Default HTG hotel image

Hotels with Swimming Pool in Montegrossi, Gaiole in Chianti

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check availability on Montegrossi Hotels with Swimming Pool

Tonight
Sep 10 - Sep 11
Tomorrow
Sep 11 - Sep 12
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Montegrossi hotels with a pool

1. Ultimo Mulino Wellness Country Hotel

Ultimo Mulino Wellness Country Hotel
Gaiole 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
Ultimo Mulino Wellness Country Hotel

2. Badia a Coltibuono

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

3. Agriturismo San Sano

Agriturismo San Sano
Gaiole 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
Agriturismo San Sano

4. Villa Sassolini Country Boutique Hotel

Villa Sassolini Country Boutique Hotel
Montevarchi
  • 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
Villa Sassolini Country Boutique Hotel

5. Relais Santa Cristina

Relais Santa Cristina
Radda in Chianti
P7,585
P8,562 total
includes taxes & fees
Sep 10 - Sep 11
Relais Santa Cristina

6. Chapter Chianti, a Member of Design Hotels

Chapter Chianti, a Member of Design Hotels
Cavriglia
P17,478
P19,662 total
includes taxes & fees
Oct 6 - Oct 7
Chapter Chianti, a Member of Design Hotels

7. Hotel Casafrassi

Hotel Casafrassi
Castellina 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
Hotel Casafrassi

8. Relais Vignale & Spa

Relais Vignale & Spa
Radda 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
Relais Vignale & Spa

9. Borgo Casa al Vento

Borgo Casa al Vento
Gaiole in Chianti
  • Tuscan poolside paradise with two outdoor pools, winery, and massage treatments.
P13,513
P15,447 total
includes taxes & fees
Sep 23 - Sep 24
Borgo Casa al Vento

10. Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World
Gaiole in Chianti
  • Serene pools with vineyard views offer both indoor and outdoor aquatic escapes.
P25,025
P28,255 total
includes taxes & fees
Oct 5 - Oct 6
Castello di Spaltenna- Small Luxury Hotels of the World
View all properties

Choose what matters most at hotels with a pool in Montegrossi

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Montegrossi Hotel Reviews

Borgo Vescine

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 !!!!"
Anna 3-night trip
Posted 10 hours ago
Borgo Vescine
Villa Pitiana

Villa Pitiana

10/10 Excellent
"We spent our honeymoon here and it was absolutely beautiful"
Rochelle 3-night trip
Posted 12 hours ago
Villa Pitiana
Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

10/10 Excellent
"The staff were very friendly and helpful. The bar service is the best."
Harley 1-night trip
Posted 1 day ago
Villa Scacciapensieri Boutique Hotel
Hotel Athena

Hotel Athena

10/10 Excellent
"Clean, well located, friendly staff, wonderful views"
Jared 3-night trip
Posted 3 days ago
Hotel Athena
Borgo San Felice Resort

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! 🇮🇹🍷✨"
Yael 2-night trip
Posted 4 days ago
Borgo San Felice Resort
Dievole Wine Resort

Dievole Wine Resort

10/10 Excellent
"Amazing hotel with the most unreal views. Staff were super friendly. Would definitely recommend!"
Tia 3-night trip
Posted 6 days ago
Dievole Wine Resort
Hotel Italia

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."
Hannah 1-night trip
Posted 7 days ago
Hotel Italia
Castello di Spaltenna- Small Luxury Hotels of the World

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"
Ashley 2-night trip
Posted 1 month ago
Castello di Spaltenna- Small Luxury Hotels of the World
COMO Castello Del Nero

COMO Castello Del Nero

10/10 Excellent
"Great staff!"
Philip 1-night trip
Posted 3 months ago
COMO Castello Del Nero

Frequently asked questions

What are some hotels with pools in Montegrossi?
La Certosa di Pontignano: Features a children's pool, a seasonal outdoor pool, and a rooftop terrace. Hotel Athena: Features a rooftop terrace, an outdoor pool, and a snack bar/deli. Grand Hotel Continental Siena – Starhotels Collezione: Provides 2 restaurants, 2 outdoor pools, and a full-service spa. Villa Pitiana: Hotel located near Piazza del Campo. Features a sauna, a seasonal outdoor pool, and a snack bar/deli. Hotel Chiusarelli: Offers 2 restaurants, a seasonal outdoor pool, and a full-service spa.
What is there to see and do in Montegrossi?
Make a point to visit attractions like Borgo di Vescine - Tenute di Castelvecchi and Chianti Observatory. During your stay, check out sights such as Badia a Coltibuono, Meleto Castle, and Castello di Albola.
When is the best time to book a hotel with a pool in Montegrossi?
You may want to consider a place to stay that has an outdoor pool if you will be visiting Montegrossi in the warmest months of August, July, or June when the average temp is 72°F. Lodging with an indoor pool may be the way to go if you come to town during the coldest months of January, February, or December when the average temp is 44°F.

Explore a world of travel with Expedia