
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. Castellina in Chianti is 2 km away. Accommodation at La Leccia comes with a unique design and handmade furniture. 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.
Exceptional
335 reviews

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.
Exceptional
274 reviews

Surrounded by vineyards, Belvedere Di San Leonino is located in Castellina in Chianti, in the heart of the Chianti area. Set in a historic country house from the 1400s, this property offers rooms decorated in a typical Tuscan style. The Belvedere features private gardens with free parking and a spacious outdoor swimming pool. The beautiful panoramic views include the vineyards, olive groves, the Elsa Valley, San Gimignano and Siena. Each room comes with terracotta flooring, high oak-beamed ceilings, antique furniture and wrought-iron beds. Il Cortile restaurant serves buffet breakfast, and Tuscan cuisine for dinner. In the evening, aperitif and drinks are served in the bar with lounge. During summer, dinner is serve in the garden. Guests can enjoy free wine tasting at a nearby shop. Florence is 45 km from Hotel Belvedere Di San Leonino, while Siena is a 20-minute drive away.
Exceptional
462 reviews

Located 5 km from Castellina In Chianti, Querceto Di Castellina is a 14th-century building and offers an outdoor pool, garden and accommodation with a patio. WiFi is free throughout, and there is also a terrace. Rustic-style apartments at the Querceto all come with a kitchenette, dining area and satellite flat-screen TV. The private bathroom includes a hairdryer and shower. Wine tasting sessions can be organised on site, as well as traditional cooking classes. Guests can enjoy typical Tuscan wine and snacks at the property's wine bar. The property provides free private parking, and is surrounded by olive groves and vineyards. Greve in Chianti is a 20-minute drive away.
Exceptional
209 reviews

Castello di Fonterutoli Wine Resort is a medieval country village in Tuscany's Chianti wine district 5 km outside Castellina in Chianti. It offers a restaurant and wine cellar to visit. The rooms are set in separate buildings located around the grounds. Each one features a private bathroom and elegant décor. You are invited for a guided tour of the wine cellar where you can buy wines from the shop. Breakfast at Castello di Fonterutoli Wine Resort is a buffet of pastries, hot dishes and cold cuts. The restaurant is open to the public and serves traditional Tuscan cuisine. Siena is a 20-minute drive away. Buses for Siena stop in Fonterutoli village centre, 200 metres away.
Exceptional
986 reviews

Managed directly by the owner, Albergo Palazzo Squarcialupi is a 15th-century building in Castellina in Chianti. It offers a garden with outdoor swimming pool, and a spa. Rooms are complete with seating area. The rooms of Palazzo Squarcialupi feature rustic terracotta floors, exposed wooden beams on the ceilings, and 18th-century furnishings. The bathrooms are in Carrara marble. Modern room facilities include air conditioning and a flat-screen TV. Free WiFi is available throughout. Breakfast is a sweet and savoury buffet, served in the breakfast room. During summer you can enjoy a drink on the terrace overlooking the pool and the Chianti Valley. The property is located in an area restricted to traffic. The bus to Siena stops 100 metres from the hotel. The nearest train station is Castellina Scalo, 6 km away.
Exceptional
520 reviews

With a pool, Villa Casalecchi is a 19th-century property 2.5 km from Castellina in Chianti. It features free Wi-Fi and a sun terrace overlooking the vineyards and olive groves. All accommodation at the Casalecchi is en suite. The Villa offers rooms with antique furnishings and a rustic décor. Each has a TV, and some are air conditioned. Breakfast is buffet style, with a combination of sweet and savoury items. Surrounded by a large terraced Italian garden, Villa Casalecchi also features a chapel with frescoes. Staff can help arranging tours to nearby attractions. In the heart of the Chianti area, the property is a 30-minute drive from Siena and 45 minutes from Florence. Riding stables are available nearby.
Exceptional
194 reviews

Borgo Vescine is located in the heart of Tuscany, right in the Chianti Classico area. The Relais has an extension of 100 acres and is 20 km from Siena and 42 km from Florence. Today, Borgo Vescine stands as a luxurious Relais, meticulously preserving the original charm of a medieval village and is surrounded by vineyards and olive trees. Guests have the opportunity to partake in a variety of authentic experiences, including exclusive wine tastings, hands-on cooking classes, exhilarating truffle hunts, scenic Vespa tours, and delightful al fresco dinners. Dinners are hosted among the olive trees or in the central square with the purpose of recreating the ancient time at the Borgo. This enchanting retreat offers: a wine room dated 1061 a.C., a heated outdoor swimming pool with stunning panoramic vistas, two distinctive bars and restaurants and a complimentary parking. Enjoy refined dishes on the open-air Terrace restaurant overlooking the Tuscan hills or experience nature firsthand at the Eco-Nature Bistrot. You will have the opportunity to sip drinks and cocktails in both the Borgo Vescine’s bars. The 28 rooms are all luxurious and decorated in classic tuscan dècor, some accommodations include a private balcony with views of the rolling hills, the forests, or the Borgo itself. Additionally, they are equipped with flat-screen TVs, free WiFi, and cozy bathrooms. Surrounded by lush gardens and verdant vegetation, Borgo Vescine also boasts its own vegetable garden, saffron fields, and lavender cultivation, adding to the allure of this idyllic retreat.
Exceptional
333 reviews

<h2>Elegant Accommodation</h2> Villa Rosa Panzano in Panzano offers a country house with a swimming pool boasting stunning views, a sun terrace, and a lush garden. Guests enjoy free WiFi in public areas, ensuring connectivity during their stay. <h2>Comfortable Amenities</h2> The property features private check-in and check-out services, a paid shuttle, a lounge, and a concierge. Additional facilities include a coffee shop, outdoor seating area, family rooms, bicycle parking, and breakfast in the room. <h2>Dining Experience</h2> A continental and Italian breakfast is served daily, including juice, fresh pastries, cheese, and fruits. The on-site restaurant caters to special diets, providing diverse dining options for all guests. <h2>Local Attractions</h2> Located 11 km from Piazza Matteotti and 48 km from Florence Airport, Villa Rosa Panzano is close to attractions such as Piazza del Campo and the Uffizi Gallery. Guests can enjoy cycling activities and relax in the serene surroundings.
Exceptional
93 reviews

Just outside the town of Radda, Villa Campomaggio Resort & SPA is surrounded by vineyards in the heart of the Chianti wine area. Dating back to 1776, the villa's grounds include a swimming pool and spa. This historic villa offers elegant rooms and apartments, all decorated with the same care and attention to detail. They feature wooden or terracotta floors and wood-beamed or arched ceilings. All include an LCD TV and minibar. Guests are served a buffet breakfast in the courtyard, where they can enjoy the tranquility of the garden. The wellness area includes a hot tub, Turkish bath, sauna and relaxation area. You can treat yourself to a massage or beauty treatment. Free parking is provided and the centre of Radda in Chianti is 5 minutes away by car.
Exceptional
648 reviews

Located in the small square of Panzano, and boasting panoramic views over the Chianti hills, La Pensione di Vignamaggio is surrounded by vineyards and olive groves. Public parking is available nearby. Featuring a stylish décor inspired by Decameron tales, the rooms come with exposed wood-beamed ceilings, terracotta floors, and a private bathroom. Some rooms also offer views of countryside. Vignamaggio is 8 km form the property, while Florence Peretola Airport is a 50-minute drive away.
Exceptional
365 reviews

<h2>Historic Charm</h2> Villa La Petraia in Panzano is housed in a historic building, offering a unique setting with a swimming pool, sun terrace, and lush garden. Guests enjoy free WiFi, a bar, and an outdoor seating area. <h2>Comfortable Accommodations</h2> Rooms feature air-conditioning, private bathrooms, and modern amenities such as flat-screen TVs and minibars. Family rooms and private check-in services ensure a comfortable stay. <h2>Delicious Breakfast</h2> A variety of breakfast options are available, including American, buffet, and gluten-free. Guests can savour local specialities, fresh pastries, and a selection of warm dishes. <h2>Convenient Location</h2> Located 43 km from Florence Airport, Villa La Petraia is near attractions like Piazza Matteotti (8 km) and Pitti Palace (37 km). Guests appreciate the scenic views and the attentive host.
Exceptional
89 reviews

Relais Vignale is a charming historic 18th-century villa located in the heart of the Chianti Classico area, with panoramic views across the Tuscan countryside and Chianti vineyards. The outdoor swimming pool is set in a floral garden, and the restaurant features a terrace. The centre of Radda is 2 minutes' walk away. The building was renovated according to the original architecture, and offers the standards of a 4-star hotel. Rooms are elegant, each is individually designed, and comes with air conditioning, heating and satellite TV. All rooms feature a minibar, while suites have a balcony or a terrace overlooking the surrounding hills. Some rooms are in the annex building. The Vignale includes a collection of antique furniture, frescoed ceilings, and grand fireplaces. There is also a TV room, lounge bar, and library. WiFi is available and there is a free internet point in the lobby. Breakfast is buffet style. The restaurant is open to the public and specialises in grilled meat and traditional Tuscan dishes, accompanied by fine local wines. A wellness centre with Turkish bath, hot tub and a relaxation area is at guests’ disposal with an extra cost. Massage treatments can also be arranged at an extra cost. The property offers free parking and is 1 hour's drive from both Florence and Siena. Volterra and Arezzo are both 58 km from the property.
Exceptional
517 reviews

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.
Exceptional
601 reviews

<h2>Elegant Accommodations</h2> Agriturismo Borgo Il Bonagino in Radda in Chianti offers family rooms with private bathrooms, balconies, and garden or mountain views. Each room includes air-conditioning, a kitchenette, and a terrace. <h2>Exceptional Facilities</h2> Guests enjoy a swimming pool with a view, sun terrace, and lush garden. Free WiFi is available throughout the property. Additional amenities include an indoor and outdoor play area, coffee shop, and barbecue facilities. <h2>Convenient Location</h2> Located 56 km from Florence Airport, the farm stay is near attractions such as Piazza Matteotti (19 km) and the Uffizi Gallery (47 km). Free on-site private parking and bicycle parking enhance the stay. <h2>Guest Satisfaction</h2> Highly rated for its attentive staff and excellent service support, the property is praised for its swimming pool and convenient location.
Exceptional
61 reviews

Set in the picturesque town of Radda in Chianti, Palazzo San Niccolò is an elegant hotel offering free Wi-Fi, a large garden and interesting interiors with original frescoes and antique furniture. Rooms at San Niccolò are air conditioned and feature a satellite LCD TV and minibar. All rooms have either a hydromassage shower or bath. Your day at San Niccolò Palazzo begins with a large buffet breakfast featuring homemade pastries and a wide variety of food. Guests can relax out in the garden with tables and chairs and enjoy a drink from the bar. Staff can recommend the best local restaurants and provide useful tourist information. Rates include use of Palazzo Leopoldo's indoor heated pool and of L'Ultimo Mulino's outdoor pool. Set amongst green hills in the Tuscan countryside, the hotel is 40 minutes' drive from Siena.
Exceptional
953 reviews

<h2>Elegant Accommodation</h2> Pieve Aldina - Relais & Châteaux in Radda in Chianti offers a 5-star hotel experience with a spa and wellness centre, infinity swimming pool, sauna, sun terrace, and lush garden. Free WiFi is available throughout the property. <h2>Comfortable Amenities</h2> Guests enjoy air-conditioning, private bathrooms with free toiletries, minibars, and soundproofed rooms. Additional facilities include a lounge, public bath, beauty services, and yoga classes. <h2>Dining Options</h2> The restaurant serves Italian cuisine with vegetarian and vegan options, offering lunch, dinner, and cocktails. Breakfast includes continental, buffet, and vegetarian selections. <h2>Prime Location</h2> Located 58 km from Florence Airport, the hotel is near attractions such as Piazza Matteotti (21 km) and Uffizi Gallery (49 km). Free on-site private parking is available.
Exceptional
147 reviews






Note: The prices for each boutique hotels in Castellina In Chianti do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.
When you stay at a luxury or boutique stay in Castellina in Chianti, Italy, you’ll have easy access to some of the most enchanting attractions in the region.
Castellina in Chianti Village: Stroll through the charming streets of this historic village, where medieval architecture and vibrant local culture come together beautifully.
Chianti Classico Wine Route: Embark on a scenic drive through the rolling hills of Chianti, dotted with vineyards and wineries that invite you to taste world-renowned Italian wines.
Castello di Brolio: Discover this stunning castle and its surrounding gardens, offering breathtaking views of the Chianti landscape and a peek into the rich history of wine production.
San Salvatore Monastery: Visit this serene monastery nestled in the hills, where you can enjoy the peaceful ambiance and captivating panoramic vistas of the countryside.
Il Palazzino: Experience traditional Tuscan cuisine at this delightful restaurant, known for its warm atmosphere and locally-sourced ingredients that showcase regional flavors.
Chianti Sculpture Park: Wander through this unique outdoor gallery featuring contemporary sculptures set against the beautiful backdrop of nature, ideal for art lovers and families alike.
Greve in Chianti Market: Immerse yourself in local life by visiting this charming market, where you can sample fresh produce, artisanal goods, and exquisite wines from the area.
Biking Tours: Take part in guided biking tours through the picturesque countryside, providing an active way to explore the stunning landscapes and quaint villages around Castellina in Chianti.
Popular boutique hotels in Castellina in Chianti that have a pool include:
Transportation/Shuttle service is available at the following boutique hotels in Castellina in Chianti:
A spa is available to guests at the following boutique hotels in Castellina in Chianti:
Families traveling in Castellina in Chianti enjoyed their stay at the following boutique hotels:
These 3 star hotels received great reviews from other travelers:
Some of the best boutique hotels in Castellina in Chianti are: