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

Tonight
Oct 22 - Oct 23
Tomorrow
Oct 23 - Oct 24
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Castellina in Chianti hotels with a pool

A poolside area with lounge chairs and a view of the night sky.
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.

1. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
  • Scenic Tuscan escape with a poolside paradise and winery at your doorstep.
$107 nightly
$124 total
Oct 27 - Oct 28
Total with taxes and fees
Belvedere di San Leonino
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.
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.
$85 nightly
$97 total
Oct 25 - Oct 26
Total with taxes and fees
Hotel Colle Etrusco Salivolpi
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.

3. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
  • Countryside farm stay's outdoor pool beckons with scenic vineyard views.
$87 nightly
$100 total
Nov 5 - Nov 6
Total with taxes and fees
Borgo di Pietrafitta Relais
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.

4. 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.
$201 nightly
$225 total
Nov 8 - Nov 9
Total with taxes and fees
Castello La Leccia
A poolside area with lounge chairs and a stone building in the background.
A bathroom with a large sink, toilet, and walk-in shower.
A garden with a gravel path leading to a white metal table and chairs, surrounded by red roses and a large terracotta pot.
A bedroom with a bed, bedside tables, a sofa, a window with curtains, and a wall with a painting.

5. 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 27 - Oct 28
Total with taxes and fees
Palazzo Squarcialupi
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 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.

6. Fattoria di Vegi

Fattoria di Vegi
Castellina in Chianti
$243 nightly
$274 total
Oct 30 - Oct 31
Total with taxes and fees
Fattoria di Vegi
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 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.

7. 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.
$136 nightly
$153 total
Nov 22 - Nov 23
Total with taxes and fees
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 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.

8. Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
  • Sun-soaked seasonal pool oasis in the heart of a Tuscan wine resort with loungers and umbrellas.
$56 nightly
$68 total
Oct 26 - Oct 27
Total with taxes and fees
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 spacious bedroom with a large bed, a desk, and a chair. There is a painting on the wall and a window with curtains.
A sculpture of two figures in a garden with a windmill in the background.

9. 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.
$204 nightly
$229 total
Oct 24 - Oct 25
Total with taxes and fees
Agriturismo Villa Godenano - Pool & Suites
A swimming pool with stone walls, lounge chairs, and a building with stone architecture.
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'.

10. Collelungo

Collelungo
Castellina in Chianti
  • Sip and splash at this enchanting farm stay, featuring a seasonal outdoor pool and attached winery.
$127 nightly
$144 total
Oct 26 - Oct 27
Total with taxes and fees
Collelungo
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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 interior with a brick archway, wooden beams, a bar area, and potted plants.
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
$85 nightly
$97 total
Oct 25 - Oct 26
Total with taxes and fees
Hotel Colle Etrusco Salivolpi
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.
A rustic stone building with a garden in front.
A poolside area with lounge chairs and a view of the night sky.

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
$107 nightly
$124 total
Oct 27 - Oct 28
Total with taxes and fees
Belvedere di San Leonino
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
$87 nightly
$100 total
Nov 5 - Nov 6
Total with taxes and fees
Borgo di Pietrafitta Relais
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
$201 nightly
$225 total
Nov 8 - Nov 9
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 traditional villa with a tiled roof, surrounded by lush greenery and hills.
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
$56 nightly
$68 total
Oct 26 - Oct 27
Total with taxes and fees
Hotel Casafrassi
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 pool area with lounge chairs and umbrellas, surrounded by greenery and trees.
A stone building with a large arched doorway, a bench, and a potted plant outside.

Albergo Il Colombaio

Albergo Il Colombaio
Castellina in Chianti
$136 nightly
$153 total
Nov 22 - Nov 23
Total with taxes and fees
Albergo Il Colombaio
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 spa area with a stone ceiling, a large bathtub, and a seating area.
A historic building with a courtyard, stone arches, and a tiled roof.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
$203 nightly
$230 total
Oct 27 - Oct 28
Total with taxes and fees
Palazzo Squarcialupi
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.
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 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
$204 nightly
$229 total
Oct 24 - Oct 25
Total with taxes and fees
Agriturismo Villa Godenano - Pool & Suites
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
$243 nightly
$274 total
Oct 30 - Oct 31
Total with taxes and fees
Fattoria di Vegi
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
$367 nightly
$411 total
Oct 28 - Oct 29
Total with taxes and fees
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.
View all properties

Top Castellina in Chianti Hotel Reviews

Villa Neroli

Villa Neroli

10/10 Excellent
"My family and I stayed at Villa Neroli for three nights in October while celebrating our wedding in Tuscany and we really loved our stay! The hotel itself is beautiful with comfortable, clean rooms and lovely grounds. Breakfast was great, with plenty of options and the location worked really well for us with some nice restaurants nearby. What stood out most was the staff. Everyone was so friendly and helpful, especially the front desk team. We had quite a few requests during our stay, and they were always happy to help. We also had several family members and friends staying at the hotel for our wedding and the staff did a great job accommodating everyone and helping coordinate our wedding shuttle. One of our favorite moments was simply sitting outside by the pool one evening enjoying a glass of wine together. It was such a peaceful spot and a nice break from all the wedding excitement. Overall, we had a fantastic experience and really appreciated how welcoming everyone was. We'd happily stay at Villa Neroli again next time we're in Florence. Highly recommend!"
Marye 3-night trip
Posted 1 day ago
Villa Neroli
Plus Florence - Hostel

Plus Florence - Hostel

8/10 Good
"i loved the location , the price , the vibe , as a first time solo traveller staying in a hostel i was a bit nervous , i thoroughly enjoyed my stay and would deffo recommend and would 100 percent stay here again , love how everyone respected everybody , had a great time and slept well"
Denise 2-night trip
Posted 1 day ago
Plus Florence - Hostel
Hu Firenze Camping In Town

Hu Firenze Camping In Town

10/10 Excellent
"On a bien aimé notre séjour. C’était très propre partout. Notre cabine était parfaite. Votre équipe s’est bien occupée de nous. Et nous avons eu un très bon service. Nous le recommandons. Et le restaurant et le service était très bon aussi. Nous avons trouvé très pratique de pouvoir acheter nos excursions au camping et d’avoir le transport pour les excursions directement du camping c’était bien pratique et zéro stress à essayer de trouver le groupe au centre ville."
Mimi 4-night trip
Posted 4 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 7 days ago
Italiana Hotels Florence

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 $68 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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