Top Boutique Hotels in Val Di Chiana Senese (2026)

Providing garden views, Stelle di Monte in Montepulciano features accommodations and a garden. This recently renovated guest house is located 31 miles from Mount Amiata and 4.5 miles from Montepulciano Terme. The guest house provides rooms with air conditioning, free private parking, and free Wifi. At the guest house, units are fitted with a wardrobe. There's a private bathroom with walk-in shower in every unit, along with slippers, a hair dryer, and free toiletries. At the guest house, all units are equipped with bed linen and towels. À la carte and continental breakfast options with warm dishes, pancakes, and fruit are available daily at the guest house. At the property, there is an romantic restaurant serving French cuisine as well as vegetarian options. Guests at Stelle di Monte can enjoy cycling and hiking nearby, or make the most of the sun terrace. Bagno Vignoni is 14 miles from the accommodation, while Bagni San Filippo is 18 miles away. The nearest airport is Perugia San Francesco d'Assisi Airport, 48 miles from Stelle di Monte.

- "We enjoyed everything about the property. Hosts Nathalie & Igor are just amazing. They made sure everything was top notch. We will be back and will definitely stay with them." - "Gorgeous views from and incredibly well kept and romantic property." - "Beautifully restored historical villa with panoramic views. Luxury bed and bathroom facilities." - "What a piece of heaven on earth" - "Stelle di Monte was more than we expected. The view was truly out of this world. The breakfast and dinner beyond delicious. Igor and Nathalie are wonderful hosts and ensure we had everything we needed."

Il Giuncheto offers accommodations in Trequanda. Free WiFi is available throughout the property and free private parking is available on site. You will find a shared lounge at the property. You can engage in various activities, such as cycling and hiking. Siena is 20 mi from Il Giuncheto, while Arezzo is 21 mi away. The nearest airport is Perugia San Francesco d'Assisi Airport, 42 mi from Il Giuncheto.

- "Everything was amazing, I think we couldn’t dream of a better place than this to stay in Tuscany. The bed was super super confortable, the room extremely clean and big, the staff was so kind (it’s a family which owns this place and they took much care of us), the food is homemade and is delicious (we ate there every single night), and the activities proposed very fun (we took the electric bikes for a day and the cooking class for another day, I recommend). Also, the place is extremely calm, away from the highway, and given that it only has 5 suites in total, it was even more peaceful. Breakfast also was DELICIOUS with only local products, and a lot of choice."

Agriturismo Sole offers a solarium and air-conditioned accommodations in Trequanda, 25 miles from Piazza del Campo. There's a private entrance at the farm stay for the convenience of those who stay. The farm stay also features free Wifi, free private parking, and facilities for disabled guests. At the farm stay, each unit comes with a wardrobe. Rooms have a kettle, while some rooms also boast a fully equipped kitchen with a dishwasher, an oven, and a microwave. At the farm stay, units have bed linen and towels. As an added convenience, the farm stay offers packed lunches for guests to bring on excursions and other trips off-property. Guests can keep up their exercise routines during yoga and fitness classes. Guests can also relax in the garden, next to the infinity pool, or on the sun terrace. Piazza Grande is 28 miles from Agriturismo Sole, while Montepulciano Terme is 16 miles from the property. The nearest airport is Perugia San Francesco d'Assisi, 51 miles from the accommodation, and the property offers a paid airport shuttle service.

- "It is amazing. The location is perfect in the heart of the Crete Senesi. It is very close to Montepulciano and Pienza. Santiago is so kind and he showed us many lovely animals such as dogs, cats and pigs. My 8 year old daughter loved them. The breakfast also has high quality. It is much better than pictures in the website." - "The hosts were unforgettably friendly and openhearted! The nature, location, views, pets, facilities were excellent! ♥️ the place is heaven!"

