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

Find Hotels with a Pool in Castellina in Chianti

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Check availability on Castellina in Chianti Hotels with a Pool

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Oct 1 - Oct 2
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Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.
A dining area with a stone wall, wooden beams, and a table set for four with wine glasses and plates.
A stone building with a courtyard, a covered seating area, and a small bell tower.

1. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
  • Countryside farm stay's outdoor pool beckons with scenic vineyard views.
$83 nightly
$96 total
Oct 25 - Oct 26
Total with taxes and fees
Borgo di Pietrafitta Relais
A clear blue pool with lounge chairs and a stone building in the background.
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.
A rustic living room with exposed wooden beams, a sofa, a coffee table, and a dining area with chairs.

2. Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
  • Sun-drenched Tuscan pool retreat offers garden-framed relaxation and poolside cocktails.
$102 nightly
$115 total
Oct 26 - Oct 27
Total with taxes and fees
Hotel Colle Etrusco Salivolpi
A pool with clear water and a row of white lounge chairs facing a scenic hillside view.
An outdoor patio with round tables and chairs, surrounded by potted plants and flowers.
A spa room with a stone ceiling, a circular hot tub, a window, and a bench.
A cozy living room with two beige sofas, a glass coffee table, and a patterned rug.

3. 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.
$203 nightly
$230 total
Oct 21 - Oct 22
Total with taxes and fees
Palazzo Squarcialupi
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.
A rustic stone building with a garden in front.

4. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
  • Scenic Tuscan escape with a poolside paradise and winery at your doorstep.
$123 nightly
$142 total
Oct 15 - Oct 16
Total with taxes and fees
Belvedere di San Leonino
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.
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.

5. 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.
$139 nightly
$159 total
Oct 13 - Oct 14
Total with taxes and fees
Villa Casalecchi Country Hotel
A pool with lounge chairs and umbrellas, surrounded by stone tiles and trees.
A sculpture of two figures in a garden with a windmill in the background.
A castle-like building with a swimming pool and a well-maintained garden.
A long table set for dining in a tunnel with wine barrels on one side.

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.
$150 nightly
$169 total
Oct 28 - Oct 29
Total with taxes and fees
Agriturismo Villa Godenano - Pool & Suites
A swimming pool with lounge chairs and an umbrella, surrounded by trees.
A room with a wooden floor, a bathtub, a chair, a bed, and large windows offering a view of the countryside.
A restaurant with stone walls, wooden furniture, and a wine cellar.
A stately building with a grand entrance, multiple arches, and a well-lit facade.

7. Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
$241 nightly
$272 total
Oct 26 - Oct 27
Total with taxes and fees
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 bedroom with a wooden ceiling, a bed with white bedding, a bedside table with a tray of items, and a window with curtains.
A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.

8. 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.
$284 nightly
$317 total
Oct 9 - Oct 10
Total with taxes and fees
Castello La Leccia
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
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.
A traditional villa with a tiled roof, surrounded by lush greenery and hills.

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.
$61 nightly
$74 total
Oct 4 - Oct 5
Total with taxes and fees
Hotel Casafrassi
A pool area with a view of vineyards and hills.
A buffet setup with various baked goods and pastries, including a bundt cake, arranged on a wooden table with a stone wall background.
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.

10. Riserva di Fizzano Residence

Riserva di Fizzano Residence
Castellina in Chianti
  • Vineyard retreat's outdoor pool offers tranquil relaxation with Tuscan sunshine and idyllic views.
$164 nightly
$182 total
Oct 8 - Oct 9
Total with taxes and fees
Riserva di Fizzano Residence
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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 stone-walled dining area with a table set for four, a bench, and a view through an open doorway to the outside.
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.
A stone building with a courtyard, a covered seating area, and a small bell tower.

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
$83 nightly
$96 total
Oct 25 - Oct 26
Total with taxes and fees
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 stone building with a wooden bench outside.
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.

