
Exceptional
60 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

Superb
354 reviews

Superb
151 reviews

Exceptional
124 reviews

Exceptional
240 reviews

Superb
410 reviews

Villa Poggiano is a 6-hectare estate in the heart of the peaceful Tuscan countryside. It offers an outdoor pool and luxurious guest rooms with free internet access and panoramic views. Surrounded by green parkland, Villa Poggiano is only 5 minutes’ drive from Montepulciano’s medieval centre, set on the Val d’Orcia hills. Enjoy panoramic views and complete silence while walking in the gardens or swimming in the marble swimming pool, surrounded by statues and fountains. Family-run, Villa Poggiano offers a warm welcome as well as beautifully decorated suites. Rooms are located in the main villa or in lodges, where they enjoy unforgettable views of olive groves and corn fields. All benefit from free Wi-Fi internet access and there is also an internet point in the lobby. To ensure your complete relaxation Villa Poggiano serves a delicious breakfast spread of cakes, pastries, meats and cheeses until 11:00. Friendly staff at Villa Poggiano can book restaurants or organise a variety of tours for you in the area. Visit vineyards and local towns or go further afield to some of Tuscany’s most famous cities of art.
Superb
222 reviews

Set just 10 minutes’ walk from Montepulciano’s historic centre, Il Rondò offers personalised service, a bar, and free garage parking. Rooms offer free WiFi and some overlook the lovely gardens. Beautifully decorated and containing antique furniture, interiors at Il Rondò maintain an 18th-century Tuscan charm. Each room offers air conditioning and satellite TV. A buffet breakfast with local products is included daily and can be served in the garden. Guests staying 4 nights or longer receive a complimentary bottle of red Montepulciano wine. A welcome drink is offered in the garden.
Superb
647 reviews

Dating back to the early Middle Ages, Villa Cicolina is now a charming hotel. Boasting fantastic views of the Tuscan countryside, it guarantees a personalised service and an unforgettable stay. Set close to Montepulciano, this was once the country retreat of a noble family. It features antique furniture, original paintings and frescoed ceilings. Explore the large, private gardens which lead down to a small church. The garden features a swimming pool with hydromassage, which is surrounded by olive groves. Villa Cicolina has lots of large open spaces where you can relax with a book. Make sure to visit the wine cellar, home to a large collection of wines and olive oil. Enjoy a delicious 4-course menu at the restaurant, specialising in traditional, Tuscan cuisine. Guest rooms are located on the ground, first and second floors. There are also separate rooms which are set in cottages and have their own garden. In the lobby there is free Wi-Fi and a free internet point.
Superb
391 reviews

Superb
649 reviews

Fabulous
751 reviews

In Tuscan countryside, Tenuta Santagnese farm offers self-catering apartments surrounded by extensive gardens with barbecue facilities and an outdoor pool. Parking is free. The family-run Santagnese farmhouse has rustic apartments with typical Tuscan kitchens, large bathrooms and bedrooms with cast-iron beds. Most furnishings are antiques, from the 18th century. Montepulciano city centre is about a 10-minute drive from the Santagnese Tenuta.
Fabulous
233 reviews

LaChiusa Tuscany is set in an ancient oil mill in the Tuscan countryside. Featuring stone walls and antique rural furniture, it enjoys lovely views of the Montepulciano landscape. The hotel offers spacious rooms with a rustic feel. They are decorated in a typical Tuscan style and overlook the relaxing garden. Some boast stone details and wood-beamed ceilings. The on-site restaurant features arched walls with red bricks. Here, guests can enjoy traditional local specialities, home-grown products and a wide range of wines. The property's garden and terrace are equipped with sun loungers and chairs. They boast panoramic views of the countryside. Providing free parking, Hotel LaChiusa Tuscany is 10 km from Pienza and Montepulciano. The A1 motorway is a 30-minute drive away.
Fabulous
385 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
234 reviews

Exceptional
22 reviews

Tenuta Santo Pietro is a working farm located in Tuscan countryside, and features an outdoor swimming pool with views of Pienza, 5 km away. The rooms are located in a 13th-century farmhouse, and come with terracotta floors and wooden beams on the ceilings. The rooms come with air conditioning and TV, and each features mosquito nets on the windows. Some rooms offer views of the valley, and some feature stone walls. Each room has a marble bathroom, complete with bath or shower, hairdryer, and toiletries. A sweet and savoury buffet is served daily for breakfast, and includes freshly baked croissants and cakes, cheese, and cold cuts. The restaurant specialises in traditional Tuscan cuisine, made using fresh local ingredients. Wine and olive oil are produced and sold on site. The Santo Pietro's well-tended gardens feature several patio areas, furnished with tables and chairs. The pool is surrounded by padded-teak deck chairs, tables, and parasols.
Superb
235 reviews

Palazzo Massaini - Cavarciano is located in the Tuscan countryside, 5 km from Pienza. It has a large garden and produces its own wheat, olives and wine. Each room features a cooling fan, desk and private bathroom with free toiletries. The apartments are equipped with a full kitchenette, seating area with a TV and 2 bathrooms. A sweet Italian breakfast is served daily at the breakfast room. Guests enjoy free access to the swimming pool of the propriety. Free on/site parking is available. San Biagio Church is a 15-minute drive from the Cavarciano, while Chianciano Terme is 18 km away.
Superb
541 reviews

Set in an 18th-century mansion, Agriturismo Podere La Rocca offers traditionally furnished accommodation with bathrooms. Located 12 km from the centre of Montepulciano, it has free Wi-Fi and a garden with a pool. The rooms and apartments are air conditioned. The apartments include a kitchenette and dining area. Some feature a hydromassage bath tub. Agriturismo Podere La Rocca provides a daily à la carte breakfast. The property also organises tours of the Montepulciano wine region. Montepulciano Station is 7 km from the property. The A1 Autostrada del Sole motorway is a 15-minute drive away.
Superb
157 reviews

Fabulous
114 reviews

Superb
608 reviews

Very Good
158 reviews


Note: The prices for each boutique hotels in Montepulciano 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.
If you’re looking for a luxury or boutique stay in Montepulciano, Italy, you'll find that the town is teeming with charming attractions that will enhance your experience.
Piazza Grande: Explore the stunning Piazza Grande, the heart of Montepulciano, where historical architecture surrounds you and vibrant local life unfolds.
Nobile Wine Cellars: Indulge your senses by touring the famed Nobile wine cellars, where you can savor exquisite tastings and learn about the winemaking process unique to this region.
Duomo di Montepulciano: Visit the Duomo di Montepulciano, a magnificent cathedral nestled in the town square, distinguished by its impressive façade and beautiful artwork inside.
La Fortezza Medicea: Discover La Fortezza Medicea, an imposing fortress offering panoramic views of the surrounding countryside, perfect for capturing breathtaking photographs.
Cinta Senese Herds: Experience the picturesque sight of Cinta Senese pigs grazing in the lush landscapes nearby, a symbol of Tuscany's rich agricultural heritage.
Val d'Orcia: Take a scenic drive through Val d'Orcia, a UNESCO World Heritage site, where rolling hills and vineyards create postcard-perfect vistas just minutes from your boutique hotel.
Local Art Galleries: Immerse yourself in the local culture by visiting the town’s charming art galleries, showcasing works from talented contemporary artists and highlighting Montepulciano's artistic legacy.
Cooking Classes: Enhance your culinary skills by joining a cooking class, where you’ll learn to prepare traditional Tuscan dishes using fresh ingredients sourced locally.
Popular boutique hotels in Montepulciano that have a pool include:
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Some of the best boutique hotels in Montepulciano are: