𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chianti Region from RM305 (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 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 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.

1. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

RM1,115

RM1,263 total

includes taxes & fees

9 Nov - 10 Nov

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

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.

A restaurant with a table set for two, overlooking a scenic landscape.

2. Relais Vignale & Spa

Radda in Chianti

Ali

RM707

RM919 total

includes taxes & fees

22 Oct - 23 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 courtyard with a stone building, wooden pergola, and raised garden beds with various plants.

3. Hotel Villa Campomaggio

Radda in Chianti

Dario

RM676

RM771 total

includes taxes & fees

20 Oct - 21 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 corridor with a wooden door at the end, a metal railing on one side, and a light fixture above.

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

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

4. La Certosa di Pontignano - Place of Charme

Castelnuovo Berardenga

Leslie

RM388

RM464 total

includes taxes & fees

16 Nov - 17 Nov

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

An outdoor dining area with stone buildings and a tower, illuminated by ambient lighting.

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

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

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

Gaiole in Chianti

Michelle

RM1,351

RM1,532 total

includes taxes & fees

30 Oct - 31 Oct

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

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

A pool area with a view of a hilly landscape.

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

6. Borgo Del Cabreo

Greve in Chianti

Brian

RM1,051

RM1,174 total

includes taxes & fees

26 Oct - 27 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 stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

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

7. Belvedere di San Leonino

Castellina in Chianti

Kevork

RM439

RM511 total

includes taxes & fees

27 Oct - 28 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 kitchen with a large window, wooden ceiling, and a view of a forested area.

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

8. Chapter Chianti, a Member of Design Hotels

Cavriglia

Michael

RM1,101

RM1,238 total

includes taxes & fees

20 Oct - 21 Oct

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

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

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

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

9. La pietra del cabreo

Greve in Chianti

Morvarid

RM899

RM1,007 total

includes taxes & fees

20 Oct - 21 Oct

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

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

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

A well-lit outdoor garden area with stone planters, a paved walkway, and a building with large windows.

10. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Saion

RM729

RM820 total

includes taxes & fees

20 Oct - 21 Oct

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

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.

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

11. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

RM475

RM550 total

includes taxes & fees

1 Nov - 2 Nov

A spa area with a stone ceiling, a pool, and two sun loungers.

A courtyard with outdoor seating, stone walls, and a staircase.

A luxurious room with ornate ceiling artwork, plush seating, and elegant lighting fixtures.

A buffet area with various fruits and a bar with bottles.

12. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

RM379

RM444 total

includes taxes & fees

17 Nov - 18 Nov

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

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

13. Villa Le Barone

Greve in Chianti

Tereza

RM1,021

RM1,150 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

14. Hotel Borgo di Cortefreda Relais - Place of Charme

Tavarnelle Val di Pesa

Sergey

RM524

RM603 total

includes taxes & fees

16 Nov - 17 Nov

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.

15. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

RM440

RM494 total

includes taxes & fees

8 Nov - 9 Nov

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

A dining area with a table set for two, featuring wine bottles and bread.

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.

16. Castello La Leccia

Castellina in Chianti

Eva

RM821

RM922 total

includes taxes & fees

4 Nov - 5 Nov

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

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

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

A stone archway leading to a window with a view of tall trees and a distant landscape.

17. Castello di Tornano Wine Resort

Gaiole in Chianti

Karina

RM578

RM673 total

includes taxes & fees

27 Oct - 28 Oct

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

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

A clear blue pool with lounge chairs and a stone building in the background.

A stone building with a wooden bench outside.

18. Hotel Colle Etrusco Salivolpi

Castellina in Chianti

Monica

RM400

RM454 total

includes taxes & fees

20 Oct - 21 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 white vehicle parked in front of a building with a stone facade and arched windows, surrounded by gravel and greenery.

A bathroom with a bathtub, a window with a view of a vineyard, and a small table with a bottle and glasses.

19. Tenuta CorteDomina

Radda in Chianti

Edgar

RM877

RM983 total

includes taxes & fees

1 Nov - 2 Nov

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

A historic estate with a central courtyard, surrounded by lush gardens and vineyards.

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

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

20. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

RM1,503

RM1,700 total

includes taxes & fees

5 Nov - 6 Nov

View all properties

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.

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

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

Relais Villa Olmo - Place of Charme

Impruneta

"Very friendly and clean."

Aparthotel

A stone building with a garden in front.

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

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

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

Borgo Argenina

Gaiole in Chianti

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

Townhouse

A 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.

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."

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 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.

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 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 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 "

Apartment

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

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

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

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

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 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.

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

Relais Villa Belvedere

Figline e Incisa Valdarno

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

Holiday Home

A stone building with multiple windows and a chimney.

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.

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

Agriturismo La Ferrozzola

Castellina in Chianti

"Very nice agriturismo. "

Townhouse

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

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

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

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

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

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

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.

