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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Pool

Villa

Spa

Apartment

Apart hotel

Farm

Hot tub

Family friendly

Waterpark

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

A room with a large window offering a view of a hilly landscape. There is a sofa with patterned upholstery and a lamp on a side table.

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

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

Gaiole in Chianti

Rama

Rp6.021.424

Rp6.827.919 total

includes taxes & fees

30 Oct - 31 Oct

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

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

2. Relais Vignale & Spa

Radda in Chianti

Ali

Rp2.929.481

Rp3.850.045 total

includes taxes & fees

26 Oct - 27 Oct

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

A reception area with a wooden ceiling, a reception desk, and seating.

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

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

3. Chapter Chianti, a Member of Design Hotels

Cavriglia

Samay

Rp4.906.436

Rp5.519.741 total

includes taxes & fees

6 Oct - 7 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.

4. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

Rp5.335.749

Rp6.032.871 total

includes taxes & fees

28 Oct - 29 Oct

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.

A resort with a swimming pool, terraced gardens, and a view of rolling hills.

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

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

5. COMO Castello Del Nero

Tavarnelle Val di Pesa

Lauren

Rp14.325.493

Rp15.921.590 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 pool area with a view of a hilly landscape.

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

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.

6. Borgo Del Cabreo

Greve in Chianti

Brian

Rp5.670.205

Rp6.319.081 total

includes taxes & fees

11 Oct - 12 Oct

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

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

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

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

7. Hotel Villa Campomaggio

Radda in Chianti

Dario

Rp3.352.731

Rp3.810.665 total

includes taxes & fees

18 Oct - 19 Oct

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

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

8. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

Rp3.326.972

Rp3.782.330 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

9. Castello Vicchiomaggio

Greve in Chianti

Maryse

Rp3.096.398

Rp3.406.038 total

includes taxes & fees

27 Oct - 28 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 stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

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

10. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

Rp2.222.411

Rp2.567.293 total

includes taxes & fees

15 Oct - 16 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 historic estate with a central courtyard, surrounded by lush gardens and vineyards.

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

11. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

GUANGMIN

Rp9.635.680

Rp10.803.683 total

includes taxes & fees

20 Oct - 21 Oct

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

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

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.

12. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

Rp10.009.130

Rp11.214.478 total

includes taxes & fees

11 Oct - 12 Oct

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

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

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

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

13. Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa

Sergey

Rp2.393.560

Rp2.755.577 total

includes taxes & fees

24 Oct - 25 Oct

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

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

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

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

14. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Saion

Rp3.513.492

Rp3.946.615 total

includes taxes & fees

1 Oct - 2 Oct

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

A spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.

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

A modern interior with a bar area, seating, and a staircase.

15. Locanda le Piazze

Castellina in Chianti

Tara

Rp6.212.017

Rp6.955.879 total

includes taxes & fees

12 Oct - 13 Oct

A historic stone building with multiple windows and a courtyard.

An outdoor dining area with tables set for two, covered by large umbrellas, and a brick wall in the background.

A room with a large window overlooking a landscape with trees and hills. There are two upholstered sofas with a patterned rug in the center.

A pool area with lounge chairs and a service person attending to a guest.

16. Borgo San Felice Resort

Castelnuovo Berardenga

Cynthia

Rp13.009.490

Rp14.514.874 total

includes taxes & fees

25 Oct - 26 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 pathway leading to a large planter.

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

17. La pietra del cabreo

Greve in Chianti

Jorge Aaron

Rp4.014.357

Rp4.497.566 total

includes taxes & fees

30 Sept - 1 Oct

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

A table set with wine glasses and a candle, viewed through a window with string lights.

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.

18. Tenuta CorteDomina

Radda in Chianti

Dustin

Rp4.702.001

Rp5.253.975 total

includes taxes & fees

5 Oct - 6 Oct

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

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

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

An indoor dining area with wooden tables and chairs, hanging baskets, and large windows offering a view of the outdoors.

19. Borgo Vescine

Radda in Chianti

Gabrielle

Rp9.433.739

Rp10.540.661 total

includes taxes & fees

20 Oct - 21 Oct

A person sitting in a hot tub with a waterfall feature in the background.

A tiled shower area with a square light fixture above the showerhead.

A dining area with tables and chairs, a chandelier, and wall-mounted lighting.

A spa area with wooden benches and a glass partition, a modern bathroom with a large sink, and a corridor leading to another room.

20. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Maria

Rp3.010.767

Rp3.393.618 total

includes taxes & fees

25 Oct - 26 Oct

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Holiday Rentals in Chianti Region

Aparthotel

A stone building with a garden in front.

