The Best Hotels with a Pool in Montegrossi from ￥22,758 in 2026

Q: What are some hotels with pools in Montegrossi?

Grand Hotel Continental Siena – Starhotels Collezione : Offers 2 restaurants, 2 outdoor pools, and a full-service spa. Borgo Scopeto Wine & Country Relais : Provides a sauna, a rooftop pool, and spa services. Hotel Athena : Features an indoor pool, an outdoor pool, and 2 restaurants. Hotel Executive : Offers a children's pool, a seasonal outdoor pool, and a rooftop terrace. Palazzo Ravizza : Offers 2 restaurants, a seasonal outdoor pool, and a full-service spa.

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Our top choices for Montegrossi hotels with a pool

Castello di Meleto

Gaiole in Chianti

Seasonal outdoor pool at Tuscan farm stay with vineyard views and sun loungers for serene relaxation amid the countryside.

￥28,120 total

includes taxes & fees

Jul 28 - Jul 29

Castello di Spaltenna- Small Luxury Hotels of the World

Gaiole in Chianti

Serene pools with vineyard views offer both indoor and outdoor aquatic escapes.

￥72,275 total

includes taxes & fees

Aug 9 - Aug 10

Borgo Casa al Vento

Gaiole in Chianti

Tuscan poolside paradise with two outdoor pools, winery, and massage treatments.

￥40,236 total

includes taxes & fees

Jul 28 - Jul 29

Castello di Tornano Wine Resort

Gaiole in Chianti

Poolside bliss awaits at this Tuscan wine resort where medieval castle meets vineyard views.

￥39,133 total

includes taxes & fees

Aug 27 - Aug 28

Seasonal outdoor pool, pool umbrellas, sun loungers

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.

￥34,804 total

includes taxes & fees

Aug 12 - Aug 13

Four Points by Sheraton Siena

Scacciapensieri

Seasonal pool retreat in Siena where vibrant summer days culminate in relaxation amidst Italian gardens and medieval views.

￥27,588 total

includes taxes & fees

Aug 7 - Aug 8

Seasonal outdoor pool, open 9:00 AM to 7:00 PM, pool umbrellas

Villa Scacciapensieri Boutique Hotel

Scacciapensieri

Dive into serenity at this Tuscan retreat, where a seasonal outdoor pool sits amid picturesque gardens and mountain views.

￥41,625 total

includes taxes & fees

Aug 14 - Aug 15

Outdoor pool, pool umbrellas, sun loungers

Villa Casalecchi Country Hotel

Castellina in Chianti

Tuscan poolside paradise boasts an outdoor swimming spot and a hot tub in scenic countryside settings.

￥29,893 total

includes taxes & fees

Jul 28 - Jul 29

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Choose what matters most at hotels with a pool in Montegrossi

Breakfast included

4 stars

Top Montegrossi Hotel Reviews

Villa Scacciapensieri Boutique Hotel

10/10 Excellent

"The pool was a big hit with our kids. The staff were kind and very helpful in getting us what we needed and making recommendations for us. It is outside the historic center but very close by. We enjoyed the serene setting and Tuscan views."

Villa Il Palagio

10/10 Excellent

"Our family of five enjoyed our time at the property very much. The rooms were comfortable and the surrounding area is beautiful. The pool is a huge plus to cool down and have a relaxing time. The Rignano train station nearby makes it easy to get around Italy, by connecting to Florence’s main station. Truly an asset. The A1 highway is also nearby connecting you within easy access to beautiful Tuscany. Restaurants in the area were very good also. I would definitely stay again at Vila Il Palagio."

Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent

"One of my favorite hotels. The rooms (at least ours) are very small. BUT... they're beautiful as is the entire property. It's a hike to town, so plan on driving or taking a cab. The views are incredible. It's the type of hotel experience you would imagine for your Italian dream vacation. Nitpicks: We booked two days in Siena as a rest in the middle of the rest of our travels. This would have been PERFECT for that, except that they were hosting a large, Indian wedding. (Which was BEAUTIFUL by the way.) But, the DJ played (accompanied by a saxophonist!) until almost midnight and the morning ceremony started pretty early as well. So, it didn't end up being as restful as we'd hoped as this was all happening right outside our window. Also, if the restaurant or bar is closed, there is no where to get a snack or drink. (Not really anywhere to get just a snack anyway.) Wouldn't be such a big deal, except you're not near any convenience stories or anything. A vending machine would be nice!"

Castello di Leonina Relais

8/10 Good

"The view from the dining area was perfect. The included breakfast was amazing and the complimentary ebike rentals were perfect to get around outside of the hotel to catch more amazing views! The food at dinner was perfect. The only thing that was lacking was the bathroom showers. Ours was leaking. Other than that it was a perfect stay."

Frequently asked questions

What are some hotels with pools in Montegrossi?

Grand Hotel Continental Siena – Starhotels Collezione: Offers 2 restaurants, 2 outdoor pools, and a full-service spa. Borgo Scopeto Wine & Country Relais: Provides a sauna, a rooftop pool, and spa services. Hotel Athena: Features an indoor pool, an outdoor pool, and 2 restaurants. Hotel Executive: Offers a children's pool, a seasonal outdoor pool, and a rooftop terrace. Palazzo Ravizza: 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 Cantalici Winery.

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.

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