Rolling hills, a line of tall cypress trees, and a misty valley.

Hotels with Swimming Pools in Asciano

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Check availability on Asciano 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 Asciano hotels with a pool

An aerial view of a property with a swimming pool, surrounded by trees and a view of the countryside.
A table set for dining with a scenic view of rolling hills and distant mountains.
A spacious dining area with round tables and wicker chairs, a patterned rug, and a wooden ceiling.
A bathroom with a large arched window, a bathtub, a sink, and a towel rack.

1. Castello di Leonina Relais

Castello di Leonina Relais
Asciano
  • Luxurious medieval castle with rooftop and natural pools offers serene countryside swims and poolside dining.
S$167
includes taxes & fees
23 Oct - 24 Oct
Castello di Leonina Relais
An indoor swimming pool with lounge chairs and a view of the countryside.
A spacious lobby with a reception desk, potted plants, and a modern architectural design.
A terrace with multiple sun loungers and a scenic view of green fields and hills.
A modern bathroom with a large sink, mirror, and glass shower enclosure. Adjacent is a bedroom with two beds, a wooden ceiling, and a view of the outdoors.

2. 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.
S$125
includes taxes & fees
1 Nov - 2 Nov
Precise House Montaperti Siena
A person in a swimming pool with a view of trees and distant hills.
A modern bathroom with a glass shower enclosure, a white sink, and a large window offering a view.
A spacious living room with a high ceiling, a sofa set, a round coffee table, and a fireplace.
A modern kitchen with a large window, stainless steel appliances, and a wall-mounted clock.

3. Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
S$314
includes taxes & fees
12 Oct - 13 Oct
Albergo Diffuso Borgo Santo
An aerial view of a large estate with multiple buildings, a swimming pool, and well-maintained gardens.
An outdoor dining area with tables and chairs, surrounded by stone walls and trees.
A stone building with a garden featuring lavender and other plants.
A kitchen with a stove, coffee maker, and a green door.

4. Hotel Borgo Casabianca

Hotel Borgo Casabianca
Asciano
S$320
includes taxes & fees
9 Oct - 10 Oct
Hotel Borgo Casabianca
A poolside area with lounge chairs and umbrellas, a stone wall, and a clear sky.
A modern bathroom with a glass-enclosed shower, a white sink, and a toilet.
A buffet setup with various food items and condiments.
A hotel room with a bed, a shower, a TV, and a cabinet.

5. Relais Cloister Pienza

Relais Cloister Pienza
Pienza
S$190
includes taxes & fees
6 Oct - 7 Oct
Relais Cloister Pienza
A swimming pool with lounge chairs and umbrellas, a stone building with a tiled roof, and a clear blue sky.
A hotel room with a bed, a sofa, a chair, a small table with a lamp, and a window with a view of a green landscape.
A table set with a bottle of wine, two wine glasses, and a vase with flowers.
A modern bathroom with a marble shower wall, a large mirror, and a wooden vanity.

6. Poggio Paradiso Resort & Spa

Poggio Paradiso Resort & Spa
Torrita di Siena
  • Summer seclusion at this Tuscan spa retreat with poolside relaxation and gourmet dining.
S$304
includes taxes & fees
3 Nov - 4 Nov
Poggio Paradiso Resort & Spa
A villa with a swimming pool, terraced garden, and a view of distant mountains.
A stone building with a tiled roof, surrounded by a grassy area and flowering plants.
A stone building with a gravel pathway leading to the entrance.
A cozy living room with a fireplace, comfortable seating, and a table set with various desserts.

7. Agriturismo Il Macchione

Agriturismo Il Macchione
Pienza
  • Luxurious Tuscan retreat with outdoor pool, on-site winery, and cycling adventures amid rolling hills near Pienza Cathedral.
S$218
includes taxes & fees
5 Nov - 6 Nov
Agriturismo Il Macchione
A pool with a stone wall, a view of the countryside, and a building with a tiled roof.
A spacious lobby with a tiled floor, a wooden reception desk, a staircase, and a large floral painting on the wall.
A hotel with a classic facade, multiple windows with shutters, and a sign indicating it is the "Hotel dei Capitani."
A terrace with outdoor seating, a view of the landscape, and a building with large windows.

