𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Chianti Region from RM420 (2026) - Fully Refundable Options

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

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Chianti Region

Pet friendly

Pool

Villa

Spa

Apartment

Hot tub

Farm

Apart hotel

Family friendly

Waterpark

Condo

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

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.

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

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

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

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

Gaiole in Chianti

Rama

RM1,598

RM1,804 total

includes taxes & fees

21 Oct - 22 Oct

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

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

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.

2. Hotel Villa Campomaggio

Radda in Chianti

Dario

RM780

RM886 total

includes taxes & fees

25 Oct - 26 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.

3. Palazzo Leopoldo Dimora Storica & Spa

Radda in Chianti

Elizabeth

RM757

RM860 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

4. Relais Vignale & Spa

Radda in Chianti

Ali

RM716

RM930 total

includes taxes & fees

8 Oct - 9 Oct

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

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

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

A cozy living room with a sofa, a dining table with chairs, a hanging lamp, and a mirror on the wall.

5. Pieve Aldina - Relais & Châteaux

Radda in Chianti

Paul

RM1,491

RM1,677 total

includes taxes & fees

25 Oct - 26 Oct

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

A bar area with a high ceiling, wooden beams, and a bar counter with stools.

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.

6. Chapter Chianti, a Member of Design Hotels

Cavriglia

Samay

RM1,115

RM1,254 total

includes taxes & fees

8 Oct - 9 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 glass table, a vase with flowers, a bottle of wine, and a chair.

7. Dievole Wine Resort

Castelnuovo Berardenga

Marissa

RM1,457

RM1,640 total

includes taxes & fees

14 Oct - 15 Oct

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

A garden with pink roses, a lawn, and a white umbrella.

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

A courtyard with outdoor seating, a gravel path, and a building covered in ivy.

8. Villa Le Barone

Greve in Chianti

Aditi

RM1,034

RM1,166 total

includes taxes & fees

25 Oct - 26 Oct

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.

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

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

9. Borgo Vescine

Radda in Chianti

Gabrielle

RM2,143

RM2,395 total

includes taxes & fees

21 Oct - 22 Oct

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

A stone building with a courtyard, a covered seating area, and a small bell tower.

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

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

10. Borgo di Pietrafitta Relais

Castellina in Chianti

Alejandro

RM368

RM423 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 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.

11. Tenuta CorteDomina

Radda in Chianti

Dustin

RM1,015

RM1,135 total

includes taxes & fees

5 Oct - 6 Oct

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

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

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.

12. Hotel Palazzo San niccolò & Spa

Radda in Chianti

Afeefa

RM617

RM706 total

includes taxes & fees

28 Sept - 29 Sept

A swimming pool with a view of a historic building surrounded by olive trees.

An aerial view of a castle with a courtyard, surrounded by vineyards and dense trees.

A formal dining room with a long table set for a meal, ornate ceiling, and classical architecture.

A stone building with a circular tower, a gravel pathway, and a metal archway leading to a wooden door.

13. Castello di Meleto

Gaiole in Chianti

Vinesh

RM933

RM1,064 total

includes taxes & fees

27 Sept - 28 Sept

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.

An indoor swimming pool with clear glass walls, wooden beams, and large windows.

14. Villa Casagrande Resort & SPA

Figline e Incisa Valdarno

Ana

RM499

RM559 total

includes taxes & fees

25 Oct - 26 Oct

A pool with a stone wall and a tree, surrounded by a clear sky and distant mountains.

A minimalist room with a wooden desk, two chairs, a mirror, and a vase with flowers.

A room with a wooden door, a white cabinet with a book and candles, and two framed pictures on the wall.

A stone wall, a pink building, and a pool with a garden.

15. Villa Barberino

Meleto

Claire

RM579

RM637 total

includes taxes & fees

26 Oct - 27 Oct

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.