Villa Cassia di Baccano

Loro Ciuffenna

"The staff were great and the villa was amazing"

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.

An outdoor dining area with wooden tables and chairs, string lights, and a view of greenery.

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

hu Firenze Certosa camping in town

Impruneta

"Friendly staff!"

Residence

A balcony with a table and chairs, a railing, and a view of a town and hills.

A dining area with white furniture, a buffet setup, and large windows offering a view of the landscape.

A bedroom with a bed, a wardrobe, a radiator, and a window with curtains.

A modern kitchen with white cabinetry, a dining area with a table and chairs, and a living area with a sofa.

Residence Il Connubio

Impruneta

"Great location if you are looking for a place quiet, great outdoor scenery. Pleasant people. "

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."

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 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.

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

Podere il Pino

Poggibonsi

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

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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.

See properties

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

Fattoria di Vegi

10/10 Excellent

"We loved our stay here! It was the perfect place to slow down and take in the beauty of Tuscany. We enjoyed the cooking class and wine tasting we took with the other couples staying there. Highly recommend booking this as part of your stay! We also enjoyed the amenities they offered like the art room - we set up easels in the grass, drank wine, and drew each other’s portraits which ended up being pretty funny. The food at the restaurant was good although it felt like some of the dishes could’ve been simpler. Our favorite dishes was the pasta with mushrooms and the pizzas on pizza night. The majority of the staff was friendly too. Highly recommend this location if you’re looking for a beautifully designed, relaxing location with amenities/activities. We hope to be back!"

Hotel Villa Cesi

10/10 Excellent

"Rooms are very clean and staff are very friendly and super helpful and above all they are caring and very accommodating especially with our elderly less abled parents for which we are very grateful. Property is in a beautiful setting. Restaurant staff also very helpful. Thank you very much to all who hosted us at Villa Cesi."

Salvadonica - Borgo del Chianti

10/10 Excellent

"Beautiful property, clean and spacious room, great service. We are so thankful for our stay at this property. We had a patio outside our room, and this was a highlight for me. The restaurant had a bar with local wines and snacks; we could then sit outside and relax in peace. We did one of the wine tastings with the hotel, which was fabulous. We ate at the restaurant; my teenage children each found something they enjoyed. It is located outside of Florence, so we did have a bit of a drive each day to see different sites, but the property made the stay very well worth it. Breakfast each day was also really wonderful,"

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"Beautiful quaint 1000 year old monastery turned into a hotel! The staff was extremely accommodating and we really enjoyed our stay. Very easy to get around all of Tuscany from this hotel."

Borgo Vescine

10/10 Excellent

"The staff was amazing and incredibly kind."

Hotel Toscana Ambassador

8/10 Good

"Close to train station"

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."

COMO Castello Del Nero

10/10 Excellent

"The most beautiful hotel in the heart of Chianti. The service was above and beyond. Everything about this charming hotel was amazing. We cannot wait to go back."

More cheap stays in Chianti Region

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

RM265

RM305 total

8 Nov - 9 Nov

includes taxes & fees

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

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

Explore a world of travel with Expedia

Province of Siena Holiday Rentals

Chianti Region hotels from RM305

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. Dievole Wine Resort

2. Relais Vignale & Spa

3. Hotel Villa Campomaggio

4. La Certosa di Pontignano - Place of Charme

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

6. Borgo Del Cabreo

7. Belvedere di San Leonino

8. Chapter Chianti, a Member of Design Hotels

9. La pietra del cabreo

10. Castello di Fonterutoli Wine Resort

11. Palazzo Leopoldo Dimora Storica & Spa

12. Hotel Palazzo San niccolò & Spa

13. Villa Le Barone

14. Hotel Borgo di Cortefreda Relais - Place of Charme

15. Villa Casagrande Resort & SPA

16. Castello La Leccia

17. Castello di Tornano Wine Resort

18. Hotel Colle Etrusco Salivolpi

19. Tenuta CorteDomina

20. Borgo Scopeto Wine & Country Relais

Holiday Rentals in Chianti Region

Relais Villa Olmo - Place of Charme

Borgo Argenina

Terre di Baccio

Chianti Village Morrocco

Rocca di Castagnoli

Casa Vacanze Squarcialupi

Relais Villa Belvedere

Agriturismo La Ferrozzola

L' Eroico

Villa Cassia di Baccano

hu Firenze Certosa camping in town

Residence Il Connubio

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

I Parigi Corbinelli

Podere il Pino

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

Fattoria di Vegi

Hotel Villa Cesi

Salvadonica - Borgo del Chianti

Castello di Spaltenna- Small Luxury Hotels of the World

Borgo Vescine

Hotel Toscana Ambassador

Villa Le Barone

Hu Norcenni Girasole Village

COMO Castello Del Nero

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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