The romanticized Italy of daydreams, the Chianti wine region sits between Tuscany’s rolling hills, vineyards and olive groves. Explore the historic hamlets, taste the flavors of the region and take in the natural beauty of the sun-streaked Italian Cypress trees.
Our top hotels.
Castles, villas, estates, oh my! Our list of Chianti hotels- from charming boutiques to mature holiday retreats- boasts of vine-covered stone dwellings, extensive wine cellars, cosmopolitan style, and timeless Chianti warmth. Borgo San Felice, COMO Castell del Nero and Villa Le Barone are some of our favorites!
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
COMO Castello Del Nero - At this 12th century castle, take in the vast 740 acres of rolling countryside and notice the detailed medieval frescos, murals and stonework. With a wine cellar and swanky pool, the COMO Castello Del Nero has a cosmopolitan style with a classic Tuscan feel.
COMO Castello Del Nero - At this 12th century castle, take in the vast 740 acres of rolling countryside and notice the detailed medieval frescos, murals and stonework. With a wine cellar and swanky pool, the COMO Castello Del Nero has a cosmopolitan style with a classic Tuscan feel.
COMO Castello Del Nero - At this 12th century castle, take in the vast 740 acres of rolling countryside and notice the detailed medieval frescos, murals and stonework. With a wine cellar and swanky pool, the COMO Castello Del Nero has a cosmopolitan style with a classic Tuscan feel.
COMO Castello Del Nero - At this 12th century castle, take in the vast 740 acres of rolling countryside and notice the detailed medieval frescos, murals and stonework. With a wine cellar and swanky pool, the COMO Castello Del Nero has a cosmopolitan style with a classic Tuscan feel.
COMO Castello Del Nero - At this 12th century castle, take in the vast 740 acres of rolling countryside and notice the detailed medieval frescos, murals and stonework. With a wine cellar and swanky pool, the COMO Castello Del Nero has a cosmopolitan style with a classic Tuscan feel.
COMO Castello Del Nero - At this 12th century castle, take in the vast 740 acres of rolling countryside and notice the detailed medieval frescos, murals and stonework. With a wine cellar and swanky pool, the COMO Castello Del Nero has a cosmopolitan style with a classic Tuscan feel.
Hotel Le Fontanelle - Perched on a hilltop, Hotel Le Fontanelle is a 13th century estate turned upscale hotel with panoramic views of the Chianti Classico region. Featuring beamed ceilings and terracotta floors, this 5-star hotel is a peaceful, rural retreat for those looking for quiet elegance.
Hotel Le Fontanelle - Perched on a hilltop, Hotel Le Fontanelle is a 13th century estate turned upscale hotel with panoramic views of the Chianti Classico region. Featuring beamed ceilings and terracotta floors, this 5-star hotel is a peaceful, rural retreat for those looking for quiet elegance.
Hotel Le Fontanelle - Perched on a hilltop, Hotel Le Fontanelle is a 13th century estate turned upscale hotel with panoramic views of the Chianti Classico region. Featuring beamed ceilings and terracotta floors, this 5-star hotel is a peaceful, rural retreat for those looking for quiet elegance.
Hotel Le Fontanelle - Perched on a hilltop, Hotel Le Fontanelle is a 13th century estate turned upscale hotel with panoramic views of the Chianti Classico region. Featuring beamed ceilings and terracotta floors, this 5-star hotel is a peaceful, rural retreat for those looking for quiet elegance.
Hotel Le Fontanelle - Perched on a hilltop, Hotel Le Fontanelle is a 13th century estate turned upscale hotel with panoramic views of the Chianti Classico region. Featuring beamed ceilings and terracotta floors, this 5-star hotel is a peaceful, rural retreat for those looking for quiet elegance.
Hotel Le Fontanelle - Perched on a hilltop, Hotel Le Fontanelle is a 13th century estate turned upscale hotel with panoramic views of the Chianti Classico region. Featuring beamed ceilings and terracotta floors, this 5-star hotel is a peaceful, rural retreat for those looking for quiet elegance.
Hotel Le Fontanelle - Perched on a hilltop, Hotel Le Fontanelle is a 13th century estate turned upscale hotel with panoramic views of the Chianti Classico region. Featuring beamed ceilings and terracotta floors, this 5-star hotel is a peaceful, rural retreat for those looking for quiet elegance.
La Canonica di Cortine - Within the heart of Chianti, set amidst centuries-old vineyards and olive trees, La Canonica di Cortine is an ancient abode for country-chic lovers. With mature gardens, a pool and shaded terrace, this Chianti villa is the dream holiday retreat.
La Canonica di Cortine - Within the heart of Chianti, set amidst centuries-old vineyards and olive trees, La Canonica di Cortine is an ancient abode for country-chic lovers. With mature gardens, a pool and shaded terrace, this Chianti villa is the dream holiday retreat.
