𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chianti Region from RM294 (2026) - Fully Refundable Options

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

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Our top choices for Chianti Region hotels

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

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

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

A swimming pool with stone walls and a stone pathway leading to a building with multiple floors and a balcony.

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

Gaiole in Chianti

Sonja

RM1,355

RM1,536 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 cozy living room with a sofa, a coffee table, and a view of greenery through large windows.

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.

2. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

RM1,200

RM1,357 total

includes taxes & fees

28 Oct - 29 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 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.

3. Hotel Villa Campomaggio

Radda in Chianti

Dario

RM677

RM773 total

includes taxes & fees

3 Nov - 4 Nov

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 stone building with a wooden door and an arched window.

4. Hotel Borgo di Cortefreda Relais

Tavarnelle Val di Pesa

Sergey

RM539

RM620 total

includes taxes & fees

24 Oct - 25 Oct

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

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

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

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

5. Tenuta CorteDomina

Radda in Chianti

Edgar

RM966

RM1,081 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

6. Relais Vignale & Spa

Radda in Chianti

Ali

RM667

RM875 total

includes taxes & fees

16 Oct - 17 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 woman in a blue bikini in a spa pool with a stone wall and a blue light fixture.

7. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

RM478

RM553 total

includes taxes & fees

2 Nov - 3 Nov

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

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

8. Chapter Chianti, a Member of Design Hotels

Cavriglia

Andon

RM1,104

RM1,242 total

includes taxes & fees

8 Oct - 9 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 person relaxing in a hot tub with a view of a building and trees in the background.

A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

A rustic stone building with a garden in front.

9. Belvedere di San Leonino

Castellina in Chianti

Michelle Reene

RM454

RM527 total

includes taxes & fees

8 Oct - 9 Oct

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

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

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.

10. Villa Le Barone

Greve in Chianti

Tereza

RM1,023

RM1,153 total

includes taxes & fees

25 Oct - 26 Oct

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

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

A cozy living room with a striped sofa, a wooden coffee table, and a bookshelf.

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

11. Castello di Fonterutoli Wine Resort

Castellina in Chianti

Saion

RM810

RM910 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

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

12. Castello di Tornano Wine Resort

Gaiole in Chianti

Lisa

RM624

RM723 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 bedroom with a large bed, a bedside table, and a chair.

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.

13. Borgo Del Cabreo

Greve in Chianti

Brian

RM1,129

RM1,260 total

includes taxes & fees

9 Oct - 10 Oct

A candle on a tray with corks, a glass with a drink and an orange slice, and a table with chairs in an outdoor setting with arches in the background.

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

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

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

14. La Certosa di Pontignano

Castelnuovo Berardenga

Leslie

RM395

RM471 total

includes taxes & fees

2 Nov - 3 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 reception area with a stone counter, a sign for SPA VILLA CASAGRANDE, and a staircase leading to a glass door.

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

15. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

RM481

RM539 total

includes taxes & fees

1 Nov - 2 Nov

A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.

A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and lush greenery, overlooking a valley.

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

A dining area with a stone wall, wooden beams, and a table set for four with wine glasses and plates.

16. Borgo di Pietrafitta Relais

Castellina in Chianti

Alejandro

RM363

RM417 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

17. La pietra del cabreo

Greve in Chianti

Jorge Aaron

RM1,129

RM1,260 total

includes taxes & fees

9 Oct - 10 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 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.

18. Castello La Leccia

Castellina in Chianti

Eva

RM823

RM924 total

includes taxes & fees

3 Nov - 4 Nov

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

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.

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

19. Castello Vicchiomaggio

Greve in Chianti

Mary Margaret

RM741

RM816 total

includes taxes & fees

9 Oct - 10 Oct

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

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

A spa area with multiple white massage chairs arranged in a row, a brick ceiling, and a staircase in the background.

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

20. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

RM433

RM504 total

includes taxes & fees

2 Nov - 3 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.

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

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

Relais Villa Olmo

Impruneta

"Very friendly and clean."

Townhouse

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

An outdoor dining area with a stone wall backdrop, metal chairs, and a table set with white tablecloths, plates, and glassware.

