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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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.

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

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

Rp7.339.184

Rp8.276.968 total

includes taxes & fees

21 Oct - 22 Oct

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

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

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

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

2. Relais Vignale & Spa

Radda in Chianti

Ali

Rp2.921.333

Rp3.839.336 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 modern living room with a white sofa, armchairs, and a coffee table.

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

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

Rp4.865.806

Rp5.474.031 total

includes taxes & fees

11 Oct - 12 Oct

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

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

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.

4. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

Rp5.320.908

Rp6.016.091 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.

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.

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

5. COMO Castello Del Nero

Tavarnelle Val di Pesa

Lauren

Rp14.285.647

Rp15.877.305 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.

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

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.

6. Hotel Villa Campomaggio

Radda in Chianti

Dario

Rp3.400.387

Rp3.862.030 total

includes taxes & fees

1 Nov - 2 Nov

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

A pool area with lounge chairs and umbrellas, a large building in the background, and a view of the countryside.

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

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.

7. Hotel Le Fontanelle

Castelnuovo Berardenga

Cristina

Rp9.981.290

Rp11.183.285 total

includes taxes & fees

11 Oct - 12 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 terraced vineyard with stone walls and a stone pathway leading to a seating area with metal chairs and tables.

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

8. Castello Vicchiomaggio

Greve in Chianti

Maryse

Rp3.070.756

Rp3.377.831 total

includes taxes & fees

27 Oct - 28 Oct

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

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

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

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

9. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

Rp2.107.040

Rp2.439.389 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 outdoor dining area with tables set for a meal, a sign indicating a wine list, and a view of the landscape.

10. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

GUANGMIN

Rp9.608.879

Rp10.773.633 total

includes taxes & fees

20 Oct - 21 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 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 pool area with a view of a hilly landscape.

11. Borgo Del Cabreo

Greve in Chianti

Brian

Rp5.654.433

Rp6.301.505 total

includes taxes & fees

11 Oct - 12 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.

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.

12. Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa

Sergey

Rp2.386.903

Rp2.747.913 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 striped sofa, a wooden coffee table, and a bookshelf.

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.

13. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Saion

Rp3.591.715

Rp4.032.474 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

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

14. La pietra del cabreo

Greve in Chianti

Jorge Aaron

Rp4.976.393

Rp5.555.129 total

includes taxes & fees

2 Oct - 3 Oct

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

A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.

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

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

15. Locanda le Piazze

Castellina in Chianti

Tara

Rp6.194.738

Rp6.936.532 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 pool area with lounge chairs and a service person attending to a guest.

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.

16. Borgo San Felice Resort

Castelnuovo Berardenga

Cynthia

Rp12.973.304

Rp14.474.500 total

includes taxes & fees

25 Oct - 26 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 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.

17. Tenuta CorteDomina

Radda in Chianti

Dustin

Rp4.257.580

Rp4.764.435 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

A hotel room with a large bed, a desk, and a chair, a view of a city through the window, and a ceiling light.

18. Hotel Palazzo San Lorenzo & SPA

Colle di Val d'Elsa

Maria

Rp2.985.836

Rp3.365.516 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

19. Borgo Vescine

Radda in Chianti

Gabrielle

Rp9.407.499

Rp10.511.342 total

includes taxes & fees

20 Oct - 21 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 rustic stone building with a garden in front.

20. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

Rp2.216.230

Rp2.560.152 total

includes taxes & fees

15 Oct - 16 Oct

View all properties

Holiday Rentals in Chianti Region

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 stone building with a wooden door and a balcony with flower planters.

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!"

Aparthotel

A stone building with a garden in front.

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

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

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."

Residence

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

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

A stone wall with a metal railing, overlooking a valley with trees and distant hills.

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"

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 hotel room with a bed, a nightstand, a lamp, and a view of a landscape through a window.

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

Villa Curina Resort

Castelnuovo Berardenga

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

Holiday Home

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

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

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

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

Borgo Argiano

Castelnuovo Berardenga

"Amazing staff, clean room, amazing pool!"

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

A group of people toasting with wine glasses at a table with a view of the countryside.

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

A stone building with arched windows and a patio area with outdoor seating.

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. "

Townhouse

An arched entrance with a lantern above, flanked by two potted plants.

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

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

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

Villa il Fedino

San Casciano in Val di Pesa

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

Residence

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

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

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

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

Palazzo Pacini

Colle di Val d'Elsa

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

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

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

Relais Villa Belvedere

Figline e Incisa Valdarno

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

Residence

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

A poolside area with lounge chairs and umbrellas, a clear sky, and a view of the landscape.

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

A building with a sign reading "MARIANI B&B" and a statue of a cherub in front.

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

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."

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"

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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

Palagina la Dimora

8/10 Good

"Was staying locally for business but the pools open too late for an early swim, which was the plan...so a bit of a disappointment, upside is that you walk to Sting's pizza place :-)"

Villa I Barronci Resort & Spa

8/10 Good

"Under renovation so it could have been better"

Fattoria di Vegi

10/10 Excellent

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

Relais Vignale & Spa

10/10 Excellent

"In a convenient location."

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"

More cheap stays in Chianti Region

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

Rp2.453.361

Rp2.759.520 total

8 Oct - 9 Oct

includes taxes & fees

8.6/10 Excellent! (276 reviews)

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

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Agriturismo Il Caggio di Sotto

Loc. Il Caggio di Sotto, 26 Colle di Val d'Elsa SI

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9.6/10 Exceptional! (16 reviews)

Castello di Pratelli

Via Di Pratelli 1/a Figline e Incisa Valdarno FI

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9.2/10 Wonderful! (5 reviews)

Hotel Albergo Italia

Via Trento, 36 Poggibonsi SI

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Quercia Al Poggio

Strada Di Quercia Al Poggio 4 Barberino Tavarnelle FI

Get rates

Explore a world of travel with Expedia

More ways to book

Book Hotels in Chianti Region on Expedia.it

Find hotels in Chianti Region from Rp1.537.457

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. Hotel Villa Campomaggio

7. Hotel Le Fontanelle

8. Castello Vicchiomaggio

9. Palazzo Leopoldo Dimora Storica & Spa

10. Borgo Scopeto Wine & Country Relais

11. Borgo Del Cabreo

12. Hotel Borgo di Cortefreda Relais

13. Castello di Fonterutoli Wine Resort

14. La pietra del cabreo

15. Locanda le Piazze

16. Borgo San Felice Resort

17. Tenuta CorteDomina

18. Hotel Palazzo San Lorenzo & SPA

19. Borgo Vescine

20. Belvedere di San Leonino

Holiday Rentals in Chianti Region

Riserva di Fizzano Residence

Borgo Argenina

Villa San Filippo

Villa Curina Resort

Borgo Argiano

Villa di Sotto

Chianti Village Morrocco

Borgo Sicelle

Villa il Fedino

Palazzo Pacini

Rocca di Castagnoli

Relais Villa Belvedere

Castello Del Nero - Podere San Filippo

Mariani Bed & Breakfast

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

Palagina la Dimora

Villa I Barronci Resort & Spa

Fattoria di Vegi

Relais Vignale & Spa

Hotel Toscana Ambassador

Villa Le Barone

Hu Norcenni Girasole Village

Villa Il Palagio

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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