
Welcome to Pieve Aldina Relais & Châteaux, a lovely retreat nestled in the beautiful town of Radda in Chianti. Just 21 kilometers from Piazza Matteotti, we offer a warm and welcoming place to stay. Enjoy our seasonal outdoor swimming pool, relax in our spacious garden, and connect with others in our shared lounge. Plus, you can rest easy knowing that free private parking is available for your convenience. We’re here to make your experience enjoyable and memorable!
Exceptional
147 reviews

Welcome to La Pieve Marsina Country Retreat, nestled in the beautiful Chianti region of Siena. Here, we invite you to experience a blend of tradition, relaxation, and delicious local flavors. Our retreat is set in a charming medieval village, thoughtfully renovated to preserve its history while providing modern comforts. Whether you’re looking to unwind in nature, explore local culture, or enjoy authentic cuisine, we strive to create a welcoming space for everyone. We can't wait to share this special place with you!
Exceptional
290 reviews

Nestled in the beautiful Tuscan countryside, Castello di Casole, A Belmond Hotel, Tuscany is a welcoming retreat that offers something for everyone. Enjoy refreshing dips in the outdoor pool, indulge in relaxing treatments at the spa, or keep active in the fitness center. With two delightful restaurants on-site, you can savor delicious meals made with local ingredients. This charming former castle has been transformed into elegant rooms and suites, ensuring a comfortable stay for all guests. Whether you're looking for adventure or relaxation, you'll find it here amidst stunning landscapes and warm hospitality.
Exceptional
91 reviews

Hotel Le Fontanelle is a welcoming 5-star hotel nestled in the beautiful Chianti Classico region, conveniently located between Siena and Florence. Here, you can enjoy breathtaking views and stunning landscapes that offer a perfect backdrop for a memorable getaway. Our goal is to create a relaxing and enjoyable experience for all our guests, where everyone feels at home amidst the beauty of Italy.
Exceptional
157 reviews

Borgo San Felice is a welcoming hotel in Castelnuovo Berardenga, nestled in the beautiful Chianti wine region. Here, you can enjoy comfortable and spacious rooms decorated with charming antique furniture. The hotel features a lovely swimming pool, perfect for relaxation, and breathtaking views of the stunning countryside. We strive to create a warm and inviting atmosphere for all our guests, ensuring that everyone feels at home during their stay.
Exceptional
28 reviews

Welcome to Villa Le Calvane, a beautiful retreat nestled in the hills of Montespertoli, where you can enjoy breathtaking views of the Chianti region. Here, you can relax in our seasonal infinity pool or unwind in the hot tub. We take pride in producing our own olive oil and wine right here on the property, offering you a taste of local flavors. Plus, we provide free private parking for your convenience. We hope you find comfort and joy during your stay with us!
Exceptional
131 reviews

Nestled in the heart of beautiful vineyards, Locanda Le Piazze is a charming boutique hotel that was once a 16th-century farmhouse. Just 6 km from Castellina in Chianti, this cozy retreat offers a peaceful escape on a hillside, conveniently located between the vibrant cities of Florence and Siena. Whether you're looking to relax in nature, explore local culture, or enjoy fine dining, our welcoming atmosphere is designed to make you feel right at home. We invite you to experience the beauty and warmth of this unique destination!
Exceptional
274 reviews

Podere Terreno, located on Via della Volpaia in Radda in Chianti, offers a welcoming place to stay along with a beautiful garden for guests to enjoy. You’ll have access to a cozy shared lounge where you can relax and connect with others. Each room is designed with your comfort in mind and includes a wardrobe for your belongings. You’ll find private bathrooms for your convenience. We strive to make your experience as enjoyable and comfortable as possible. Come and unwind in our peaceful setting!
Exceptional
147 reviews

Villa Il Fedino is a beautiful place to stay, featuring comfortable and stylish suites in a charming 14th-century building. Here, you can relax by the outdoor swimming pool and enjoy the scenic views of the lush green park that surrounds the property, all set against the stunning backdrop of the famous Chianti hills. We invite you to experience a warm and welcoming atmosphere where your comfort and enjoyment are our top priorities.
Exceptional
516 reviews

