Find Hotels with a Pool in Castellina in Chianti

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Check availability on Castellina in Chianti Hotels with a Pool

Our top choices for Castellina in Chianti hotels with a pool

Outdoor pool, sun loungers
Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais

Borgo di Pietrafitta Relais
Castellina in Chianti
9.4 out of 10, Exceptional, (169)
"Wonderful setting."
United Kingdom
Simon
The price is ￥17,738
￥20,240 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Borgo di Pietrafitta Relais
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers
Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi

Hotel Colle Etrusco Salivolpi
3.0 star property
Castellina in Chianti
9.6 out of 10, Exceptional, (114)
"Friendly staff and walking distance to town"
United States
Scott
The price is ￥35,152
￥39,214 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Hotel Colle Etrusco Salivolpi
Seasonal outdoor pool, open 9 AM to 8 PM, pool umbrellas, sun loungers
Residenzia del Sogno

Residenzia del Sogno

Residenzia del Sogno
Castellina in Chianti
9.8 out of 10, Exceptional, (14)
"Beautiful and authentic place, lovely couple running the place that care about you and your stay. "
Canada
Katherine
The price is ￥21,537
￥24,420 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Residenzia del Sogno
Exterior
Agriturismo La Ferrozzola

Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9)
"Very nice agriturismo. "
United States
Ruth
Agriturismo La Ferrozzola
Aerial view
Albergo Il Colombaio

Albergo Il Colombaio

Albergo Il Colombaio
3.0 star property
Castellina in Chianti
8.4 out of 10, Very Good, (58)
"I was a little hesitant about staying outside a "major city," but I'm so glad we did. Very cute hotel and room. It was a short walk to the local town, which had lots of options for dinner and chianti tasting. "
United States
Christine
The price is ￥20,578
￥23,183 total
includes taxes & fees
Dec 22 - Dec 23
Albergo Il Colombaio
A heated pool
Casa La Misura, garden and pool in the heart of Chianti

Casa La Misura, garden and pool in the heart of Chianti

Casa La Misura, garden and pool in the heart of Chianti
Castellina in Chianti
10.0 out of 10, Exceptional, (2)
"What a beautiful stay in the enchanting Tuscan countryside! Every detail was attended to and we could not have felt more at home. We can only dream of returning sometime!"
United States
Jami B.
Casa La Misura, garden and pool in the heart of Chianti
Exterior
PODERE 1384

PODERE 1384

PODERE 1384
Castellina in Chianti
The price is ￥89,460
￥99,499 total
includes taxes & fees
Dec 15 - Dec 16
PODERE 1384
Pool
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18

VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
Castellina in Chianti
The price is ￥856,606
￥947,725 total
includes taxes & fees
Jan 1 - Jan 2, 2026
VILLA IL PRINCIPE - Nine Bedroom Villa, Sleeps 18
A heated pool
OLIVE TREES HOUSE WITH POOL

OLIVE TREES HOUSE WITH POOL

OLIVE TREES HOUSE WITH POOL
Castellina in Chianti
OLIVE TREES HOUSE WITH POOL
Seasonal outdoor pool
The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini

The Social Hub Florence Lavagnini
4.0 star property
San Lorenzo
9.0 out of 10, Wonderful, (1284)
"Super friendly staff! Great location! "
United States
Jutta
The price is ￥11,793
￥15,523 total
includes taxes & fees
Dec 14 - Dec 15
The Social Hub Florence Lavagnini
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

Villa Neroli

Villa Neroli

10/10 Excellent
"Most was good"
Emir 1-night trip
Posted 2 weeks ago
Villa Neroli
Plaza Hotel Lucchesi

Plaza Hotel Lucchesi

10/10 Excellent
"Clean, comfortable room/beds. Great location. Staff was very, very attentive. Very good breakfast. A special shout out to Concierge Extraordinaire Walter, who helped us out way beyond what I expected! I "
Naomi 3-night trip
Posted 3 weeks ago
Plaza Hotel Lucchesi

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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 11 places to stay with pools. While you're here, you can explore attractions like City Hall Castellina In Chianti and Buondonno Winery, and then unwind poolside at one of the accommodations in Castellina in Chianti that guests like for their pools.
What are some hotels with pools in Castellina in Chianti?
IQ Hotel Firenze: Hotel, 12-minute walk from Cathedral of Santa Maria del Fiore. Features a full-service spa, a seasonal outdoor pool, and a sauna. Bernini Palace: Hotel, 13-minute walk from Piazza di Santa Maria Novella. Provides 2 bars, a seasonal outdoor pool, and a rooftop terrace. The Social Hub Florence Lavagnini: Hotel, 8-minute walk from Palazzo Vecchio. Offers a rooftop terrace, a seasonal outdoor pool, and a snack bar/deli. Grand Hotel Baglioni: Hotel located near Cathedral of Santa Maria del Fiore. Offers a full-service spa, a seasonal outdoor pool, and a snack bar/deli.
How many hotels with pools are there in Castellina in Chianti?
Expedia has 11 hotels in Castellina in Chianti for your poolside break.
What is there to see and do in Castellina in Chianti?
The picturesque setting of Chianti Sculpture Park and Sentierelsa Trail showcase the area's natural beauty. Discover sights such as City Hall Castellina In Chianti, Buondonno Winery, and Casa Vinicola Luigi Cecchi 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 an accommodation with an outdoor swimming pool if you will be visiting Castellina in Chianti in the warmest months of August, July, or June when the average temperature is 72°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 44°F.