𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chianti Region from RM304 (2026) - Fully Refundable Options

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 swimming pool with a stone deck, surrounded by trees and a castle-like building in the background.

A stone building with a garden, tall trees, and a clear blue sky.

A restaurant with stone walls and a high ceiling, featuring tables set for dining.

A sunlit patio with a glass roof, stone walls, and outdoor seating.

1. Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

Sonja

RM1,348

RM1,528 total

includes taxes & fees

30 Oct - 31 Oct

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

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

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

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

2. Hotel Villa Campomaggio

Radda in Chianti

Dario

RM674

RM769 total

includes taxes & fees

3 Nov - 4 Nov

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

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

A cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

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

3. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

RM1,112

RM1,260 total

includes taxes & fees

9 Nov - 10 Nov

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.

4. Tenuta CorteDomina

Radda in Chianti

Edgar

RM502

RM570 total

includes taxes & fees

8 Nov - 9 Nov

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

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.

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

5. Relais Vignale & Spa

Radda in Chianti

Ali

RM705

RM916 total

includes taxes & fees

19 Oct - 20 Oct

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

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

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.

6. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

Sergey

RM580

RM665 total

includes taxes & fees

9 Nov - 10 Nov

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

A room with a view of a valley, a stone shelf with flowers, a wooden bench, and a fireplace.

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.

7. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

RM450

RM523 total

includes taxes & fees

1 Nov - 2 Nov

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

A pool area with a view of a hilly landscape.

8. Borgo Del Cabreo

Greve in Chianti

Brian

RM899

RM1,007 total

includes taxes & fees

11 Oct - 12 Oct

A bedroom with a canopy bed, a bedside table, a chair, a potted plant, and a large mirror.

An aerial view of a rural village with traditional stone buildings, terraced fields, and a prominent villa with a swimming pool.

A modern living room with a white sofa, armchairs, and a coffee table.

A compact living space with a wooden ceiling, a white sofa, a small table, a potted plant, and a cabinet with circular designs.

9. Chapter Chianti, a Member of Design Hotels

Cavriglia

Andon

RM1,098

RM1,235 total

includes taxes & fees

11 Oct - 12 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 stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

A rustic stone building with a garden in front.

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

10. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

RM452

RM525 total

includes taxes & fees

15 Oct - 16 Oct

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

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

A 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.

11. Villa Le Barone

Greve in Chianti

Tereza

RM1,018

RM1,147 total

includes taxes & fees

25 Oct - 26 Oct

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

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.

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

12. Castello Vicchiomaggio

Greve in Chianti

Mary Margaret

RM746

RM821 total

includes taxes & fees

27 Oct - 28 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 modern spa area with a wooden sauna, a glass-enclosed shower, and a marble-floored pool.

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

13. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

RM441

RM494 total

includes taxes & fees

8 Nov - 9 Nov

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.

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

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

14. Castello di Tornano Wine Resort

Gaiole in Chianti

Lisa

RM621

RM720 total

includes taxes & fees

25 Oct - 26 Oct

A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

A courtyard with stone buildings, outdoor tables set for dining, and a gravel ground.

A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.

A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a tray of items, and a window with curtains.

15. Castello La Leccia

Castellina in Chianti

Eva

RM724

RM815 total

includes taxes & fees

17 Oct - 18 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.

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

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

16. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Leslie

RM387

RM463 total

includes taxes & fees

2 Nov - 3 Nov

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

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

A terrace with wicker furniture, a pool, and a vineyard view.

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

17. La pietra del cabreo

Greve in Chianti

Jorge Aaron

RM973

RM1,089 total

includes taxes & fees

13 Oct - 14 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 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.

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

18. Borgo di Pietrafitta Relais

Castellina in Chianti

Alejandro

RM362

RM416 total

includes taxes & fees

25 Oct - 26 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.

19. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Saion

RM727

RM818 total

includes taxes & fees

11 Oct - 12 Oct

A large building with multiple rooms, surrounded by a field of lavender.

An arched brick corridor leading to a dining area with tables set for a meal.

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

An outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.

20. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

RM1,576

RM1,780 total

includes taxes & fees

6 Nov - 7 Nov

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Holiday Rentals in Chianti Region

Residence

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

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

A stone building with a garden, outdoor seating, and a large tree.

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

Relais Villa Olmo - Place of Charme

Impruneta

"Very friendly and clean."

Townhouse

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

A bedroom with a stone wall, a large mirror, a bed with white linens, a potted plant, and a view through a window with curtains.

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

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

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."

Apartment

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

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

A bedroom with a bed, bedside tables, a chair, and a window with curtains.

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

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. "

Residence

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

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

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.

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 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 "

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

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

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

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

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

La Locanda di Pietracupa

Tavarnelle Val di Pesa

"Great place, wonderful restaurant"

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 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.

B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

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

Townhouse

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

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

A stone building with a wooden door and shutters, a sign reading "b.v. eroico", and a number "19" on the wall.

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."

Holiday Home

A stone building with multiple windows and a chimney.

A stone staircase leading up to a rustic stone building with a flat roof, surrounded by greenery and trees.