16. Borgo Scopeto Wine & Country Relais

Castelnuovo Berardenga

Hannah

RM2,191

RM2,457 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 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.

A pool area with a view of a hilly landscape.

17. Borgo Del Cabreo

Greve in Chianti

Brian

RM1,288

RM1,436 total

includes taxes & fees

18 Oct - 19 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 terraced vineyard with stone walls and a stone pathway leading to a seating area with metal chairs and tables.

18. Castello Vicchiomaggio

Greve in Chianti

Maryse

RM656

RM721 total

includes taxes & fees

27 Sept - 28 Sept

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

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

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

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

19. La Certosa di Pontignano

Castelnuovo Berardenga

Roberto

RM407

RM485 total

includes taxes & fees

16 Oct - 17 Oct

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

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

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

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

20. La pietra del cabreo

Greve in Chianti

Jorge Aaron

RM1,289

RM1,437 total

includes taxes & fees

15 Oct - 16 Oct

View all properties

Holiday Rentals in Chianti Region

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."

Residence

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

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

Riserva di Fizzano Residence

Castellina in Chianti

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

Residence

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

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

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

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

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 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.

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."

Holiday Home

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

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.

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

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

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

Villa di Sotto

Castelnuovo Berardenga

"Great spot"

Townhouse

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

A living room with a blue sofa, a coffee table, and a potted plant.

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

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

Terre di Baccio

Greve in Chianti

"Amazing property. Air conditioning works. Dinner and breakfast is first class. Free parking"

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

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."

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

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 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."

Villa

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

A bedroom with a stone wall, a bed with a white bedspread, a television mounted on the wall, and a window with curtains.

A staircase leading to a room with a stone wall, a green chair, a sofa, and a view through a large window.

A gravel path leading through a vineyard with stone pillars and a potted plant at the entrance.

Relais Badia a Passignano

Tavarnelle Val di Pesa

"A beautiful estate in a scenic Chianti location. The villa was freshly renovated and perfect for a few days of relaxation and wine tours."

Townhouse

A garden with a stone pathway, wooden benches, and various potted plants.

An aerial view of a residential area with a large house, a swimming pool, and surrounding greenery.

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

A room with two beds, a desk with a chair, a television, and a window with curtains.

Antico Borgo il Cardino

San Gimignano

"It was perfect for my one night stop before moving on to another location in Toscana."

Townhouse

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

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.

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 dining area with a table set for two, featuring a view of greenery through a window.

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

A sign reading "CAMERE" against a clear blue sky.

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

La Locanda di Pietracupa

Tavarnelle Val di Pesa

"Great place, wonderful restaurant"

Residence

A courtyard with a fountain, a pergola with flowers, and a building with a bell tower.

A two-story building with a symmetrical facade, green shutters, and a central arched entrance.

A swimming pool with a stone wall and a metal fixture on the right.

A room with a large arched window offering a view of a tree and landscape.

Relais Villa Belpoggio - Residenza d'Epoca

Loro Ciuffenna

"Excellent getaway- beautiful property - great staff - extremely clean - I give it a 100"

See all holiday rentals

Save an average of 15% on thousands of hotels when you're signed in

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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.

See properties

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

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.

See properties

Learn more about Chianti Region

Take a sightseeing trip of Tuscany's renowned wine region and visit its vineyards, wineries, ancient churches, castles and hilltop villages.

See all hotels in Chianti Region

Terraced vineyards on a hillside, a small village, and rolling green hills.

Top Chianti Region Hotel Reviews

Fattoria di Vegi

10/10 Excellent

"This is a newly renovated and opened property cared for by a wonderful family. Everything has been taken care of down to the last detail. The food is delicious, the rooms are well appointed and till we thoroughly enjoyed exploring the property and every interesting nook! There's lots to do including a ping pong table and a beautiful pool. My only regret was not staying longer"

Castello Vicchiomaggio

8/10 Good

"Really liked the location! Helpful staff."

