Hotels logo

Hotels in Castellina in Chianti

October 2026
9
November 2026

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Where to stay in Castellina in Chianti?

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 dining area with a stone wall, wooden beams, and a table set for four with wine glasses and plates.
A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and lush greenery, overlooking a valley.

1. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
$89
$102 total
includes taxes & fees
Oct 25 - Oct 26
Borgo di Pietrafitta Relais
A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.
A rustic living room with exposed wooden beams, a sofa, a coffee table, and a dining area with chairs.
A stone building with a wooden bench outside.
A rustic interior with a brick archway, wooden beams, a bar area, and potted plants.

2. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
$108
$122 total
includes taxes & fees
Oct 21 - Oct 22
Hotel Colle Etrusco Salivolpi
A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.
A courtyard with stone buildings, outdoor tables set for dining, and a gravel ground.
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.

3. Castello La Leccia

Castello La Leccia
Castellina in Chianti
$201
$225 total
includes taxes & fees
Nov 2 - Nov 3
Castello La Leccia
A spa area with a stone ceiling, a large bathtub, and a seating area.
A bedroom with a bed, bedside tables, a sofa, a window with curtains, and a wall with a painting.
A rectangular pool with clear water, surrounded by white lounge chairs and a grassy area.
A historic building with a courtyard, stone arches, and a tiled roof.

4. Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
$198
$225 total
includes taxes & fees
Oct 18 - Oct 19
Palazzo Squarcialupi
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 well-lit outdoor garden area with stone planters, a paved walkway, and a building with large windows.
A stone building with wooden shutters, a bench, and hanging purple flowers.

5. Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
$178
$201 total
includes taxes & fees
Oct 11 - Oct 12
Castello di Fonterutoli Wine Resort
A stately building with a grand entrance, multiple arches, and a well-lit facade.
A well-decorated living room with a sofa, a coffee table, and a vase with flowers.
A spacious living room with two sofas, a coffee table, and a mural of trees on the walls.
A swimming pool with lounge chairs and an umbrella, surrounded by trees.

6. Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
$244
$276 total
includes taxes & fees
Oct 27 - Oct 28
Fattoria di Vegi
A stone building with an arched entrance, a wooden door, and a small balcony with a railing.
A pool area with lounge chairs and umbrellas, surrounded by greenery and trees.
A stone staircase leading to a wooden balcony with a view of a mountainous landscape.
A stone-walled room with tables set for dining, a staircase, and a lamp.

7. Albergo Il Colombaio

Albergo Il Colombaio
Castellina in Chianti
$153
$172 total
includes taxes & fees
Oct 13 - Oct 14
Albergo Il Colombaio
A stone building with a staircase leading up to a window, surrounded by lush greenery and flowering plants.
A stone building with a gravel path leading to a wooden door. There are potted plants and a metal gate in the foreground.
A stone building with a balcony and a garden with pink flowers.
A stone-walled dining area with tables set for a meal, a stone fireplace, and a sign indicating 'Colleluono'.

8. Collelungo

Collelungo
Castellina in Chianti
$127
$144 total
includes taxes & fees
Oct 10 - Oct 11
Collelungo
A long table set for dining in a tunnel with wine barrels on one side.
A pool with lounge chairs and umbrellas, surrounded by stone tiles and trees.
A spacious bedroom with a large bed, a desk, and a chair. There is a painting on the wall and a window with curtains.
A castle-like building with a swimming pool and a well-maintained garden.

9. Agriturismo Villa Godenano - Pool & Suites

Agriturismo Villa Godenano - Pool & Suites
Castellina in Chianti
$166
$187 total
includes taxes & fees
Oct 26 - Oct 27
Agriturismo Villa Godenano - Pool & Suites
A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.
A rustic stone building with a garden in front.
A poolside area with lounge chairs and a view of the night sky.
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

10. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
$110
$128 total
includes taxes & fees
Oct 15 - Oct 16
Belvedere di San Leonino
A historic building with a stone facade, multiple windows with shutters, and a well-maintained garden with potted plants and flowers.
A hallway with a wooden altar, benches, and a carpet with a floral pattern.
A spacious living room with striped sofas, a coffee table, and a chandelier.
A clear blue pool with lounge chairs and umbrellas, surrounded by lush greenery and a forested hillside.

11. Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti
$148
$169 total
includes taxes & fees
Oct 11 - Oct 12
Villa Casalecchi Country Hotel
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 bedroom with a bed, bedside tables, a chair, and a window with curtains.
A modern two-story residential building with a stone facade, a well-maintained garden with hedges and grass, and a clear sky.

12. Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
$114
$132 total
includes taxes & fees
Nov 6 - Nov 7
Casa Vacanze Squarcialupi
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.
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.
A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.

13. Locanda le Piazze

Locanda le Piazze
Castellina in Chianti
$338
$378 total
includes taxes & fees
Oct 21 - Oct 22
Locanda le Piazze
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.
A stone building with outdoor seating, potted plants, and flags.
An open door leading to a patio with a round wooden table and chairs, overlooking a hilly landscape.
A stone building with a sign reading "del sogno RESIDENZIA DEL SOGNO".

14. Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
$133
$150 total
includes taxes & fees
Oct 10 - Oct 11
Residenzia del Sogno
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 room with a window featuring sheer curtains, a radiator below, and a view of a green landscape.

15. Mariani Bed & Breakfast

Mariani Bed & Breakfast
Castellina in Chianti
$87
$100 total
includes taxes & fees
Oct 14 - Oct 15
Mariani Bed & Breakfast
A stone building with multiple windows and a chimney.
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, set against a stone building with a garden.
A stone staircase leading up to a rustic stone building with a flat roof, surrounded by greenery and trees.
A rustic interior with exposed wooden beams, a wooden dining table with wine bottles, a sofa, and a staircase leading to an upper level.

16. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
$128
$146 total
includes taxes & fees
Nov 8 - Nov 9
Agriturismo La Ferrozzola
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.
A pool area with a view of vineyards and hills.
An outdoor dining area with tables and chairs, a pergola structure, and potted plants.

17. Riserva di Fizzano Residence

Riserva di Fizzano Residence
Castellina in Chianti
$176
$195 total
includes taxes & fees
Oct 19 - Oct 20
Riserva di Fizzano Residence
A stone corridor leading to a wooden archway with a view of a green landscape and a red chair.
An outdoor terrace with tables and chairs, overlooking a hilly landscape with vineyards.
A modern bedroom with a large bed, a chandelier, and a view of greenery outside.
A narrow stone pathway between buildings with a clear view of the countryside.

18. PODERE 1384

PODERE 1384
Castellina in Chianti
$495
$552 total
includes taxes & fees
Nov 1 - Nov 2
PODERE 1384
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
A view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.
A bar area with brick arches, wooden barrels, leather seating, and a wine rack.
A building with arched windows, a courtyard with a pond, and a metal fence.

19. Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
$60
$73 total
includes taxes & fees
Oct 11 - Oct 12
Hotel Casafrassi
A historic square with a central fountain, surrounded by stone buildings with arched windows and a prominent tower.
A lobby with a reception desk, a staircase, and seating areas.
A hotel room with a bed, a desk, a chair, a TV, and a balcony with a view.
A historic square with stone buildings, a central fountain, and a tower.

20. La Cisterna

La Cisterna
San Gimignano City Centre
$99
$116 total
includes taxes & fees
Nov 5 - Nov 6
La Cisterna
View all properties

You may also like pet-friendly hotels in Castellina in Chianti

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 dining area with a stone wall, wooden beams, and a table set for four with wine glasses and plates.
A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and lush greenery, overlooking a valley.

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
$89
$102 total
includes taxes & fees
Oct 25 - Oct 26
Borgo di Pietrafitta Relais
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 well-lit outdoor garden area with stone planters, a paved walkway, and a building with large windows.
A stone building with wooden shutters, a bench, and hanging purple flowers.

Castello di Fonterutoli Wine Resort

Castello di Fonterutoli Wine Resort
Castellina in Chianti
$178
$201 total
includes taxes & fees
Oct 11 - Oct 12
Castello di Fonterutoli Wine Resort
A long table set for dining in a tunnel with wine barrels on one side.
A pool with lounge chairs and umbrellas, surrounded by stone tiles and trees.
A spacious bedroom with a large bed, a desk, and a chair. There is a painting on the wall and a window with curtains.
A castle-like building with a swimming pool and a well-maintained garden.

