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

Hotels with Swimming Pool in Roccastrada, Tuscany

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Check availability on Roccastrada Hotels with Swimming Pool

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 large stone house with a swimming pool, surrounded by lush greenery and hills.
A cozy living room with a fireplace, bookshelves, and a dining area.

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.
P5,382
P6,133 total
includes taxes & fees
Oct 25 - Oct 26
La Melosa Resort & Spa - Adults Only
A swimming pool with a view of a valley and mountains.
A rustic stone house with a balcony, surrounded by tall grasses and trees, during sunset.
An outdoor dining area with tables set for a meal, surrounded by greenery and a wooden pergola.
A spacious room with a long wooden table, large windows offering a view of the outdoors, and a modern chandelier.

2. Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
  • Swim in Tuscan splendor at this vineyard-adjacent farm stay featuring a seasonal outdoor pool with 24-hour access.
P9,900
P11,103 total
includes taxes & fees
Oct 27 - Oct 28
Valdonica Winery & Vineyard Residence
A group of people dining at a table with a view of a valley and mountains.
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.
A long table set for a formal outdoor event, surrounded by a vineyard.

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.
P11,739
P13,055 total
includes taxes & fees
Oct 11 - Oct 12
Valdonica Winery - Chill in Nature Lodge
A rectangular pool with lounge chairs and umbrellas, surrounded by a brick patio.
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.
A hotel with a swimming pool, surrounded by greenery and adjacent to a road.

4. Country House il Ciliegio

Country House il Ciliegio
Roccastrada
  • Tuscan paradise awaits with private poolside bar service and children's splash area.
P5,587
P6,288 total
includes taxes & fees
Nov 1 - Nov 2
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.
An outdoor patio with a pergola, tables, chairs, and a view of rolling hills.

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.
P5,173
P7,251 total
includes taxes & fees
Oct 6 - Oct 7
Agriturismo Podere Ristella - Wine&Food
A historic stone building with multiple windows and a courtyard.
A breakfast buffet with various food items and beverages, set in a room with stone walls and a large window.
A stone staircase leading to an arched doorway, surrounded by stone walls and potted plants.
An outdoor patio with stone arches, terracotta flooring, and tables set for dining.

6. 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.
Agriturismo Tenuta di Montemassi La Fattoria
A rectangular swimming pool with a clear blue water, surrounded by a well-maintained lawn and several lounge chairs.
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.
A historic building with a stone facade, surrounded by a well-maintained garden with yellow flowers and tall trees.

7. Antico Casale L'Impostino

Antico Casale L'Impostino
Civitella Paganico
  • Tuscan farm stay's seasonal pool invites leisurely escapes amid winery and hiking trails.
P8,273
P9,100 total
includes taxes & fees
Oct 19 - Oct 20
Antico Casale L'Impostino
A pool with a modern water feature and a stone structure.
An indoor swimming pool with clear glass walls, a tiled floor, and a stone wall with a mosaic pattern.
A large, multi-story building with a swimming pool, surrounded by lush greenery.
A buffet table with various desserts and a long dining area with tables and chairs.

8. 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.
P5,324
P5,857 total
includes taxes & fees
Oct 4 - Oct 5
Mercure Petriolo Siena Terme Spa Hotel
A stone house with a swimming pool, red shutters, and a covered patio.
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 hotel room with a bed, towels, a painting, and a vase with flowers.
A stone building with a red shuttered window, a colorful mosaic, and a staircase leading to a hilltop view.

9. NonnaNara

NonnaNara
Grosseto
P8,131
P8,945 total
includes taxes & fees
Oct 23 - Oct 24
NonnaNara
A swimming pool with clear blue water, a person standing on the edge, and another person swimming. There are lounge chairs and an umbrella in the background.
A stone staircase leading up to a structure, surrounded by lush greenery and trees.
A Mediterranean-style villa with a gravel driveway, a covered patio, and lush greenery surrounding the property.
A hotel room with a fireplace, a desk with a chair, a bed with a blue and white bedspread, and a view of the outdoors through large windows.

10. Tenuta il Sassone - Wine & Food

Tenuta il Sassone - Wine & Food
Gavorrano
  • Vineyard retreat with seasonal outdoor pool and children's splash area makes family-friendly Tuscan escapes come alive.
P7,947
P9,239 total
includes taxes & fees
Oct 6 - Oct 7
Tenuta il Sassone - Wine & Food
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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 large stone house with a swimming pool, surrounded by lush greenery and hills.
A spa area with two hot tubs, a decorative bowl with candles, and a person in a robe.

