The Best Castle
Hotels near Pienza

Great views. Offering an outdoor pool, garden, and free bike rentals, Agriturismo Palazzo Massaini is situated in the Tuscan countryside, 5 km from Pienza. The farm specialises in Chianti wine and olive oil production. Palazzo Massaini Agriturismo serves a sweet daily breakfast of homemade cakes, coffee, and other items. The apartments are located 500 metres from the ancient stone palace and share a spacious patio with outdoor furniture. They each include a TV, free toiletries, and a fully equipped kitchen with a dishwasher. On request, this can be savoury. Set over 300 hectares of maintained land, the property has numerous opportunities for long walks in the countryside. Montepulciano is 10 km away, while Siena can be reached in about an hour’s drive. Show full description

Historic. Great location. How many people can say they’ve stayed in a 15th-century convent? You can if you book Relais Chiostro di Pienza, a charming hotel set right in the heart of Pienza. Set just 100 metres from Pienza’s cathedral, this historic hotel has well-kept gardens and a panoramic terrace offering lovely views of the Tuscan countryside. Relais Chiostro di Pienza’s rooms feature views of the old town, the Val d’Orcia countryside or the old convent itself. La Terrazza del Chiostro, the Relais’s restaurant, serves Tuscan and Italian dishes out on the terrace. What could be better than a refreshing dip in Chiostro di Pienza’s outdoor pool after an afternoon exploring the old churches and monuments nearby? Sun loungers are available for free. All come with tea and coffee-making facilities, minibars and satellite TV and some feature original ceiling frescoes. Take in the panoramic views while enjoying your meal. Show full description

Highly elegant. Great restaurant. Set just inside San Quirico d'Orcia's historic town walls, Palazzo del Capitano is a charming 15th-century building. It features a wellness centre and 1000-m² garden with vegetable patches and fountains. Breakfast is served at Trattoria Toscana Al Vecchio Forno, a few steps from Palazzo del Capitano Relais & Wellness. This property is surrounded by olive groves and Mediterranean gardens where you will find plenty of sun loungers. The wellness centre includes a hot tub, a Turkish bath or a massage. It is available upon reservation and comes at extra charge. The rooms are decorated in a rustic style, with wooden-beamed ceilings, antique furniture and terracotta floors. They all have satellite TV and free Wi-Fi. There is also the relaxing living room which was once the stables and the Vecchio Forno restaurant. This Michelin-recommended restaurant serves Tuscan food and wine indoors by the fireplace or outside in the beautiful garden, under the olive trees. Set in the Val d'Orcia area of Tuscany, the hotel is 25 minutes' drive from Montepulciano, famous for its wine. Show full description

Great location. Set in 50 hectares of private land, Il Macchione is an 18th-century stone farmhouse. Just 1.5 km outside Pienza, it features a swimming pool that overlooks Val d'Orcia Natural Park. Apartments have a rustic style with wood-beamed ceilings and antique furniture. They all feature a comfortable living and dining area with a fully equipped kitchenette. You will also have air conditioning, satellite TV channels and free Wi-Fi. Outdoors, you will find the 70-m² terrace featuring a swimming pool with hydromassage area and plenty of sun loungers, chairs and tables. The grounds also include a children's playground, gazebos and lots of vineyards, olive trees and colourful flowers. Agriturismo Il Macchione serves a buffet breakfast each morning and a BBQ is available in the garden. Parking is free and the farmhouse is an hour's drive from historic Siena. Show full description

Luxurious. Comfortable beds. Popular among couples. 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. Show full description

Very stylish. Cosy rooms. Popular among couples. Villa Le Prata - Wine Resort - Adults Only- Enoturismo is housed in an 18th-century restored villa in the peaceful Tuscan countryside, a 5-minute drive from Montalcino. It offers a lush garden, free private parking, and free WiFi in public areas. Overlooking the private park or the vineyards, the air-conditioned rooms at Villa Le Prata all come with antique furnishings. They include a private bathroom fitted with a shower, a flat-screen TV and a minibar. The property is in an area ideal for hiking, cycling, and wine/food-tasting tours. You can also visit the Sant'Antimo Abbey, located 13 km away. Show full description

Beach front location. Charming. Comfortable beds. 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. Show full description

Beach front location. Luxurious. Cosy rooms. 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. Show full description

Charming. Set on Mount Amiata in the south of Tuscany, Castello Di Potentino is a working organic farm that produces award-winning wines and olive oil. Its grounds include a private chapel and beautiful garden. Staff can arrange wine tastings and other tours around the castle and in the surrounding area. Castello Di Potentino is 5 minutes' drive from the small town of Seggiano. The rooms all have different designs, some with wooden beams and others with frescoes on the ceiling. Each one has antique furniture and plenty of old world charm. A sweet breakfast of bread, jams, fruit and yoghurts is served in the breakfast room each morning. Parking is free and the Abbey of Sant'Antimo is 20 minutes' drive away. The nearest bus stop is 1 km away for buses to Grosseto, 1 hour away. Show full description

Close to beach front. Relaxing atmosphere. Superb breakfast. 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. Show full description

Lovely property. Stunning pool facilities. 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. Show full description

Great value. This Agriturismo with spring-water swimming pool is located on a hill just outside Pienza. All rooms and the restaurant offer a panoramic view of the Tuscan countryside. Parking is free. The rustic rooms come with exposed oak-wood beams on the ceilings and underfloor heating and cooling system. Each features a private bathroom and a satellite TV. Some are located in the annex building just a few meters away. Breakfast is continental style. The restaurant serves typical regional cuisine and it is open on request for dinner. Horseback riding excursions can be organised on site. The public bus to/from the centre of Pienza stops outside Agriturismo La Collina. It runs at scheduled times during the day. Show full description

Delightful property. Great location. Set in a former post office from the 16th century, the 4-star Relais Osteria Dell'Orcia is located in the UNESCO-protected Val d'Orcia Nature Reserve, along the historic Via Francigena road. The property offers an outdoor swimming pool, elegant rooms with satellite TV, and free Wi-Fi. Air-conditioned rooms at the family-run Osteria Dell'Orcia are decorated in a traditional Tuscan style, with original wood-beamed ceilings, silk brocades, and cool tiled floors. With views of Pienza and Bagno Vignoni, all rooms include a private bathroom with hairdryer. Breakfast is a sweet and savoury buffet of freshly baked bread, croissants and homemade yoghurt. Featuring traditional stone walls, the à la carte restaurant is managed by the chef Eliana and offers Tuscan cuisine and an extensive wine list including Brunello and Nobile di Montepulciano wines. Show full description

Historic. Friendly staff. A jewel of the Tuscan countryside, luxurious Castello delle Serre sits majestically at the top of the charming medieval town of Serre di Rapolano, 40 minutes from Siena and Montepulciano. The hotel has incorporated modern comforts into this grandiose residence which offers oversized beds and spacious marble bathrooms, not to mention a spectacular swimming pool. Picturesque countryside views are the norm as you wander around the beautiful gardens of this exceptional property, perhaps sitting under ancient trees, or lounging in the vast park. The surrounding area offers you all that Tuscany is famous for. Just 4 km away you will find Rapolano Terme, a spa town famous for its healing waters and the Chianti and Montalcino vineyards and wine cellars are nearby, perfect for wine-tasting trips. Unspoilt old hill towns such as San Gimignano and cultural hotspots like Siena, where you can really soak up the art and history of the area are all just a short drive away too. Show full description

Beach front location. Romantic. Superb interior design. Surrounded by vineyards, Argiano Dimore Wine Relais is a working farmstay in Val D’Orcia, a 10-minute drive from Montalcino and 25 km from San Quirico D'orcia. It features a restaurant, a bar, a seasonal outdoor pool and free Wi-Fi. Guests of Argiano Dimore Wine Relais have access to a garden with barbecue facilities. Argiano Dimore Wine Relais offers free parking. The air conditioned rooms come with a wooden beamed ceiling and offer garden views and a private bathroom with a hairdryer and complimentary toiletries. À la carte breakfast is available daily. An array of activities can be enjoyed on site or in the surroundings, including horse riding, cycling and hiking. Show full description

Luxurious. Outstanding SPA facilities. Set on a hill overlooking Val d’Orcia, Castello di Velona Resort, Thermal SPA & Winery features a restaurant and a spa centre for an additional charge. The property is also reachable via helicopter and there is a helipad on site. The rooms located in the new wing of the castle include a patio and a spa bath in the bathroom. The Castello offers regional cuisine, accompanied by the property's own wines and olive oil. The Velona’s rooms offers views of Tuscan vineyards. Each one is air conditioned and features a log fire, a marble bathroom, and satellite TV channels. Both the Lounge Bar and the restaurant feature a terrace. Sant’Antimo Abbey is 2 km from the property, and Siena is a 30-minute drive away. Parking is free at the Velona. Show full description

Historic property. Great interior design. Convento San Bartolomeo is a restored 13th-century Franciscan monastery offering traditional rooms with wood-beam ceilings. Located in Piancastagnaio, it features original frescoes in its dining hall and free internet access. It also boosts a brand new heated external swimming pool which is open also during winter time. With terracotta floors and natural wood furniture, the rooms at the Convento San Bartolomeo preserve many original features of the monastery. Breakfast at the property is served in the Friar’s kitchen, overlooking the gardens. Guests can enjoy discounted rates at local wineries and restaurants, tennis courts, horse-riding and thermal baths centre. Chianciano Terme Station is 37 km from the San Bartolomeo Convento. The A1 Autostrada del Sole motorway is a one-hour drive away. Show full description

Good breakfast. Immersed in the peaceful greenery of Val d'Orcia Valley, the elegant Borgo Canalicchio features 2 outdoor pools, free Wi-Fi and a large garden. All self-catering apartments offer air conditioning and a flat-screen TV, 2 km from historic Montalcino. Wrought-iron beds and wood-beamed ceilings characterise apartments at Borgo Canalicchio Di Sopra Relais. This family-run estate produces and sells its own Brunello wine. Each has a fully equipped kitchen and comfortable lounge area. Nearby Montalcino hosts a range of restaurants, shops and bars. Show full description

Unique. Great breakfast. 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 a partner property 1.5 km away. Free on/site parking is available. San Biagio Church is a 15-minute drive from the Cavarciano, while Chianciano Terme is 18 km away. Show full description

Beautiful. Great restaurant. Offering an outdoor seasonal pool, a garden and free WiFi, Abbadia Sicille Relais is set in Trequanda. Guests can enjoy the property's sun terrace and free private parking. Both Siena and Arezzo are within 50 km of Abbadia Sicille Relais. The rustic-style rooms are equipped with a flat-screen TV. The private bathroom has free toiletries and a hairdryer. Some rooms have seating area. Perugia Airport can reached by car in 1 hour. Show full description