La Canonica di Cortine - Within the heart of Chianti, set amidst centuries-old vineyards and olive trees, La Canonica di Cortine is an ancient abode for country-chic lovers. With mature gardens, a pool and shaded terrace, this Chianti villa is the dream holiday retreat.
La Canonica di Cortine - Within the heart of Chianti, set amidst centuries-old vineyards and olive trees, La Canonica di Cortine is an ancient abode for country-chic lovers. With mature gardens, a pool and shaded terrace, this Chianti villa is the dream holiday retreat.
La Canonica di Cortine - Within the heart of Chianti, set amidst centuries-old vineyards and olive trees, La Canonica di Cortine is an ancient abode for country-chic lovers. With mature gardens, a pool and shaded terrace, this Chianti villa is the dream holiday retreat.
La Canonica di Cortine - Within the heart of Chianti, set amidst centuries-old vineyards and olive trees, La Canonica di Cortine is an ancient abode for country-chic lovers. With mature gardens, a pool and shaded terrace, this Chianti villa is the dream holiday retreat.
La Canonica di Cortine - Within the heart of Chianti, set amidst centuries-old vineyards and olive trees, La Canonica di Cortine is an ancient abode for country-chic lovers. With mature gardens, a pool and shaded terrace, this Chianti villa is the dream holiday retreat.
Locanda di Piazze - This stone farmhouse circa 1540 has been transformed into a rustic-chic hotel with surrounding gardens, sundeck and pool with panoramic views. With a high-end regional restaurant on site, there may be no need to venture off the garden terrace at all.
Locanda di Piazze - This stone farmhouse circa 1540 has been transformed into a rustic-chic hotel with surrounding gardens, sundeck and pool with panoramic views. With a high-end regional restaurant on site, there may be no need to venture off the garden terrace at all.
Locanda di Piazze - This stone farmhouse circa 1540 has been transformed into a rustic-chic hotel with surrounding gardens, sundeck and pool with panoramic views. With a high-end regional restaurant on site, there may be no need to venture off the garden terrace at all.
Locanda di Piazze - This stone farmhouse circa 1540 has been transformed into a rustic-chic hotel with surrounding gardens, sundeck and pool with panoramic views. With a high-end regional restaurant on site, there may be no need to venture off the garden terrace at all.
Locanda di Piazze - This stone farmhouse circa 1540 has been transformed into a rustic-chic hotel with surrounding gardens, sundeck and pool with panoramic views. With a high-end regional restaurant on site, there may be no need to venture off the garden terrace at all.
Locanda di Piazze - This stone farmhouse circa 1540 has been transformed into a rustic-chic hotel with surrounding gardens, sundeck and pool with panoramic views. With a high-end regional restaurant on site, there may be no need to venture off the garden terrace at all.
Locanda di Piazze - This stone farmhouse circa 1540 has been transformed into a rustic-chic hotel with surrounding gardens, sundeck and pool with panoramic views. With a high-end regional restaurant on site, there may be no need to venture off the garden terrace at all.
Villa Le Barone - This charming boutique hotel consists of quaint cottages, barns and a 16th century villa covered in ivy. With antique furnishings and a down-to-earth Tuscan restaurant, Villa Le Barone has an unspoiled ambiance of timeless Chianti warmth.
Villa Le Barone - This charming boutique hotel consists of quaint cottages, barns and a 16th century villa covered in ivy. With antique furnishings and a down-to-earth Tuscan restaurant, Villa Le Barone has an unspoiled ambiance of timeless Chianti warmth.
Villa Le Barone - This charming boutique hotel consists of quaint cottages, barns and a 16th century villa covered in ivy. With antique furnishings and a down-to-earth Tuscan restaurant, Villa Le Barone has an unspoiled ambiance of timeless Chianti warmth.
Villa Le Barone - This charming boutique hotel consists of quaint cottages, barns and a 16th century villa covered in ivy. With antique furnishings and a down-to-earth Tuscan restaurant, Villa Le Barone has an unspoiled ambiance of timeless Chianti warmth.
Villa Le Barone - This charming boutique hotel consists of quaint cottages, barns and a 16th century villa covered in ivy. With antique furnishings and a down-to-earth Tuscan restaurant, Villa Le Barone has an unspoiled ambiance of timeless Chianti warmth.
Villa Le Barone - This charming boutique hotel consists of quaint cottages, barns and a 16th century villa covered in ivy. With antique furnishings and a down-to-earth Tuscan restaurant, Villa Le Barone has an unspoiled ambiance of timeless Chianti warmth.
La Canonica di Cortine - Within the heart of Chianti, set amidst centuries-old vineyards and olive trees, La Canonica di Cortine is an ancient abode for country-chic lovers. With mature gardens, a pool and shaded terrace, this Chianti villa is the dream holiday retreat.
La Canonica di Cortine - Within the heart of Chianti, set amidst centuries-old vineyards and olive trees, La Canonica di Cortine is an ancient abode for country-chic lovers. With mature gardens, a pool and shaded terrace, this Chianti villa is the dream holiday retreat.
La Canonica di Cortine - Within the heart of Chianti, set amidst centuries-old vineyards and olive trees, La Canonica di Cortine is an ancient abode for country-chic lovers. With mature gardens, a pool and shaded terrace, this Chianti villa is the dream holiday retreat.
La Canonica di Cortine - Within the heart of Chianti, set amidst centuries-old vineyards and olive trees, La Canonica di Cortine is an ancient abode for country-chic lovers. With mature gardens, a pool and shaded terrace, this Chianti villa is the dream holiday retreat.
La Canonica di Cortine - Within the heart of Chianti, set amidst centuries-old vineyards and olive trees, La Canonica di Cortine is an ancient abode for country-chic lovers. With mature gardens, a pool and shaded terrace, this Chianti villa is the dream holiday retreat.
La Canonica di Cortine - Within the heart of Chianti, set amidst centuries-old vineyards and olive trees, La Canonica di Cortine is an ancient abode for country-chic lovers. With mature gardens, a pool and shaded terrace, this Chianti villa is the dream holiday retreat.
La Canonica di Cortine - Within the heart of Chianti, set amidst centuries-old vineyards and olive trees, La Canonica di Cortine is an ancient abode for country-chic lovers. With mature gardens, a pool and shaded terrace, this Chianti villa is the dream holiday retreat.
Villa Le Barone - This charming boutique hotel consists of quaint cottages, barns and a 16th century villa covered in ivy. With antique furnishings and a down-to-earth Tuscan restaurant, Villa Le Barone has an unspoiled ambiance of timeless Chianti warmth.
Villa Le Barone - This charming boutique hotel consists of quaint cottages, barns and a 16th century villa covered in ivy. With antique furnishings and a down-to-earth Tuscan restaurant, Villa Le Barone has an unspoiled ambiance of timeless Chianti warmth.
Villa Le Barone - This charming boutique hotel consists of quaint cottages, barns and a 16th century villa covered in ivy. With antique furnishings and a down-to-earth Tuscan restaurant, Villa Le Barone has an unspoiled ambiance of timeless Chianti warmth.
Villa Le Barone - This charming boutique hotel consists of quaint cottages, barns and a 16th century villa covered in ivy. With antique furnishings and a down-to-earth Tuscan restaurant, Villa Le Barone has an unspoiled ambiance of timeless Chianti warmth.
Villa Le Barone - This charming boutique hotel consists of quaint cottages, barns and a 16th century villa covered in ivy. With antique furnishings and a down-to-earth Tuscan restaurant, Villa Le Barone has an unspoiled ambiance of timeless Chianti warmth.
Villa Le Barone - This charming boutique hotel consists of quaint cottages, barns and a 16th century villa covered in ivy. With antique furnishings and a down-to-earth Tuscan restaurant, Villa Le Barone has an unspoiled ambiance of timeless Chianti warmth.
Hotel Le Fontanelle - Perched on a hilltop, Hotel Le Fontanelle is a 13th century estate turned upscale hotel with panoramic views of the Chianti Classico region. Featuring beamed ceilings and terracotta floors, this 5-star hotel is a peaceful, rural retreat for those looking for quiet elegance.
Hotel Le Fontanelle - Perched on a hilltop, Hotel Le Fontanelle is a 13th century estate turned upscale hotel with panoramic views of the Chianti Classico region. Featuring beamed ceilings and terracotta floors, this 5-star hotel is a peaceful, rural retreat for those looking for quiet elegance.
Hotel Le Fontanelle - Perched on a hilltop, Hotel Le Fontanelle is a 13th century estate turned upscale hotel with panoramic views of the Chianti Classico region. Featuring beamed ceilings and terracotta floors, this 5-star hotel is a peaceful, rural retreat for those looking for quiet elegance.
Hotel Le Fontanelle - Perched on a hilltop, Hotel Le Fontanelle is a 13th century estate turned upscale hotel with panoramic views of the Chianti Classico region. Featuring beamed ceilings and terracotta floors, this 5-star hotel is a peaceful, rural retreat for those looking for quiet elegance.
Hotel Le Fontanelle - Perched on a hilltop, Hotel Le Fontanelle is a 13th century estate turned upscale hotel with panoramic views of the Chianti Classico region. Featuring beamed ceilings and terracotta floors, this 5-star hotel is a peaceful, rural retreat for those looking for quiet elegance.
Hotel Le Fontanelle - Perched on a hilltop, Hotel Le Fontanelle is a 13th century estate turned upscale hotel with panoramic views of the Chianti Classico region. Featuring beamed ceilings and terracotta floors, this 5-star hotel is a peaceful, rural retreat for those looking for quiet elegance.
Hotel Le Fontanelle - Perched on a hilltop, Hotel Le Fontanelle is a 13th century estate turned upscale hotel with panoramic views of the Chianti Classico region. Featuring beamed ceilings and terracotta floors, this 5-star hotel is a peaceful, rural retreat for those looking for quiet elegance.
Locanda di Piazze - This stone farmhouse circa 1540 has been transformed into a rustic-chic hotel with surrounding gardens, sundeck and pool with panoramic views. With a high-end regional restaurant on site, there may be no need to venture off the garden terrace at all.
Locanda di Piazze - This stone farmhouse circa 1540 has been transformed into a rustic-chic hotel with surrounding gardens, sundeck and pool with panoramic views. With a high-end regional restaurant on site, there may be no need to venture off the garden terrace at all.
Locanda di Piazze - This stone farmhouse circa 1540 has been transformed into a rustic-chic hotel with surrounding gardens, sundeck and pool with panoramic views. With a high-end regional restaurant on site, there may be no need to venture off the garden terrace at all.
Locanda di Piazze - This stone farmhouse circa 1540 has been transformed into a rustic-chic hotel with surrounding gardens, sundeck and pool with panoramic views. With a high-end regional restaurant on site, there may be no need to venture off the garden terrace at all.
Locanda di Piazze - This stone farmhouse circa 1540 has been transformed into a rustic-chic hotel with surrounding gardens, sundeck and pool with panoramic views. With a high-end regional restaurant on site, there may be no need to venture off the garden terrace at all.
Locanda di Piazze - This stone farmhouse circa 1540 has been transformed into a rustic-chic hotel with surrounding gardens, sundeck and pool with panoramic views. With a high-end regional restaurant on site, there may be no need to venture off the garden terrace at all.
Locanda di Piazze - This stone farmhouse circa 1540 has been transformed into a rustic-chic hotel with surrounding gardens, sundeck and pool with panoramic views. With a high-end regional restaurant on site, there may be no need to venture off the garden terrace at all.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
Borgo San Felice - Surrounded by vineyards and olive groves, Borgo San Felice is a restored 8th century building with stone walls, terracotta floors and exposed beams for your visual pleasure. This 5-star wine resort also features a piano bar with a fireplace, two restaurants, tennis courts, pool and sauna. Luxury and authenticity at its finest.
COMO Castello Del Nero - At this 12th century castle, take in the vast 740 acres of rolling countryside and notice the detailed medieval frescos, murals and stonework. With a wine cellar and swanky pool, the COMO Castello Del Nero has a cosmopolitan style with a classic Tuscan feel.
COMO Castello Del Nero - At this 12th century castle, take in the vast 740 acres of rolling countryside and notice the detailed medieval frescos, murals and stonework. With a wine cellar and swanky pool, the COMO Castello Del Nero has a cosmopolitan style with a classic Tuscan feel.
COMO Castello Del Nero - At this 12th century castle, take in the vast 740 acres of rolling countryside and notice the detailed medieval frescos, murals and stonework. With a wine cellar and swanky pool, the COMO Castello Del Nero has a cosmopolitan style with a classic Tuscan feel.
COMO Castello Del Nero - At this 12th century castle, take in the vast 740 acres of rolling countryside and notice the detailed medieval frescos, murals and stonework. With a wine cellar and swanky pool, the COMO Castello Del Nero has a cosmopolitan style with a classic Tuscan feel.
COMO Castello Del Nero - At this 12th century castle, take in the vast 740 acres of rolling countryside and notice the detailed medieval frescos, murals and stonework. With a wine cellar and swanky pool, the COMO Castello Del Nero has a cosmopolitan style with a classic Tuscan feel.
COMO Castello Del Nero - At this 12th century castle, take in the vast 740 acres of rolling countryside and notice the detailed medieval frescos, murals and stonework. With a wine cellar and swanky pool, the COMO Castello Del Nero has a cosmopolitan style with a classic Tuscan feel.
Explore more hotels by selecting a region below:
Top tours.
Chianti Villages with Winery Lunch Day Trip
Roll up and down the lush hills of Tuscany on your way from one charming village to another, and round out your day with a winery visit complete with a homecooked lunch paired with impeccable wine.
Siena & Monteriggioni Day Trip
Turn back time to Italy’s medieval period with visits to the quaint hilltop towns of Monteriggioni and Siena. Your day will be broken up with a stop for a cellar tour and home-cooked lunch along with tastings of wine, olive oil, and balsamic vinegar at a winery.
Tuscan Cooking Class
Prepare a traditional 4-course Tuscan meal under the guidance of an experienced local chef. Following your lesson, you will sit down and savor the dishes you just created along with some wine.
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