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Castellina in Chianti Hotels with Swimming Pool

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Check availability on Castellina in Chianti Hotels with Swimming Pools

Tonight
17 Sept - 18 Sept
Tomorrow
18 Sept - 19 Sept
This weekend
18 Sept - 20 Sept
Next weekend
25 Sept - 27 Sept

Our top choices for Castellina in Chianti hotels with a pool

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 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 striped sofa.

1. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
  • Countryside farm stay's outdoor pool beckons with scenic vineyard views.
RM370
RM426 total
includes taxes & fees
14 Oct - 15 Oct
Borgo di Pietrafitta Relais
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 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
  • Sun-drenched Tuscan pool retreat offers garden-framed relaxation and poolside cocktails.
RM463
RM524 total
includes taxes & fees
20 Sept - 21 Sept
Hotel Colle Etrusco Salivolpi
A poolside area with lounge chairs and a view of the night sky.
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.
A rustic stone building with a garden in front.
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.

3. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
  • Scenic Tuscan escape with a poolside paradise and winery at your doorstep.
RM518
RM598 total
includes taxes & fees
7 Oct - 8 Oct
Belvedere di San Leonino
A pool with clear water and a row of white lounge chairs facing a scenic hillside view.
A cozy living room with two beige sofas, a glass coffee table, and a patterned rug.
A stone-walled hallway with a staircase, a glass table with a red cushion, and a wooden cabinet.
A spa room with a stone ceiling, a circular hot tub, a window, and a bench.

4. 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.
RM935
RM1,057 total
includes taxes & fees
26 Sept - 27 Sept
Palazzo Squarcialupi
A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.
A dining area with a table set for two, featuring wine bottles and bread.
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.

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.
RM1,312
RM1,462 total
includes taxes & fees
9 Oct - 10 Oct
Castello La Leccia
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
A traditional villa with a tiled roof, surrounded by lush greenery and hills.
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.

6. Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
  • Sun-soaked seasonal pool oasis in the heart of a Tuscan wine resort with loungers and umbrellas.
RM253
RM306 total
includes taxes & fees
17 Sept - 18 Sept
Hotel Casafrassi
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 spacious bedroom with a large bed, a desk, and a chair. There is a painting on the wall and a window with curtains.

7. Agritourism Villa [EXACT MATCH] Godenano - Pool & Suites

Agritourism Villa [EXACT MATCH] Godenano - Pool & Suites
Castellina in Chianti
  • Dive into this Tuscan paradise with a seasonal pool and umbrellas for ultimate summer relaxation.
RM686
RM774 total
includes taxes & fees
30 Sept - 1 Oct
Agritourism Villa [EXACT MATCH] Godenano - Pool & Suites
A clear blue pool with lounge chairs and umbrellas, surrounded by lush greenery and a forested hillside.
A spacious living room with striped sofas, a coffee table, and a chandelier.
A bench in a park with a lamp post and a building in the background.
A hallway with a wooden altar, benches, and a carpet with a floral pattern.

8. 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.
RM577
RM663 total
includes taxes & fees
15 Oct - 16 Oct
Villa Casalecchi Country Hotel
A swimming pool with stone walls, lounge chairs, and a building with stone architecture.
A stone-walled dining area with tables set for a meal, a stone fireplace, and a sign indicating 'Colleluono'.
A stone building with a staircase leading up to a window, surrounded by lush greenery and flowering plants.
A stone building with a balcony and a garden with pink flowers.

9. Collelungo

Collelungo
Castellina in Chianti
  • Sip and splash at this enchanting farm stay, featuring a seasonal outdoor pool and attached winery.
RM532
RM604 total
includes taxes & fees
21 Sept - 22 Sept
Collelungo
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 an arched entrance, a wooden door, and a small balcony with a railing.
A stone-walled room with tables set for dining, a staircase, and a lamp.

10. 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.
RM643
RM721 total
includes taxes & fees
20 Sept - 21 Sept
Albergo Il Colombaio
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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 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 clear blue pool with lounge chairs and a stone building in the background.
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
RM463
RM524 total
includes taxes & fees
20 Sept - 21 Sept
Hotel Colle Etrusco Salivolpi
A stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.
A cozy living room with a stone fireplace, striped sofas, and a coffee table.
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 striped sofa.

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
RM370
RM426 total
includes taxes & fees
14 Oct - 15 Oct
Borgo di Pietrafitta Relais
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
A traditional villa with a tiled roof, surrounded by lush greenery and hills.
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.

Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
RM253
RM306 total
includes taxes & fees
17 Sept - 18 Sept
Hotel Casafrassi
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 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
RM518
RM598 total
includes taxes & fees
7 Oct - 8 Oct
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 spacious living room with striped sofas, a coffee table, and a chandelier.
A bench in a park with a lamp post and a building in the background.
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
RM577
RM663 total
includes taxes & fees
15 Oct - 16 Oct
Villa Casalecchi Country Hotel
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.

Castello La Leccia

Castello La Leccia
Castellina in Chianti
RM1,312
RM1,462 total
includes taxes & fees
9 Oct - 10 Oct
Castello La Leccia
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 spacious bedroom with a large bed, a desk, and a chair. There is a painting on the wall and a window with curtains.

Agritourism Villa [EXACT MATCH] Godenano - Pool & Suites

Agritourism Villa [EXACT MATCH] Godenano - Pool & Suites
Castellina in Chianti
RM686
RM774 total
includes taxes & fees
30 Sept - 1 Oct
Agritourism Villa [EXACT MATCH] Godenano - Pool & Suites
A pool with clear water and a row of white lounge chairs facing a scenic hillside view.
A stone-walled hallway with a staircase, a glass table with a red cushion, and a wooden cabinet.
A spa room with a stone ceiling, a circular hot tub, a window, and a bench.
An outdoor patio with round tables and chairs, surrounded by potted plants and flowers.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
RM935
RM1,057 total
includes taxes & fees
26 Sept - 27 Sept
Palazzo Squarcialupi
A stone building with an arched entrance, a wooden door, and a small balcony with a railing.
A stone-walled room with tables set for dining, a staircase, and a lamp.
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.

Albergo Il Colombaio

Albergo Il Colombaio
Castellina in Chianti
RM643
RM721 total
includes taxes & fees
20 Sept - 21 Sept
Albergo Il Colombaio
A stone building with a courtyard, a swimming pool, and vineyard fields in the background.
A stone building with a wooden door and a balcony with flower planters.
A buffet setup with various baked goods and pastries, including a bundt cake, arranged on a wooden table with a stone wall background.
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
RM988
RM1,096 total
includes taxes & fees
23 Sept - 24 Sept
Riserva di Fizzano Residence
View all properties

4-star hotels with pools in Castellina in Chianti

An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
A traditional villa with a tiled roof, surrounded by lush greenery and hills.
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.

Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
RM253
RM306 total
includes taxes & fees
17 Sept - 18 Sept
Hotel Casafrassi
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 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
RM518
RM598 total
includes taxes & fees
7 Oct - 8 Oct
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 spacious living room with striped sofas, a coffee table, and a chandelier.
A bench in a park with a lamp post and a building in the background.
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
RM577
RM663 total
includes taxes & fees
15 Oct - 16 Oct
Villa Casalecchi Country Hotel
A pool with clear water and a row of white lounge chairs facing a scenic hillside view.
A stone-walled hallway with a staircase, a glass table with a red cushion, and a wooden cabinet.
A spa room with a stone ceiling, a circular hot tub, a window, and a bench.
An outdoor patio with round tables and chairs, surrounded by potted plants and flowers.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
RM935
RM1,057 total
includes taxes & fees
26 Sept - 27 Sept
Palazzo Squarcialupi
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
RM1,543
RM1,726 total
includes taxes & fees
24 Sept - 25 Sept
Locanda le Piazze
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.
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Top Castellina in Chianti Hotel Reviews

Plus Florence - Hostel

Plus Florence - Hostel

8/10 Good
"The indoor pool was undergoing maintenance and the outdoor pool closed at 7, not the 10pm advertised in the hostel’s messages after checking in. The restaurant advertises itself online as being flexible for gluten free/ vegetarian/ vegan. When sitting down and asking, nothing was completely gluten free and only the three meat dishes and one pasta dish could be made gluten free. We ate elsewhere. Clean rooms and friendly staff, good for a basic hostel stay. Air conditioning in the rooms, however it is very loud (might just be an issue in the room we stayed in). Great location for the train station."
Maisie 2-night trip
Posted 9 hours ago
Plus Florence - Hostel
Villa Neroli

Villa Neroli

10/10 Excellent
"My cousin and I were on a month trip with many stops in 4 countries. Florence was our 2nd last stop. Villa Nerolli was my favorite overall stay. It was so very relaxing with the scents of roses, bamboo, jasmine and wisteria everywhere. Simply beautiful and a symphony for all the senses. The food, service, pool, and drinks were fabulous πŸ’– I hope to make it back one day πŸ™"
Susan 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 such as City Hall Castellina In Chianti and Castellina Fortress, and then kick back and relax poolside at one of the accommodation options 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 should I expect to find 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 settings 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 Walls of Monteriggioni 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 accommodation that offers an outdoor pool if you plan to visit Castellina in Chianti in the warmest months of August, July or June, when the average temperature is 22Β°C. Accommodation with an indoor pool may be what you want if you visit during the coldest months of January, February or December, when the average temp is 6Β°C.

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