Top Boutique Hotels in Siena Area (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."

Featuring garden views, Casanova di Campriano in Lupompesi features accommodations, an open-air bath, and a garden. This property offers a pool with a view and free private parking. Every room is equipped with a flat-screen TV with satellite channels. The air-conditioned units have a fully equipped kitchenette with dining area, a microwave, kettle, and a toaster. Every room comes with a coffee machine, a private bathroom, and free Wifi, while certain rooms are fitted with a terrace and some have mountain views. At the vacation home, every unit comes with bed linen and towels. Piazza del Campo is 15 miles from the vacation home, while Palazzo Chigi-Saracini is 13 miles from the property.

- "We had originally booked for 3 days and 2 nights, but upon arriving at the villa and seeing how perfectly maintained it was with its stunning view, we immediately asked if we could extend our stay for an additional night. Marco and Tania gave us a warm welcome and Tania connected with us daily to check in on how we were doing and to offer suggestions on places to visit, including an amazing restaurant. Tania treated us like family rather than just guests, and we highly recommend this villa."

This enchanting 15th century property, nestled in the rolling hills of Tuscany, offers an exceptional view of the surrounding countryside and San Gimignano. A free outdoor pool is available on site. The Tuscan-style rooms have handcrafted furniture and original features from the 16th century, such as wood-beamed ceilings and terracotta floors. Each includes a satellite flat-screen TV, air conditioning and a mini-bar. Each bathroom includes a spacious shower. A breakfast consisting of homemade cakes and local products is provided daily, served on the terrace during summer. The on site restaurant serves seasonal local dishes and homemade pasta, and should be reserved in advance. Light lunches are also available. Surrounded by lavender bushes and grape vines, the hotel’s location is not only picturesque, it is ideal for day-trips; San Gimignano is 2.2 mi from Agriturismo Il Segreto di Pietrafitta, and Florence and Siena are accessible in 45 minutes. Chianti is a 20-minute drive away.

- "Had a fantastic weekend. Everything was perfect, from the arrival to the dinner, breakfast and even a chilly swim the next day! Thank you Diego and Pedro for giving us a magical experience we will remember for a long time." - "Absolutely beautiful agriturismo situated in stunning gardens. Our room was really lovely with a comfortable bed, nice bathroom and plenty of room for suitcases. Our booking included half board which included a delicious buffet breakfast and three course dinner. The owners are very welcoming and the in-house chef is amazing. The location is only a few minutes drive to San Gimignano and 35 mins drive to Siena. We hired a car in Siena and did day trips each day. Stunning part of Tuscany."

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."

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."

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 3-star accommodations, Torre del Fuggisole is located in Siena, 0.7 mi from Piazza Matteotti and 2625 feet from San Cristoforo Church. The 3-star hotel has air-conditioned rooms with a private bathroom and free WiFi. The property is 1969 feet from Piazza del Campo, and within 1969 feet of the city center. At the hotel, each room comes with a wardrobe. Rooms are equipped with a flat-screen TV, and some rooms at Torre del Fuggisole have a city view. All rooms will provide guests with a fridge. Popular points of interest near the accommodations include Palazzo Chigi-Saracini, National Museum of Etruscan Archaeology and National Picture Gallery Siena. The nearest airport is Florence Airport, 47 mi from Torre del Fuggisole.

- "The hotel is new, clean and comfortable. The staff was really nice as well, we loved our stay there! The location is perfect to walk around Siena." - "The staff was wonderful; very friendly with great recommendations. The room was clean and comfortable." - "The hotel was very clean and fresh. The room was airy and bed was very comfortable. There was also many toiletries and complementary water bottles in the room. Staff was so helpful and wonderful."

Borgo Argiano in Castelnuovo Berardenga provides adults-only accommodations with pool with a view, a garden, and barbecue facilities. With pool views, this accommodation offers a balcony. The farm stay also features free Wifi, free private parking, and facilities for disabled guests. All units at the farm stay come with air conditioning, a flat-screen TV with streaming services, a kitchen, a dining area, a safety deposit box, and a private bathroom with a shower, slippers, and a hair dryer. A terrace with an outdoor dining area and mountain views is offered in all units. At the farm stay, every unit is fitted with bed linen and towels. There is a coffee shop and lounge. Guests can take advantage of yoga classes held in house. A bicycle rental service is available at the farm stay, while cycling and walking tours can be enjoyed nearby. Piazza del Campo is 8.3 miles from Borgo Argiano, while Piazza Matteotti is 26 miles from the property. The nearest airport is Florence Airport, 53 miles from the accommodation.

- "Everything was perfect - great hospitality, location, scenery, an unforgettable experience." - "An absolute dream in the hills of Tuscany. With views over Chianti, you can also see Siena Montalcino and Montepulciano. The setting is beyond stunning, quiet yet in the dynamics of a working vineyard. Fantastic pool area with the views and a heated pool when summer hasn’t kicked in yet. The room has been like home away from home, well equipped kitchen and beautiful outdoor seating to enjoy your breakfast or a candlelight dinner, drink in the evening watching the stars. They also have a social area which is full of books, entertainment and open fire and a bar. You simply can’t find a single here to not enjoy. Highly recommend! By far one of the best stays in Tuscany."

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!"

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."

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."

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"

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!"

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 center. Chianciano Terme Station is 23 mi from the San Bartolomeo Convento. The A1 Autostrada del Sole motorway is a one-hour drive away.

- "It was just great, al the members of the staff are kind and helpful, breakfast was also good and the place is charming. The owner showed and explained us the history of the convent for 1 hour aprox and it was amazing. They even gave us a sample of their local honey, there were so many details and it’s such a different experience that I would recommend it to everyone." - "Our stay at Convento San Bartolomeo was the highlight of our 6-day trip to Tuscany! Staying at this historic building is an experience of its own. We would like to take this opportunity and congratulate the owner and the employees of this hotel for doing such an amazing job. The restoration is spotless and made with respect to the building's identity but also with modern touches when necessary. You can tell that everything is done here with love and respect for the cultural history of the place. At the same time, the guests are welcome to enjoy every corner of the Convento. Last but not least, the service provided to the guests is exceptional! Delicious breakfast, dinner in the best room one can imagine, and a heated swimming pool and jacuzzi which was the cherry on top of an exceptional stay!"

With an outdoor pool, Podere Cunina is located in Buonconvento, 19 mi from Siena, surrounded by the Tuscan hills. Honey, saffron and olive oil are produced on site. Rooms come with air conditioning. The bathrooms feature free toiletries and a hairdryer. Arezzo is 30 mi from Podere Cunina, while Montalcino is a 30-minute drive from the property. The nearest airport is Florence Airport, 68 mi from the property.

- "Love everything, the property itself, the cleanliness, the amazing view, the hosts were very accommodating, very sweet and friendly couple." - "The property is beautiful and the room was spacious and clean. The host was wonderful. Great property!!!" - "Wonderful, serene and relaxing stay on a working farm. The apartment we stayed in was large, with a loft, with all the facilities of a typical home. As our host Silvana mentioned….one comes to the Tuscany to enjoy the country side, to slow down and relax. Podere Cunina was one of our favourite accommodations while travelling through the Tuscany. Every morning, we wake up to a misty country side view, and in the evening, we faced a picturesque sunset, something you won’t catch staying in the city. Restaurants are easy to find in the area, or you can plan to cook and enjoy a slow dinner in the apartment. Definitely a choice accommodation when we return to the Tuscany."

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!"

Villa Le Prata - Farm House & Winery - Adults Only 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 mini-bar. The property is in an area ideal for hiking, cycling, and wine/food-tasting tours. You can also visit the Sant'Antimo Abbey, located 8.1 mi away.

- "Amazing stay!" - "This villa is completely restored with 8 beautiful and spacious guest rooms. The room had shuttered windows overlooking the Tuscan countryside and includes a modern bathroom with large tiled shower. The property is gorgeous with a small wine vineyard and chestnut grove both of which guests are free to roam. The chef is excellent. We ate very good traditional Tuscan dinner there both evenings we stayed. The staff is great - - friendly and available when needed."