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"

Hu Norcenni Girasole Village

10/10 Excellent

"Perfect can’t fault it. Maybe a bigger train/bus at peak times would help. Lovely restaurant, bars, ice cream. Clean swimming pools. Good, kind, friendly staff. Safe place. Clean accommodation. Peaceful environment. Must take mosquito treatment as they’re bad out here. Lovely bonus is the pump at the pools to pump donuts up. Can’t fault it. Will 100000% return."

Salvadonica - Borgo del Chianti

10/10 Excellent

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

Relais Vignale & Spa

10/10 Excellent

"Beautiful small medieval town with castle and narrow streets. Close to wineries but not much else to do….location is very beautiful on top of hill."

Park Hotel Chianti

10/10 Excellent

"The staff are very helpful and kind."

Palagina la Dimora

8/10 Good

"Nice property to relax. Pool is nice. Breakfast is meh but works. Room was spacious although felt outdated and lacking lighting. Some staff were very helpful while some could have been more friendly."

More cheap stays in Chianti Region

Villa Castiglione

Via Colle Ramole 20 Impruneta FI

RM675

RM757 total

29 Sept - 30 Sept

includes taxes & fees

8.6/10 Excellent! (276 reviews)

Villa Norcenni Aparthotel

Via Norcenni 7 Figline e Incisa Valdarno FI

Get rates

Agriturismo Il Caggio di Sotto

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

Get rates

9.6/10 Exceptional! (16 reviews)

Castello di Pratelli

Via Di Pratelli 1/a Figline e Incisa Valdarno FI

Get rates

9.2/10 Wonderful! (5 reviews)

Hotel Albergo Italia

Via Trento, 36 Poggibonsi SI

Get rates

Quercia Al Poggio

Strada Di Quercia Al Poggio 4 Barberino Tavarnelle FI

Get rates

Explore a world of travel with Expedia

Province of Siena Holiday Rentals

Chianti Region hotels from RM420

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. Hotel Villa Campomaggio

3. Palazzo Leopoldo Dimora Storica & Spa

4. Relais Vignale & Spa

5. Pieve Aldina - Relais & Châteaux

6. Chapter Chianti, a Member of Design Hotels

7. Dievole Wine Resort

8. Villa Le Barone

9. Borgo Vescine

10. Borgo di Pietrafitta Relais

11. Tenuta CorteDomina

12. Hotel Palazzo San niccolò & Spa

13. Castello di Meleto

14. Villa Casagrande Resort & SPA

15. Villa Barberino

16. Borgo Scopeto Wine & Country Relais

17. Borgo Del Cabreo

18. Castello Vicchiomaggio

19. La Certosa di Pontignano

20. La pietra del cabreo

Holiday Rentals in Chianti Region

Villa Curina Resort

Riserva di Fizzano Residence

Villa San Filippo

Chianti Village Morrocco

Borgo Argiano

Villa di Sotto

Terre di Baccio

Villa il Fedino

Borgo Sicelle

B&B La Fonte del Machiavelli

Relais Badia a Passignano

Antico Borgo il Cardino

Rocca di Castagnoli

La Locanda di Pietracupa

Relais Villa Belpoggio - Residenza d'Epoca

Stay near popular Chianti Region attractions

Antinori nel Chianti Classico

The Mall Luxury Outlet

Tenuta Torciano Winery

Verrazzano Castle

Castle of Brolio

Castello di Albola

Meleto Castle

Piazza Matteotti

Learn more about Chianti Region

Top Chianti Region Hotel Reviews

Fattoria di Vegi

Castello Vicchiomaggio

Villa Il Palagio

Hotel Villa Campomaggio

Hu Norcenni Girasole Village

Salvadonica - Borgo del Chianti

Relais Vignale & Spa

Park Hotel Chianti

Palagina la Dimora

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

Explore a world of travel with Expedia

Go further with the Expedia app