In 1511, Niccolò Machiavelli, who had family land near Bibbione in a place called Sant’Andrea in Percussina, purchased a castle along with some farmland. He turned this space into a hunting lodge, where he could enjoy time in nature and share moments with friends and family. The story reflects how people in that time valued their connection to the land and the joy of gathering together.
Exceptional
426 reviews

Just a short distance from the charming town of Radda, you'll find Villa Campomaggio Resort & SPA, nestled among beautiful vineyards in the heart of Chianti. This historic villa, which dates back to 1776, offers a welcoming atmosphere where you can unwind and connect with nature. Enjoy relaxing by the inviting swimming pool or exploring the stunning surroundings. Whether you’re looking for a peaceful getaway or an adventure in the countryside, this resort is designed with your comfort and enjoyment in mind.
Exceptional
648 reviews

COMO Castello Del Nero is located in the beautiful Chianti wine area, nestled between Florence and Siena. This stunning 12th-century castle offers a relaxing COMO Shambhala retreat, complete with an inviting outdoor pool. For your convenience, there is free parking available on-site. We want to ensure that your stay is comfortable and enjoyable!
Exceptional
98 reviews

At Villa Lecchi Hotel Wellness, we strive to create a welcoming and relaxing experience for all our guests. Nestled in the beautiful greenery of Tuscany, our hotel features a stunning outdoor pool, a cozy restaurant, and a soothing spa where you can unwind and rejuvenate. We make it easy for you to stay connected with complimentary WiFi and provide hassle-free private parking for your convenience. Whether you're here for a peaceful retreat or an adventure, we’re committed to making your stay enjoyable and memorable.
Exceptional
254 reviews

Discover a special place that’s just a short walk from the charming village of Radda in Chianti. Enjoy stunning views of the beautiful Chianti countryside while experiencing a peaceful and relaxing atmosphere. It's the perfect spot to unwind without straying far from the heart of the village.
Exceptional
517 reviews

Albergo Palazzo Squarcialupi is a charming hotel located in the heart of Castellina in Chianti, housed in a historic building from the 15th century. Managed by its owner, this welcoming place offers a beautiful garden where you can relax and enjoy the sunshine, as well as an outdoor swimming pool for refreshing dips. For those looking to unwind, there’s also a spa available to help you relax and rejuvenate. Each room is thoughtfully designed to provide a comfortable stay, ensuring you feel right at home during your visit.
Exceptional
520 reviews

Welcome to this incredible historical site! Here, you'll find a post office that dates back to 1000 AD. Imagine horses arriving along the boulevard, where they would stop to rest in the central yard. They could even enjoy a refreshing drink from the trough nearby. This place not only tells a story of transportation and communication from the past but also invites you to step into history and appreciate what life was like back then. We hope you enjoy exploring this unique piece of our heritage!
Exceptional
210 reviews

Palazzo San Lorenzo is located in the charming medieval village of Colle di Val d'Elsa. Our hotel features comfortable rooms designed with a modern touch, equipped with amenities like a 32-inch LCD TV and a relaxing hydro-massage bath or shower. We also provide spacious accommodations that include complimentary Wi-Fi, ensuring you stay connected during your visit. We welcome everyone and strive to make your stay enjoyable and memorable!
Exceptional
1929 reviews

Borgo Scopeto is a charming Tuscan estate that offers stunning views of the beautiful city of Siena, just a short drive away. This lovely property has been thoughtfully restored to reflect its rich history while providing modern comforts. Whether you're looking for a peaceful retreat or a base to explore the surrounding area, Borgo Scopeto welcomes everyone with open arms and a warm atmosphere.
Exceptional
389 reviews

Welcome to our beautifully restored building! We’ve worked hard to preserve the elegant charm of the Renaissance while ensuring you have all the modern comforts you need for a relaxing stay. Enjoy convenient amenities like electronic key access, TV, and Wi-Fi. You can also take advantage of our lovely swimming pool, soothing jacuzzi, restaurant, and spa area. We’re here to make your experience enjoyable and memorable!
Exceptional
2327 reviews