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
Castellina in Chianti
$102 nightly
$115 total
Oct 26 - Oct 27
Total with taxes and fees
Hotel Colle Etrusco Salivolpi
A pool with clear water and a row of white lounge chairs facing a scenic hillside view.
A spa room with a stone ceiling, a window with frosted glass, a bed with pillows, and a wall-mounted artwork.
An outdoor patio with round tables and chairs, surrounded by potted plants and flowers.
A stone-walled hallway with a staircase, a glass table with a red cushion, and a wooden cabinet.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
$203 nightly
$230 total
Oct 21 - Oct 22
Total with taxes and fees
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 rustic stone building with a garden in front.
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.
A poolside area with lounge chairs and a view of the night sky.

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
$123 nightly
$142 total
Oct 15 - Oct 16
Total with taxes and fees
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 bench in a park with a lamp post and a building in the background.

Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti
$139 nightly
$159 total
Oct 13 - Oct 14
Total with taxes and fees
Villa Casalecchi Country Hotel
A long table set for dining in a tunnel with wine barrels on one side.
A sculpture of two figures in a garden with a windmill in the background.
A castle-like building with a swimming pool and a well-maintained garden.
A pool with lounge chairs and umbrellas, surrounded by stone tiles and trees.

Agriturismo Villa Godenano - Pool & Suites

Agriturismo Villa Godenano - Pool & Suites
Castellina in Chianti
$150 nightly
$169 total
Oct 28 - Oct 29
Total with taxes and fees
Agriturismo Villa Godenano - Pool & Suites
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
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.
A traditional villa with a tiled roof, surrounded by lush greenery and hills.

Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
$61 nightly
$74 total
Oct 4 - Oct 5
Total with taxes and fees
Hotel Casafrassi
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 restaurant with stone walls, wooden furniture, and a wine cellar.
A swimming pool with lounge chairs and an umbrella, surrounded by trees.

Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
$241 nightly
$272 total
Oct 26 - Oct 27
Total with taxes and fees
Fattoria di Vegi
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 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.

Castello La Leccia

Castello La Leccia
Castellina in Chianti
$284 nightly
$317 total
Oct 9 - Oct 10
Total with taxes and fees
Castello La Leccia
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.
A stone building with a wooden door and a balcony with flower planters.

Riserva di Fizzano Residence

Riserva di Fizzano Residence
Castellina in Chianti
$164 nightly
$182 total
Oct 8 - Oct 9
Total with taxes and fees
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 rustic stone building with a garden in front.
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.
A poolside area with lounge chairs and a view of the night sky.

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
$123 nightly
$142 total
Oct 15 - Oct 16
Total with taxes and fees
Belvedere di San Leonino
A pool with clear water and a row of white lounge chairs facing a scenic hillside view.
A spa room with a stone ceiling, a window with frosted glass, a bed with pillows, and a wall-mounted artwork.
An outdoor patio with round tables and chairs, surrounded by potted plants and flowers.
A stone-walled hallway with a staircase, a glass table with a red cushion, and a wooden cabinet.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
$203 nightly
$230 total
Oct 21 - Oct 22
Total with taxes and fees
Palazzo Squarcialupi
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 bench in a park with a lamp post and a building in the background.

Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti
$139 nightly
$159 total
Oct 13 - Oct 14
Total with taxes and fees
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 spacious dining area with wooden tables and chairs, a fireplace, and a modern kitchen in the background.
A modern interior with a bar area, seating, and a staircase.

Locanda le Piazze

Locanda le Piazze
Castellina in Chianti
$342 nightly
$383 total
Oct 21 - Oct 22
Total with taxes and fees
Locanda le Piazze
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
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.
A traditional villa with a tiled roof, surrounded by lush greenery and hills.

Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
$61 nightly
$74 total
Oct 4 - Oct 5
Total with taxes and fees
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

Italiana Hotels Florence

Italiana Hotels Florence

8/10 Good
"Greta place and friendly staff. Pool closed early in the month due to rain that was disappointing"
Jodie 2-night trip
Posted 2 days ago
Italiana Hotels Florence
Villa Neroli

Villa Neroli

10/10 Excellent
"The staff was amazing and very helpful on recommendations for dining/attractions. I will be back for breakfast - excellent selections and the staff was excellent!!"
Jennifer 3-night trip
Posted 4 days ago
Villa Neroli

