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
Sep 23 - Sep 24
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Sep 24 - Sep 25
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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 cozy living room with a stone fireplace, striped sofas, and a coffee table.

1. Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
  • Countryside farm stay's outdoor pool beckons with scenic vineyard views.
$77 nightly
$89 total
Oct 14 - Oct 15
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 rustic interior with a brick archway, wooden beams, a bar area, and potted plants.
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.
$116 nightly
$131 total
Oct 21 - Oct 22
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 circular hot tub, a window, and a bench.
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.

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.
$187 nightly
$212 total
Oct 21 - Oct 22
Total with taxes and fees
Palazzo Squarcialupi
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 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.

4. 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.
$144 nightly
$163 total
Sep 30 - Oct 1
Total with taxes and fees
Agritourism Villa [EXACT MATCH] Godenano - Pool & Suites
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 balcony and a garden with pink flowers.
A stone building with a staircase leading up to a window, surrounded by lush greenery and flowering plants.

5. Collelungo

Collelungo
Castellina in Chianti
  • Sip and splash at this enchanting farm stay, featuring a seasonal outdoor pool and attached winery.
$106 nightly
$121 total
Oct 24 - Oct 25
Total with taxes and fees
Collelungo
A pool area with lounge chairs and umbrellas, surrounded by lush greenery and hills in the background.
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.
A courtyard with stone buildings, tables with white tablecloths, and chairs arranged for dining.

6. 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.
$261 nightly
$291 total
Oct 9 - Oct 10
Total with taxes and fees
Castello La Leccia
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 person relaxing in a hot tub with a view of a building and trees in the background.

7. Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
  • Scenic Tuscan escape with a poolside paradise and winery at your doorstep.
$124 nightly
$144 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 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.

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.
$140 nightly
$161 total
Oct 9 - Oct 10
Total with taxes and fees
Villa Casalecchi Country Hotel
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
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.
A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

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.
$57 nightly
$69 total
Oct 22 - Oct 23
Total with taxes and fees
Hotel Casafrassi
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.

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.
$156 nightly
$175 total
Sep 24 - Sep 25
Total with taxes and fees
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 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 cozy living room with a stone fireplace, striped sofas, and a coffee table.

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
$77 nightly
$89 total
Oct 14 - Oct 15
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 rustic interior with a brick archway, wooden beams, a bar area, and potted plants.
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
$116 nightly
$131 total
Oct 21 - Oct 22
Total with taxes and fees
Hotel Colle Etrusco Salivolpi
An aerial view of a villa with a swimming pool, surrounded by lush greenery and a hilly landscape.
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.
A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
$57 nightly
$69 total
Oct 22 - Oct 23
Total with taxes and fees
Hotel Casafrassi
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 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.

Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti
$140 nightly
$161 total
Oct 9 - Oct 10
Total with taxes and fees
Villa Casalecchi Country Hotel
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 window with frosted glass, a bed with pillows, and a wall-mounted artwork.
A spa room with a stone ceiling, a circular hot tub, a window, and a bench.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
$187 nightly
$212 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 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.
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
$124 nightly
$144 total
Oct 15 - Oct 16
Total with taxes and fees
Belvedere di San Leonino
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 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.

Agritourism Villa [EXACT MATCH] Godenano - Pool & Suites

Agritourism Villa [EXACT MATCH] Godenano - Pool & Suites
Castellina in Chianti
$144 nightly
$163 total
Sep 30 - Oct 1
Total with taxes and fees
Agritourism Villa [EXACT MATCH] Godenano - Pool & Suites
A historic stone building with multiple levels, surrounded by lush greenery and yellow flowering plants.
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, tables with white tablecloths, and chairs arranged for dining.

Castello La Leccia

Castello La Leccia
Castellina in Chianti
$261 nightly
$291 total
Oct 9 - Oct 10
Total with taxes and fees
Castello La Leccia
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 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
$156 nightly
$175 total
Sep 24 - Sep 25
Total with taxes and fees
Albergo Il Colombaio
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.
An outdoor dining area with tables and chairs, a pergola structure, and potted plants.
A stone building with a wooden door and a balcony with flower planters.

Riserva di Fizzano Residence

Riserva di Fizzano Residence
Castellina in Chianti
$202 nightly
$224 total
Sep 29 - Sep 30
Total with taxes and fees
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 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.
A bar area with brick arches, wooden barrels, leather seating, and a wine rack.

Hotel Casafrassi

Hotel Casafrassi
Castellina in Chianti
$57 nightly
$69 total
Oct 22 - Oct 23
Total with taxes and fees
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 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.
A stone building with ivy-covered walls, a stone pathway, and a garden with flowers.

Belvedere di San Leonino

Belvedere di San Leonino
Castellina in Chianti
$124 nightly
$144 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 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.

Villa Casalecchi Country Hotel

Villa Casalecchi Country Hotel
Castellina in Chianti
$140 nightly
$161 total
Oct 9 - Oct 10
Total with taxes and fees
Villa Casalecchi Country Hotel
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 window with frosted glass, a bed with pillows, and a wall-mounted artwork.
A spa room with a stone ceiling, a circular hot tub, a window, and a bench.

Palazzo Squarcialupi

Palazzo Squarcialupi
Castellina in Chianti
$187 nightly
$212 total
Oct 21 - Oct 22
Total with taxes and fees
Palazzo Squarcialupi
A large stone building with a tower, surrounded by lush greenery and a well-maintained lawn.
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.
A vineyard landscape with rows of grapevines and a person holding a glass.

Locanda le Piazze

Locanda le Piazze
Castellina in Chianti
$341 nightly
$382 total
Oct 16 - Oct 17
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

Italiana Hotels Florence

Italiana Hotels Florence

10/10 Excellent
"Very convenient, great breakfast and location. Would 100% stay here again"
Daniel 3-night trip
Posted 3 days ago
Italiana Hotels Florence
Plus Florence - Hostel

Plus Florence - Hostel

8/10 Good
"We were a couple who stayed the first night in a 3 single beds room, and the other three nights we were in a private room with a large bed. One issue is that there is only one singular outlet in the rooms. In the private room, we only had one free electrical outlet which was in the bathroom. We had to disconnect the TV in order to have any outlet in the bedroom. We really feel this is inadequate, especially in bedroom with more than two beds. On the day we left we found bugs under the bedside cube. I also had multiple bites on my leg, luckily they were not itchy so I don't know what they were. They were NOT bedbugs. There is no facility to iron at all, not a single iron on the whole property They staff was really friendly and helpful over all, even when faced with large groups who were waiting to check in they were very professional, kind and helpful, 5 starts for any staff interaction. We would definitely stay again but would really wish they would install more outlets and stay on top of ants/bugs. All towels and beddings were clean. We didn't eat from their restaurant or use the pool so we have no comments to share."
Charlotte 3-night trip
Posted 3 days ago
Plus Florence - Hostel

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 $69 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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