19 Best Wine hotels in Chianti

Borgo Pignano

Chianti’s borders are as wonderfully fluid as its main export, with the name actually referring to the hills and valleys between Florence and Siena where the grapes are grown that go into Chianti and Chianti Classico. And if you draw a loopy line around that region it includes some of Tuscany’s most scenic spots. So the best wine hotels in Chianti offer incredible views of vineyards, medieval hilltop towns, sunburnt wheat fields, rows of poplars and cypresses and olive groves — as well as opportunities to taste incredible wines grown against this backdrop. And if you’re thinking “well, that’s nice but I’m a bit peckish”, the best wine hotels in Chianti definitely have the menu sorted too. Some of our Gurus’ recommendations are restaurants with rooms, or hotels offering cooking classes; there are a couple of castles too, not to mention villas and converted farmhouses. So whatever your taste or budget, we should be able to recommend a great option!

For the Album

Borgo Pignano

  • The Borgo Pignano is a handsome, traditional villa on a private Tuscan estate turned luxury haven. Set on a hilltop, overlooking 750 acres of farmland, the views around are beautiful, both from the villa, and from the terraces that descend the hill, with their pool, vines and romantic corners. Inside are 17 rooms and suites, beautifully decorated in the Tuscan style, with frescoes, vast fireplaces, high ceilings and terracotta tiled floors — some are in the main house, but there are also separate cottages and maisonettes, perfect for groups of families. Then there are the added extras, like the infinity pool, private-feeling cinema, art classes, yoga classes and billiard table.

For a Special Occasion

Vitiglano Relais and Spa

  • The Vitigliano Relais & Spa has been built in the ruins of the old hamlet of Vitigliano, occupying an idyllic hilltop position overlooking Chianti country. There are only six rooms and suites, all individually designed and elegantly decorated, but all huge, with charming traditional features, roomy bathrooms and all the mod cons. There’s a beautiful pool and terrace, complete with hot tub, plus a small spa. And a gourmet restaurant. Refined, remote and romantic.

For the Views

La Locanda

  • The Relais Borgo san Felice is a sprawling country house hotel, overlooking its own vineyards from a glorious hilltop position. It also has a billiards room, tennis courts and pool. Plus an extremely well regarded Mediterranean restaurant. Accommodation is in 33 spacious rooms and suites, elegantly decorated in pale shades that make the most of the original features. Expect plenty of space everywhere you go, and a long, long wine list — which they use for their comprehensive tastings.
  • La Locanda is a small, hilltop hotel, with wonderful traditional Tuscan charm, and incredible vineyard and valley views. Inside this converted villa are seven beautiful rooms and suites, which feature original details like terracotta floors, beamed ceilings and exposed stone floors, plus a collection of elegant but homely antiques. Each room is different, but our favourites have private terraces. There’s also a delightful library, a bar and lounge. Outside is a shaded terrace and a divine infinity-pool-with-a-view.

For Foodies

Villa Sassolini

  • Villa Sassolini is a charmingly rural gastronomic restaurant with rooms in the hills of Chianti. In addition to the gourmet menu, cooking classes, and incredible views, Villa Sassolini has five spacious and elegant rooms and suites, with a muted neutral colour scheme, large bathrooms and romantic details. There’s also a beautiful pool with wonderful views, gardens drenched in lavender and rosemary, and a collection of sunny terraces.
  • The Villa Bordoni is a beautifully decorated country villa, with 11 rooms and suites, and wonderful views over the hills of Chianti. The blue exterior feels a little Mediterranean — especially beside the palm trees, but inside the terracotta floors, beamed ceilings, and canopied beds feel very Tuscan. There’s an excellent restaurant, complete with a cooking school, and there are a number of vineyards within walking distance.

