Our top pick of the best small boutique hotels, luxury hotels, charming bed & breakfasts, agritourism and holiday homes in Siena province
The province of Siena in south-eastern Tuscany, perfectly encapsulates the charm and history of Italy. Explore our collection of beautiful boutique hotels in Siena, charming country retreats, and lavish luxury hotels in Siena, each of which perfectly captures the character of this spectacular location. For those looking for a self-catering getaway, we invite you to explore our quaint vacation homes and chic holiday villas in Siena, which offer the ideal backdrop to create your own authentic Tuscan experience. Alternately, spend some time in one of our charming wine hotels or castle retreats in Chianti, where the charm of genuine Tuscany is waiting.
Selection of small boutique hotels, luxury hotels, charming bed & breakfasts, romantic getaways, stylish and cool holiday flats in Siena province:
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Manor House - High BudgetEnjoy your summer in this beautiful Tuscan vacation home with a swimming pool. This 17th-century country inn offers a timeless atmosphere and modern comfort. The garden with an olive grove and saltwater pool promises relaxation. Ideally located in the Orcia Valley, near thermal baths and Fonteverde Natural Spa Resort.- Countryside
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- 8 rooms
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- from 221 EUR
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Holiday Apartments - Medium Budget
- Italy
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- Tuscany
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- Siena
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- San Giovanni D'Asso
Authentic vacation homes in a historic Tuscan village. Masterfully restored, they offer modern comfort, rustic charm and panoramic views. Ideal for romantic getaways and weddings. The pool and Casale Sarageto are best suited for larger groups. An unforgettable Tuscan experience!- Countryside
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- 6 properties
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- from 210 EUR
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Design Hotel - Medium Budget- Italy
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- Tuscany
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- Siena
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- Montepulciano
Fattoria San Martino – An idyllic farmhouse inn where hospitality is at the heart of everything. Bright, spacious rooms, sustainable design and personalised service. Enjoy the harmonious connection with nature, relaxation or conviviality. An unforgettable stay awaits you!- Countryside
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- 6 rooms
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- from 255 EUR
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Bed and Breakfast & self-catering - Low Budget- Italy
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- Tuscany
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- Siena
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- Gaiole in Chianti
In a lovingly restored village in Chianti, Argenina offers self-catering country houses and elegant rooms in a charming B&B. Vineyards, stillness, homemade breakfasts and family-style cooking in one of central Italy’s most authentic regions.- Wine Country
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- 17 rooms
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- from 115 EUR
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Holiday home villa - Medium Budget- Italy
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- Tuscany
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- Siena
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- Montalcino
This design villa in Tuscany is a modern work of art surrounded by nature. With 2 bedrooms, a swimming pool, a sauna and original artworks, it offers a contemporary style and maximum comfort. Ideal for art and nature lovers.- Countryside
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- 4 people
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- from 540 EUR
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Bed and Breakfast - Medium BudgetSiena klingt leise – Glockenschläge aus der Ferne, Schritte auf Kopfsteinpflaster, Stimmen zwischen gotischen Bögen. Nur wenige Meter vom pulsierenden Zentrum entfernt liegt Le Logge Luxury Rooms in wohltuender Zurückgezogenheit. Die Räume sind s...- Historic Quarters
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- 4 rooms
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- from 160 EUR
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Hotel & Self-Catering - Medium BudgetThe charming country hotel in the heart of Chianti, near Siena, offers 4 rustic apartments for relaxing stays. Experience the timelessness of Tuscany amidst vineyards and olive groves, surrounded by traditional flair and tranquillity.- Countryside
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- 4 rooms
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- from 85 EUR
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Castle hotel - Medium Budget- Italy
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- Tuscany
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- Siena
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- Gaiole in Chianti
Discover the mediaeval heritage at the luxury hotel Castello di Spaltenna in Chianti. Historic charm, knight's armour and modern comforts await you at this time-travel destination. Enjoy views of both beautiful vineyards and vast forests from the outdoor pool and terrace.- Countryside
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- 37 rooms
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- from 280 EUR