8. Hotel Dei Capitani

Hotel Dei Capitani
Montalcino
  • Soak up Italian sunshine in this charming hillside hotel with inviting outdoor pool.
S$181
includes taxes & fees
7 Oct - 8 Oct
Hotel Dei Capitani
A poolside area with lounge chairs, a table with wine glasses and a bottle, and a view of a mountainous landscape.
A hotel room with a large bed, a bedside table, a lamp, a window with curtains, and a view of greenery outside.
A wicker table with a candle, surrounded by greenery and stone walls.
A kitchen with a buffet setup, including a variety of food items and glassware.

9. SI Montalcino Hotel

SI Montalcino Hotel
Montalcino
  • Sparkling tuscan poolside retreat offers a refreshing escape with scenic vineyard views.
S$157
includes taxes & fees
1 Nov - 2 Nov
SI Montalcino Hotel
A garden pathway leading to a rustic building with a tiled roof, surrounded by lush greenery and red flowers.
A modern bedroom with a large bed, a TV, a fireplace, and a bathtub.
An outdoor restaurant with tables and chairs, covered by a wooden roof, and surrounded by greenery.
A spa setting with a stone wall, a fireplace, and a massage table.

10. Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso

Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso
San Quirico d'Orcia
  • Dive into garden poolside paradise with sparkling waters amid charming historical villa setting.
S$181
includes taxes & fees
2 Nov - 3 Nov
Boutique Villa Liberty - Depandance Hotel - Borgo Capitano Collection - Albergo diffuso
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Choose what matters most at hotels with a pool in Asciano

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Asciano Hotel Reviews

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

10/10 Excellent
"Stunning property; a real representation of Tuscany with the long driveway of tall trees; staff was amazing; food was excellent; gardens, picturesque! We would highly recommend! Overall amazing !!!"
lynda 3-night trip
Posted 3 hours ago
Villa di Piazzano - Small Luxury Hotel of the World
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 12 hours ago
Castiglion del Bosco, A Rosewood Hotel
Castello di Leonina Relais

Castello di Leonina Relais

10/10 Excellent
"We loved staying here. The hotel was full of history and in a beautiful location. The views overlooking the Tuscan hills were spectacular. We loved the quiet location and enjoyed walks on and near the property. Renting a car is a must and was perfect to take day trips to the beautiful historic Tuscan hill towns. The included breakfast was a beautiful spread with so much to choose from. We got quite spoiled between the delicious breakfasts and the dinners at the property restaurant. The staff was very helpful and friendly. Grazie mille! :) This hotel is a must and we will definitely be back when we visit Tuscany again."
Kendra 4-night trip
Posted 3 days ago
Castello di Leonina Relais
Castello di Spaltenna- Small Luxury Hotels of the World

Castello di Spaltenna- Small Luxury Hotels of the World

10/10 Excellent
"This was a beautiful hotel! Everything from the room to the amenities to the staff. Most of the amenities are complimentary (sauna, steam room, pool, gym, etc). The staff were very helpful as well. We would absolutely stay here again."
Sonja 3-night trip
Posted 3 days ago
Castello di Spaltenna- Small Luxury Hotels of the World
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 8 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 Asciano?
If taking it easy by the pool is your idea of the perfect getaway, you may want to consider relaxing Asciano, which has 16 places to stay with pools. During your trip, you can explore sights such as Monte Oliveto Maggiore Abbey and Val di Chiana, and then relax poolside at one of the accommodation options in Asciano that guests like for their pools.
What are some accommodation options with pools in Asciano?
Castello di Leonina Relais: Features a sauna, a rooftop pool and a rooftop terrace. Precise House Montaperti Siena: Offers a seasonal outdoor pool, an indoor pool and a full-service spa.
How many pool hotels are there in Asciano?
Expedia's 16 hotels in Asciano give you a great choice for your poolside getaway.
What is there to see and do in Asciano?
The picturesque setting of Val di Chiana showcases the area's natural beauty. Discover sights such as Monte Oliveto Maggiore Abbey and Museo Cassioli during your stay. Take in the natural beauty of Asciano with the countryside.
When is the best time to book a hotel with a pool in Asciano?
You may want to consider a place to stay that has an outdoor pool if you'll be visiting Asciano in the hottest months of August, July or June, when the average temp is 22°C. Accommodation 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 6°C.
What's the best way to travel around Asciano?
Knowing the transportation options in and around Asciano can help you enjoy the area beyond your hotel pool. If you want to travel outside the area, take a train from Asciano Monte Oliveto Maggiore Station, Asciano Station or Castelnuovo Berardenga Station. Asciano may not have many public transport options to choose from, so consider a car rental to maximise your time.

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