We have created a list with cool, unusual and unique hotels in Tuscany, Italy. We have also included accommodation in farm stays, villas, historic buildings, "relais" (mansions), apartments, old "castellos", hamlets, residences, boutique hotels, country estates, monasteries, romantic hotels, wineries, ancient castles, "agriturismos" and manor houses. Hope you enjoy it. We think it might be the best of its kind around. Tip: Set your dates to see room prices!
A list by Ella Hofer & Maryna Kravets. Updated January 2024.
Farm Stay.Popular among women. 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
Lupaia is a luxurious resort in the heart of Tuscany. It has a beautiful outdoor pool with stunning countryside views and well-maintained gardens. The on-site restaurant serves delicious meals with an open kitchen concept.
Farm Stay.Unique. Great views. Immersed in the green of southern Tuscany's Maremma hills, Castello di Vicarello is a former castle transformed into a luxurious Mediterranean retreat. This pet-friendly property features free WiFi, a spa and a swimming pool surrounded by lush gardens. All the elegant suites and rooms at the Castello di Vicarello feature the highest standard of furniture and objects gathered through years of travelling. Each unit has an en-suite bathroom with a bathtub. A restaurant with outdoor seating is available at the property. The gourmet menus are based on local recipes, using the own Castle’s production and wines from the local vineyards. Guests can enjoy summer dinners under the stars, whilst the winter season offers warm meals by the fireplace. Cooking lessons and wine tasting are available on request. A sweet and savoury breakfast is served daily. Roses, jasmine and countless native flowers mix themselves with ancient lemon and olive trees in the castle's garden. Less than one hour's drive from the hotel guests can also enjoy 2 golf course facilities. Hunting excursions are possible during the season. The village of Paganico is 11 km away, whilst Grosseto's town centre is 36 km away. The picturesque coastal town of Castiglione della Pescaia is 57 km from the property. Siena is less than 1 hour away by car.Show full description
Farm Stay.Great value. Popular among women. 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 minibar. 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 3.5 km from Agriturismo Il Segreto di Pietrafitta, and Florence and Siena are accessible in 45 minutes. Chianti is a 20-minute drive away.Show full description
Il Segreto di Pietrafitta is a charming farmstay in San Gimignano. It provides comfortable rooms, a delightful restaurant, and a refreshing pool. What sets it apart is the breathtaking view of the town and countryside.
Boutique hotel.Delightful property. Superb interior design. The Badia di Pomaio is a restored 17th-century abbey with a hillside location, 5 km from Arezzo. An infinity pool is available here, as well as free WiFi. Air-conditioned rooms at the Badia di Pomaio feature wood-beamed ceilings and artisan furnishings made from iron, stone and wood. Traditional Tuscan cuisine is served at the Campo Badia restaurant with an outdoor dining area. Vegetables are produces on site. The property also has a wine cellar in a natural cave with a vaulted ceiling. Guests can relax out in the garden and enjoy the views over the Tuscan hills towards Arezzo.Show full description
Badia di Pomaio is a unique hotel nestled in the hills. Once an old abbey, it has been transformed into a modern boutique hotel. The beautifully designed rooms and well-maintained grounds provide a stunning view.
Bed and Breakfast.Highly elegant. Great interior design. Villa la Moresca Relais de Charme B&B Adults only B&B Adults only - B&B is located at the southern end of the fortified village of Montecatini Alto between Florence and Pisa, in a dominant position over much of Tuscany. The Borgo boasts some enchanting corners such as the Medieval Fortress, the ancient Clock Tower, the Museum of Santa Barbara and ‘La Piazzetta’ (the Montecatini living room) with some of the most renowned restaurants and cafes in the area. The Rooms and Suites of Villa la Moresca Relais de Charme B&B Adults only B&B Adults only - B&B, are all finely decorated and furnished with original antiques from the structure or from the most sophisticated Italian and French antiques markets. The Moresca Breakfast (included in the price) is an important moment, not only to start the day well, with energy and well-being, but also to be pampered by the delights of our cuisine and some products of our Region. They have the names of Italian composers: Verdi, Bellini, Puccini, Rossini and each has its own soul and taste that differentiates it from the others for style, originality and refinement. All rooms have a bathroom (the Verdi with an exclusive whirlpool tub) and air conditioning. Depending on the season in which you are as our guest, it can be served in the frescoed dining room overlooking the valley, or in the garden between the cool and the scent of flowers and the singing of birds.Show full description
Villa La Moresca Relais de Charme B&B Adults Only is a unique and exclusive accommodation. It has a lovely interior design and is located in a fortified village. The hosts, Luca and Andrea, prepare delicious Italian meals.
Farm Stay.Great location. Castello La Leccia is a restored mediaeval hamlet, featuring an 11th-century castle, an outdoor swimming pool, and free Wi-Fi. The property is set on a hill, and offers a terrace with views of the Tuscan countryside. Accommodation at La Leccia comes with a unique design and handmade furniture. Castellina in Chianti is 2 km away. Some rooms boast original stuccoes and four-poster beds. The restaurant serves traditional dishes of Tuscany, along with great local wines. The breakfast buffet features both sweet and savoury items, including homemade cakes, Tuscan bread, fresh fruit, cheese and cold cuts. The property organises tastings of its own wine and olive oil. Castello La Leccia is at the end of an unpaved road off the SP51 road. Parking is free.Show full description
Apartment hotel.Charming. Castelletto di Montebenichi is a 12th-century castle with frescoed walls and a garden. Located halfway between Siena and Arezzo, its swimming pool offers panoramic views across the Chianti hills and vineyards. All apartments include satellite TV, air conditioning, and a fully equipped kitchen. Each room has a unique design and lots of space. Set in Montebenichi, a pretty hamlet, Castelletto is surrounded by medieval villages and wineries for wine tasting tours. Parking and WiFi are free at the Castelletto. You will also find a gym. Surrounded by a large private park, there are plenty of places where you can relax both indoors and outdoors.Show full description
This unique castle hotel, dating back to the 12th century, stands out with its antique art collections and beautiful surroundings of vineyards and olive groves. The refined rooms, outdoor pool, and gym with a hot tub provide a one-of-a-kind experience, combining historical architecture with modern amenities.
Luxury Hotel.Elegant. Set on a hilltop 10 km from Montalcino overlooking its own vineyards, Castello Banfi - Il Borgo offers elegant rooms. This hotel boasts an outdoor pool, gym and its own winery and cellar. The restaurant serves Tuscan cuisine and local wines. Guests will have discounts on wine at the Cantine Banfi wine cellar. Offering views of the Ombrone valley and the vineyards, each room comes with free Wi-Fi, a flat-screen TV with Sky channels, and a walk-in rainfall shower. Some rooms have a bath. Rooms are furnished with wood-beamed ceilings and Tuscan-style interiors. With stone arches and antique chandeliers, the restaurant provides local specialities at lunch and dinner. Breakfast is provided as a buffet. Siena is a 1-hour drive away and Montepulciano is 50 km from the Castello Banfi hotel.Show full description
Boutique hotel.Charming. Great value. Located in Cortona, 36 km from Piazza Grande, Borgo Solamore provides accommodation with a seasonal outdoor swimming pool, free private parking, a garden and a terrace. The air-conditioned rooms provide a garden view and come with a wardrobe and free WiFi. At the hotel, each room comes with a patio. Each room has a coffee machine and a private bathroom with a bidet and free toiletries, while selected rooms come with a kitchen equipped with a fridge. Guest rooms in Borgo Solamore are fitted with a flat-screen TV and a hairdryer. Guests at the accommodation can enjoy an Italian breakfast. Terme di Montepulciano is 42 km from Borgo Solamore, while Perugia Train Station is 49 km away. The nearest airport is Perugia San Francesco d'Assisi Airport, 60 km from the hotel.Show full description
I would describe this as the most relaxing and romantic boutique hotel in Tuscany.
Bed and Breakfast.Hip. Great views. Enjoy a majestic setting in the Tuscan countryside and relax within the walls of this ancient castle, just 2 km outside the historic walls of Siena. Castello delle Quattro Torra is a comfortable bed and breakfast. For more independence, book Quattro Torra’s charming apartment, located on the first floor. Start your day in the impressive breakfast room and enjoy the welcoming, family-run atmosphere and free breakfast. Admire the medieval courtyard. Furnishings include antique objects, exposed wood-beam ceilings, original stone walls and terracotta floors. Quattro Torra’s main living area is located on the third floor. Here you can choose to stay in the Tower Room, with its 360-degree view of the surrounding countryside, or the very spacious Blue Room, with a view of Siena. Here you will have a cosy kitchen, a comfortable living room, and a large double room. Friendly staff will assist you with booking tours and day trips to nearby sites. There are cosy lounges, relaxing gardens and children’s play areas. Enjoy free Wi-Fi. Take advantage of the large, free car park.Show full description
I rate this as one of the coolest bed and breakfasts in Tuscany.
