
Welcome to Lupaia, a beautiful inn located in the heart of Tuscany. Nestled between the charming towns of Montepulciano and Pienza, our inn offers stunning views of the rolling hills that make this region so special. Whether you’re seeking a romantic getaway or a peaceful retreat, Lupaia is designed to provide a warm and welcoming experience for everyone. We invite you to relax, unwind, and immerse yourself in the natural beauty and rich culture that Tuscany has to offer.
Exceptional
134 reviews

Welcome to Borgo San Vincenzo, located in the beautiful town of Montepulciano, just 13 km from Terme di Montepulciano. We’re excited to offer you a comfortable stay with a range of amenities designed to make your experience enjoyable and relaxing. Here, you can take advantage of our complimentary bikes to explore the stunning surroundings at your own pace. We also provide free private parking for your convenience. Take a dip in our outdoor swimming pool or unwind in our lovely garden—both are perfect spots to enjoy the fresh air and natural beauty. We look forward to welcoming you and ensuring you have a memorable visit!
Exceptional
163 reviews

Welcome to Vignacce, a place I’m proud to call home. I pay attention to all the little details because I want everyone who visits to experience the beauty and tranquility that this wonderful spot has to offer. We have a cozy space that comfortably accommodates up to 12 guests, ensuring an intimate and peaceful atmosphere for everyone. My goal is to create a warm and inviting environment where you can relax and enjoy your stay.
Exceptional
82 reviews

At Fonteliving, we believe in creating a welcoming and relaxing environment for everyone. Our beautifully designed apartments provide you with comfort and style, making it the perfect place to unwind. Enjoy our outdoor pool, which is nestled in the lush greenery of the Tuscan countryside—ideal for soaking up the sun or taking a refreshing dip. For those looking for a little extra relaxation, the popular thermal pools are just a short 700-meter walk away. Our spacious apartments are equipped with air conditioning to ensure your stay is as comfortable as possible. We’re here to help you create memorable experiences in a serene and friendly setting.
Exceptional
283 reviews

Welcome to our property, where your safety and comfort are our top priorities. We have a Special Protection Program in place, designed to ensure a secure environment for both our guests and staff. Nestled within the historic walls of medieval Cortona, our beautiful 18th-century space invites you to experience the charm and culture of this amazing town. We look forward to making your stay enjoyable and memorable!
Exceptional
333 reviews

Welcome to Agriturismo Merigge Wellness & Spa Montepulciano, a charming farm stay located in a beautifully restored historic building. Enjoy breathtaking views while relaxing by our infinity pool. Situated just 12 km from the serene Terme di Montepulciano, this is the perfect place to unwind and connect with nature. We invite you to experience the warmth of our hospitality and the tranquility of our surroundings. Your comfort and enjoyment are our top priorities!
Exceptional
240 reviews

Experience the charm of Tuscany at Villa San Sanino - Relais, a welcoming family-run getaway just 3 km from the heart of Torrita di Siena. Here, you can enjoy beautifully designed suites that come with your own private garden, perfect for relaxing in nature. Indulge in delicious meals at our traditional restaurant and take a dip in the refreshing saltwater infinity pool. We’re dedicated to making your stay comfortable and memorable, ensuring everyone feels at home.
Exceptional
13 reviews

Poggio Piglia is a charming destination located in the lovely hamlet of Macciano, nestled in the beautiful Tuscan countryside. Our property features spacious gardens where you can relax and unwind, complete with a swimming pool that provides stunning views of the surrounding valleys. Each room at Poggio Piglia is designed for your comfort, ensuring a welcoming and cozy atmosphere for all our guests. Whether you’re here for a peaceful retreat or to explore the rich culture of Tuscany, we are dedicated to making your stay enjoyable and memorable.
Exceptional
215 reviews

Welcome to Foresteria Il Giardino di Fontarronco, a beautiful retreat in Alberoro, just 15 km from Arezzo. Here, you can enjoy our refreshing outdoor pool, explore our spacious garden, and relax on the terrace. Our accommodations are designed for your comfort, featuring self-catering options and free WiFi to keep you connected during your stay. We invite you to experience a peaceful getaway where you can feel at home.
Exceptional
97 reviews

Welcome to Siena House, located in the beautiful village of Torrita di Siena, nestled in the stunning Tuscan countryside. Here, you'll find a lovely garden with a refreshing swimming pool, perfect for relaxing and enjoying the outdoors. Our spacious rooms are designed with your comfort in mind, offering elegant décor and breathtaking views of the surrounding hills. Whether you're here for a peaceful retreat or an adventure in Tuscany, we aim to make your stay enjoyable and memorable. We look forward to welcoming you!
Exceptional
10 reviews

The name Leopoldina honors Pietro Leopoldo d’Asburgo Lorena, the Grand Duke of Tuscany. He commissioned the construction of these unique homes in the valley during a project to reclaim and develop the Valdich area.
Exceptional
71 reviews

Welcome to La Fontaiola, a charming 18th-century country house nestled in the serene countryside of Umbria. Here, you can enjoy the beauty of nature while taking advantage of our complimentary bike rentals to explore the area at your own pace. Our expansive garden is perfect for relaxing or having a delightful barbecue with family and friends. Every morning, we serve a delicious Italian breakfast to help you start your day on a tasty note. We strive to create a warm and inviting atmosphere where everyone feels at home.
Exceptional
91 reviews

Welcome to our charming country house boutique hotel! We pride ourselves on providing a warm and welcoming atmosphere where every detail is thoughtfully considered. Our dedicated team is here to ensure your stay feels personal and special, offering hands-on support throughout your visit. Nestled in a beautiful location, our hotel serves as the perfect base for exploring the stunning hilltop villages and vibrant towns of Tuscany. Whether you're seeking adventure, relaxation, or cultural experiences, we're excited to help you create unforgettable memories during your stay. We can't wait to welcome you!
Exceptional
21 reviews

At I Grandi Di Toscana, we invite you to experience our wonderful wine tours and tastings. Our estate is dedicated to producing high-quality Chianti wines that we’re proud to share with you. In addition to our wines, enjoy a refreshing swim in our pool or a fun round of golf on our 2-hole course. We look forward to welcoming you and making your visit memorable!
Exceptional
201 reviews

Welcome to Villa Svetoni Wine Resort, located in the beautiful town of Montepulciano, just 13 km from the relaxing Terme di Montepulciano. Here, you can enjoy a comfortable stay with plenty of amenities designed for your enjoyment and relaxation. Take a dip in our seasonal outdoor swimming pool, unwind in our lovely garden, or maintain your fitness routine at our well-equipped fitness center. We also offer free private parking for your convenience. Our goal is to create a welcoming atmosphere where you can feel at home while exploring the stunning surroundings. We look forward to making your stay memorable!
Exceptional
410 reviews

Just a short 10-minute walk from the heart of Montepulciano, Il Rondò is here to provide you with a warm and welcoming experience. Our friendly staff is dedicated to offering personalized service to ensure your stay is enjoyable. You can relax at our bar or take advantage of our convenient free garage parking. Our comfortable rooms come with free WiFi, and many of them feature beautiful views of our lovely gardens. We invite everyone to come and enjoy the hospitality we have to offer!
Exceptional
672 reviews

Villa Cicolina offers a unique experience that goes beyond the standard luxury hotel. Set in a beautiful 16th-century villa, we aim to provide warm and welcoming hospitality that feels both elegant and familiar. Our goal is to help you fully enjoy your time in Tuscany, embracing all the wonderful aspects of this beautiful region. We strive to create a space where you feel at home while soaking in the rich culture and history around you.
Exceptional
421 reviews

Villa Schiatti is a welcoming retreat nestled in the beautiful area of Castiglion Fiorentino, just a short 10-minute drive from the charming town of Cortona. Here, you can enjoy the convenience of free parking and complimentary WiFi throughout your stay. The villa boasts stunning panoramic views, allowing you to immerse yourself in nature’s beauty. We offer a variety of comfortable rooms and apartments equipped with cable TV and private bathrooms, ensuring you have everything you need for a relaxing visit. Whether you're seeking a peaceful getaway or an adventure in the surrounding area, Villa Schiatti provides a cozy and inclusive environment for everyone to feel at home. We look forward to welcoming you!
Exceptional
748 reviews

Welcome to Locanda agli Amici! We’re delighted to invite you to enjoy our seasonal outdoor swimming pool, beautiful garden, and inviting shared lounge and terrace, all located in the charming town of Cortona. Our hotel is designed with your comfort in mind. We offer complimentary WiFi so you can stay connected during your visit. Our team is here to assist you with room service and concierge support, ensuring that your stay is as enjoyable and stress-free as possible. Whether you're relaxing by the pool, exploring the gardens, or unwinding in the lounge, we want you to feel at home. We look forward to welcoming you soon!
Exceptional
310 reviews