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Holiday home villa - Medium BudgetThe 16th century Fattoria Tregole winery in Chianti is a Tuscan-style villa. Ideally located with a garden, swimming pool and close to Castellina. Experience authentic Tuscany and relax in the heart of picturesque vineyards.- Countryside
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- 4 properties
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- from 220 EUR
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Country Hotel - High Budget- Italy
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- Tuscany
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- Siena
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- Torrita di Siena
This characteristic rural hotel Follonico is a place where you can feel the authenticity of Italy in a warm and hospitable environment, while exploring the magnificent countryside and historical treasures to be found in Tuscany.- Countryside
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- 6 rooms
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- from 285 EUR
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Luxury Hotel - LuxuryThe luxury hotel Grand Hotel Continental in Siena enchants with baroque elegance and splendid furnishings from times gone by. Enjoy royal comfort in heavenly rooms and exquisite culinary delights in the hotel's own restaurant and legendary wine bar Sapordivino.- City
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- 51 rooms
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- from 279 EUR
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Hotel - Medium Budget- Italy
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- Tuscany
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- Siena
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- San Quirico d'Orcia
Discover Hotel Relais Palazzo del Capitano amidst the unspoiled beauty of Val d'Orcia, with charming rooms and gardens, ideal for a relaxing stay. Whether exploring the surrounding countryside or relaxing in the cosy rooms, this hotel promises an authentic experience in Tuscany.- Village
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- 16 rooms
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- from 147 EUR
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Hotel - Low Budget- Italy
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- Tuscany
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- Siena
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- San Giovanni D'Asso
A lovely little Tuscany hotel still off the beaten track. Unless you are a connoisseur of fine white truffles, you may never have heard of San Giovanni d’Asso, a small hamlet nestled comfortably in the hills of this beautiful and relatively u...- Village
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- 9 rooms
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- from 150 EUR
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Spa Hotel - High Budget- Italy
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- Tuscany
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- Siena
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- Monteriggioni
The romantic Relais la Costa wellness hotel in Monteriggioni offers relaxation surrounded by Tuscan nature. Enjoy charming suites, homemade breakfast, sauna, a Turkish bath and a heated pool. A perfect place for a relaxing retreat near Siena and Florence.- Countryside
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- 7 rooms
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- from 189 EUR
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Boutique Hotel - High Budget- Italy
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- Tuscany
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- Siena
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- San Gimignano
The i Pini Biotique Agrivilla is the ideal vegan hotel for sustainable luxury in the Tuscan countryside. Enjoy exclusive rooms, only organic and vegan cuisine and green surroundings. Welcome to your Secretplace.- Countryside
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- 11 rooms
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- from 460 EUR
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Holiday home villa - High BudgetThe dreamlike villa in the middle of the Tuscan countryside offers space for 14 people, a modern pool and an in-house restaurant. Discover the beauty of San Casciano dei Bagni and enjoy the Italian dream.- Countryside
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- 6 rooms
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- from 180 EUR
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Country Hotel - High BudgetIn the heart of the Chianti region, the 16th century buildings of Wine Resort Dievole overlook 400 hectares of stunning vineyards and olive groves. The resort features 27 elegantly renovated rooms and suites, each adorned with antique furnishings and offering breathtaking views. Guests can indulge in authentic Tuscan cuisine, enjoy wine tastings, or simply relax by the pool while iconic cities such as Siena or Florence are only short car trip away.- Countryside
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- 27 rooms
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- from 298 EUR
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Country Hotel - High BudgetThis unique Tuscan retreat is the perfect place for a romantic getaway in the heart of Italy. If you are looking to relax place from the everyday grind, La Saracina, a stylish hotel in Val d'Orica, is the place to be. The rooms have been carefully designed with cosy elements and décor from around the world to create a peaceful and comfortable atmosphere.- Countryside
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- 5 rooms
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- from 286 EUR