For Romantics

Castello di Tornano

  • The Castello di Tornano, is perched on a hilltop near Lecce, and has magnificent panoramic views over the vineyards and olive groves of the surrounding area. And it ticks all the boxes a castle should: bedrooms in turrets, four-poster beds, beamed ceilings, and a pool where the moat would be. There are even stables, should you choose to arrive on horseback, and tennis courts. There are 11 rooms and eight apartments, and you can either self-cater or enjoy locally grown local cuisine in the traditional restaurant.
  • The Castelletto di Montebenichi is an historic 12th century castle hamlet in the Chianti hills, with nine charming apartments. This is a really special place to stay, complete with wonderful antiques, stained glass windows, an ornately carved stone exterior, wonderful tiled roofs, and terraces running down the side of the hill like steps. The grounds around the castelletto are large, and there are so many places to enjoy the view.
  • Salvadonica is a small, and delightful, farmhouse-turned-hotel, surrounded by vineyards and overlooking a beautiful valley. The hotel has just 19 rooms and suites, decorated with contemporary minimalism set against the farmhouse’s original features — the terracotta tiles, exposed beams and stone walls, and frescoes. There’s also an excellent Tuscan restaurant which spills out onto an idyllic terrace, with views of the pool, the boules green, olives groves, and the hotel’s tennis courts. Relaxed and romantic.

For a Rural Retreat

Castel Monastero

  • The Castel Monastero is a magnificently restored 11th century hamlet tucked into the Chianti hills, complete with 61 guest rooms and suites arranged, village-style, amongst beautiful gardens, in cottages, villas and larger buildings. As well as beautiful places to sleep and relax, the Castel Monastero has two restaurants, one overseen by Gordon Ramsay, and an impressive cellar bar. Plus postcard perfect waterfall pools, and a wellness centre and spa. Ideal for visitors to the Chianti hills who want to return home at the end of a day’s explorations to a luxurious, pampering cocoon.

For Families

Hotel le Fontanelle

  • Discreet yet sprawling, Hotel Le Fontanelle is a collection of 25 rustic rooms, villas and cottages in a hamlet-style setting, surrounded by olive groves, lemon trees and vineyards. It sounds simple, but it’s a five star experience, with luxurious, but homely decor, and all sorts of added extras. There are incredible views from the pool and the gardens surrounding it, a fantastic restaurant known for its local specialities, and a spa complete with indoor pool, sauna and hot tub.
  • The Castello di Spaltenna is a stunning country house resort, near Gaiole in the peacefully rural Chianti hills. The castello has 37 beautiful rooms, suites and apartments, all traditionally decorated, featuring exposed stone, beamed ceilings and antique furnishings, and many with fantastic views over vineyards and sunburnt wheat fields. Some of the apartments comfortably sleep four, and have their own kitchens. The wine cellar is huge, and there are two restaurants on site, including a very creative Tuscan restaurant with a Michelin star, plus both indoor and outdoor pools, and a state-of-the-art spa and fitness centre. And they offer babysitting.
  • Castello di Bibbione is a traditional Tuscan castle, in a hilltop spot that affords glorious views of the Chianti region. There are 13 apartments, some in farmhouse-style outbuildings, and all traditionally decorated, with terracotta floors, whitewashed stone walls and exposed beam ceilings, and furnished with antiques. Apartments sleep between two and six, and there’s one whole farmhouse, which sleeps 12 — ideal for groups or extended families. The large grounds incorporate gardens, terraces and a huge infinity pool.

For a Countryside Escape

Villa Le Barone

  • Enquiring minds might try the the Villa Le Barone, a gorgeous, 14th century Tuscan villa near Panzano, known for its tutored wine tastings and cookery lessons. Its kitchen and restaurant are impressive places, and there’s an onsite winery, you’re also able to learn about. Accommodation is in 28 rooms and two suites, all carefully, and romantically, decorated with antiques, and many offering beautiful views. Outside there are gardens and a heated, salt-water pool.
  • Il Borgo di Vescine is a collection of 13th century stone buildings connected by cobbled paths into a little hamlet, and now turned charming hotel. There’s plenty of privacy, space and peace, but also the opportunity to enjoy the company of fellow guests in the restaurant or on the terrace, where local cuisine is served, paired with local wines. You’re just 20 minutes from Siena, but there’s plenty to do onsite, including wine tastings, cooking classes, horse riding, using the gym and pool, or exploring the grounds. Explore further afield on the hotel’s bikes.