La Chiusa is a warm and inviting guest house located in the beautiful countryside of Montefollonico. Once an ancient oil mill, it features fifteen charming rooms and a delightful gourmet restaurant, where you can enjoy delicious meals made with local ingredients. Our goal is to create a cozy atmosphere where everyone feels welcome and at home. Whether you're looking to relax, explore the area, or indulge in great food, we’re here to make your stay memorable and enjoyable.
Exceptional
391 reviews

Nestled in the beautiful Tuscan countryside, just 3 kilometers from the charming town of Cortona, Agriturismo I Pagliai invites you to enjoy a relaxing getaway. Here, you can unwind by the outdoor pool during the warm summer months and stay connected with complimentary WiFi throughout your stay. This lovely estate, which dates back to the 15th century, also produces its own delicious olive oil, allowing you to savor the flavors of the region. We look forward to welcoming you to our peaceful retreat!
Exceptional
278 reviews

Welcome to Agriturismo Podere La Rocca, a charming retreat nestled in an 18th-century mansion. Here, you’ll find comfortable accommodations, each with its own bathroom, designed to make you feel right at home. We are located just 12 kilometers from the heart of Montepulciano, making it easy for you to explore the area. Enjoy complimentary Wi-Fi throughout your stay and relax in our beautiful garden. We can't wait to welcome you and help you create wonderful memories!
Exceptional
157 reviews

Casa M Tuscany is a welcoming retreat located just 46 kilometers from the beautiful Mount Amiata. Our accommodations are designed to make you feel right at home. Enjoy delicious meals in our restaurant, take a refreshing dip in the outdoor swimming pool, and relax in our cozy shared lounge or bar area. We provide free WiFi and private parking to ensure your stay is comfortable and convenient. Whether you’re here for adventure or relaxation, we’re here to support your needs and help create wonderful memories during your visit.
Exceptional
588 reviews

Welcome to Villa Borgo San Pietro! Nestled in a beautiful historic farmhouse surrounded by the lush green hills of Tuscany, just 4 km from the charming town of Cortona, our villa is a perfect getaway for everyone. Enjoy a refreshing dip in our outdoor pool or take advantage of the free WiFi available in public areas to stay connected. Plus, we offer free parking for your convenience. We look forward to welcoming you to our inviting space where you can relax, explore, and create wonderful memories with your loved ones.
Exceptional
643 reviews

Welcome to Monastero San Silvestro, a beautiful retreat with a rich history that dates back to the 14th century. Here, you can enjoy cozy self-catering apartments that reflect the charming Tuscan style, offering you a comfortable and inviting place to stay. Take advantage of our lovely outdoor saltwater pool, where you can relax and take in stunning views of the surrounding countryside. Whether you're looking for a peaceful getaway or an adventure-filled trip, we have something for everyone. We can't wait to welcome you!
Exceptional
331 reviews


Note: The prices for each boutique hotels in Val Di Chiana 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 or Boutique stay in Val di Chiana, Italy: When you choose a luxury or boutique stay in Val di Chiana, Italy, you'll be perfectly positioned to explore these stunning attractions that enhance your travel experience.
Cortona: This charming hilltop town is known for its medieval architecture, breathtaking views, and art galleries, making it a must-visit during your stay.
Lake Trasimeno: Enjoy a peaceful retreat at Lake Trasimeno, where you can partake in boat rides, cycling, or simply relaxing by the serene waters surrounded by lush landscapes.
Montepulciano: Famous for its Vino Nobile wine, Montepulciano offers wine tours and tastings while revealing stunning Renaissance architecture and picturesque streets.
Pienza: Recognized as a UNESCO World Heritage site, Pienza captivates visitors with its elegant squares, exquisite cheese shops, and beautiful surrounding countryside.
Castiglione del Lago: Explore the enchanting medieval castle and take a leisurely stroll along the shores of Lake Trasimeno in this delightful lakeside town.
Val d'Orcia: Known for its rolling hills and striking landscapes, you can take scenic drives or bike rides through Val d'Orcia to immerse yourself in the region's natural beauty.
Thermal Baths of San Casciano dei Bagni: Indulge in relaxation and rejuvenation at these luxurious thermal baths that promise soothing experiences amidst beautiful natural surroundings.
Local Cuisine Tours: Savor the flavors of Tuscany by joining local cuisine tours that allow you to sample authentic dishes and learn cooking secrets from talented chefs.
Popular boutique hotels in Val di Chiana that have a pool include:
Transportation/Shuttle service is available at the following boutique hotels in Val di Chiana:
A spa is available to guests at the following boutique hotels in Val di Chiana:
Families traveling in Val di Chiana enjoyed their stay at the following boutique hotels:
These 3 star hotels received great reviews from other travelers: