 Nov - 4 Nov

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

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

10. Villa I Barronci Resort & Spa

San Casciano in Val di Pesa

Haris

S$113

includes taxes & fees

3 Nov - 4 Nov

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

A person relaxing on a sun lounger by a pool with a table beside them holding a drink and a bowl.

11. Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa

Sergey

S$194

includes taxes & fees

24 Oct - 25 Oct

A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.

A poolside area with lounge chairs and a view of the night sky.

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

A rustic stone building with a garden in front.

12. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

S$181

includes taxes & fees

15 Oct - 16 Oct

A narrow stone pathway leading to a rustic building with a wooden door and a window.

A cozy living room with a striped sofa, a wooden coffee table, and a bookshelf.

A cozy living room with a fireplace, wooden beams, and comfortable seating.

A stone building with wooden shutters, a bench, and hanging purple flowers.

13. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Saion

S$268

includes taxes & fees

6 Oct - 7 Oct

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

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.

A bedroom with a large bed, a bedside table, and a chair.

A pool area with a view of a hilly landscape.

14. Borgo Del Cabreo

Greve in Chianti

Brian

S$410

includes taxes & fees

15 Oct - 16 Oct

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

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

A 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.

15. Tenuta CorteDomina

Radda in Chianti

Edgar

S$338

includes taxes & fees

1 Nov - 2 Nov

A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.

A stone building with a wooden bench outside.

A rustic living room with exposed wooden beams, a sofa, a coffee table, and a dining area with chairs.

A rustic interior with a brick archway, wooden beams, a bar area, and potted plants.

16. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

Monica

S$146

includes taxes & fees

26 Oct - 27 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.

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

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

17. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

S$146

includes taxes & fees

3 Nov - 4 Nov

A stone-walled room with a table set for breakfast, featuring pastries, fruits, and a coffee station.

A poolside area with lounge chairs and umbrellas, surrounded by stone flooring and greenery.

A bedroom with a large bed, wooden beams, stone wall, and a stone fireplace.

An outdoor dining area with stone walls, tables, and chairs, surrounded by greenery and a stone building in the background.

18. Ultimo Mulino Wellness Country Hotel

Gaiole in Chianti

Ariel

S$143

includes taxes & fees

22 Oct - 23 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.

19. Villa Le Barone

Greve in Chianti

Tereza

S$361

includes taxes & fees

25 Oct - 26 Oct

A stone building with a circular window and a door, surrounded by purple flowers.

A stone building with a tiled roof, arched windows, and a well-maintained lawn.

A stone building with a tiled pathway leading to a large planter.

A bottle of wine and two glasses on a windowsill with a vineyard view.

20. La pietra del cabreo

Greve in Chianti

Jorge Aaron

S$427

includes taxes & fees

25 Oct - 26 Oct

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Holiday Rentals in Chianti Region

Residence

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

An outdoor dining area with tables set for a meal, large windows, and a stone wall in the background.

A stone pathway leading to a terrace with potted plants and flowers, overlooking a hillside with houses.

A swimming pool with a clear blue water surface, surrounded by a brick deck and a grassy area with trees.

Relais Villa Olmo

Impruneta

"Very friendly and clean."

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 olive trees and a vineyard in the background.

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

Borgo Argiano

Castelnuovo Berardenga

"Amazing staff, clean room, amazing pool!"

Residence

An outdoor dining area with tables and chairs, candles, and a view of palm trees and greenery.

A bedroom with a large bed, a sofa, a television, and a painting on the wall.

A dining area with wooden chairs and tables, a chandelier, and potted plants.

A view through a window of a stone staircase leading to a building with arched windows and a tower, overlooking a hilly landscape.

Palazzo Pacini

Colle di Val d'Elsa

"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "

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

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

Villa il Fedino

San Casciano in Val di Pesa

"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

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

A hotel room with a bed, two bedside lamps, a TV, a window with curtains, a wooden wardrobe, and a tray with glasses and a bottle.

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

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

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 "

Residence

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

A large, modern building with a blue roof, surrounded by lush green fields and trees.

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

A 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."

Apartment

A balcony with a table, chairs, and a bottle of wine, overlooking a vineyard and distant hills.

A modern two-story residential building with a stone facade, a well-maintained garden with hedges and grass, and a clear sky.

A modern kitchen with dark wooden cabinets, a dining table with chairs, and a vase of flowers on the table.

A dining area with a wooden table and chairs, a white sofa with cushions, and a staircase with a metal railing.

Casa Vacanze Squarcialupi

Castellina in Chianti

"Staff was very helpful. Was a bit bummed the pool was closed as that was part of the reason for choosing the hotel. "

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 kitchen with wooden cabinets, a dining table with chairs, a chandelier, and a view of the outdoors through a glass door.

Relais Villa Belvedere

Figline e Incisa Valdarno

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

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.

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 and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."

Townhouse

A stone building with a yellow sign reading "b&b erioico".

A modern dining area with a wooden table, glass vases, and a staircase with glass railings.