Spaltenna is a charming little village with a rich history. At its heart, you'll find a beautiful church with a bell tower that dates back to the year 1000, along with an impressive castle nearby. The village also has a small collection of cozy homes, all showcasing stunning medieval architecture. It's a wonderful place for anyone who appreciates history and beauty in their surroundings.
Exceptional
130 reviews

The RossHotels Group includes four welcoming hotels. Palazzo Leopoldo and Palazzo San Niccolò are situated in the charming historic area of Radda in Chianti, where you can explore beautiful streets and local culture. L’Ultimo Mulino, on the other hand, is nestled in the peaceful countryside, offering a serene escape surrounded by nature. We strive to provide a comfortable and enjoyable experience for all our guests, making every stay memorable.
Exceptional
1051 reviews

Nestled in the charming town of Gaiole in Chianti, often praised as one of the best places to live by Forbes magazine, Ultimo Mulino truly embodies this beautiful reputation. Housed in a lovingly restored old mill, it features original stonework that adds to its unique character. Here, we invite you to experience a warm and welcoming environment, where comfort and community come together.
Exceptional
864 reviews

At RossHotels Group, we are proud to welcome you to our four unique hotels. Palazzo Leopoldo and Palazzo San Niccolò are nestled in the charming historical center of Radda in Chianti, where you can immerse yourself in the rich culture and history of the area. For those seeking a peaceful countryside escape, L’Ultimo Mulino offers a serene retreat surrounded by nature. We’re dedicated to providing a warm and inviting experience for everyone who stays with us, ensuring that your needs are met and your visit is memorable.
Exceptional
953 reviews

Welcome to Castel Monastero, a charming retreat nestled in a beautifully restored medieval village dating back to the 10th century. Here, you can enjoy stunning views of the Tuscan landscape, relax by our inviting pool, and rejuvenate at our wellness center. We offer two delightful restaurants where you can savor delicious meals made from fresh, local ingredients. Each of our comfortable rooms provides free amenities to ensure your stay is enjoyable and stress-free. We invite you to experience the warmth and beauty of this unique destination.
Exceptional
146 reviews






Note: The prices for each boutique hotels 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.
Luxury Vineyards: When you indulge in a luxury or boutique stay in Chianti, Italy, you'll be perfectly situated to explore the region's enchanting vineyards that offer tastings of some of the finest wines in the world.
Castello di Brolio: This historic castle, surrounded by stunning gardens and scenic views, allows you to delve into the rich heritage of Chianti while learning about its celebrated wine production.
Greve in Chianti: Known as the gateway to Chianti, Greve is a charming town where you can wander through its picturesque squares, vibrant markets, and enjoy delectable local cuisine and wines.
San Polo in Chianti: Nestled in the heart of the countryside, this quaint village invites you to experience authentic Tuscan life with its rustic charm and breathtaking landscapes ideal for leisurely strolls.
Chianti Sculpture Park: An artistic oasis in the countryside, this unique park showcases contemporary sculptures amidst nature, making it a perfect spot for art lovers seeking inspiration.
Badia a Passignano: Visit this beautiful abbey dating back to the 11th century, where you can marvel at its architecture and enjoy peaceful walks in the surrounding vineyards and olive groves.
Wine Tours: Embark on a guided wine tour that offers insider access to exclusive vineyards, where you can learn about winemaking processes and taste exquisite vintages right from the source.
Cooking Classes: Engage in delightful cooking classes where you’ll learn to prepare traditional Tuscan dishes using fresh, local ingredients, a perfect complement to your luxury or boutique stay in Chianti, Italy.
Popular boutique hotels in Chianti that have a pool include:
Transportation/Shuttle service is available at the following boutique hotels in Chianti:
A spa is available to guests at the following boutique hotels in Chianti:
Families traveling in Chianti enjoyed their stay at the following boutique hotels:
Some of the best boutique hotels in Chianti are: