A stone building with a clock tower, steps leading up to it, and people walking around.

Hotels with Swimming Pool in Castellina in Chianti, Tuscany

  • 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

Check availability on Castellina in Chianti Hotels with Swimming Pool

Tonight
Oct 4 - Oct 5
Tomorrow
Oct 5 - Oct 6
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for Castellina in Chianti hotels with a pool

A spa room with a stone ceiling, a window with frosted glass, a bed with pillows, and a wall-mounted artwork.
A pool area with lounge chairs, surrounded by well-maintained lawns and trees, with a view of rolling hills in the background.
A historic building with a courtyard, stone arches, and a tiled roof.
A bedroom with a wooden headboard, a large bed, two bedside tables with lamps, a wooden bench, a desk with a chair, and a window with curtains.

1. Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
  • Dive into the tranquil waters of a seasonal outdoor pool surrounded by the charm of this Beaux Arts hotel and attached winery.
P12,598
P14,280 total
includes taxes & fees
Oct 21 - Oct 22
Palazzo Squarcialupi
A clear blue pool with lounge chairs and a stone building in the background.
A rustic living room with exposed wooden beams, a sofa, a coffee table, and a dining area with chairs.
A spacious lobby with a stone archway, wooden ceiling beams, a bar area with a wine rack, and a reception desk.
A stone building with a wooden bench outside.

2. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
  • Sun-drenched Tuscan pool retreat offers garden-framed relaxation and poolside cocktails.
P6,872
P7,771 total
includes taxes & fees
Oct 19 - Oct 20
Hotel Colle Etrusco Salivolpi
A person in a white hat and white top walking towards a building with a pool, surrounded by greenery and a hilly landscape.
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.
A vineyard landscape with rows of grapevines and a person holding a glass.
A modern interior with a bar area, seating, and a staircase.

3. Locanda le Piazze

Locanda le Piazze
Castellina in Chianti
  • Savor countryside luxury at the outdoor pool, where vineyard views and poolside cocktails create an idyllic Tuscan escape.
P23,041
P25,767 total
includes taxes & fees
Oct 12 - Oct 13
Locanda le Piazze
A swimming pool with lounge chairs and umbrellas, surrounded by a stone wall and lush greenery, overlooking a valley.
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 stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.

4. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
  • Countryside farm stay's outdoor pool beckons with scenic vineyard views.
P5,181
P5,981 total
includes taxes & fees
Oct 25 - Oct 26
Borgo di Pietrafitta Relais
A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.
A courtyard with stone buildings, tables with white tablecloths, and chairs arranged for dining.
A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.
A dining area with a table set for two, featuring wine bottles and bread.

5. Castello La Leccia

Castello La Leccia
Castellina in Chianti
  • Castello La Leccia's seasonal pool offers Tuscan countryside refreshment and vineyard views all summer long.
P14,784
P16,544 total
includes taxes & fees
Nov 2 - Nov 3
Castello La Leccia
A pool with lounge chairs and umbrellas, surrounded by stone tiles and trees.
A long table set for dining in a tunnel with wine barrels on one side.
A castle-like building with a swimming pool and a well-maintained garden.
A sculpture of two figures in a garden with a windmill in the background.

6. Agriturismo Villa Godenano - Pool & Suites

Agriturismo Villa Godenano - Pool & Suites
Castellina in Chianti
  • Dive into this Tuscan paradise with a seasonal pool and umbrellas for ultimate summer relaxation.
P9,288
P10,498 total
includes taxes & fees
Oct 27 - Oct 28
Agriturismo Villa Godenano - Pool & Suites
A swimming pool with lounge chairs and an umbrella, surrounded by trees.
A spacious living room with two sofas, a coffee table, and a mural of trees on the walls.
A room with a wooden floor, a bathtub, a chair, a bed, and large windows offering a view of the countryside.
A stately building with a grand entrance, multiple arches, and a well-lit facade.

7. Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
P15,350
P17,308 total
includes taxes & fees
Oct 26 - Oct 27
Fattoria di Vegi
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 building with a large arched doorway, a bench, and a potted plant outside.
A stone-walled room with tables set for dining, a staircase, and a lamp.

