
Hotels with Swimming Pool in Montegrossi, Gaiole in Chianti
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Sep 18 - Sep 20Our top choices for Montegrossi hotels with a pool




1. Ultimo Mulino Wellness Country Hotel
Ultimo Mulino Wellness Country HotelGaiole in Chianti
- Tuscan retreat offers sparkling outdoor pool with free cabanas, loungers, and refreshing poolside bar service.
P7,256
P8,564 total
includes taxes & fees
Oct 6 - Oct 7




2. Badia a Coltibuono
Badia a ColtibuonoGaiole in Chianti
- Rustic Tuscan farm stay captivates with a seasonal outdoor pool and garden views in the heart of wine country.




3. Agriturismo San Sano
Agriturismo San SanoGaiole in Chianti
- Tuscan vineyard retreat with sun-kissed seasonal pool beckons outdoor adventurers for summer splashing.
P6,098
P6,999 total
includes taxes & fees
Oct 7 - Oct 8




4. Villa Sassolini Country Boutique Hotel
Villa Sassolini Country Boutique HotelMontevarchi
- Splash and relax at this Tuscan retreat with dreamy indoor and outdoor pools for any season.
P14,465
P15,912 total
includes taxes & fees
Oct 7 - Oct 8
P7,585
P8,562 total
includes taxes & fees
Sep 10 - Sep 11
P17,478
P19,662 total
includes taxes & fees
Oct 6 - Oct 7




7. Hotel Casafrassi
Hotel CasafrassiCastellina in Chianti
- Sun-soaked seasonal pool oasis in the heart of a Tuscan wine resort with loungers and umbrellas.
P3,906
P4,734 total
includes taxes & fees
Sep 11 - Sep 12




8. Relais Vignale & Spa
Relais Vignale & SpaRadda in Chianti
- Discover a seasonal rooftop sanctuary with dual pools, poolside bar service, and stunning vineyard views in historic wine country.
P11,227
P14,586 total
includes taxes & fees
Oct 8 - Oct 9
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Top Montegrossi Hotel Reviews
Borgo Vescine
10/10 Excellent
"This place is simply perfection From the moment you check in to the moment you leave , you feel like royalty . Staff is impressive how polite , accommodating and welcoming Thank you Lorenzo at the bar ! Honestly no words besides EXCELLENT Anna /Canada !!!!"
Villa Pitiana
10/10 Excellent
"We spent our honeymoon here and it was absolutely beautiful"
Villa Scacciapensieri Boutique Hotel
10/10 Excellent
"The staff were very friendly and helpful. The bar service is the best."
Hotel Athena
10/10 Excellent
"Clean, well located, friendly staff, wonderful views"
Borgo San Felice Resort
10/10 Excellent
"An unforgettable stay in Tuscany!** Our stay at Borgo San Felice was truly incredible from beginning to end. From the moment our private driver picked us up at the train station and brought us through the beautiful Tuscan countryside to the resort, everything felt seamless and special. The property itself is absolutely breathtaking pictures truly don’t do it justice. We enjoyed dinner on the property, a wonderful couples massage, a private wine tour and tasting, and a relaxing pool day. We especially loved the live piano music in the evenings; it added such a romantic and elegant touch to the entire experience. The service was one of the highlights of our stay. A special shout-out to **Herman at the pool**, who was always attentive and completely on point with everything we needed. We also had an amazing experience at **Poggio Rosso**, where **Matia provided top-notch service** and made our Michelin-starred dinner feel even more memorable. Every detail from the beautiful grounds and peaceful atmosphere to the food, wine, spa, and exceptional hospitality—made our time here unforgettable. Borgo San Felice gave us exactly the Tuscany experience we were hoping for and more. We absolutely loved our stay and would return in a heartbeat. Highly recommend! 🇮🇹🍷✨"
Dievole Wine Resort
10/10 Excellent
"Amazing hotel with the most unreal views. Staff were super friendly. Would definitely recommend!"
Hotel Italia
10/10 Excellent
"Our stay was fantastic. The room was genuinely luxurious with marble fittings everywhere. The staff were brilliant and really knew what to recommend. The breakfast was good but rather crowded on the day we were there."
Castello di Spaltenna- Small Luxury Hotels of the World
10/10 Excellent
"Just an amazing overall experience, super welcoming and hospitable staff. Vacationing in an estate that is 1100 years old makes it even more memorable. Thank you Spaltena"
COMO Castello Del Nero
10/10 Excellent
"Great staff!"