For Traditional Charms

Relais Vignale

  • Relais Vignale is an 18th century country house, carefully and sympathetically restored to its traditional elegance, and transformed into a 42 room country hotel. Rooms have terracotta-tiled floors, whitewashed walls, and exposed beams on the ceilings, plus a collection of simple, locally made antiques. Outside there are gardens, a lovely outdoor pool, and a Tuscan terrace restaurant with vineyard and olive grove views. They offer wine tastings onsite, but you’re surrounded by vineyards and cellar doors.

For Great Value

Palazzo Leopoldo

  • The Palazzo Leopoldo is a traditional Tuscan hilltop hotel with just 14 rooms and suites, and a beautiful restaurant with incredible valley views and a welcoming terrace. The decor is perfectly Tuscan, with terracotta-tiled floors, exposed beams on high ceilings, and a collection of antiques. There are hot tubs on the terrace, and an indoor pool in the cellars, along with a luxurious spa.
  • The Castello di Fonterutoli is a medieval villa in charming Castellina, with 12 smartly decorated rooms and a wonderful restaurant with an exceptional wine list. While the exterior is certainly wonderfully traditional, the interiors are stylishly decorated in Farrow&Ball-esque colours, with art on the walls, and a sitting room packed with books.

Best B&Bs

Agriturismo Poggiacolle

  • The Agriturismo Poggiacolle is a Tuscan farmhouse B&B with its own vineyards and saffron farm, just outside San Gimignano. It has just four guest apartments, self-catering, with rustic, romantic details: think beamed ceilings, terracotta-tiled floors, four-poster beds and wonderful views of the surrounding countryside. To share between just these four apartments are a tennis court, gardens, a children’s play area, and an infinity pool.

Still not sure where to book?

  • You could expand your search to include the best wine hotels in Tuscany, or the best Tuscan hotels for food and wine
  • Or expand your search even further to the best places to stay in Tuscan, or all our wine hotels in Italy
  • Or refine your search to just the for the best hotels in Florence, or the best places to stay in Siena
  • Alternatively, you could contact one of our friendly Gurus for personalised advice.
    • Villa le Barone Panzano in Chianti Greve in Chianti, Tuscany 28 rooms from £156

      Views  -  Stunning views over the Chianti countryside
      Country Escape
      Great walks  -  Fitness trail for walking or jogging, plus many walking and hiking paths close by.
      Air conditioningTennisRestaurantSwimming PoolGardenViewsParkingNo pets
      Recommended by  -  Sawdays

      Gorgeous Tuscan villa with spectacular views over the surrounding countryside. Traditional, romantic bedrooms and suites with oak floors, soft fabrics and antique furniture. New heated salt water swimming pool for 2017, winery, restaurant, wine tasting and cookery classes. See More

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    • Castello di Tornano Gaiole in Chianti Siena, Tuscany 11 rooms from £134

      Restaurant  -  Serving traditional Chianti cuisine and featuring vegetables grown in their own garden
      Air conditioningTennisRestaurantSwimming PoolGardenPet friendlyViewsParking
      Recommended by  -  I Escape

      A beautiful castle serenely perched on a hilltop. Traditional rooms and apartments, some in turrets, with oak floors, four poster beds, and magnificent valley views. Ideal for weddings, groups or family holidays. See More

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    • Castello di Spaltenna Gaiole In Chianti Siena, Tuscany 37 rooms from £190

      Foodies  -  Two restaurants offer the choice of informal or formal dining, the latter of which has been awarded one Michelin Star
      Families  -  Apartments sleep four and have their own kitchens, ideal for families wanting a little privacy
      Sights nearby  -  The church of San Sigismondo, Gaiole in Chianti Stadium, and Medieval Tower of Barbischio are all easily accessible
      Restaurant  -  There are various dining options from Michelin starred to Pizzeria!
      Air conditioningTennisSpaRestaurantSwimming PoolGardenViewsParking

      A striking stone castle set in the Chianti hills offering a peaceful rural escape. Elegant rooms feature exposed stonework, beamed ceilings and antiques. The expansive grounds house a large pool and there's an indulgent spa to aid total relaxation. Best yet there's two good restaurants to pick from. See More

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    • Relais Borgo San Felice Castelnuovo Berardenga SI, Tuscany 33 rooms from £486