A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, set against a stone building with a garden.

A stone building with a gravel driveway leading to a table set for dining, surrounded by greenery and a vineyard in the background.

Agriturismo La Ferrozzola

Castellina in Chianti

"Very nice agriturismo. "

Camping

A water park with a pool, slides, and a wooden deck area.

A row of wooden cabins with white canopies, each with a wooden deck and a small porch.

A modern bedroom with a bed, an air conditioning unit, a bedside lamp, a laptop, and a mirror.

An indoor dining area with tables and chairs, a bar in the background, and large green plants.

hu Firenze Certosa camping in town

Impruneta

"Friendly staff!"

Townhouse

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

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.

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

I Parigi Corbinelli

Florence

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

Aparthotel

A stone building with a tiled roof, a chimney, and a circular window.

A dining area with a table and chairs, a large vase with flowers, and a view through an open archway.

A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

A stone staircase leading to a door, surrounded by a well-maintained garden with various plants and a clear view of the countryside.

Podere il Pino

Poggibonsi

"Beautiful place to stay. Great for kids and has an amazing view. "

Holiday Home

A historic stone building with a central tower, surrounded by well-manicured gardens and a gravel courtyard.

A garden pathway with a stone archway, surrounded by various plants and trees.

An outdoor dining area with tables and chairs, a white canopy, and stone buildings in the background.

Chianti Romantic Retreat

Greve in Chianti

"This is a lovely, quiet place to stay in with the benefit of a pool. We wished we gad booked for longer. It was a great self catering place and a 10 minute drive from the town of Greve in Chianti. You are in the Chianti hills and amongst vineyards. A car is essential to get to local sites, shops and restaurants."

Residence

A swimming pool with a stone fountain, surrounded by a grassy area and trees.

A modern kitchen with white cabinetry, a built-in microwave, and an oven. There is a white dining table with a vase of flowers.

A stone fountain with a tiered design, surrounded by a well-maintained lawn and a stone wall.

A modern living room with a fireplace, a dining area, and a kitchen.

Rocca Palazzaccio

Impruneta

"A lovely stay at this property with our 2 year old.The apartment had everything we needed and communication with the host was very good There are steep hills to access the property by car or foot so bear that in mind but we managed fine with a pram and a car its just worth noting Handy to have laundry facilities on site aswell. There is a coop just a few minutes down the road Lovely views and a clean pool which was perfect for our little one to use and toys there that he could play in the...

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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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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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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.

See properties

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

Villa I Barronci Resort & Spa

10/10 Excellent

"Great spot and friendly staff."

Castello Vicchiomaggio

10/10 Excellent

"A unique stay with a picturesque view. Breakfast, lunch, and dinner were fantastic. The property was great for relaxing at but also a good launching spot for exploring some of the nearby towns and sites."

Fattoria di Vegi

10/10 Excellent

"LOVE LOVE LOVE This was the highlight of our 2.5 week Toscana trip!! You won't regret booking. The space is stunning and newly opened and staff are welcoming and wonderful!"

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"

Relais Vignale & Spa

10/10 Excellent

"In a convenient location."

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

RM264

RM304 total

8 Nov - 9 Nov

includes taxes & fees

8.6/10 Excellent! (278 reviews)

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

Get rates

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

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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

Province of Siena Holiday Rentals

Chianti Region hotels from RM304

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. Castello di Spaltenna- Small Luxury Hotels of the World

2. Hotel Villa Campomaggio

3. Dievole Wine Resort

4. Tenuta CorteDomina

5. Relais Vignale & Spa

6. Hotel Borgo di Cortefreda Relais - Place of Charme

7. Palazzo Leopoldo Dimora Storica & Spa

8. Borgo Del Cabreo

9. Chapter Chianti, a Member of Design Hotels

10. Belvedere di San Leonino

11. Villa Le Barone

12. Castello Vicchiomaggio

13. Villa Casagrande Resort & SPA

14. Castello di Tornano Wine Resort

15. Castello La Leccia

16. La Certosa di Pontignano - Place of Charme

17. La pietra del cabreo

18. Borgo di Pietrafitta Relais

19. Castello di Fonterutoli Wine Resort

20. Borgo Scopeto Wine & Country Relais

Holiday Rentals in Chianti Region

Relais Villa Olmo - Place of Charme

Terre di Baccio

Casa Vacanze Squarcialupi

Chianti Village Morrocco

Rocca di Castagnoli

Relais Villa Belvedere

La Locanda di Pietracupa

B&B La Fonte del Machiavelli

L' Eroico

Agriturismo La Ferrozzola

hu Firenze Certosa camping in town

I Parigi Corbinelli

Podere il Pino

Chianti Romantic Retreat

Rocca Palazzaccio

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

Piazza Matteotti

Meleto Castle

Learn more about Chianti Region

Top Chianti Region Hotel Reviews

Villa I Barronci Resort & Spa

Castello Vicchiomaggio

Fattoria di Vegi

Borgo Vescine

Castello di Spaltenna- Small Luxury Hotels of the World

Hotel Toscana Ambassador

Relais Vignale & Spa

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

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