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

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

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

Borgo Argenina

Gaiole in Chianti

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

Residence

A stone building with a courtyard, a swimming pool, and vineyard fields in the background.

An outdoor dining area with tables and chairs, a pergola structure, and potted plants.

A pool area with a view of vineyards and hills.

A buffet setup with various baked goods and pastries, including a bundt cake, arranged on a wooden table with a stone wall background.

Riserva di Fizzano Residence

Castellina in Chianti

"Great place to stay in Tuscany! Very nice breakfast also!"

Townhouse

A villa with a swimming pool, outdoor seating, and a tennis court.

A pool area with lounge chairs and umbrellas, a stone planter with flowers, and a building with balconies in the background.

A lobby with a stone archway, a reception desk, and a seating area with a sofa and armchairs.

An aerial view of a property with a swimming pool, tennis court, and vineyard.

Villa Curina Resort

Castelnuovo Berardenga

"Beautiful resort in the hills, lovely and charming room, incredibly spacious."

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"

Holiday Home

A bedroom with a large bed, a wooden ceiling, and a brick archway.

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

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

A villa with a swimming pool surrounded by olive trees and a vineyard in the background.

Borgo Argiano

Castelnuovo Berardenga

"Amazing staff, clean room, amazing pool!"

Townhouse

A pool area with two rectangular pools, surrounded by lounge chairs and umbrellas, set against a backdrop of vineyards and tall cypress trees.

A stone-walled sauna with a wooden interior and a hot tub in the foreground.

A restaurant with tables set for dining, large windows offering a view of the landscape, and a wooden ceiling structure.

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

Villa di Sotto

Castelnuovo Berardenga

"Great spot"

Residence

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

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

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

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

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."

Residence

A hillside villa with a swimming pool, terraced gardens, and a church tower.

A kitchen with wooden cabinets, a brick archway, and a vase with sunflowers.

A spacious room with a foosball table, a billiards table, a bookshelf, and a bench.

A swimming pool with a view of rolling hills in the background.

Borgo Sicelle

Castellina in Chianti

"Beautiful stay if you want to live the real Tuscany feeling. Hotel staff was extremely friendly, helpful and the overall property is extremely neat, always keeping the Italian style. "

Residence

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

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

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

An arched entrance to a building with a tiled floor and a staircase leading inside.

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

A hammock suspended between trees in a garden with a view of a hilly landscape.

Villa il Fedino

San Casciano in Val di Pesa

"Tha parking was easy on the property. It was within walking distance to the villages with shops, restaurants and cafes. The best part was the staff. The owners were incredibly helpful, friendly and made you feel like family. Breakfast outside was lovely overlooking the hills of Tuscany. We met many people and had lovely conversations with other travelers during breakfast. A gem in Tuscany."

Townhouse

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

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.

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.

Rocca di Castagnoli

Gaiole in Chianti

"It was wonderful to stay in a castle in Tuscany no less Every person we met was attentive and kind We were staying near friends and didn’t hang around the grounds much or use the pool but everything seemed well kept It’s really a place to retreat to eat at and sleep at which served our purpose well "

Townhouse

A kitchen with wooden cabinets, a glass display case, and a dining area with a table and chairs.

A covered outdoor seating area with wicker furniture and potted plants.

A room with a window featuring sheer curtains, a radiator below, and a view of a green landscape.

A bedroom with a bed, a painting, and a bathroom door.

Mariani Bed & Breakfast

Castellina in Chianti

"Beautiful view, very clean and everything in great condition. Friendly service. We will definitely stay again."

Aparthotel

A swimming pool with lounge chairs and umbrellas, surrounded by stone walls and a landscaped area with trees.

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

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.

Relais Villa Belvedere

Figline e Incisa Valdarno

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

Residence

An outdoor dining area with a table and chairs, surrounded by greenery and trees, overlooking a scenic landscape.

A room with a large window, a cabinet, and a person sitting by the window.

A dining area with a table, chairs, a television, and a view of the outdoors.

A large villa with a swimming pool, surrounded by lush greenery and a well-maintained lawn.

Castello Del Nero - Podere San Filippo

Tavarnelle Val di Pesa

"The hotel and property was soo beautiful!"

Townhouse

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

A spa room with a bathtub, candles, towels, and a bottle of wine.

A modern kitchen with stone countertops, built-in shelves, and a large window.

A dining area with white tables and chairs, stone walls, and large windows with curtains.

Villa Cassia di Baccano

Loro Ciuffenna

"The staff were great and the villa was amazing"

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Stay near popular Chianti Region attractions

A spiral staircase with a person standing on it.

Antinori nel Chianti Classico

9.4/10 (16 reviews)

You can enjoy a tasting or tour at Antinori nel Chianti Classico during your travels to Bargino. Visit the churches and wineries in this walkable area.