Frequently asked questions

What are the best hotels in Castellina In Chianti with outdoor pools?
In the heart of Castellina In Chianti, Castello La Leccia shines as a premier choice for travellers seeking a serene escape. This stunning property boasts a great review rating of 10.0, where guests rave about the excellent and friendly staff, as well as the amazing breakfast featuring fresh local produce. Adding to its charm, the outdoor pool is consistently noted for its cleanliness, making it an ideal spot for families looking to unwind under the Tuscan sun.For those interested in a blend of relaxation and luxury, Locanda le Piazze offers a beautiful outdoor pool complemented by a poolside bar. Rated 9.8 by visitors, guests enjoy spacious rooms and fantastic food, ensuring a memorable stay. The spa services, including body scrubs and massages, provide an extra touch of indulgence for parents looking for some pampering while the kids splash around.Another delightful option is Belvedere di San Leonino, a cozy 4-star hotel that enjoys a rating of 9.6. With its welcoming atmosphere, friendly staff, and an outdoor pool that invites guests to relax, this hotel also features an onsite winery, adding a great experience to your stay. The views of the vineyard are simply breathtaking, great for family photos.Families will appreciate the lovely outdoor pool at Palazzo Squarcialupi, which also has a winery onsite. With a review score of 9.8, it's celebrated for its friendly and helpful staff, good amenities, and a lovely garden that enhances the overall experience.Lastly, Hotel Colle Etrusco Salivolpi is a charming 3-star option. Guests give it a great rating of 9.6, praising the wonderful breakfast and first-class service from the staff. Its outdoor pool is a great place for families, providing a secure and relaxing environment to enjoy time together.
How much does a hotel with outdoor pool in Castellina In Chianti cost?
Enjoy staying in a hotel in Castellina In Chianti with an outdoor pool. You can find a great deal from $74 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels in Castellina In Chianti that have private outdoor pools?
In the charming landscape of Castellina In Chianti, the "Charming Chianti Hilltop House" stands out as a premier option for travellers seeking luxury and privacy with its exceptional views and a large outdoor swimming pool. With a superb traveller rating of 10.0, this property offers a secured private pool that ensures both relaxation and safety for families, alongside amenities like a fully equipped kitchen and outdoor play areas that cater to children.Another delightful choice is the "Chianti: Farm 4 Forest with Swimming Pool," which boasts a traveller review score of 8.8. This hotel features a beautiful outdoor pool, providing a serene setting for families to unwind. The property combines the rustic charm of the Tuscan countryside with modern comforts, including a kitchen for convenient meal preparation and its proximity to local museums, superb for enriching family adventures.
Are there hotels in Castellina In Chianti with outdoor pool cabanas or loungers?
The Chianti: Farm 4 Forest with Swimming Pool is a charming option for travellers seeking relaxation in Castellina In Chianti. This lovely property features a shared outdoor pool surrounded by the stunning Tuscan landscape, providing a picturesque setting for unwinding under the sun.Guests particularly appreciate the availability of beach sun loungers, superb for soaking up the warm Italian sun after a refreshing swim. With an excellent review rating of 8.8, this hotel strikes a balance between comfort and quality, making it an ideal retreat for families looking to enjoy the beauty of Tuscany while having convenient access to outdoor leisure activities.
Which Castellina In Chianti hotels offer poolside service for food and drinks?
Locanda le Piazze is a charming 4-star hotel in Castellina In Chianti that not only features a beautiful outdoor pool but also offers a delightful poolside bar where guests can enjoy refreshing drinks and light snacks. With an impressive traveller rating of 9.8, guests rave about the fantastic food and great service, making it a great spot for families and adventure-seekers alike to unwind after a day of exploring Tuscany.Another excellent option is Hotel Colle Etrusco Salivolpi, a cozy 3-star hotel boasting an inviting outdoor pool and a poolside bar as well. Rated 9.6 by travellers, this hotel is praised for its wonderful breakfast and comfy beds, ensuring a relaxing stay for families looking to recharge. The pool area is a great place for parents to relax while enjoying a drink, knowing their children are having fun in a safe environment.
Is it cheaper to book flights and a Castellina In Chianti hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Castellina In Chianti for you.

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