Bed and Breakfast.Popular among couples. Set just 15 minutes drive from the seaside, peaceful Relais Sant'Elena is surrounded by beautiful Tuscan countryside. Relax and enjoy lovely views from this historic residence. Wine tastings, cooking classes and visits to the farm are also available. Take a walk around Relais Sant'Elena's simple gardens or sit by the outdoor swimming pool and enjoy both the views and the silence surrounding you. Add to the magic by enjoying an aperitif by the poolside or a holistic treatment. Free mountain bikes are also available. The establishment is comprised of 2 different buildings, the Manor House and the Foresteria. Inside both you will find elegantly decorated rooms, furnished with antiques. Breakfast is served in the winter garden or under the pretty, covered veranda and features typical Tuscan products. Guests can enjoy traditional Tuscan dishes prepared with local products and fine wines at the on-site restaurant. Relais Sant'Elena's location makes it easy for you to go on unforgettable trips to important Tuscan cities or nearby villages. You can even enjoy wine tasting in the famous Bolgheri vineyards, located just 10 minutes' drive away.Show full description
Relais Sant'Elena is a beautiful hotel in a peaceful countryside setting. It provides a farm stay experience with lovely gardens and a refreshing pool. The restaurant serves delicious meals made with local ingredients, and guests have the opportunity to take cooking lessons.
Farm Stay.Lively. Nice surroundings. Popular among couples. Agriturismo Humile has air-conditioned guest accommodation in Chianciano Terme, 46 km from Mount Amiata, 5.3 km from Terme di Montepulciano and 26 km from Bagno Vignoni. This farm stay features a pool with a view, a garden and free private parking. The farm stay provides garden views and a sun terrace. At the farm stay, units are equipped with a desk. All units come with a private bathroom, a safety deposit box and free WiFi, while selected rooms are fitted with a patio and some have pool views. At the farm stay, units include bed linen and towels. Buffet and continental breakfast options with warm dishes, local specialities and fresh pastries are available daily at the farm stay. Bagni San Filippo is 27 km from Agriturismo Humile. The nearest airport is Perugia San Francesco d'Assisi Airport, 81 km from the accommodation.Show full description
This farm stay is popular among couples travelling to Tuscany.
Bed and Breakfast.Very cosy. Lovely interior design. Offering a terrace and inner courtyard view, Dimora delle Muse is situated in Montalcino, 40 km from Mount Amiata and 28 km from Bagno Vignoni. Among the facilities at this property are a concierge service and a housekeeping service, along with free WiFi throughout the property. The bed and breakfast will provide guests with air-conditioned units with a desk, a safety deposit box, a flat-screen TV and a private bathroom with a bidet. Guests can have wine or champagne delivered to their room. At the bed and breakfast, every unit comes with bed linen and towels. Bagni San Filippo is 34 km from the bed and breakfast, while Terme di Montepulciano is 48 km from the property.Show full description
I think this place could be the most COSY bed and breakfast in Tuscany.
Resort.Creative. Nice surroundings. 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
This is likely the most CREATIVE resort in Tuscany.
Boutique hotel.Elegant. Lovely surroundings. Popular among couples. A former 16th-century farmhouse surrounded by vineyards, Locanda Le Piazze is now a small, luxurious, boutique hotel 6 km from Castellina in Chianti. Located on a hill, between Florence and Siena, it offers panoramic views of the countryside. The Locanda's extensive gardens feature an outdoor pool set in an olive grove. On site parking is free. The simple, individually decorated rooms come with air conditioning, and a flat-screen TV. The minibars are stocked with free mineral water, and the en suite bathrooms are complete with a hairdryer. The Tavola by Guido Haverkock restaurant offers a variation of traditional Tuscan cuisine, using organic local ingredients. A generous breakfast is served daily.Show full description
Locanda Le Piazze is a one-of-a-kind boutique hotel in a farmhouse dating back to the 16th century. Surrounded by vineyards, it has a peaceful environment. The hotel has a high-end restaurant and a lovely pool. Its historical allure, eco-friendly initiatives, and gourmet experience distinguish itself.