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A grand, illuminated building with arched windows and a central fountain.

The Mall Luxury Outlet

8.8/10 (355 reviews)

During your visit to Leccio, you can enjoy retail therapy at The Mall Luxury Outlet. Discover the acclaimed art galleries and stunning cathedral in this walkable area.

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Tenuta Torciano Winery

9.2/10 (40 reviews)

You can enjoy a tasting or tour at Tenuta Torciano Winery during your travels to Ulignano. Discover the beautiful countryside and wineries in this quaint area.

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Verrazzano Castle

9.8/10 (10 reviews)

You can find out about the history of Greve in Chianti when you stop by Verrazzano Castle. Discover the area's countryside and wineries.

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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

Fattoria di Vegi

10/10 Excellent

"We had a lovely night stay at this villa in September. It is a 900 year-old hunting lodge that has been converted to spacious rooms many with balconies. The views are incredible, the rooms have been renovated with character fixtures, but includes excellent air-conditioning. The view from the pool was out of a storybook. Staff was attentive and very nice to deal with. The grounds have endless opportunities for photos at every turn. Try to explore the grounds a little - including the painters studio with is exquisite. It has only been open four months so there are a few bugs but overall, the stay was excellent. The one area they need to improve however is the food. The selections are pretty limited and the quality was not to the standard of the property. My recommendation is have the breakfast on site and lunch by the pool, but try the surrounding towns for dinner. Castellini in Chianti is a small town 15 minutes away with great choices. One Belvedere and their sister property Locanda are both within 2 kms and have high end dining. Overall I highly recommend this villa for a unique Tuscan experience."

Villa I Barronci Resort & Spa

10/10 Excellent

"Excellent dinner, spacious rooms, pol and jacuzzi, and incredible views!"

Relais Vignale & Spa

10/10 Excellent

"In a convenient location."

Hotel Toscana Ambassador

8/10 Good

"Friendly staff. Property is dated and needs some repairs. Location is convenient and the breakfast is amazing."

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 Il Palagio

10/10 Excellent

"The check in went great and the property is amazingly managed, a beautiful villa in the hills of Tuscany. It felt magic just walking to it, I would absolutely recommend renting a car if you want to go into Florence often."

Hotel Villa Campomaggio

10/10 Excellent

"Great hotel"

Salvadonica - Borgo del Chianti

10/10 Excellent

"Beautiful escape weekend. I would go back again and again. The staff was amazing. Food was incredible."

More cheap stays in Chianti Region

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

Rp1.134.892

Rp1.279.046 total

30 Sept - 1 Oct

includes taxes & fees

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

Rp1.931.909

Rp2.186.430 total

14 Oct - 15 Oct

includes taxes & fees

8.6/10 Excellent! (276 reviews)

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

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Book Hotels in Chianti Region on Expedia.it

Find hotels in Chianti Region from Rp1.279.046

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. Relais Vignale & Spa

3. Chapter Chianti, a Member of Design Hotels

4. Dievole Wine Resort

5. COMO Castello Del Nero

6. Borgo Del Cabreo

7. Hotel Villa Campomaggio

8. Palazzo Leopoldo Dimora Storica & Spa

9. Castello Vicchiomaggio

10. Belvedere di San Leonino

11. Borgo Scopeto Wine & Country Relais

12. Hotel Le Fontanelle

13. Hotel Borgo di Cortefreda Relais

14. Castello di Fonterutoli Wine Resort

15. Locanda le Piazze

16. Borgo San Felice Resort

17. La pietra del cabreo

18. Tenuta CorteDomina

19. Borgo Vescine

20. Hotel Palazzo San Lorenzo & SPA

Holiday Rentals in Chianti Region

Borgo Argenina

Riserva di Fizzano Residence

Villa Curina Resort

Villa San Filippo

Borgo Argiano

Villa di Sotto

Chianti Village Morrocco

Borgo Sicelle

Palazzo Pacini

Villa il Fedino

Rocca di Castagnoli

Mariani Bed & Breakfast

Relais Villa Belvedere

Castello Del Nero - Podere San Filippo

Villa Cassia di Baccano

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

Fattoria di Vegi

Villa I Barronci Resort & Spa

Relais Vignale & Spa

Hotel Toscana Ambassador

Villa Le Barone

Hu Norcenni Girasole Village

Villa Il Palagio

Hotel Villa Campomaggio

Salvadonica - Borgo del Chianti

More cheap stays in Chianti Region

Villa Norcenni Aparthotel

Villa Castiglione

Agriturismo Il Caggio di Sotto

Castello di Pratelli

Hotel Albergo Italia

Quercia Al Poggio

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