Agriturismo Villa Godenano - Pool & Suites

Agriturismo Villa Godenano - Pool & Suites
Castellina in Chianti
$166
$187 total
includes taxes & fees
Oct 26 - Oct 27
Agriturismo Villa Godenano - Pool & Suites
A spa area with a stone ceiling, a large bathtub, and a seating area.
A bedroom with a bed, bedside tables, a sofa, a window with curtains, and a wall with a painting.
A rectangular pool with clear water, surrounded by white lounge chairs and a grassy area.
A historic building with a courtyard, stone arches, and a tiled roof.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
$198
$225 total
includes taxes & fees
Oct 18 - Oct 19
Palazzo Squarcialupi
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 bedroom with a bed, bedside tables, a chair, and a window with curtains.
A modern two-story residential building with a stone facade, a well-maintained garden with hedges and grass, and a clear sky.

Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti
$114
$132 total
includes taxes & fees
Nov 6 - Nov 7
Casa Vacanze Squarcialupi
A stone building with an arched entrance, a wooden door, and a small balcony with a railing.
A pool area with lounge chairs and umbrellas, surrounded by greenery and trees.
A stone staircase leading to a wooden balcony with a view of a mountainous landscape.
A stone-walled room with tables set for dining, a staircase, and a lamp.

Albergo Il Colombaio

Albergo Il Colombaio
Castellina in Chianti
$153
$172 total
includes taxes & fees
Oct 13 - Oct 14
Albergo Il Colombaio
A stone building with a staircase leading up to a window, surrounded by lush greenery and flowering plants.
A stone building with a gravel path leading to a wooden door. There are potted plants and a metal gate in the foreground.
A stone building with a balcony and a garden with pink flowers.
A stone-walled dining area with tables set for a meal, a stone fireplace, and a sign indicating 'Colleluono'.

Collelungo

Collelungo
Castellina in Chianti
$127
$144 total
includes taxes & fees
Oct 10 - Oct 11
Collelungo
A historic building with a stone facade, multiple windows with shutters, and a well-maintained garden with potted plants and flowers.
A hallway with a wooden altar, benches, and a carpet with a floral pattern.
A spacious living room with striped sofas, a coffee table, and a chandelier.
A clear blue pool with lounge chairs and umbrellas, surrounded by lush greenery and a forested hillside.

Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti
$148
$169 total
includes taxes & fees
Oct 11 - Oct 12
Villa Casalecchi Country Hotel
A pool area with lounge chairs and umbrellas, surrounded by greenery and a stone building.
A stone building with outdoor seating, potted plants, and flags.
An open door leading to a patio with a round wooden table and chairs, overlooking a hilly landscape.
A stone building with a sign reading "del sogno RESIDENZIA DEL SOGNO".

Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
$133
$150 total
includes taxes & fees
Oct 10 - Oct 11
Residenzia del Sogno
A stone building with multiple windows and a chimney.
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, set against a stone building with a garden.
A stone staircase leading up to a rustic stone building with a flat roof, surrounded by greenery and trees.
A rustic interior with exposed wooden beams, a wooden dining table with wine bottles, a sofa, and a staircase leading to an upper level.

Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
$128
$146 total
includes taxes & fees
Nov 8 - Nov 9
Agriturismo La Ferrozzola
View all properties

Go beyond your typical stay in Castellina in Chianti

Pool image
Pool
Pool
spa image
Spa
Spa
hot tub image
Hot tub
Hot tub
pet friendly image
Pet friendly
Pet friendly
apart-hotel image
Apart hotel
Apart hotel
Apartment image
Apart­ment
Apart­ment
villa image
Villa
Villa
farm image
Farm
Farm
Family friendly image
Family friendly
Family friendly
Condo image
Condo
Condo
Cottage image
Cottage
Cottage
campsite image
Campsite
Campsite
Our prices for hotels in Castellina in Chianti are cheapest in February

Price trends for hotels in Castellina in Chianti

Pricing is based on two traveler single night rates
View properties in October

October

High 20°C / low 11°C. Sunny most days.
20°
11°
14°
7°
10°
3°
9°
2°
11°
2°
14°
4°
18°
7°
21°
10°
27°
15°
31°
18°
31°
18°
26°
14°
Monthly weather averages (˚C)