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

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

Terre di Baccio

Greve in Chianti

"Amazing property and room, only issue is it’s very understaffed so it’s hard to get anything without chasing down workers. They also don’t stay on the property so after like 11pm you’re on your own. Besides that it was a wonderful location and very peaceful."

Apartment

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

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

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

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

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 stone building with a garden in front.

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

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

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 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 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 "

Residence

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

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

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

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

Chianti Village Morrocco

Tavarnelle Val di Pesa

"It’s seen its best day a while ago. Basic necessities for an overnight, but I wouldn’t choose it again."

Residence

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

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.

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

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 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.

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

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

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

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

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

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

B&B La Fonte del Machiavelli

San Casciano in Val di Pesa

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

Townhouse

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

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

An aerial view of a town with a central square, surrounding buildings, and vineyards.

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

L' Eroico

Gaiole in Chianti

"Monica is a very gracious host. We very much enjoyed our stay. The village is also very quaint and within walking distance. We appreciate the hospitality and highly recommend staying here if you’re coming to the area."

Holiday Home

A stone building with multiple windows and a chimney.

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

A rustic interior with exposed wooden beams, a wooden dining table with wine bottles, a sofa, and a staircase leading to an upper level.

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

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"

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 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.

Villa Cassia di Baccano

Loro Ciuffenna

"The staff were great and the villa was amazing"

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."

Camping

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

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

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

"Lovely location in the hills. Really nice pool and bar."

See all holiday rentals

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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

Castello Vicchiomaggio

10/10 Excellent

"What a gorgeous place! We loved it here and can’t wait to go back!"

Villa I Barronci Resort & Spa

8/10 Good

"We quite enjoyed the heated pool and views. Thank you for having us."

Fattoria di Vegi

10/10 Excellent

"The entire estate was perfectly curated, every aspect was completely flawless. Food and wine…. 10/10. Best place we’ve ever stayed."

Salvadonica - Borgo del Chianti

10/10 Excellent

"Property was beautiful staff was great last time with my family"

Borgo Vescine

10/10 Excellent

"The staff was amazing and incredibly kind."

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent

"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."

Hotel Toscana Ambassador

8/10 Good

"Close to train station"

Relais Vignale & Spa

10/10 Excellent

"In a convenient location."

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."

More cheap stays in Chianti Region

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

RM279

RM321 total

2 Nov - 3 Nov

includes taxes & fees

8.6/10 Excellent! (277 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

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

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Quercia Al Poggio

Strada Di Quercia Al Poggio 4 Barberino Tavarnelle FI

Get rates

Explore a world of travel with Expedia

Province of Siena Holiday Rentals

Chianti Region hotels from RM294

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. Dievole Wine Resort

3. Hotel Villa Campomaggio

4. Hotel Borgo di Cortefreda Relais

5. Tenuta CorteDomina

6. Relais Vignale & Spa

7. Palazzo Leopoldo Dimora Storica & Spa

8. Chapter Chianti, a Member of Design Hotels

9. Belvedere di San Leonino

10. Villa Le Barone

11. Castello di Fonterutoli Wine Resort

12. Castello di Tornano Wine Resort

13. Borgo Del Cabreo

14. La Certosa di Pontignano

15. Villa Casagrande Resort & SPA

16. Borgo di Pietrafitta Relais

17. La pietra del cabreo

18. Castello La Leccia

19. Castello Vicchiomaggio

20. Hotel Palazzo San niccolò & Spa

Holiday Rentals in Chianti Region

Relais Villa Olmo

Terre di Baccio

Casa Vacanze Squarcialupi

Borgo Argenina

Rocca di Castagnoli

Chianti Village Morrocco

Palazzo Pacini

Villa il Fedino

B&B La Fonte del Machiavelli

L' Eroico

Agriturismo La Ferrozzola

La Locanda di Pietracupa

Villa Cassia di Baccano

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

hu Firenze Certosa camping in town

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

Castello Vicchiomaggio

Villa I Barronci Resort & Spa

Fattoria di Vegi

Salvadonica - Borgo del Chianti

Borgo Vescine

Castello di Spaltenna- Small Luxury Hotels of the World

Hotel Toscana Ambassador

Relais Vignale & Spa

Villa Le Barone

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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