We have created a list with cool, unusual and unique hotels in Chianti, Italy. We have also included accommodation in historic buildings, farm stays, villas, apartments, wineries, country estates, hamlets, country houses, manor houses, old "castellos", romantic hotels and boutique hotels. 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.Historic. Great views. Popular among couples. 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
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.Highly elegant. Great bar. 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.
Boutique hotel.Charming. Nice interior design. Offering an outdoor pool with views of the Tuscan hills, Villa Bordoni is located in Greve in Chianti. The property features free Wi-Fi, and an on-site restaurant with cooking lessons. The 16th-century ornate villa is surrounded by vineyards and olive groves. Guests can enjoy bike rentals as well as a free fitness centre. There is also abundant outdoor space with furniture for relaxing. The spacious air-conditioned rooms are equipped with an iPod docking centre and Flat-screen TV with a DVD player. The rooms also have a minibar and private bathroom with bathrobes and free toiletries. The buffet breakfast includes an array of items, such as fresh pastries, fruit, and hot drinks. The restaurant serves regional cuisine, and is open for lunch and dinner. It features hand-painted walls and an original fireplace and wood oven. Santa Croce is a 10 minute drive away, while Peretola Airport in Florence is 40 km from Bordoni.Show full description
Boutique hotel. COMO Castello Del Nero is set in the Chianti wine area, between Florence and Siena, and dates back to the 12th century. It features a COMO Shambhala retreat with outdoor pool and offers free parking. The uniquely designed rooms of Castello Del Nero come with original frescoes or beamed ceilings. Every part of the castle offers panoramic views across the Tuscan countryside, with vineyards and olive groves. All feature a plasma-screen TV, air conditioning, and a bathrobe and slippers. La Torre Restaurant, a Michelin-starred restaurant, is set in what was once the castle's stable. It has an à la carte menu accompanied by a selection of local wines. La Taverna Restaurant serves Tuscan specialities. Castello Del Nero offers a shuttle service to and from Florence and Sienna, which operates according to a schedule.Show full description
Boutique hotel.Cool. Set amongst the timeless landscape of Chianti, Villa Le Barone is an historic manor house property of the famous Della Robbia family since the 16th century. Thoroughly renovated, the hotel is now an inviting and intimate establishment yet maintaining the character of a private house. The hotel boasts a romantic atmosphere in all its common areas and a unique character in each of the individually decorated rooms. The swimming pool, tennis court and terraces are set amongst enchanting rose gardens, with views on the surrounding countryside, featuring olive groves and Chianti Classico vineyards. The restaurant is set in the old winery and it serves typical Tuscan food made with fresh, local and natural products.Show full description
Country House.Great value. Popular among women. Set in 600 hectares of beautiful Chianti countryside 20 minutes from Siena, Wine Resort Dievole offers different types of recently renovated apartment-suites and rooms in a large complex. Once home to Tuscan nobility, these 16th-century buildings overlook vineyards and olive groves, as do Wine Resort Dievole 2 lovely swimming pools. All rooms and suites have antique furnishings and some offer kitchen facilities as well as private gardens. Wine Resort Dievole is perfect for exploring Tuscany, whether by bike (itineraries, transfers, guides and maps can be provided) or car. Florence is just an hours drive away. In the evening relax back at home at Wine Resort Dievole. Of course, typical Tuscan cuisine is always available. Dishes are made with local, organic ingredients and some of the villas own produce is also served, including olive oil and wines.Show full description
Apartment.Charming. Superb interior design. Situated in San Gusmè, Borgo San Gusmè features accommodation with free WiFi and access to a garden with a terrace. The units come with tiled floors and feature a fully equipped kitchen with a fridge, a flat-screen TV with cable channels, and a private bathroom with bidet and free toiletries. There is a seating and/or dining area in some units. The property is 25 km from Siena and 70 km from Florence. The nearest airport is Florence Airport, 87 km away.Show full description
Based on my research this is one of the most charming, creative and cosy apartments in Chianti! WOW!