8. Albergo Il Colombaio

Albergo Il Colombaio
Castellina in Chianti
  • Lounge beneath Italian sunshine at the inviting outdoor pool, where rural charm meets relaxation at this countryside retreat.
P9,600
P10,771 total
includes taxes & fees
Oct 7 - Oct 8
Albergo Il Colombaio
A clear blue pool with lounge chairs and umbrellas, surrounded by lush greenery and a forested hillside.
A bench in a park with a lamp post and a building in the background.
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.

9. Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti
  • Tuscan poolside paradise boasts an outdoor swimming spot and a hot tub in scenic countryside settings.
P8,618
P9,902 total
includes taxes & fees
Oct 9 - Oct 10
Villa Casalecchi Country Hotel
A poolside area with lounge chairs and a view of the night sky.
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 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.

10. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
  • Scenic Tuscan escape with a poolside paradise and winery at your doorstep.
P7,653
P8,841 total
includes taxes & fees
Oct 15 - Oct 16
Belvedere di San Leonino
View all properties

Choose what matters most at hotels with a pool in Castellina in Chianti

Breakfast included
4 stars
5 stars
Spa
Hot tub

Hotels with pools and free breakfast 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
P5,181
P5,981 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 clear blue pool with lounge chairs and a stone building in the background.

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
P6,872
P7,771 total
includes taxes & fees
Oct 19 - Oct 20
Hotel Colle Etrusco Salivolpi
A spa room with a stone ceiling, a window with frosted glass, a bed with pillows, and a wall-mounted artwork.
A pool area with lounge chairs, surrounded by well-maintained lawns and trees, with a view of rolling hills in the background.
A historic building with a courtyard, stone arches, and a tiled roof.
A bedroom with a wooden headboard, a large bed, two bedside tables with lamps, a wooden bench, a desk with a chair, and a window with curtains.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
P12,598
P14,280 total
includes taxes & fees
Oct 21 - Oct 22
Palazzo Squarcialupi
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 stone building with ivy-covered walls, a stone pathway, and a garden with flowers.
A rustic stone building with a garden in front.
A person relaxing in a hot tub with a view of a building and trees in the background.

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
P7,653
P8,841 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 bench in a park with a lamp post and a building in the background.
A clear blue pool with lounge chairs and umbrellas, surrounded by lush greenery and a forested hillside.
A hallway with a wooden altar, benches, and a carpet with a floral pattern.

Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti
P8,618
P9,902 total
includes taxes & fees
Oct 9 - Oct 10
Villa Casalecchi Country Hotel
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 castle-like building with a swimming pool and a well-maintained garden.
A sculpture of two figures in a garden with a windmill in the background.

Agriturismo Villa Godenano - Pool & Suites

Agriturismo Villa Godenano - Pool & Suites
Castellina in Chianti
P9,288
P10,498 total
includes taxes & fees
Oct 27 - Oct 28
Agriturismo Villa Godenano - Pool & Suites
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.

Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
P3,776
P4,576 total
includes taxes & fees
Oct 6 - Oct 7
Hotel Casafrassi
A stately building with a grand entrance, multiple arches, and a well-lit facade.
A spacious living room with two sofas, a coffee table, and a mural of trees on the walls.
A well-decorated living room with a sofa, a coffee table, and a vase with flowers.
A swimming pool with lounge chairs and an umbrella, surrounded by trees.

Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
P15,350
P17,308 total
includes taxes & fees
Oct 26 - Oct 27
Fattoria di Vegi
A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.
A courtyard with stone buildings, tables with white tablecloths, and chairs arranged for dining.
A dining area with a table set for two, featuring wine bottles and bread.
A bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a tray of items, and a window with curtains.

Castello La Leccia

Castello La Leccia
Castellina in Chianti
P14,784
P16,544 total
includes taxes & fees
Nov 2 - Nov 3
Castello La Leccia
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.
An outdoor dining area with tables and chairs, a pergola structure, and potted plants.
A pool area with a view of vineyards and hills.
A stone building with a wooden door and a balcony with flower planters.