Farm Stay.Lively. Popular among couples. Set in the Chianti area, in the middle of the Tuscan countryside, Villa Di Capovento is an antique stone villa with outdoor pool. It is a 30-minute drive from Siena. All rooms at Capovento feature classic-style décor and antique Tuscan furniture. They all have free WiFi and a flat-screen TV with satellite and cable channel. Some rooms have a balcony. Capovento's restaurant and wine bar uses its own olive oil and serves traditional Tuscan specialities, along with famous wines from the Chianti area. Guests can rent bikes in the village and ride around the countryside, or just relax in the large garden with sun loungers. The Villa is a 10-minute drive from the town of Castellina in Chianti and 20 minutes by car from the Siena-Florence motorway.Show full description
Villa Di Capovento is housed in an ancient stone villa with a romantic atmosphere. Guests can relax by the outdoor swimming pool and enjoy the beautiful Tuscan countryside. The hotel also has free parking.
Boutique hotel.Lively. Great bar. Certosa Di Maggiano is a former monastery located in the Tuscan countryside, 2 km from Siena's famous Piazza del Campo. It offers unique rooms, free internet and free parking. Surrounded by olive groves and vineyards, the elegant indoor lounges with free internet point were designed by the famous architect Renzo Mongiardino. Built in 1314, Hotel Certosa di Maggiano features an outdoor swimming pool and a tennis court, all free of charge. Rooms are former monastic cells with a minibar. You can request a personal trainer and practise activities such as yoga, Pilates, Qi Gong and meditation. Breakfast is served in an historic kitchen and outdoors under the pergola.Show full description
This is likely one of the most LIVELY boutique hotels in Tuscany.
Farm Stay.Relaxing atmosphere. Great value. This charming country estate has been transformed into luxury accommodation with a swimming pool overlooking the breathtaking Tuscan countryside. It offers suites with patios. Your suite at Tenuta Pianirossi Relais is uniquely furnished with hand-crafted furniture and original features. Surrounded by vineyards and greenery, Tenuta Pianirossi Relais is a great place to sample Tuscan specialities and fine wines. Breakfast includes local products and staff arrange wine tasting sessions. The restaurant is open on request for dinner. Each suite has a lounge area with fridge and tea and coffee-making facilities, plus a private patio with a view of the countryside. A car is recommended for guests at Tenuta Pianirossi Relais. Located just outside Cinigiano, it is 40 minutes' drive from Grosseto. The hill town of Montalcino, famous for its Brunello di Montalcino wine, is 25 km away. Terme di Petriolo thermal spa is 30 km away.Show full description
This farm stay has great affordability and outstanding views.
Bed and Breakfast.Beautiful. Great location. Popular among women. Eat breakfast on the terrace at Campo Regio Relais while enjoying unforgettable views of Siena’s famous Torre del Mangia and Cathedral. Rooms are elegantly decorated with antique furniture. This luxury bed and breakfast provides quiet accommodation on one of Siena’s main streets, La Via della Sapienza, connecting Piazza del Campo to Siena's most important churches and museums. Residenza d’Epoca Campo Regio Relais’s friendly staff are sure to make you feel right at home in this historic building. Made up of just 6 rooms, the residence also contains a reception, an elegant drawing room perfect for reading and a bar with antique furniture. Rooms at Campo Regio are spacious and stylish and bathrooms are modern. Each one features free Wi-Fi and an LCD TV with satellite channels. Some rooms offer panoramic views and one has a four-poster bed and private terrace. Staff can book excursions or walking tours for you on request and will be on hand from 07:00 until 20:00 to help you. Wine tastings are also organized at the property.Show full description
Residenza d'Epoca Campo Regio Relais is a charming boutique hotel situated in the heart of Siena. It provides breathtaking views of the city and its cathedral from the balcony. The rooms are beautifully decorated and there is a comfortable communal lounge.
Apartment.Historic. Great location. Popular among women. Italian Maison de Charme in a former 15th century palace. The property will give you a taste of grand Italian life and will be an fantastic to experience Lucca and Tuscany. The Apartment includes three beautiful striking bedrooms with en-suite bathrooms. Our main living space surrounds our 18th century kitchen and leads to our idyllic private Terrace (covered by a Wisteria). This will become your peaceful Tuscan hideaway in a bustling modern Italian town. Steps to top-rated restaurants, bars, shopping districts and of course gelato. The space is made of an open living area leading to a hidden enchanting terrace.Show full description
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