An ancient stone tower with a view of rolling hills and fields in the background.

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Check availability on Roccastrada Hotels with Pool

This weekend
3 Jul - 5 Jul
Next weekend
10 Jul - 12 Jul

Our top choices for Roccastrada hotels with a pool

Front of property

Agriturismo Tenuta di Montemassi La Fattoria

Agriturismo Tenuta di Montemassi La Fattoria
3.0 star property
Roccastrada
9.6 out of 10, Exceptional, (9 reviews)
  • cleanliness
    Serene seasonal pool surrounded by Tuscan countryside views awaits at this charming farmstay offering rooftop terrace relaxation.
The price is Rp1.731.641
Rp1.945.703 total
includes taxes & fees
2 Jul - 3 Jul
Agriturismo Tenuta di Montemassi La Fattoria
Outdoor pool, pool loungers

La Melosa Resort & Spa - Adults Only

La Melosa Resort & Spa - Adults Only
4.0 star property
Roccastrada
9.2 out of 10, Wonderful, (42 reviews)
  • cleanliness
    Poolside paradise creates an oasis of serenity at this resort with mountain views.
The price is Rp1.746.429
Rp1.982.417 total
includes taxes & fees
2 Jul - 3 Jul
La Melosa Resort & Spa - Adults Only
Seasonal outdoor pool

Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
9.6 out of 10, Exceptional, (35 reviews)
  • cleanliness
    Swim in Tuscan splendour at this vineyard-adjacent farm stay featuring a seasonal outdoor pool with 24-hour access.
The price is Rp2.614.123
Rp2.936.883 total
includes taxes & fees
21 Jul - 22 Jul
Valdonica Winery & Vineyard Residence
Living area

Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
  • cleanliness
    Wine country retreat with a seasonal outdoor pool and on-site vineyard makes for a splendid Tuscan escape.
The price is Rp3.374.212
Rp3.752.421 total
includes taxes & fees
5 Jul - 6 Jul
Valdonica Winery - Chill in Nature Lodge
Seasonal outdoor pool, pool umbrellas, pool loungers

Country House il Ciliegio

Country House il Ciliegio
Roccastrada
9.2 out of 10, Wonderful, (7 reviews)
  • cleanliness
    Tuscan paradise awaits with private poolside bar service and children's splash area.
The price is Rp2.093.867
Rp2.344.104 total
includes taxes & fees
13 Jul - 14 Jul
Country House il Ciliegio
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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Choose what matters most at hotels with a pool in Roccastrada

Breakfast included
4 stars

Hotels with pools and free breakfast in Roccastrada

Outdoor pool, pool loungers
La Melosa Resort & Spa - Adults Only

La Melosa Resort & Spa - Adults Only

La Melosa Resort & Spa - Adults Only
4.0 star property
Roccastrada
9.2 out of 10, Wonderful, (42)
The price is Rp1.746.429
Rp1.982.417 total
includes taxes & fees
2 Jul - 3 Jul
La Melosa Resort & Spa - Adults Only
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 Roccastrada Hotel Reviews

Hotel Italia

Hotel Italia

10/10 Excellent
"Hotel Italia was an absolute gem. The staff were incredibly friendly and helpful — they understood we were tired from traveling with teens and even nailed a salon recommendation that turned out to be the best hair wash of my life, just minutes from the hotel. Our room was spotless, quiet, and the A/C worked perfectly; we didn’t hear a sound from neighbors or stair traffic. The location is a sweet spot — only 5 to 10 minutes from the tourist sights, yet tucked in a local neighborhood with bakeries and grocery stores, giving us that refreshing, peaceful feeling of being disconnected from the tourist rush. Breakfast was amazing, and the little teen-approved Duomo and gelato challenges made exploring even more fun. Bottom line: we’d come back and stay here again in a heartbeat. For anyone visiting Siena, Hotel Italia at Porta Camollia gives you that perfect “live like a local” buffer before diving into the Duomo and Piazza del Campo — and if you need a salon, just ask reception; their pick is solid."
darya 2-night trip
Posted 4 days ago
Hotel Italia

Frequently asked questions

What's it like visiting Roccastrada?
If spending time by the pool is your idea of the perfect getaway, you may want to explore historic Roccastrada, which has 17 places to stay with pools. During your visit, you can explore sights such as I Canaloni del Torrente Farma and Podere Ristella Vineyards and Winery, and then kick back and relax poolside at one of the accommodation options in Roccastrada that guests like for their pools.
What are some accommodation options with pools in Roccastrada?
Hotel Athena: Offers 2 outdoor swimming pools, an indoor pool and 3 restaurants. Grand Hotel Continental Siena – Starhotels Collezione: Offers a children's pool, a seasonal outdoor pool and a private beach. Palazzo Ravizza: Offers a rooftop terrace, a seasonal outdoor pool and spa services. Hotel Chiusarelli: Features 2 restaurants, 2 outdoor swimming pools and a full-service spa. Castello di Velona Resort Thermal SPA & Winery: Offers a rooftop terrace, a seasonal outdoor pool and a snack bar/deli.
How many pool hotels will I find in Roccastrada?
Expedia's 17 hotels in Roccastrada give you a great choice for your poolside getaway.
What is there to see and do in Roccastrada?
The picturesque setting of I Canaloni del Torrente Farma and Val di Merse showcase the area's natural beauty. Discover sights such as Podere Ristella Vineyards and Winery, Sassoforte Castle and Castello del Belagaio during your stay.
When is the best time to book a hotel with a pool in Roccastrada?
You may want to think about a place to stay with an outdoor swimming pool if you're planning to visit Roccastrada in the hottest months of August, July or June, when the average temp is 23°C. Accommodation offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February or March, when the average temp is 9°C.
What's the best way to travel around Roccastrada?
Knowing the transportation options in Roccastrada can help you enjoy the area beyond your hotel pool. To see more of the surrounding area, hop aboard a train at Roccastrada Station or Sticciano Station. Roccastrada might not have very many public transport options to choose from, so consider renting a car to explore more.