
Exceptional
60 reviews

Exceptional
288 reviews

Exceptional
282 reviews

Exceptional
193 reviews

On a hilltop in the heart of Tuscany, Lupaia, a converted stone farmhouse overlooking Montepulciano, will offer you a warm welcome. The hotel is made up of 12 charming and unique guest rooms, each of which have beautiful hand painted walls, original wooden beams, antique furnishings and paintings and restored fireplaces. All enjoy independent access and have private terraces or gardens as well as extraordinary views of the surrounding Tuscan landscape with its hills and medieval villages. These breathtaking views can also be appreciated from the hotel’s outdoor swimming pool which is set into the hillside. Original Tuscan recipes and exquisite wines from the surrounding Vino Nobile di Montepulciano vineyards will be served in the restaurant or on the patio during the summer months. The restaurant also uses olive oil produced by its own olive groves. The hotel can arrange for you to attend cooking classes or cheese tasting events and pride themselves on their hospitality and personal service. Close to important tourist destinations such as Florence, Siena and Arezzo yet immersed in the most tranquil of surroundings, Lupaia is the perfect place from which to discover the beauty of Tuscany.
Exceptional
95 reviews

Exceptional
101 reviews

Exceptional
243 reviews

Surrounded by stunning Tuscan countryside in Pienza, La Saracina offers rooms and apartments decorated in traditional style. The property offers a swimming pool, free Wi-Fi and free parking. All rooms at La Saracina offer views of the garden and feature vaulted ceilings. They are painted in pastel colours, and some of them offer a hot tub. The property’s staff can arrange meals with traditional dishes upon request, and offer cooking lessons to those who are interested. This country house also has a sun terrace. Guided trekking is available on the paths that surround La Saracina. The city centre is located 8 km from the property, and Siena is a 1-hour drive away.
Exceptional
148 reviews

Superb
354 reviews

Superb
82 reviews

Superb
151 reviews

Superb
78 reviews

Exceptional
122 reviews

Exceptional
75 reviews

Set at an altitude of 470 metres, Agriturismo Cerreto offers 360° views of the Val d'Orcia and Mount Amiata. This 15th-century farmhouse offers cosy accommodation with fireplaces, 4 km outside Pienza. Cerreto is a working farmhouse that produces its own olive oil, wine and jams. Breakfast is brought to your room in a basket each morning and includes homemade cakes, natural jams and other produce from the farm. Rooms and apartments have a classic design with tiled floors and arched ceilings. Each one has a private entrance and a kitchenette. Outdoors, you will find a swimming pool with natural spring water, a BBQ area and children's games such as table tennis and football. Bikes are available to rent and free parking is provided.
Exceptional
272 reviews

Exceptional
209 reviews

Superb
82 reviews

Fonteliving RestArt offers very elegant design apartments, plus an outdoor pool surrounded by the green Tuscan countryside. The popular thermal pools are 700 metres away. Apartments are spacious, air conditioned and nicely decorated. In your living area you will find a fully equipped kitchen, LCD satellite TV and free Wi-Fi access. Each has a furnished balcony or terrace. Guests can relax on a deck chair by the pool. Fonteliving RestArt is 150 metres from a bus stop linking with Chiusi and Montepulciano. The spa town of Chianciano Terme can be reached by car in 30 minutes, and the centre of San Casciano Dei Bagni is 800 metres away.
Exceptional
327 reviews

Superb
495 reviews

Exceptional
124 reviews


Note: The prices for each boutique hotels in Val Di Chiana Senese do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here>) to get the latest prices.
When planning your luxury or boutique stay in Val di Chiana senese, Italy, you'll discover an array of captivating attractions waiting to be explored.
Montepulciano: This picturesque hilltop town is famous for its stunning Renaissance architecture and exquisite wine, making it a perfect day trip from your boutique hotel.
Pienza: Known as the 'Ideal City,' Pienza offers breathtaking views of the Tuscan countryside alongside charming streets filled with local artisan shops and delicious pecorino cheese.
Cortona: Just a short drive away, Cortona enchants visitors with its ancient Etruscan walls, quaint cafes, and vibrant art scene, ensuring a memorable experience during your stay.
Thermal Springs: Indulge in relaxation at the natural thermal springs in Rapolano Terme, where you can unwind in soothing waters just a stone's throw from your luxury accommodation.
Castiglione del Lago: Nestled on the shores of Lake Trasimeno, this charming lakeside town invites you to stroll along scenic paths or explore its historic castle while enjoying stunning lake views.
Val d'Orcia National Park: A UNESCO World Heritage site, this idyllic landscape showcases rolling hills, vineyards, and cypress trees, ideal for hiking and photography enthusiasts staying nearby.
Local Vineyards: Embark on a wine-tasting tour through the local vineyards surrounding Val di Chiana senese, where you can savor exquisite wines and learn about the region’s winemaking traditions.
Cooking Classes: Immerse yourself in the rich culinary culture of Tuscany by enrolling in a cooking class, where you’ll create authentic Italian dishes using fresh local ingredients during your boutique stay.
Transportation/Shuttle service is available at the following boutique hotels in Val di Chiana senese:
A spa is available to guests at the following boutique hotels in Val di Chiana senese:
Families traveling in Val di Chiana senese enjoyed their stay at the following boutique hotels:
These 3 star hotels received great reviews from other travelers:
Some of the best boutique hotels in Val di Chiana senese are: