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Top Ten Luxury Accommodations in Chianti

The ingredients to a fabulous vacation in Chianti include the fantastic combination of Tuscany with its unique and world famous landscapes, vineyards, olive groves and farms together with a luxury accommodation.

We have put together a list of the best ten luxury hotels, apartments, B&B and villa rentals located within the traditional boundaries of Chianti for the perfect Tuscany holiday vacation. Choose between 5 star hotels, an exclusive bed & breakfast set in a sprawling country home or wine estate or an extravagant, historical castle; each choice is perfect to make your holiday in Chianti an indulgent and enchanting experience.

1. Borgo di Pietrafitta Relais

Resort at Loc. Pietrafitta, Castellina in Chianti (Siena)

Poolside view for Borgo Pietrafitta near Castellina in ChiantiPoolside view of the Chianti landscape from Borgo Pietrafitta.

This little Tuscany hamlet uses its country chic decor, modern amenities and its warm hospitality to help you create a memorable vacation. Whether traveling on your own, for a romantic escape or with family or friends, Borgo di Pietrafitta Relais has the perfect elegant solution to your request. The lush settings are you what you need to relax and enjoy your holiday.

2. Villa il Poggiale

Agritourism at San Casciano in Val di Pesa (Florence)

A dreamy bathroom with tub at Villa il Poggiale in San CascianoA dreamy bathroom with tub at Villa il Poggiale holiday rentals in San Casciano.

A splendid 14th century villa situated in the heart of Chianti Classico area, among vineyards and olives trees which showcase the beauty of the Tuscan landscape is the perfect setting for a luxurious adventure in Tuscany. Villa il Poggiale will surround your senses with the breathtaking vistas, sumptuous decor and delicious flavors of Tuscany.

3. Villa Dianella

B&B at Vinci (Florence)

Wine cellar at B&B Villa Daniella near FlorenceEnjoy a tour and taste testing at Villa Dianella B&B near Florence.

At this beautiful Medicean villa from the 16th century, you will love the attention paid to details: plush linens, meticulously kept gardens and only the highest quality food….and of course, their very own wine cellar. The select decor, the fantastic hospitality and the elegant atmosphere at Villa Dianella are sure to enchant you from the very first moment when you arrive

4. Torre a Cona

Resort at Rignano sull'Arno (Florence)

Resort accomodations at Torre A Cona at Rignano sull'ArnoAccommodations at Torre a Cona in the typical Tuscany decor.

The classical vacation rental apartments are set on a 400-acre wine estate of Torre a Cona is dominated by the monumental eighteenth-century villa. Enjoy Tuscany 360° with splendid views, luxury accommodations and an on-site restaurant with authentic Tuscan cuisine and a “cantina” for guided wine tasting.

5. Villa Piaggia

Villa rental at Montaione (Florence)

Relax in the shadey loggia at the holiday vacation rental Villa Piaggia near MontaioneRelax in the shade of the elegant loggia at the holiday Villa Piaggia.

The combination of glamorous living spaces, marble bathrooms, magical green gardens, and elegant decors will have falling in love with Villa Piaggia. The perfect place to gather family and friends together and enjoy a holiday of indulgence and laughter; plan your

6. Villa Vianci

Historic Villa Rental at Poggibonsi (Siena)

Romantic skyline at night will light up your evening under the stars at vacation rental Villa Vianci near Siena, TuscanyRomantic skyline at night will light up your evening under the stars at Villa Vianci.

This villa ha the perfect position in Chianti for all of your adventures! Explore the history of Villa Vianci and you will fall in love with it. Beautiful set on two floors, the owners thought only of their guests comfort including lots of open spaces for spending time together, air conditioning in all of the bedrooms and fully equipped kitchen.

7. Villa di Cabbiavoli

Historic Vacation Villa at Castelfiorentino (Florence)

Elegant and comfortable bedrooms with lots of natural light at vacation villa rental Cabbiavoli in CastelfiorentinoElegant and comfortable bedrooms with lots of natural light at Cabbiavoli.

This exclusive opportunity to vacation inside the magnificent family home between Florence, Siena and Pisa is a holiday dream come true. The entire Villa di Cabbiavoli and its splendid gardens are at your disposal with room for up to 12 persons. The glamorous decor will have you feeling like royalty while exploring the lovely Tuscany landscape.

8. Villa Medicea di Lilliano

B&B and Villa Rentals at Grassina (Florence)

Courtyard gardens of B&B Villa Medicea di Lilliano near Florence ItalyRelax in the perfume of the courtyard gardens of B&B Villa Medicea di Lilliano.

The 400 year old villa offers 6 self catering solutions as well as the possibility of B&B suites with stunning views and a deluxe decor. Villa Medicea di Liliano is a wine producing estate caters especially to romantic getaways, resort style vacations and destination events and weddings.Between the position so close to Florence an major roadways and the friendly and efficient hospitality you may never want to go home.

9. Hotel Le Fontanelle

Hotel at Castelnuovo Berardenga (Siena)

Enjoy a panoramic sunset at Hotel Le Fontanelle near Siena TuscanyEnjoy a panoramic sunset at Hotel Le Fontanelle.

Nothing beats a fully equipped gym, with indoor heated pool, Jacuzzi, sauna and massage spa to help put you in full relax mode! The beautiful Siena hills, the lovely restored farmhouse and the delicious onsite restaurant give Hotel Le Fontanelle the glamour and elegance that one would associate with a luxury vacation. Enjoy a full service hotel while vacationing in Tuscany.

10. Villa Humbourg

Self catering Apartments at Certaldo (Florence)

Stylized green garden surrounding holiday rental Villa Humborg in TuscanyStylized green garden surrounding holiday rental Villa Humborg.

These two self catering apartments are nestled in an extensive 17th century villa and estate of over 100 hectares of lush green forest, olive groves and vineyards...but that’s not what is the only thing that ranks Villa Humbourg as one of the top ten luxurious stays in Chianti. The elegant bedrooms combined with spacious bathrooms, magnificent garden area for meals and relax and the warm Tuscany hospitality are the tipping points for this splendid accommodation.

Author: Donna Scharnagl

It has been more than 25 years since I took my first steps in Italy and I still haven’t found a good reason to leave.  Between the food, the culture, the history, the art, the landscapes … did I mention the food? I have become a lifelong student. It didn't take long to learn that Italians all have stories that long to be told; stories that paint a picture of how hard work produces character, how life is made of ups and downs and how good it feels to laugh.


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