Top landmarks in Castellina in Chianti

Buondonno Winery

9.6/10 (4 reviews)
Travelers might want a tour of Buondonno Winery, just one of the places to visit, and located 3.9 mi (6.3 km) from central Castellina in Chianti.
See properties

Casa Vinicola Luigi Cecchi

9.0/10 (4 reviews)
Travelers might want a tour of Casa Vinicola Luigi Cecchi, just one of the places to visit, and located 5 mi (8 km) from central Castellina in Chianti.
See properties

Castellina Fortress

9.4/10 (3 reviews)
If you're planning a bit of sightseeing during your trip, head to Castellina Fortress— just one of the monuments in central Castellina in Chianti.
See properties

Archaeological Museum of Chianti

8.0/10 (6 reviews)
If visiting museums in Castellina in Chianti are on your list, you might want to check out the upcoming exhibitions at Archaeological Museum of Chianti, located in the heart of town. If you want to experience more of the culture Castellina in Chianti has to offer, head to City Hall Castellina In Chianti, Isole e Olena Winery, and Il Molino di Grace Winery.
See properties

Lilliano Estate Winery

Travelers might want a tour of Lilliano Estate Winery, just one of the places to visit in the heart of Lilliano.
See properties

Walls of Monteriggioni

9.2/10 (5 reviews)
If museums are on your list of things to see in Castellina in Chianti, then you might want to head to Walls of Monteriggioni. If you want to experience more of the culture Castellina in Chianti has to offer, head to City Hall Castellina In Chianti, Isole e Olena Winery, and Archaeological Museum of Chianti.
See properties

Mazzei Winery

Travelers might want a tour of Mazzei Winery, just one of the places to visit in the heart of Fonterutoli.
See properties

Necropolis of Poggino

Necropolis of Poggino is 3 mi (4.8 km) from central Castellina in Chianti, why not stop by during your stay.
See properties

Learn more about Castellina in Chianti

Notable for its wineries, Castellina in Chianti features attractions such as City Hall Castellina In Chianti and Castellina Fortress. This relaxing city has something for everyone including sights like Archaeological Museum of Chianti and Walls of Monteriggioni within a rural setting.

See all hotels in Castellina in Chianti
A stone building with a clock tower, steps leading up to it, and people walking around.

Check out reviews of Castellina in Chianti hotels guests love

A stately building with a grand entrance, multiple arches, and a well-lit facade.
A well-decorated living room with a sofa, a coffee table, and a vase with flowers.
A spacious living room with two sofas, a coffee table, and a mural of trees on the walls.
A swimming pool with lounge chairs and an umbrella, surrounded by trees.

Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti

10/10 Exceptional

United States
Patrick
Fattoria di Vegi
A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.
A courtyard with stone buildings, outdoor tables set for dining, and a gravel ground.
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.

Castello La Leccia

Castello La Leccia
Castellina in Chianti

10/10 Exceptional

United States
Sarah
Castello La Leccia
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.
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.
A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.

Locanda le Piazze

Locanda le Piazze
Castellina in Chianti

10/10 Exceptional

United States
Anonymous traveler
Locanda le Piazze
A spa area with a stone ceiling, a large bathtub, and a seating area.
A bedroom with a bed, bedside tables, a sofa, a window with curtains, and a wall with a painting.
A rectangular pool with clear water, surrounded by white lounge chairs and a grassy area.
A historic building with a courtyard, stone arches, and a tiled roof.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti

10/10 Exceptional

United States
Jacqueline
Palazzo Squarcialupi
A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.
A rustic living room with exposed wooden beams, a sofa, a coffee table, and a dining area with chairs.
A stone building with a wooden bench outside.
A rustic interior with a brick archway, wooden beams, a bar area, and potted plants.

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti

10/10 Exceptional

United States
Samantha
Hotel Colle Etrusco Salivolpi
A rustic cellar with brick walls, wooden barrels, and a stone ceiling. There is a wooden table with a wine bottle and glasses, and a television mounted on the wall.
A rustic stone building with a garden in front.
A poolside area with lounge chairs and a view of the night sky.
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti

10/10 Exceptional

United States
Lior
Belvedere di San Leonino
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.
A pool area with a view of vineyards and hills.
An outdoor dining area with tables and chairs, a pergola structure, and potted plants.

Riserva di Fizzano Residence

Riserva di Fizzano Residence
Castellina in Chianti

10/10 Exceptional

United States
C
Riserva di Fizzano Residence
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 dining area with a stone wall, wooden beams, and a table set for four with wine glasses and plates.
A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and lush greenery, overlooking a valley.

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti

10/10 Exceptional

United States
Renee
Borgo di Pietrafitta Relais
A stone building with multiple windows and a chimney.
A swimming pool with clear blue water, surrounded by lounge chairs and umbrellas, set against a stone building with a garden.
A stone staircase leading up to a rustic stone building with a flat roof, surrounded by greenery and trees.
A rustic interior with exposed wooden beams, a wooden dining table with wine bottles, a sofa, and a staircase leading to an upper level.

Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti

10/10 Exceptional

United States
Kai
Agriturismo La Ferrozzola
A historic building with a stone facade, multiple windows with shutters, and a well-maintained garden with potted plants and flowers.
A hallway with a wooden altar, benches, and a carpet with a floral pattern.
A spacious living room with striped sofas, a coffee table, and a chandelier.
A clear blue pool with lounge chairs and umbrellas, surrounded by lush greenery and a forested hillside.

Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti

10/10 Exceptional

United States
George H
Villa Casalecchi Country Hotel
A stone building with a staircase leading up to a window, surrounded by lush greenery and flowering plants.
A stone building with a gravel path leading to a wooden door. There are potted plants and a metal gate in the foreground.
A stone building with a balcony and a garden with pink flowers.
A stone-walled dining area with tables set for a meal, a stone fireplace, and a sign indicating 'Colleluono'.

Collelungo

Collelungo
Castellina in Chianti

10/10 Exceptional

United States
Omar
Collelungo
A stone building with an arched entrance, a wooden door, and a small balcony with a railing.
A pool area with lounge chairs and umbrellas, surrounded by greenery and trees.
A stone staircase leading to a wooden balcony with a view of a mountainous landscape.
A stone-walled room with tables set for dining, a staircase, and a lamp.

Albergo Il Colombaio

Albergo Il Colombaio
Castellina in Chianti

10/10 Exceptional

United States
Christine
Albergo Il Colombaio
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 bedroom with a bed, bedside tables, a chair, and a window with curtains.
A modern two-story residential building with a stone facade, a well-maintained garden with hedges and grass, and a clear sky.

Casa Vacanze Squarcialupi

Casa Vacanze Squarcialupi
Castellina in Chianti

10/10 Exceptional

United States
Lindsay
Casa Vacanze Squarcialupi
A table with breakfast items and a wicker chair, overlooking a scenic landscape.
A bar area with a counter, bottles, and glasses.
A hotel room with a bed, a desk, a chair, a window with curtains, a lamp, and a view of the landscape.
A dining area with checkered flooring, tables set with white tablecloths, and wicker chairs.

Palazzo Ravizza

Palazzo Ravizza
Siena Historical Center

10/10 Exceptional

United States
Anonymous traveler
Palazzo Ravizza

Frequently Asked Questions

What accommodations do travelers like in Castellina in Chianti?

Guests like Borgo Vescine.

Where can I find free parking with my stay in Castellina in Chianti?

Park your car for free at Castello di Fonterutoli Wine Resort.

Can I book a refundable hotel in Castellina in Chianti?

If you need the flexibility to change your plans to Castellina in Chianti, most properties provide refundable* bookable rates. You can see these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.

Where can I stay in Castellina in Chianti if I want a vacation home instead of a traditional hotel?

If you're looking for a good alternative to a hotel, browse our selection of 31 vacation homes. You can also book one of 16 apartments or 27 villas.

What will the weather in Castellina in Chianti be like during my visit?

August and July are typically the warmest months in Castellina in Chianti when the average temp is 72°F. January and February are the coldest months when the average temperature is 44°F. November and October are the months with the most rain.

Why should I book my Castellina in Chianti accommodation with Hotels.com?

There are lots of reasons to book your Castellina in Chianti trip with us: our free cancellations on selected hotels* gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™** on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.