Riserva di Fizzano Residence

Riserva di Fizzano Residence
Castellina in Chianti
P11,431
P12,715 total
includes taxes & fees
Oct 6 - Oct 7
Riserva di Fizzano Residence
View all properties

4-star hotels with pools in Castellina in Chianti

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 stone building with ivy-covered walls, a stone pathway, and a garden with flowers.
A rustic stone building with a garden in front.
A person relaxing in a hot tub with a view of a building and trees in the background.

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
P7,653
P8,841 total
includes taxes & fees
Oct 15 - Oct 16
Belvedere di San Leonino
A spa room with a stone ceiling, a window with frosted glass, a bed with pillows, and a wall-mounted artwork.
A pool area with lounge chairs, surrounded by well-maintained lawns and trees, with a view of rolling hills in the background.
A historic building with a courtyard, stone arches, and a tiled roof.
A bedroom with a wooden headboard, a large bed, two bedside tables with lamps, a wooden bench, a desk with a chair, and a window with curtains.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
P12,598
P14,280 total
includes taxes & fees
Oct 21 - Oct 22
Palazzo Squarcialupi
A historic building with a stone facade, multiple windows with shutters, and a well-maintained garden with potted plants and flowers.
A bench in a park with a lamp post and a building in the background.
A clear blue pool with lounge chairs and umbrellas, surrounded by lush greenery and a forested hillside.
A hallway with a wooden altar, benches, and a carpet with a floral pattern.

Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti
P8,618
P9,902 total
includes taxes & fees
Oct 9 - Oct 10
Villa Casalecchi Country Hotel
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.
A vineyard landscape with rows of grapevines and a person holding a glass.
A modern interior with a bar area, seating, and a staircase.
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
P23,041
P25,767 total
includes taxes & fees
Oct 12 - Oct 13
Locanda le Piazze
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.

Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
P3,776
P4,576 total
includes taxes & fees
Oct 6 - Oct 7
Hotel Casafrassi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Castellina in Chianti Hotel Reviews

Hu Firenze Camping In Town

Hu Firenze Camping In Town

8/10 Good
"A very well maintained campsite with good amenities and a bustling friendly atmosphere on the whole. The only downside is beyond the control of the campsite and was the bus service into central Florence. Appalling service with infrequent and misleading times. Overall other than the logistics of going to central Florence I would recommend the campsite highly"
David 3-night trip
Posted 17 hours ago
Hu Firenze Camping In Town
Villa Neroli

Villa Neroli

10/10 Excellent
"Definitely will return. The staff was so helpful in communicating before our trip like offering to schedule car service and local events. We had a large group and we enjoyed the excellent breakfast to start our day!"
Roxane 3-night trip
Posted 1 day ago
Villa Neroli

Frequently asked questions

What's it like visiting Castellina in Chianti?
If spending time by the pool is your idea of the perfect getaway, you might want to think about relaxing Castellina in Chianti, which has 7 places to stay with pools. While you're here, you can explore attractions like City Hall Castellina In Chianti and Castellina Fortress, and then unwind poolside at one of the accommodations in Castellina in Chianti that guests like for their pools.
What are some hotels with pools in Castellina in Chianti?
Residenzia del Sogno: Features free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Podere Palazzolo: Offers a sauna, a seasonal outdoor pool, and spa services.
How many hotels with pools are there in Castellina in Chianti?
Expedia has 7 hotels in Castellina in Chianti for your poolside break.
What is there to see and do in Castellina in Chianti?
The picturesque setting of Chianti Sculpture Park and Sentierelsa Trail showcase the area's natural beauty. Discover sights such as City Hall Castellina In Chianti, Castellina Fortress, and Archaeological Museum of Chianti during your stay. The countryside and wineries are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Castellina in Chianti?
You may want to consider an accommodation with an outdoor swimming pool if you will be visiting Castellina in Chianti in the warmest months of August, July, or June when the average temperature is 72°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 44°F.

Explore a world of travel with Expedia