Top Country Houses in Province of Siena in 2026

A historic town with a prominent tower and a rainbow arching over it.

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Top Cities in Province of Siena

A narrow street with stone buildings, Italian flags, and a shop with ceramic plates.

A hillside town with historic buildings and a prominent church.

Our top choices for Province of Siena country houses

A stone building with a tiled roof, a paved pathway, and a well-maintained garden.

1. Podere Brizio

Montalcino

Aseem

HK$1,794 total

includes taxes & fees

16 Nov - 17 Nov

A spacious living room with a leather sofa, a wooden coffee table, and a view through large arched windows.

2. Relais Villa Grazianella - UNA Esperienze

Montepulciano

Maribel

HK$1,885 total

includes taxes & fees

5 Nov - 6 Nov

A stone building with a swimming pool, surrounded by trees and a view of the landscape.

3. Relais la Costa - Dimora Storica

Monteriggioni

Doug

HK$1,473 total

includes taxes & fees

26 Oct - 27 Oct

A stone building with a tiled roof surrounded by vineyards.

4. Cordella in Montalcino Wine Resort

Montalcino

Marcelo

HK$647 total

includes taxes & fees

27 Oct - 28 Oct

A stone building with a swimming pool, outdoor seating, and trees.

5. Il Castagnolo Country B&B

San Gimignano

Paul

HK$845 total

includes taxes & fees

13 Nov - 14 Nov

A dining area with a table set for four, chairs, a television mounted on the wall, and a cabinet with glass doors.

6. L'Aia di Argia

Monteroni d'Arbia

mario

HK$669 total

includes taxes & fees

26 Oct - 27 Oct

A pool with a wooden deck and lounge chairs, surrounded by trees and hills in the background.

7. Fattoria Pieve a Salti

Montalcino

Marko

HK$1,063 total

includes taxes & fees

9 Nov - 10 Nov

A room with a view of a vineyard, a table with cups and saucers, and a window with curtains.

8. Wine Estate Paradiso di Cacuci

Montalcino

Tony

HK$2,426 total

includes taxes & fees

26 Oct - 27 Oct

A hot tub on a wooden deck surrounded by a white gravel border, set in a grassy area with a view of rolling hills in the background.

9. Podere Sant'Antonio

Asciano

Robi

A table with a bottle of wine, two glasses, and a plate of food on a balcony overlooking a historic cityscape.

10. Tenuta Guardastelle

San Gimignano

Mary

A terrace with stone arches, green plants, and a table set for dining with a scenic mountain view.

11. Podere L'Aquila

Gaiole in Chianti

Heather

A stone building with a staircase leading to a second floor, a small garden area, and a red brick courtyard.

12. Locanda Casalta

Strove

Alexander

HK$1,028 total

includes taxes & fees

26 Oct - 27 Oct

Two people performing a yoga pose on a reflective pool with a sunset in the background.

13. Podere Poggio al Sole

Montepulciano

Lauren

A rustic stone wall with a wooden door, a small window, and a table with two chairs and a bottle of wine.

14. Querceto di Castellina

Castellina in Chianti

hugh

A stone building with a rustic stone wall, a wooden bench, a wicker basket, and potted plants.

15. Borghetto Poggio Bianco - Antico casale

Radicondoli

wolfgang

A tranquil lakeside setting with a gazebo, a bench, and a pool reflecting the structure.

16. Rinidia Bio

Sovicille

Kristen

A poolside area with a view of rolling hills and a clear sky.

17. Apartment with a Beautiful Sunset at the Pascianella Farmhouse

Castelmuzio

"We spent a week at this beautiful farmhouse. The views were amazing both inside and outside the property. Sunsets were awesome and the stillness and serenity was breathtaking. The property was large and comfortable. Our hosts Giacomo and Cinzia were lovely and so welcoming and helpful. Our children fell in love with their little dog, Pimpa and each morning our son would walk up the drive to find her. On our last night they invited us for dinner and we sat in the garden, with wine, Parma ham,...

Victoria B.

A stone building with a garden and outdoor seating area.

18. La Tresa Country Living

Montepulciano

"Un vrai coup de cœur. Logement pour nous tout seuls, au calme total dans la campagne toscane, loin de tout et des touristes. Ancienne ferme magnifiquement restaurée, décoration typique et authentique. Le bruit des insectes, la nature tout autour. La propriétaire est vraiment arrangeante. On a eu de la chance d'y être seuls. Seul bémol , les lits sont un peu fermes et pas eu d'eau chaude, mais en été ça ne dérange pas du tout, ça fait partie de la campagne."