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

Hotels with Swimming Pools in Roccastrada

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Check availability on Roccastrada Hotels with Swimming Pools

Tonight
5 Oct - 6 Oct
Tomorrow
6 Oct - 7 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Roccastrada hotels with a pool

A swimming pool with lounge chairs and umbrellas, surrounded by brick flooring and a hedge.
A rustic interior with exposed wooden beams, a central island with seating, and a stone wall.
A cozy living room with a fireplace, bookshelves, and a dining area.
A bedroom with a stone wall, a bed with white linens, a wooden chair, a desk with a computer, and a window with curtains.

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.
S$117
includes taxes & fees
7 Oct - 8 Oct
La Melosa Resort & Spa - Adults Only
A swimming pool with a view of a valley and mountains.
A spacious room with a long wooden table, large windows offering a view of the outdoors, and a modern chandelier.
A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.
A rustic stone house with a balcony, surrounded by tall grasses and trees, during sunset.

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.
S$199
includes taxes & fees
5 Nov - 6 Nov
Valdonica Winery & Vineyard Residence
A group of people dining at a table with a view of a valley and mountains.
A long table set for a formal outdoor event, surrounded by a vineyard.
A bedroom with a bed, a desk with a bottle and glasses, a red cabinet, and a view of the outdoors.
A garden with a wooden chair and a table, surrounded by a stone wall and a wooden fence.

3. 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.
S$233
includes taxes & fees
11 Oct - 12 Oct
Valdonica Winery - Chill in Nature Lodge
A rectangular pool with lounge chairs and umbrellas, surrounded by a brick patio.
A cozy kitchen with a brick ceiling, wooden furniture, and a dining area with a table set for breakfast.
A window with a view of buildings and a plant on the windowsill.
A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.

4. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
  • Tuscan paradise awaits with private poolside bar service and children's splash area.
S$120
includes taxes & fees
5 Nov - 6 Nov
Country House il Ciliegio
A swimming pool with a view of a hilltop castle.
A kitchen with wooden cabinets, a tiled backsplash, and a dining table with a fruit bowl.
A modern bathroom with a glass-enclosed shower, a white sink, and a large mirror.
A courtyard with a stone column, potted plants, and a view of a hilltop castle.

5. 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.
S$140
includes taxes & fees
10 Oct - 11 Oct
Agriturismo Podere Ristella - Wine&Food
A rectangular swimming pool with a clear blue water, surrounded by a well-maintained lawn and several lounge chairs.
A historic building with a stone facade, surrounded by a well-maintained garden with yellow flowers and tall trees.
A rustic stone building with a tiled roof, a covered patio with outdoor seating, and well-maintained gardens.
A covered outdoor seating area with stone pillars, a table, and chairs.

6. Antico Casale L'Impostino

Antico Casale L'Impostino
Civitella Paganico
  • Tuscan farm stay's seasonal pool invites leisurely escapes amid winery and hiking trails.
S$184
includes taxes & fees
19 Oct - 20 Oct
Antico Casale L'Impostino
A pool with a modern water feature and a stone structure.
A wicker dining table set with breakfast items, a vase of flowers, and a scenic view.
A buffet table with various desserts and a long dining area with tables and chairs.
A large, multi-story building with a swimming pool, surrounded by lush greenery.

7. Mercure Petriolo Siena Terme Spa Hotel

Mercure Petriolo Siena Terme Spa Hotel
Civitella Paganico
  • Bubbling mineral pools meet luxury at this spa hotel with indoor and outdoor swimming options.
S$119
includes taxes & fees
6 Oct - 7 Oct
Mercure Petriolo Siena Terme Spa Hotel
A stone house with a swimming pool, red shutters, and a covered patio.
A hotel room with a bed, towels, a painting, and a vase with flowers.
A bathroom with a glass shower enclosure, a white toilet, a vanity with a sink, and a window with a view of greenery outside.
A stone building with a red shuttered window, a colorful mosaic, and a staircase leading to a hilltop view.

8. NonnaNara

NonnaNara
Grosseto
S$156
includes taxes & fees
23 Oct - 24 Oct
NonnaNara
A swimming pool with lounge chairs and umbrellas, surrounded by trees and buildings.
A large estate with multiple buildings, expansive fields, and a winding road connecting them.
An outdoor patio with wooden tables and chairs, stone walls, and potted plants.
A long table set for a meal outdoors with white tablecloths, woven placemats, and potted plants.

9. Agriturismo San Galgano

Agriturismo San Galgano
Chiusdino
  • Tranquil Tuscan farmhouse invites pool lounging amid rustic countryside scenery.
S$120
includes taxes & fees
7 Oct - 8 Oct
Agriturismo San Galgano
A stone building with a pool, lounge chairs, and a garden with flowers.
A room with a wooden ceiling, a dining table with chairs, a bed, and a window with curtains.
A stone building with a tiled roof, a paved pathway, and a well-maintained garden.
A stone building with a wooden deck and white lounge chairs.