La Melosa Resort & Spa - Adults Only

La Melosa Resort & Spa - Adults Only
Roccastrada
P5,382
P6,133 total
includes taxes & fees
Oct 25 - Oct 26
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 balcony with two wooden chairs overlooking a vineyard and distant mountains.
A room with a large window overlooking a vineyard and mountains. There is a stone wall and a wooden shelf with wine bottles and glasses.
A rustic stone house with a balcony, surrounded by tall grasses and trees, during sunset.

Valdonica Winery & Vineyard Residence

Valdonica Winery & Vineyard Residence
Roccastrada
P9,900
P11,103 total
includes taxes & fees
Oct 27 - Oct 28
Valdonica Winery & Vineyard Residence
A group of people dining at a table with a view of a valley and mountains.
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.
A long table set for a formal outdoor event, surrounded by a vineyard.

Valdonica Winery - Chill in Nature Lodge

Valdonica Winery - Chill in Nature Lodge
Roccastrada
P11,739
P13,055 total
includes taxes & fees
Oct 11 - Oct 12
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 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.
A hotel with a swimming pool, surrounded by greenery and adjacent to a road.

Country House il Ciliegio

Country House il Ciliegio
Roccastrada
P5,587
P6,288 total
includes taxes & fees
Nov 1 - Nov 2
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.
An outdoor patio with a pergola, tables, chairs, and a view of rolling hills.

Agriturismo Podere Ristella - Wine&Food

Agriturismo Podere Ristella - Wine&Food
Roccastrada
P5,173
P7,251 total
includes taxes & fees
Oct 6 - Oct 7
Agriturismo Podere Ristella - Wine&Food
A historic stone building with multiple windows and a courtyard.
A bedroom with a large bed, wooden beams, a TV, and framed pictures on the wall.
A stone staircase leading to an arched doorway, surrounded by stone walls and potted plants.
An outdoor patio with stone arches, terracotta flooring, and tables set for dining.

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

10/10 Excellent
"Castiglion del Bosco is truly exquisite, the perfect way to experience Tuscany in luxury while still feeling completely surrounded by nature. The property is impeccable, from the beautiful gardens and grounds to the elegant rooms. Everything feels authentically Italian, refined and incredibly well maintained. The service is exceptional and very personalized. The staff genuinely goes out of their way to make you feel welcome. General Manager Nicola Migheli even greeted us personally upon arrival, which was a lovely touch. We also saw him regularly walking the property with his team, and it was clear how hands-on he is with every detail. One thing to know is that getting in and out requires about 40 minutes on a bumpy dirt road. It wasn’t terrible, but worth mentioning if you plan to explore frequently. That said, this is a hotel you don’t need to leave. It’s a beautiful place to slow down, relax and enjoy Tuscany in a truly special setting. We absolutely loved our stay!"
Carole 5-night trip
Posted 22 hours ago
Castiglion del Bosco, A Rosewood Hotel
Hotel Athena

Hotel Athena

10/10 Excellent
"The hotel is wonderful! The staff is extremely friendly and helpful. The location is great…jut a short walk to shopping, restaurants, and the cathedral. Our room was very clean and the beds were comfortable. The view from the terrace is stunning."
Michele 2-night trip
Posted 2 days ago
Hotel Athena
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 5 days ago
Castello di Velona Resort Thermal SPA & Winery
Villa Ermellina Siena, a Tribute Portfolio Hotel

Villa Ermellina Siena, a Tribute Portfolio Hotel

10/10 Excellent
"Beautiful hotel that is close to a bus line to get into the city. The views and accommodations make this a wonderful place to stay."
Heather 6-night trip
Posted 6 days ago
Villa Ermellina Siena, a Tribute Portfolio Hotel
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 2 weeks ago
Villa Scacciapensieri Boutique 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 3 weeks ago
Hotel Italia

Frequently asked questions

What's it like visiting Roccastrada?
If lounging by a pool is your idea of the perfect getaway, you might want to think about 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 relax and unwind poolside at one of the accommodations in Roccastrada that guests like for their pools.
What are some accommodations with pools in Roccastrada?
Hotel Athena: Features a children's pool, a seasonal outdoor pool, and a private beach. Hotel Executive: Offers 2 outdoor pools, an indoor pool, and 3 restaurants. NH Siena: Features 2 restaurants, 2 outdoor 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 that has an outdoor pool if you're planning to visit Roccastrada in the hottest months of August, July, or June when the average temp is 74°F. Lodging offering an indoor pool may be the way to go if you come to town during the coldest months of January, February, or March when the average temp is 48°F.
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 many public transit choices so consider renting a car to explore more.

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