Boutique hotel.Beautiful. Great value. Popular among women. Offering a seasonal outdoor pool with panoramic views, Borgo Del Cabreo has a tranquil lcoation in the Tuscan countryside, 1 km from the town centre of Greve in Chianti. The property takes its name from the wine that is produced in the surrounding vineyards. Every room is fitted with a flat-screen TV with satellite channels. Certain units include a seating area for your convenience. You will find a kettle in the room. Every room includes a private bathroom equipped with a bidet. For your comfort, you will find free toiletries and a hairdryer. There is a shared lounge at the property, as well as free WiFi and free parking. The nearest airport is Florence Airport, 25 km from Borgo Del Cabreo.Show full description
Farm Stay.Lovely property. Great interior design. Popular among women. Featuring a garden and views of garden, Tenuta Cortedomina is a farm stay situated in a historic building in Radda in Chianti, 19 km from Piazza Matteotti. The air-conditioned accommodation is 34 km from Piazza del Campo. At the farm stay, the romantic restaurant is open for dinner and cocktails and serves Italian cuisine. Free private parking is available and the farm stay also offers bike hire for guests who want to explore the surrounding area. At the farm stay, units are fitted with a desk. The units have a coffee machine, a flat-screen TV, a safety deposit box and free WiFi, while selected rooms will provide you with a terrace and some have mountain views. The units feature a private bathroom, bathrobes and bed linen. You can play table tennis at Tenuta Cortedomina, and the area is popular for cycling. The farm stay has a picnic area where you can spend a day out in the open. The Mall Luxury Outlet is 38 km from the accommodation, while Piazzale Michelangelo is 46 km away. The nearest airport is Florence Airport, 56 km from Tenuta Cortedomina.Show full description
Farm Stay.Romantic. Great views. Popular among women. Surrounded by the vineyards of Chianti, this family-run organic farm produces wine and olive oil. It offers a saltwater outdoor pool, and spacious accommodation with parquet floors. The bright apartments offers a fully equipped kitchen with a microwave. Wi-Fi and parking are free. With views of the medieval town of Greve in Chianti, all suites have colourful décor and warm wooden furnishings. Tuscan cookery classes can be arranged on request at Podere Campriano Winery. Guests can try local wines and olive oil, and purchase the farm's own organic produce. Piazza Matteotti in the town's historic centre is a 5-minute walk away. Both Siena and Florence are around a 45-minute drive away.Show full description
Boutique hotel.Lively. Great bar. Borgo Vescine is located in the heart of the Chianti Classico's Gallo Nero area, famous for its wines, vineyards and wine cellars. The estate is 20 km from Siena and 42 from Florence. The 13th-century village of Vescine is today a country resort preserving the original structure of a mediaeval village, in perfect harmony with the surrounding countryside. The main features of this charming establishment include a wine shop and a heated outdoor swimming pool with panoramic views. The restaurant serves traditional Tuscan and Chianti cuisine, combined with fine wines from Chianti Area. Cooking courses and wine tasting sessions are available. The 21 rooms and 7 suites are all independent from each other, and are set within the original houses of the Medieval hamlet. With period furniture, the rooms offer views of the charming park surrounding Vescine. Free Wi-Fi is available in public areas.Show full description
Boutique hotel.Trendy. Great value. Borgo San Felice is located in Castelnuovo Berardenga in the heart of the Chianti wine district. It offers spacious rooms with antique furnishings, a swimming pool, and panoramic views. The hotel boasts 2 restaurants. Il Poggio Rosso restaurant offers gourmet cuisine and has a selection of over 500 fine wines. The more informal Osteria del Grigio offers modern Tuscan cuisine and is open for lunch and dinner. There is also a bar on site. In summer, guests can enjoy a drink or a snack by the heated outdoor pool. Bikes are available to rent and you will find a tennis court, gym and bowls court on site. The health centre offers a number of beauty treatments and specialises in wine therapy, massages and other beauty treatments. Rooms here come with air conditioning and satellite TV. Parking is free and free Wi-Fi throughout are available. Borgo San Felice is set on a hill amongst olive groves and vineyards. The local area is full of interesting churches and abbeys, and the town of Siena is just a 30-minute drive away.Show full description
Bed and Breakfast.Historic property. Great bar. Immersed in a 20-hectare park with olive trees and vineyards, Terre di Baccio is nestled on a hill in the Chianti area. It is a country house of the 16th century, located less than 1 km from Greve in Chianti. Rooms and apartments come with wood-beamed ceiling and include a satellite TV, an electric kettle, and a private bathroom. Walking and cycling trails along the hills of the Chianti region start right on the doorstep. The property offers a panoramic swimming pool. The property boasts a mix of antique Tuscan features and Guatemalan furnishings. Some units are air conditioned. A continental buffet breakfast is served to guests staying in the rooms and suites. The property produces oils and wines, which can be enjoyed in Terre di Baccio’s historic wine cellar. Bicycles can be rented at the Terre di Baccio. A public bus with links to Florence, 31 km from the property, stops 300 metres away. San Casciano In Val di Pesa can be reached in 30 minutes by car.Show full description
I think this place could be the most HISTORIC bed and breakfast in Chianti.
Farm Stay.Delightful property. Gorgeous surroundings. Set in the Chianti hills, Santa Maria a Poneta is 5 minutes' drive from the medieval village of Barberino di Val d’Elsa. This historic property is a working farm that produces olive oil and wine. Santa Maria a Poneta is an elegant manor house that features a chapel from the 9th century. Apartments are set on 2 floors and feature a 20 m² terrace with views of the garden. Its grounds include a swimming pool, open from May until September, sun loungers, parasols and a BBQ. Each one includes free Wi-Fi, satellite TV and a kitchenette with kettle and toaster. The manor house has been lovingly restored and original features such as terracotta floors and wood-beamed ceilings have been beautifully preserved. Homemade olive oil and wine are available to taste on site. Staff can reserve a table in the best local restaurants and arrange horse riding lessons, museum visits and much more. Free parking is provided and the pretty hill town of San Gimignano is 15 minutes' drive away. The nearest bus stop is 4 km away in Barberino di Val d’Elsa for buses to Siena and Florence.Show full description
Based on my research this is one of the most BEAUTIFUL farm stays in Chianti.
Country House.Hip. Great location. Located on a hillside and surrounded by vineyards and cypress trees, Capanelle Wine Resort is around 500mt from Gaiole in Chianti's town centre. It offers a panoramic outdoor swimming pool and free Wi-Fi throughout. Featuring a typical Tuscan style, the air-conditioned rooms come with terracotta floors, wood beamed ceilings and wooden furnishings. Each has a flat-screen TV and private bathroom equipped with free toiletries and a hairdryer. An Italian breakfast, with hot drinks, juice and pastries, is served daily. A tour of the winery, including wine tasting, is available on request. Siena is 30 km from Capanelle Wine Resort. Greve in Chianti is a 40-minute drive away.Show full description
Bed and Breakfast.Relaxing atmosphere. Nice surroundings. La Valletta Boutique Wine Estate has air-conditioned guest accommodation in Panzano, 10 km from Piazza Matteotti, 36 km from Pitti Palace and 37 km from Piazzale Michelangelo. This bed and breakfast features a pool with a view, a garden and free private parking. The property offers services including meeting and banquet facilities and walking tours. At the bed and breakfast, some units have a private entrance, dining area, fireplace and dishwasher. The units come with a coffee machine, a TV, a safety deposit box and free WiFi, while some rooms come with a terrace and some have garden views. The units feature a private bathroom, free toiletries and bed linen. Buffet and continental breakfast options with warm dishes, local specialities and fresh pastries are available every morning at the bed and breakfast. There is a coffee shop and lounge. Guests at La Valletta Boutique Wine Estate will be able to enjoy activities in and around Panzano, like cycling. The bed and breakfast has a picnic area where you can spend a day out in the open. Ponte Vecchio is 37 km from the accommodation, while Uffizi Gallery is 37 km away. The nearest airport is Florence Airport, 43 km from La Valletta Boutique Wine Estate.Show full description
Farm Stay.Very stylish. Lovely interior design. Boasting a seasonal outdoor swimming pool and views of garden, Rietine24 is a farm stay set in a historic building in Gaiole in Chianti, 28 km from Piazza del Campo. The property was built in 19th century and has air-conditioned accommodation with a patio. Featuring family rooms, this property also provides guests with an outdoor fireplace. At the farm stay, units come with a wardrobe. Featuring a private bathroom with a shower and a hair dryer, units at the farm stay also have free WiFi, while selected rooms also offer a terrace. At the farm stay, the units include bed linen and towels. Guests may wind down in the in-house lounge, while packed lunches are also available. Yoga classes and fitness classes are provided at the fitness room in house. Guests at the farm stay can enjoy cycling nearby, or make the most of the garden. Piazza Matteotti is 30 km from Rietine24, while The Mall Luxury Outlet is 41 km from the property. The nearest airport is Florence, 78 km from the accommodation, and the property offers a paid airport shuttle service.Show full description
Boutique hotel.Elegant. Great views. Hotel Le Fontanelle enjoys panoramic views from its exceptional location in the Chianti Hills, 20 minutes drive from Siena. Relax and enjoy wellness and sports facilities in this peaceful location. Hotel Le Fontanelle's pretty main building dates back to the 13th century, part of an old country estate. All rooms have beamed ceilings and terracotta floors. They overlook the surrounding vineyards, woods, and valley. Modern facilities such as LCD satellite television and internet access are also provided. Enjoy a refreshing swim and stunning views in Hotel Le Fontanelle's outdoor pool or borrow one of the hotel's bikes free of charge, and go exploring the countryside. Guests can visit Tuscany from Hotel Le Fontanelle as the resort is located in the Chianti Region which is famous for sightseeing. Indoors you can work out in the gym, go for a swim in the indoor pool with hydromassage area or really pamper yourself and go to the wellness area. Relax in the sauna or the Turkish bath, or request one of a range of beauty treatments or massages. Hotel Le Fontanelle's La Colonna restaurant has a panoramic terrace and serves traditional Italian cuisine with a creative twist. Florence is 80 km from Hotel Le Fontanelle, while Siena is 20 km from the property. The nearest airport is Florence, 90 km from the hotel, and the property offers an airport shuttle service on request with extra charge.Show full description
Boutique hotel.Lively. Great location. Villa Curina has a countryside location, close to the Chianti hilly area, and is set in a 16th-century hamlet. A garden surrounds the entire property, including its large outdoor pool and tennis court. Rooms at Villa Curina Resort are located in the 18th-century villa or in separate refurbished farmhouses. All are elegantly decorated with antique furnishings. Modern comforts include an LCD TV and free Wi-Fi. Il Convito di Curina restaurant serves traditional Tuscan dishes and gourmet recipes, accompanied by a wide range of fine, local wines and champagne. You can enjoy a candle-lit dinner on the panoramic terrace. Siena can be reached in 20 minutes by car.Show full description
This is one of the most LIVELY boutique hotels in Chianti. It also has a great location.
We do our best to keep this list as up-to-date as possible. We last updated it in January 2024. If you know of a unique hotel that should be on the list, let us know. Click here to contact us. Thanks!
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