10. Podere Brizio

Podere Brizio
Montalcino
  • Vineyard paradise offers blissful pool lounging amidst Tuscan farm stay serenity.
S$294
includes taxes & fees
31 Oct - 1 Nov
Podere Brizio
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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

A swimming pool with lounge chairs and umbrellas, surrounded by brick flooring and a hedge.
A rustic interior with exposed wooden beams, a central island with seating, and a stone wall.
A spa area with two hot tubs, a decorative bowl with candles, and a person in a robe.
A bedroom with a stone wall, a bed with white linens, a wooden chair, a desk with a computer, and a window with curtains.

La Melosa Resort & Spa - Adults Only

La Melosa Resort & Spa - Adults Only
Roccastrada
S$117
includes taxes & fees
7 Oct - 8 Oct
La Melosa Resort & Spa - Adults Only
A spacious dining area with a large table and chairs, stone walls, and a view of the mountains.
A rustic stone house with a balcony, surrounded by tall grasses and trees, during sunset.
A swimming pool with a view of a valley and mountains.
A balcony with two wooden chairs overlooking a vineyard and distant mountains.

Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
S$199
includes taxes & fees
5 Nov - 6 Nov
Valdonica Winery & Vineyard Residence
A group of people dining at a table with a view of a valley and mountains.
A long table set for a formal outdoor event, surrounded by a vineyard.
A bedroom with a bed, a desk with a bottle and glasses, a red cabinet, and a view of the outdoors.
A garden with a wooden chair and a table, surrounded by a stone wall and a wooden fence.

Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
S$233
includes taxes & fees
11 Oct - 12 Oct
Valdonica Winery - Chill in Nature Lodge
A courtyard with stone steps leading to a small building, surrounded by lush greenery and stone buildings in the background.
A cozy kitchen with a brick ceiling, wooden furniture, and a dining area with a table set for breakfast.
A window with a view of buildings and a plant on the windowsill.
A rectangular pool with lounge chairs and umbrellas, surrounded by a brick patio.

Country House il Ciliegio

Country House il Ciliegio
Roccastrada
S$120
includes taxes & fees
5 Nov - 6 Nov
Country House il Ciliegio
A swimming pool with a view of a hilltop castle.
A wine cellar with wooden barrels, a wine rack, and a table set for dining.
A kitchen with wooden cabinets, a tiled backsplash, and a dining table with a fruit bowl.
A courtyard with a stone column, potted plants, and a view of a hilltop castle.

Agriturismo Podere Ristella - Wine&Food

Agriturismo Podere Ristella - Wine&Food
Roccastrada
S$140
includes taxes & fees
10 Oct - 11 Oct
Agriturismo Podere Ristella - Wine&Food
A historic stone building with multiple windows and a courtyard.
An outdoor patio with stone arches, terracotta flooring, and tables set for dining.
A stone staircase leading to an arched doorway, surrounded by stone walls and potted plants.
A bedroom with a large bed, wooden beams, a TV, and framed pictures on the wall.

Agriturismo Tenuta di Montemassi La Fattoria

Agriturismo Tenuta di Montemassi La Fattoria
Roccastrada
Agriturismo Tenuta di Montemassi La Fattoria
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

Castiglion del Bosco, A Rosewood Hotel

Castiglion del Bosco, A Rosewood Hotel

8/10 Good
"Although the property and the staff were great, our room was a bit of a disappointment. Junior Sweet was just a giant room with furniture that was uncomfortable to use. In general the room needs an update. Not exactly what we expected. We unfortunately had a neighbor who opened up the gate outside in between our terrace which should have never happen if it had been locked. He did that because he said my husbands iPad was too loud when in fact, his was too loud and my husband who had headphones on could not hear his show so took them off so he could hear it. Needless to say we avoided our terrace after that. Shout out to Chiara and Samantha who took a desert request seriously and made two of my evenings! Michael and David’s were also wonderful!"
Ellen 5-night trip
Posted 22 hours ago
Castiglion del Bosco, A Rosewood Hotel
Castello di Velona Resort Thermal SPA & Winery

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent
"Amazing views. Relaxing stay! A very romantic hotel, though I was surprised by the number of families there; given its location and amenities, I had assumed it was geared towards couples. That isn't a negative comment, though—it was simply a case of my own mistaken perception."
Erick 2-night trip
Posted 9 days ago
Castello di Velona Resort Thermal SPA & Winery
Hotel Italia

Hotel Italia

8/10 Good
"Clean, well maintained property that you’ll feel safe spending the night."
Shaji 1-night trip
Posted 3 weeks 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. Provides a children's pool, a seasonal outdoor pool and free self parking. Hotel Chiusarelli: Hotel located near Piazza del Campo. Features a rooftop terrace, a seasonal outdoor pool and a snack bar/deli.
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.

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