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

Search Hotels with Pool in Roccastrada

  • 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 Roccastrada Hotels with Pool

Tonight
22 Sept - 23 Sept
Tomorrow
23 Sept - 24 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 Oct

Our top choices for Roccastrada hotels with a pool

1. La Melosa Resort & Spa - Adults Only

La Melosa Resort & Spa - Adults Only
Roccastrada
  • Poolside paradise creates an oasis of serenity at this resort with mountain views.
Rp1.741.842
Rp1.977.212 total
includes taxes & fees
15 Oct - 16 Oct
La Melosa Resort & Spa - Adults Only

2. Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
  • Swim in Tuscan splendour at this vineyard-adjacent farm stay featuring a seasonal outdoor pool with 24-hour access.
Rp2.607.120
Rp2.929.018 total
includes taxes & fees
11 Oct - 12 Oct
Valdonica Winery & Vineyard Residence

3. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
  • Tuscan paradise awaits with private poolside bar service and children's splash area.
Rp1.564.175
Rp1.761.517 total
includes taxes & fees
23 Oct - 24 Oct
Country House il Ciliegio

4. Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
  • Wine country retreat with a seasonal outdoor pool and on-site vineyard makes for a splendid Tuscan escape.
Rp3.374.367
Rp3.752.594 total
includes taxes & fees
18 Oct - 19 Oct
Valdonica Winery - Chill in Nature Lodge

5. Agriturismo Tenuta di Montemassi La Fattoria

Agriturismo Tenuta di Montemassi La Fattoria
Roccastrada
  • Serene seasonal pool surrounded by Tuscan countryside views awaits at this charming farmstay offering rooftop terrace relaxation.
Rp1.817.132
Rp2.039.635 total
includes taxes & fees
27 Sept - 28 Sept
Agriturismo Tenuta di Montemassi La Fattoria

6. Agriturismo Podere Ristella - Wine&Food

Agriturismo Podere Ristella - Wine&Food
Roccastrada
  • Wine country farm stay with a seasonal pool perfect for summer dips in the Tuscan sunshine.
Rp1.486.802
Rp2.084.174 total
includes taxes & fees
5 Oct - 6 Oct
Agriturismo Podere Ristella - Wine&Food

7. SI Montalcino Hotel

SI Montalcino Hotel
Montalcino
  • Sparkling tuscan poolside retreat offers a refreshing escape with scenic vineyard views.
Rp1.889.976
Rp2.548.061 total
includes taxes & fees
29 Sept - 30 Sept
SI Montalcino Hotel

8. Antico Casale L'Impostino

Antico Casale L'Impostino
Civitella Paganico
  • Tuscan farm stay's seasonal pool invites leisurely escapes amid winery and hiking trails.
Rp2.377.863
Rp2.615.670 total
includes taxes & fees
19 Oct - 20 Oct
Antico Casale L'Impostino

9. Borgo Grondaie

Borgo Grondaie
Siena
  • Seasonal pool with Tuscan views invites summer dips in tranquil garden setting surrounded by Italian charm.
Rp2.171.240
Rp2.490.674 total
includes taxes & fees
19 Oct - 20 Oct
Borgo Grondaie

10. Precise House Montaperti Siena

Precise House Montaperti Siena
Asciano
  • Float in warmth year-round at this Italian retreat, where two pools complement soothing spa treatments in the Siena countryside.
Rp1.998.173
Rp2.320.762 total
includes taxes & fees
2 Oct - 3 Oct
Precise House Montaperti Siena
View all properties

Choose what matters most at hotels with a pool in Roccastrada

Breakfast included
4 stars
5 stars
Hot tub
Spa

Hotels with pools and free breakfast in Roccastrada

La Melosa Resort & Spa - Adults Only

La Melosa Resort & Spa - Adults Only
Roccastrada
Rp1.741.842
Rp1.977.212 total
includes taxes & fees
15 Oct - 16 Oct
La Melosa Resort & Spa - Adults Only

Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
Rp2.607.120
Rp2.929.018 total
includes taxes & fees
11 Oct - 12 Oct
Valdonica Winery & Vineyard Residence

Country House il Ciliegio

Country House il Ciliegio
Roccastrada
Rp1.564.175
Rp1.761.517 total
includes taxes & fees
23 Oct - 24 Oct
Country House il Ciliegio

Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
Rp3.374.367
Rp3.752.594 total
includes taxes & fees
18 Oct - 19 Oct
Valdonica Winery - Chill in Nature Lodge

Agriturismo Tenuta di Montemassi La Fattoria

Agriturismo Tenuta di Montemassi La Fattoria
Roccastrada
Rp1.817.132
Rp2.039.635 total
includes taxes & fees
27 Sept - 28 Sept
Agriturismo Tenuta di Montemassi La Fattoria

Agriturismo Podere Ristella - Wine&Food

Agriturismo Podere Ristella - Wine&Food
Roccastrada
Rp1.486.802
Rp2.084.174 total
includes taxes & fees
5 Oct - 6 Oct
Agriturismo Podere Ristella - Wine&Food
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

Villa Scacciapensieri Boutique Hotel

Villa Scacciapensieri Boutique Hotel

10/10 Excellent
"The villa is amazing and the perfect little world in itself. Its closeness to Siena makes it easier to visit the city. The patio is the perfect place to view Siena at sunset. The staff was very courteous and ready to help. This hotel is a gem."
Federica 1-night trip
Posted 5 days ago
Villa Scacciapensieri Boutique Hotel
Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent
"Very warm and friendly service."
Abdel 2-night trip
Posted 9 days ago
Castiglion del Bosco, A Rosewood Hotel
Hotel Italia

Hotel Italia

8/10 Good
"Clean, well maintained property that you’ll feel safe spending the night."
Shaji 1-night trip
Posted 10 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 12 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: Features a children's pool, a seasonal outdoor pool and a private beach. Hotel Executive: Offers 2 outdoor swimming pools, an indoor pool and 3 restaurants. NH Siena: Features 2 restaurants, 2 outdoor swimming pools and a full-service spa. The Sense Experience Resort - Preferred Hotels & Resorts: Hotel located near Piazza del Campo. Offers a rooftop terrace, a seasonal outdoor pool and a snack bar/deli. Hotel Chiusarelli: Hotel located near Piazza del Campo. Features a children's pool, a seasonal outdoor pool and free self parking.
How many pool hotels will I find in Roccastrada?
Expedia has 12 hotels in Roccastrada for your poolside break.
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, Castello del Belagaio and Sassoforte Castle 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.

Explore a world of travel with Expedia