Chianti Region Holiday Rentals, Tuscany: Private House Rentals

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

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Go beyond your typical stay in Chianti Region

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Farm

Waterpark

Apartment

Apart hotel

Family friendly

Pool

Hot tub

Condo

Spa

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Our top choices for Chianti Region hotels

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.

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

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

1. Relais Vignale & Spa

Radda in Chianti

Ali

Rp3.083.939

Rp4.006.436 total

includes taxes & fees

24 Oct - 25 Oct

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

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

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

Gaiole in Chianti

Michelle

Rp5.924.488

Rp6.718.000 total

includes taxes & fees

30 Oct - 31 Oct

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

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.

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

3. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

Rp4.860.815

Rp5.506.924 total

includes taxes & fees

14 Nov - 15 Nov

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

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

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

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

4. Hotel Villa Campomaggio

Radda in Chianti

Dario

Rp2.962.299

Rp3.379.214 total

includes taxes & fees

3 Nov - 4 Nov

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

A modern kitchen with a large window, wooden ceiling, and a view of a forested area.

A rustic outdoor setting with a stone building, round tables, and outdoor seating.

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

5. Chapter Chianti, a Member of Design Hotels

Cavriglia

Michael

Rp4.800.804

Rp5.400.904 total

includes taxes & fees

19 Oct - 20 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 spacious room with high arched ceilings, a wooden dining table, chairs, and a bookshelf.

6. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Rp2.090.430

Rp2.420.159 total

includes taxes & fees

2 Nov - 3 Nov

A spacious interior with high arched ceilings, stone walls, and a central round mirror reflecting the room. Tables and chairs are arranged for dining or socializing.

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

A garden with tall cypress trees, a variety of shrubs, and a stone pathway.

An outdoor dining area with tables and chairs, a chef preparing food, and a scenic view in the background.

7. COMO Castello Del Nero

Tavarnelle Val di Pesa

Lauren

Rp13.001.201

Rp14.462.236 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 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.

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

8. Tenuta CorteDomina

Radda in Chianti

Edgar

Rp3.824.823

Rp4.287.318 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

9. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Scott

Rp6.592.978

Rp7.453.420 total

includes taxes & fees

5 Nov - 6 Nov

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

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

10. Castello Vicchiomaggio

Greve in Chianti

Mary Margaret

Rp3.944.624

Rp4.339.087 total

includes taxes & fees

29 Oct - 30 Oct

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

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

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

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 - Place of Charme

Tavarnelle Val di Pesa

Sergey

Rp2.295.782

Rp2.646.046 total

includes taxes & fees

16 Nov - 17 Nov

A stone building with arched windows, a grassy courtyard, and outdoor seating.

An aerial view of a residential property with multiple buildings, a swimming pool, and landscaped gardens.

A person relaxing in a clear pool surrounded by natural scenery.

A bedroom with a wooden ceiling, a stone wall, a bed, a desk, a chair, a sofa, and a window with curtains.

12. Pieve Aldina - Relais & Châteaux

Radda in Chianti

Paul

Rp6.240.887

Rp7.025.951 total

includes taxes & fees

28 Oct - 29 Oct

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

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

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.

13. Castello La Leccia

Castellina in Chianti

Eva

Rp3.601.187

Rp4.041.764 total

includes taxes & fees

4 Nov - 5 Nov

A large, historic building with a tiled roof and multiple windows, surrounded by lush gardens and a stone pathway.

A table set for breakfast with various dishes, drinks, and a newspaper.

A spacious living room with a high ceiling, exposed wooden beams, and a large arched brick structure. There are multiple seating areas with floral-patterned sofas and armchairs. A fireplace and bookshelves are visible in the background.

A restaurant with stone pillars, wooden beams, and white tablecloths. Tables are arranged for dining.

14. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

Rp9.793.641

Rp10.973.040 total

includes taxes & fees

25 Oct - 26 Oct

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

A pool area with a view of a hilly landscape.

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.

15. Borgo Del Cabreo

Greve in Chianti

Brian

Rp5.548.130

Rp6.183.036 total

includes taxes & fees

27 Oct - 28 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 well-lit outdoor garden area with stone planters, a paved walkway, and a building with large windows.

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

16. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Saion

Rp2.848.927

Rp3.214.278 total

includes taxes & fees

18 Oct - 19 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 rustic stone building with a garden in front.

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.

17. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

Rp1.916.473

Rp2.228.140 total

includes taxes & fees

27 Oct - 28 Oct

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

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

18. La pietra del cabreo

Greve in Chianti

Jorge Aaron

Rp4.255.258

Rp4.760.797 total

includes taxes & fees

17 Oct - 18 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 restaurant with multiple tables set for dining, featuring wooden beams and a chandelier.

19. Villa Le Barone

Greve in Chianti

Tereza

Rp4.433.652

Rp4.997.037 total

includes taxes & fees

31 Oct - 1 Nov

A restaurant with a glass ceiling, wicker hanging decorations, and a tiled floor.

An aerial view of a villa surrounded by vineyards, with a swimming pool and outdoor seating area.

A bedroom with a bed, a wooden chair, a desk with a lamp, and a wardrobe.

A rural property with terracotta-roofed buildings, a paved driveway, and lush greenery.

20. Borgo Vescine

Radda in Chianti

Natalie

Rp8.248.582

Rp9.233.547 total

includes taxes & fees

27 Oct - 28 Oct

View all properties

Holiday Rentals in Chianti Region

Residence

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

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.

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

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

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

Borgo Argenina

Gaiole in Chianti

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

Townhouse

A 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.

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.

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."

Residence

A balcony with a view of rolling hills, a table with a book and a bottle, and a chair.

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

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

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

Villa San Filippo

Barberino Val d'Elsa

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

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 grassy area with a stone wall and a wooden fence.

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 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.

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 buffet with various food items, including cheeses, meats, and condiments.

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.

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 sign reading "CAMERE" against a clear blue sky.

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

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

La Locanda di Pietracupa

Tavarnelle Val di Pesa

"Great place, wonderful restaurant"

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. "

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

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

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

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. "

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.

A swimming pool surrounded by stone walls and lush greenery, with a view of distant hills.

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."

Residence

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

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

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.

Residence Il Connubio

Impruneta

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

Townhouse

An outdoor dining area with tables and chairs, covered by umbrellas, overlooking a scenic landscape.

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

A swimming pool surrounded by lush greenery and a forested hillside.

A dining area with tables set for meals, a bar area with shelves of bottles, and a wooden cabinet.

B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

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

Residence

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

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

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.

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.

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

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,"

Villa I Barronci Resort & Spa

10/10 Excellent

"Great spot and friendly staff."

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."

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."

Villa Casagrande Resort & SPA

8/10 Good

"Restaurant was great. Towels have too much use"

Camping Village Il Poggetto.

8/10 Good

"This property was nice. We enjoyed our two nights in a home on property. The home was a little dated but overall nice. Getting to Florence was a bit challenging, due to the property being in an isolated area. On the weekends there are only two busses that so by the property... one in the morning and one at night, so plan accordingly."

More cheap stays in Chianti Region

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

Rp1.160.233

Rp1.336.599 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

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Book Hotels in Chianti Region on Expedia.it

Find hotels in Chianti Region from Rp1.010.169

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. Relais Vignale & Spa

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

3. Dievole Wine Resort

4. Hotel Villa Campomaggio

5. Chapter Chianti, a Member of Design Hotels

6. Palazzo Leopoldo Dimora Storica & Spa

7. COMO Castello Del Nero

8. Tenuta CorteDomina

9. Borgo Scopeto Wine & Country Relais

10. Castello Vicchiomaggio

11. Hotel Borgo di Cortefreda Relais - Place of Charme

12. Pieve Aldina - Relais & Châteaux

13. Castello La Leccia

14. Hotel Le Fontanelle

15. Borgo Del Cabreo

16. Castello di Fonterutoli Wine Resort

17. Belvedere di San Leonino

18. La pietra del cabreo

19. Villa Le Barone

20. Borgo Vescine

Holiday Rentals in Chianti Region

Relais Villa Olmo - Place of Charme

Borgo Argenina

Terre di Baccio

Villa San Filippo

Chianti Village Morrocco

Rocca di Castagnoli

Relais Villa Belvedere

La Locanda di Pietracupa

Casa Vacanze Squarcialupi

L' Eroico

Agriturismo La Ferrozzola

I Parigi Corbinelli

Residence Il Connubio

B&B La Fonte del Machiavelli

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

Salvadonica - Borgo del Chianti

Villa I Barronci Resort & Spa

Fattoria di Vegi

Borgo Vescine

Hotel Toscana Ambassador

Villa Le Barone

Hu Norcenni Girasole Village

Villa Casagrande Resort & SPA

Camping Village Il Poggetto.

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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