Featuring a shared lounge, bar and views of city, Antico Sipario Boutique Hotel, BW Signature Collection is located in Paciano, 25 miles from Perugia Cathedral. With a garden, the 3-star hotel has air-conditioned rooms with free WiFi, each with a private bathroom. The hotel has family rooms. At the hotel, the rooms are equipped with a desk. Antico Sipario Boutique Hotel, BW Signature Collection has some rooms with garden views, and every room has an electric tea pot. All rooms in the accommodation are equipped with a flat-screen TV and free toiletries. The daily breakfast offers continental, Italian or gluten-free options. San Severo Church is 25 miles from Antico Sipario Boutique Hotel, BW Signature Collection, while Montepulciano Terme is 20 miles from the property. The nearest airport is Perugia San Francesco d'Assisi Airport, 30 miles from the hotel.

- "Absolutely everything. Amazing place and host." - "The Hotel is Amazing 10/10. I stayed in the Opera room and it was a lovely beautifully decorated room. claudio was extremely helpful and professional, Thank You" - "Claudio the manager was an excellent host and was very attentive and helpful. Antico Sipario is a beautiful place in an equally beautiful village of Paciano. Everything about the accommodation was high quality." - "Unique design, very comfortable, Claudio is extremely helpful and kind. Amazing breakfast! very comfortable beds. Location is like a painting."

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.

- "Beautiful property, with an amazing and attentive staff. They food was delicious." - "Absolutely amazing place. Great location. Beautiful grounds. Excellent service and food. Really helpful staff. Perfect Tuscan experience" - "Quality of service and the exclusiveness of the experience" - "Excellent service Beautiful rooms Great food" - "The location, the ground and the staff was absolutely exceptional. The attention to perfection was in every detail of the hotel, our room, pool, dinner and more. We are planning to return with our adult children for a longer stay."

29 miles from Mount Amiata in Sarteano, Palazzo Pio III - Residenza d'epoca provides accommodations with access to wellness packages and beauty services. The property is around 9.2 miles from Montepulciano Terme, 20 miles from Bagni San Filippo, and 20 miles from Bagno Vignoni. The accommodation features a spa facilities, free Wifi throughout the property, and family rooms. The bed and breakfast will provide guests with air-conditioned units offering a desk, a kettle, a safety deposit box, a flat-screen TV, and a private bathroom with a bidet. There's also a dressing room in some of the units. At the bed and breakfast, each unit has bed linen and towels. Buffet and continental breakfast options with warm dishes, local specialities, and fresh pastries are available each morning at the bed and breakfast. Both a bicycle rental service and a car rental service are available at Palazzo Pio III - Residenza d'epoca. The nearest airport is Perugia San Francesco d'Assisi Airport, 45 miles from the accommodation.

- "Wonderful palace recently renewed, with great attention to detail both in the common areas and in the room. We’ve loved everything: the style, the atmosphere, the comfort, the silence, the breakfast, the suggestions for nearby activities. Chiara is a lovely host dedicated to preserve the roots of this historical building. Highly recommended for its authenticity and uniqueness!" - "This is really an 11. It is a beautifully restored historical property where Pope Pius III was born. Much attention has been paid to detail and Chiara is the sweetest most wonderful host. She makes the most delicious jams and pastries for breakfast. Our room (for 4 of us) was so beautiful, clean and spacious. The bathroom was large with high quality fittings. The property had a pretty living room and a cosy nook with armchairs for guests to utilise. There was nothing at all to fault. And this is a great quiet base from which to explore the southern part of Tuscany. Truly amazing stay!"

Sce Quiríc in San Quirico dʼOrcia provides adults-only accommodations with an infinity pool, an open-air bath, and a garden. The air-conditioned accommodations are 27 miles from Mount Amiata. Free private parking is available, and the farm stay also provides bike rental for guests who want to explore the surrounding area. At the farm stay, some units have a private entrance, dining area, fireplace, and dishwasher. Every room has a private bathroom, a safety deposit box, and free Wifi, while certain rooms include a terrace and some have mountain views. At the farm stay, every unit has bed linen and towels. Buffet and à la carte breakfast options with warm dishes, local specialities, and fresh pastries are available daily at the farm stay. There is a coffee shop, and packed lunches are also available. Guests at Sce Quiríc will be able to enjoy activities in and around San Quirico dʼOrcia, like hiking. Guests can also warm up near the outdoor fireplace after a day of cycling. Piazza del Campo is 29 miles from the accommodation, while Bagno Vignoni is 5.2 miles away.

- "We had an amazing three-night retreat at Sce Quiric. The rooms are beautifully modern and tastefully decorated, equipped with all the essentials for a comfortable stay in the stunning Val d'Orcia region. The infinity pool is simply breathtaking, offering unparalleled views that seem to stretch into infinity. The atmosphere is incredibly serene, providing a luxurious and relaxing experience. Breakfast was a highlight, featuring a delightful spread including made-to-order eggs, freshly squeezed fruit juice, and delicious bakery treats. A special thanks to Danny and Sophia for their warm hospitality. We're already eagerly anticipating our next visit!"

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 colors, 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 center is located 5 mi from the property, and Siena is a 1-hour drive away.

- "We love the room and the property very much from the interior decoration to the big and comfortable bed. The breakfast area is so lovely like out of the magazine picture perfect with nice spread of homemade breakfast stuff (bread, eggs cooked to your likes, yogurt, jams). The view from the breakfast nook over Val d’orcia is very charming. we feel that the owners are thoughtful about all the details and it really delivers a perfect cozy staying experience for us, wish we could come back next time"

Delcorto Suites is offering accommodations in Montepulciano. This 4-star hotel offers free WiFi. The property is non-smoking throughout and is located 30 miles from Mount Amiata. At the hotel, every room includes a closet. Complete with a private bathroom equipped with a bidet and free toiletries, guest rooms at Delcorto Suites have a flat-screen TV and air conditioning, and some rooms are equipped with a terrace. At the accommodation each room is equipped with bed linen and towels. Breakfast is available daily, and includes buffet, à la carte and continental options. At Delcorto Suites you'll find a restaurant serving Italian and Local cuisine. Vegetarian and vegan options can also be requested. Montepulciano Terme is 3.5 miles from the hotel, while Bagno Vignoni is 13 miles away. The nearest airport is Perugia San Francesco d'Assisi Airport, 47 miles from Delcorto Suites.

- "Spacious, quiet rooms right in the centre of town. Helpful staff provided guidance for nearby public parking. Simple but delicious breakfast in the central dining room." - "1- Easy check-in procedure and communication with the facility 2- Excellent welcome directly from the owners of the facility with helpful tips for the stay 3- Historical building masterfully renovated 4- Very spacious room with modern facilities 5- Beautiful and modern bathroom (we were in the "Flora" suite) 6- Room temperature quickly adjustable despite the size of the room 7- Excellent breakfast with some dishes prepared on the spot 8- Kindness of the staff"

Located in Castelmuzio, 13 miles from Bagno Vignoni, La Moscadella has accommodations with a garden, free private parking, a terrace and a restaurant. Among the facilities at this property are a shared kitchen and room service, along with free WiFi throughout the property. The property provides a concierge service, and luggage storage for guests. Rooms have an electric tea pot and a private bathroom with a shower and free toiletries, while certain rooms come with a kitchen equipped with a fridge. The rooms at the hotel have air conditioning and a safety deposit box. The area is popular for cycling, and bike rental is available at La Moscadella. Montepulciano Terme is 15 miles from the accommodation, while Bagni San Filippo is 22 miles from the property.

- "Great service, beautifully decorated rooms, lots of attention to details, good breakfast" - "Location of the property is in a Tuscan version of heaven, magnificent and large rooms and the design is pure genius. Incredible food, courteous staff and overall a magical and romantic experience. Would come again and again." - "We loved everything about La Moscadella - the facility, the room, the food, the staff, the location and even the guests that we met while staying there! Isabella is a fabulous host, and Caterina was tremendously helpful when planning our days and visits to sites and villages in Tuscany. If (or when) we go back, we will definitely stay at La Moscadella again or one of Isabella’s other villas."

Located in Montepulciano, 7.9 miles from Montepulciano Terme, Borgo San Vincenzo provides accommodations with free bikes, free private parking, an outdoor swimming pool and a garden. Among the facilities of this property are a restaurant, a shared lounge and a 24-hour front desk, along with free WiFi throughout the property. Guests can use a bar. All guest rooms features air conditioning, a fridge, a minibar, a coffee machine, a bidet, free toiletries and a closet. The hotel has some units that feature a terrace, and every room includes a private bathroom with a shower and a hairdryer. At Borgo San Vincenzo rooms come with bed linen and towels. A buffet, continental or Italian breakfast is available every morning at the property. The area is popular for hiking and cycling, and car rental is available at this 4-star hotel. Bagno Vignoni is 17 miles from the accommodation, while Bagni San Filippo is 22 miles away. The nearest airport is Perugia San Francesco d'Assisi Airport, 43 miles from Borgo San Vincenzo.

- "This property is perfection. It is more beautiful than any of the pictures. The staff are incredible and so helpful, the food is delicious, and it's located near so many towns to explore in Tuscany. Do yourself a favor and book it." - "Everything about this hotel is really good, super helpful and friendly owners on site ever day, excellent staff, great pool and perfect weather 😄😄" - "Everything!" - "Absolutely everything! The location the cleanliness, the spacious rooms, the pool, the food and drinks, the friendliness of the owner and the stuff...I have probably forgotten to mention something, but Literally Everything was Pure Pleasure!"

Located 1969 feet from Lake Trasimeno, Antico Casale Tiravento offers a 1-hectare garden with BBQ facilities and sun loungers as well as free Wi-Fi. Its air-conditioned apartments have views of the lake and a patio, or balcony or terrace, some feature a spa tub. The elegant-style apartments feature a fully-equipped kitchenette with dishwasher, a private entrance and a satellite TV. Each has a patio and free access to a laundry area with washing machine, clothes dryer and ironing board. Some have a hot tub. A heated jacuzzi with a wonderful view of the lake and islands, is available in the garden, free of charge for our guests. During the summer months, guests can relax in the garden with lake views. Passignano sul Trasimeno Train Station is 0.6 mi from the Tiravento. Cortona is 12 mi away.

- "Ideal location on the edge of town with the supermarket a short walk away. The apartments were very clean with a bathroom and kitchen in each, plenty of space for our group of 11. Antonella was fantastic making multiple trips to the station to collect our group and arranging transport to and from the wedding we were attending. Everyone said how they would love to have stayed for longer!" - "Everything was perfect. The house is beautiful, the view fenominal and Antonella's hospitality outstanding !!!"

Located in Pienza, 20 miles from Mount Amiata, Podere Gonzaga provides accommodations with a garden, free private parking and a terrace. Located around 7.9 miles from Bagno Vignoni, the hotel with free WiFi is also 8.2 miles away from Bagni San Filippo. The property has evening entertainment and a concierge service. The hotel will provide guests with air-conditioned rooms offering a closet, an electric tea pot, a minibar, a safety deposit box, a flat-screen TV and a private bathroom with a bidet. Selected rooms here will provide you with a kitchenette with a fridge, a microwave and a stovetop. At Podere Gonzaga all rooms come with bed linen and towels. Montepulciano Terme is 10 miles from the accommodation.

- "Beautiful property, very well presented room. Charming with lots of character. Room was very spacious and modern and well presented with everything needed. The hosts are very warm and welcoming. Was great chatting to learn more about their background and the area. The breakfast was delicious and included lots of local produce such as the cheese the area is famous for. I wouldn’t hesitate to recommend Podere Gonzaga. 5*" - "The best Host!Very polite and helpful! The room was very spacious with amazing decoration to the detail. It was even better in person than the photos. Also very good location near to all the beautiful villages and of course the landscapes of Val D’Orcia."

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 oversize 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 2.5 mi 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. Unspoiled 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.

- "We recently stayed at a charming castle run by its dedicated owners, and our experience was nothing short of extraordinary. From the moment we arrived, the owners and their exceptional staff went above and beyond to ensure our stay was memorable. The historic ambiance of the castle, combined with modern comforts, made for a unique and luxurious experience. One highlight was the hosted four-course dinner, which was absolutely awesome. The owner, who had the best wine recommendations, even took us to the cellar to personally pick our wine. The attention to detail, warm hospitality, and personalized service made us feel like royalty. If you're looking for a truly special getaway, we highly recommend booking a stay at this enchanting castle."

Set at an altitude of 1542 ft, Agriturismo Cerreto offers 360° views of the Val d'Orcia and Mount Amiata. This 15th-century farmhouse offers cozy accommodations with fireplaces, 2.5 miles 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 cake, 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, guests will find a swimming pool with natural spring water, a BBQ area and children's games such as ping-pong and soccer. Bikes are available to rent and free parking is available.

- "Love the location, the facilities, and Monica was a great host. We thoroughly enjoyed our stay." - "We were weary travelers upon arriving and were treated extremely well by Monica. She made sure we had everything we needed and more. The property is gorgeous and relaxing. Close to many places but quiet and remote. The breakfast baskets were beyond generous and kept us fed for breakfast, lunch and snacks. I recommend the Pientino Toscana!" - "Excellent location close to Pienza. Spacious room with nice amenities. Beautiful property"

Featuring a garden and free WiFi in all areas, Castello di Spedaletto da Laura offers air-conditioned rooms in a peaceful area in Pienza. Olive oil, wine, pasta and legumes are produced at the on-site mill. All the rooms are located in the former grain store just outside the castle's walls, and come with a fan and a TV. The private bathroom is complete with a shower and free toiletries. A sweet and savory breakfast is offered daily. It includes hot drinks, pastries, cold meats and homemade products. Castello di Spedaletto da Laura is a 20-minute drive from Montepulciano, famous for its red wine. Lucciolabella Natural Reserve is 3.4 mi away.

- "Breakfast was excellent. Especially Italian salumi was excellent. Access to Pienza, Montalcino and Montepulciano was perfect." - "Everything. Laura is a nice and warm host, she offered us the unforgettable experience." - "Staff were friendly, setting was beautiful, food was delicious." - "The place was worth the money in every way. Very nice rooms, everything was incredibly clean, great breakfast, sweet staff (Elena) and a charming host. And then the surroundings were fantastic."

Villa Vignacce - Boutique Country Resort enjoys a location in Bettolle, 25 miles from Piazza Grande and 13 miles from Montepulciano Terme. This country house features free private parking and bicycle parking. The country house provides inner courtyard views and a picnic area. At the country house, some units have a private entrance, dining area, fireplace, and dishwasher. Rooms have a kettle, a private bathroom, and free Wifi, while some rooms also boast a terrace and some have mountain views. In some units there's a dressing room for guests to change in. Italian and vegetarian breakfast options are available each morning at the country house. You can play table tennis at Villa Vignacce - Boutique Country Resort, and the area is popular for walking tours. Guests can swim in the pool with a view, go cycling or hiking, relax in the garden, and use the barbecue facilities. Bagno Vignoni is 22 miles from the accommodation, while Bagni San Filippo is 30 miles from the property. The nearest airport is Perugia San Francesco d'Assisi Airport, 42 miles from Villa Vignacce - Boutique Country Resort.

- "Everything was just wonderful. The location, beautiful gardens, decor in the rooms, warm and friendly welcome from Anna Licia the host of the Villa. Kitchen was fully equipped, which was convenient to prepare all our meals. Bedrooms were spacious and had beautiful view over the gardens. We could chill out in the gardens or by the pool." - "Amazing hosts - Anna was spectacular and catered to every request. It was a lovely, spacious and homely resort. It had all the facilities that a family would require. Super central to all the major Tuscan towns. Great pool, BBQ facilities and a lovely grassed, contained courtyard (especially with roaming children) to spend the evenings were stand outs."