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

Search Hotels with Swimming Pool in Castellina in Chianti

  • 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
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for Castellina in Chianti hotels with a pool

A poolside area with lounge chairs and a stone building in the background.
A bedroom with a bed, bedside tables, a sofa, a window with curtains, and a wall with a painting.
A round table with a white tablecloth, two white chairs, and a vase of flowers on a terrace with a stone wall and a scenic view of green hills.
A historic building with a courtyard, stone arches, and a tiled roof.

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.
₹17,616
₹20,016 total
includes taxes & fees
27 Oct - 28 Oct
Palazzo Squarcialupi
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.

2. Locanda le Piazze

Locanda le Piazze
Castellina in Chianti
  • Savour countryside luxury at the outdoor pool, where vineyard views and poolside cocktails create an idyllic Tuscan escape.
₹34,807
₹38,926 total
includes taxes & fees
31 Oct - 1 Nov
Locanda le Piazze
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 rustic interior with a brick archway, wooden beams, a bar area, and potted plants.

3. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
  • Sun-drenched Tuscan pool retreat offers garden-framed relaxation and poolside cocktails.
₹10,699
₹12,088 total
includes taxes & fees
26 Oct - 27 Oct
Hotel Colle Etrusco Salivolpi
A swimming pool with lounge chairs and an umbrella, surrounded by trees.
A restaurant with stone walls, wooden furniture, and a wine cellar.
A spacious living room with two sofas, a coffee table, and a mural of trees on the walls.
A stately building with a grand entrance, multiple arches, and a well-lit facade.

4. Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
₹23,042
₹25,984 total
includes taxes & fees
30 Oct - 31 Oct
Fattoria di Vegi
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 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.

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.
₹19,041
₹21,371 total
includes taxes & fees
4 Nov - 5 Nov
Castello La Leccia
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 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.

6. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
  • Countryside farm stay's outdoor pool beckons with scenic vineyard views.
₹8,981
₹10,305 total
includes taxes & fees
1 Nov - 2 Nov
Borgo di Pietrafitta Relais
A poolside area with lounge chairs and a view of the night sky.
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.
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.

7. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
  • Scenic Tuscan escape with a poolside paradise and winery at your doorstep.
₹10,190
₹11,847 total
includes taxes & fees
27 Oct - 28 Oct
Belvedere di San Leonino
A pool area with lounge chairs and umbrellas, surrounded by greenery and trees.
A stone building with an arched entrance, a wooden door, and a small balcony with a railing.
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.

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.
₹12,472
₹14,039 total
includes taxes & fees
26 Oct - 27 Oct
Albergo Il Colombaio
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 building with arched windows, a courtyard with a pond, and a metal fence.
A view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.

9. Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
  • Sun-soaked seasonal pool oasis in the heart of a Tuscan wine resort with loungers and umbrellas.
₹5,704
₹6,913 total
includes taxes & fees
26 Oct - 27 Oct
Hotel Casafrassi
A swimming pool with stone walls, lounge chairs, and a building with stone architecture.
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'.
A stone building with a gravel path leading to a wooden door. There are potted plants and a metal gate in the foreground.

10. Collelungo

Collelungo
Castellina in Chianti
  • Sip and splash at this enchanting farm stay, featuring a seasonal outdoor pool and attached winery.
₹12,007
₹13,634 total
includes taxes & fees
26 Oct - 27 Oct
Collelungo
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 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.

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
₹8,981
₹10,305 total
includes taxes & fees
1 Nov - 2 Nov
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.

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
₹10,699
₹12,088 total
includes taxes & fees
26 Oct - 27 Oct
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 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 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
₹10,190
₹11,847 total
includes taxes & fees
27 Oct - 28 Oct
Belvedere di San Leonino
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 building with arched windows, a courtyard with a pond, and a metal fence.
A view through a wooden-framed window with a stone archway, a brick wall, and a tiled roof.

Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
₹5,704
₹6,913 total
includes taxes & fees
26 Oct - 27 Oct
Hotel Casafrassi
A round table with a white tablecloth, two white chairs, and a vase of flowers on a terrace with a stone wall and a scenic view of green hills.
A historic building with a courtyard, stone arches, and a tiled roof.
A spa area with a stone ceiling, a hot tub, and a seating area.
A poolside area with lounge chairs and a stone building in the background.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
₹17,616
₹20,016 total
includes taxes & fees
27 Oct - 28 Oct
Palazzo Squarcialupi
A stone building with an arched entrance, a wooden door, and a small balcony with a railing.
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.
A stone building with a large arched doorway, a bench, and a potted plant outside.

Albergo Il Colombaio

Albergo Il Colombaio
Castellina in Chianti
₹12,472
₹14,039 total
includes taxes & fees
26 Oct - 27 Oct
Albergo Il Colombaio
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 courtyard with stone buildings, outdoor tables set for dining, and a gravel ground.
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
₹19,041
₹21,371 total
includes taxes & fees
4 Nov - 5 Nov
Castello La Leccia
A stately building with a grand entrance, multiple arches, and a well-lit facade.
A restaurant with stone walls, wooden furniture, and a wine cellar.
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
₹23,042
₹25,984 total
includes taxes & fees
30 Oct - 31 Oct
Fattoria di Vegi
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
₹34,807
₹38,926 total
includes taxes & fees
31 Oct - 1 Nov
Locanda le Piazze
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.

PODERE 1384

PODERE 1384
Castellina in Chianti
₹46,989
₹52,326 total
includes taxes & fees
4 Nov - 5 Nov
PODERE 1384
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

Plus Florence - Hostel

Plus Florence - Hostel

10/10 Excellent
"Great Stay been there twice. Will be back next time in Florence"
Warren 1-night trip
Posted 10 hours ago
Plus Florence - Hostel
Hu Firenze Camping In Town

Hu Firenze Camping In Town

10/10 Excellent
"I really enjoyed my stay here. The room was clean and comfortable, and the staff was very friendly and helpful. I also enjoyed having the bar available to relax after a long day it was really good with plenty of options. Everything felt welcoming and well taken care of. I would happily stay here again!"
Jesus G. 2-night trip
Posted 2 days ago
Hu Firenze Camping In Town
Italiana Hotels Florence

Italiana Hotels Florence

10/10 Excellent
"Was our second time there so it must be good for that alone."
Gregory 3-night trip
Posted 10 days ago
Italiana Hotels Florence

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 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 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 22°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 6°C.

Explore a world of travel with Expedia