A hotel room with neatly folded towels on the bed, a wooden headboard, and a green pendant light.

An aerial view of a town with a central square, surrounding buildings, and vineyards.

L' Eroico

Gaiole in Chianti

"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."

Townhouse

A courtyard with a stone building featuring an arched entrance, potted plants, and outdoor seating.

A rustic stone building with ivy-covered walls, outdoor seating, and gravel ground.

A garden with potted plants and a wrought iron gate.

An interior space with a wooden bench, a potted plant, and two framed pictures on the wall.

I Parigi Corbinelli

Florence

"Beautiful setting, stunning views, incredible pool and gardens and so easy to jump on the bus into the city."

Townhouse

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

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

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

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"

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 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"

Holiday Home

A hallway leading to an outdoor patio with a table and chairs, framed artwork on the walls, and a rustic ceiling.

A stone staircase leading up a hill, surrounded by olive trees and greenery.

A stone building with a tiled roof, a covered patio with outdoor seating, and a garden with potted plants.

A swimming pool with a clear view of a mountainous landscape and greenery in the background.

Casale di Villore

Poggibonsi

"Fantastic property. Can’t wait to return next year. "

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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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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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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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

Borgo Vescine

10/10 Excellent

"The staff was amazing and incredibly kind."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

Hotel Toscana Ambassador

8/10 Good

"Close to train station"

Villa I Barronci Resort & Spa

8/10 Good

"Under renovation so it could have been better"

Fattoria di Vegi

10/10 Excellent

"Booked this as a last minute decision to shorten our time in Milan (and fine a place close to Florence on our way to Montepulciano) We only stayed one night, but wish it had been longer. If you are looking for informal luxury, you will find it at this idyllic Tuscan Estate. They are still expanding their amenities to include a gym, tennis court, and Spa (planned for a 2027 open) what they DO offer is a quiet, thoughtful experience. The room was perfection and the restaurant on the property - delicious. There were a few artists there taking advantage of the atelier, or painting on the property. The estate is located an hour’s drive outside of Florence and is well worth the trip if you are looking for a place to relax. We hope to return with more time to enjoy it."

Relais Vignale & Spa

10/10 Excellent

"In a convenient location."

Villa Le Barone

10/10 Excellent

"Charming place in Tuscany! Everything was absolutely perfect. We highly suggest to dine at the villa, it was exceptional. Breakfast was delicious as well."

Hu Norcenni Girasole Village

10/10 Excellent

"My family and I had such a great time. Such a kid friendly place and at check in they even had a little playground while you waiting and gave the kids bubbles. So great to be in nature and all of the amenities were lovely. The waterparks that were padded on the ground were genius and we did a family wine tasting which was such a lovely memory. Our stay was so nice with the deck and the grocery store is so affordable for dinners in. Love love love! My toddler played all day and there were so many times we got to relax because they had everything that we wanted or needed right on property."

Hotel Villa Campomaggio

10/10 Excellent

"Great hotel"

More cheap stays in Chianti Region

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

S$97

3 Nov - 4 Nov

includes taxes & fees

8.6/10 Excellent! (277 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

Hotels in Chianti Region with star rating

Explore a world of travel with Expedia

L'ugolino Holiday Rentals

Chianti Region Hotels from S$97

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. La Certosa di Pontignano

2. Borgo di Pietrafitta Relais

3. Castello Vicchiomaggio

4. Castello di Tornano Wine Resort

5. Relais Vignale & Spa

6. Dievole Wine Resort

7. Salvadonica - Borgo del Chianti

8. Palazzo Leopoldo Dimora Storica & Spa

9. Hotel Villa Campomaggio

10. Villa I Barronci Resort & Spa

11. Hotel Borgo di Cortefreda Relais

12. Belvedere di San Leonino

13. Castello di Fonterutoli Wine Resort

14. Borgo Del Cabreo

15. Tenuta CorteDomina

16. Hotel Colle Etrusco Salivolpi

17. Villa Casagrande Resort & SPA

18. Ultimo Mulino Wellness Country Hotel

19. Villa Le Barone

20. La pietra del cabreo

Holiday Rentals in Chianti Region

Relais Villa Olmo

Borgo Argiano

Palazzo Pacini

Villa il Fedino

Rocca di Castagnoli

Chianti Village Morrocco

Casa Vacanze Squarcialupi

Relais Villa Belvedere

Terre di Baccio

L' Eroico

I Parigi Corbinelli

La Locanda di Pietracupa

Villa Cassia di Baccano

Casale di Villore

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

Castello di Albola

Castle of Brolio

Meleto Castle

Piazza Matteotti

Learn more about Chianti Region

Top Chianti Region Hotel Reviews

Borgo Vescine

Castello di Spaltenna- Small Luxury Hotels of the World

Hotel Toscana Ambassador

Villa I Barronci Resort & Spa

Fattoria di Vegi

Relais Vignale & Spa

Villa Le Barone

Hu Norcenni Girasole Village

Hotel Villa Campomaggio

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

Hotels in Chianti Region with star rating

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