      Good wine list  -  Excellent choice from the hotel's own vintages.
      Wine tasting  -  The hotel is surrounded by its own vineyards.
      Foodies  -  Fantastic Mediterranean cuisine.
      Romantic Break
      Air conditioningTennisRestaurantSwimming PoolGardenViewsParking
      Recommended by  -  Relais & Chateaux, Michelin Travel, Tablet

      A stunning country house surrounded by its own vines and parkland. A hilltop position with fantastic valley views. Sumptuous elegant rooms and suites with lots of space and big bath tubs. Fantastic Mediterranean restaurant, billiards, tennis, wine tasting, swimming pool, and views for miles. Wow! See More

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    • Castel Monastero Castelnuovo Berardenga, Tuscany 61 rooms from £467

      Sights nearby  -  Situated between Siena and Arezzo and ideally located for exploring many Tuscan villages
      Cooking classes  -  Book a class and learn to create the Castel's own gourmet dishes at home
      Swimming Pool  -  There are three swimming pools, both indoor and outdoor
      Restaurant  -  There are two restaurants on site
      Air conditioningTennisSpaRestaurantSwimming PoolGardenPet friendlyViews
      Recommended by  -  Tablet

      Castel Monastero is a magnificently restored 11th century hamlet turned exclusive hotel and spa, in the peaceful Tuscan hills. Elegant rooms and suites, pool, wellness centre and two restaurants provide the ultimate in luxury relaxation. See More

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    • Campo Regio Relais Siena, Tuscany 6 rooms from £165

      Sights nearby  -  Conveniently located for the Piazza del Campo, one of Europe's most beautiful and architecturally interesting squares.
      Great walks  -  Wander around the streets of the Medieval town and absorb the architecture and beauty.
      Views  -  Stunning views over the Duomo
      Full of character
      Air conditioningViews
      Recommended by  -  Sawdays

      Romantic, stylish hotel furnished with antiques and enjoying splendid views over Siena. Elegant and spacious individually decorated bedrooms with parquet floors, four poster beds, antique furniture and beautiful fabrics. Lovely breakfast terrace. A romantic spot from which to explore Siena. See More

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    • Borgo Pignano San Gimignano 17 rooms from £277

      Families  -  With excellent family friendly accommodation and a wide range of activities for all ages it's perfect for family stay
      Views  -  The property enjoys breathtaking views over the surrounding Tuscan countryside
      Restaurant  -  Fine dining Tuscan style in Villa Pignano, or for something more relaxed try the Fireplace Restaurant or Trattoria Al Fresco
      Kids Club  -  During the summer months there are dedicated staff who organise a wide range of children's activities
      Air conditioningSpaRestaurantSwimming PoolGardenPet friendlyViewsParking
      Recommended by  -  Sawdays

      A private Tuscan estate and luxury haven set amid 750 acres of organic farmland. Sensitively restored throughout, bedrooms and suites feature original architectural details and traditional Tuscan style interiors plus stunning views. A magical spot for couples, weddings, and family holidays. See More

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    • Hotel Le Fontanelle Castelnuovo Berardenga SI, Tuscany 25 rooms from £346

      Intimate  -  The hotel is built as a hamlet so that accommodations are homely rather than hotel-like.
      Outstanding location  -  Stunning; surrouned by vineyards, rolling hills, and lemon groves.
      Country Escape
      5* Luxury  -  Very high service standards.
      Air conditioningSpaRestaurantSwimming PoolGardenParking

      A wonderful Five Star property surrounded by olive groves, lemon trees and vineyards. Homely accommodation spread through a hamlet-style setting. Each room and suite is beautifully decorated, some with private balconies and views. Fantastic restaurant and spa facilities. See More

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    • Agriturismo Poggiacolle San Gimignano 4 rooms from £82

      Groups  -  Some apartments sleep up to 10 people.
      Great walks  -  Plenty of walking on the doorstep
      Sights nearby  -  Just 2km from San Gimignano
      TennisSwimming PoolGardenPet friendlyViewsParking

      A gorgeous Tuscan farmhouse B&B with its own vineyards and saffron farm. Four separate self-catering apartments occupy the farmhouse. Rustic-romantic rooms, infinity pool, tennis courts, and spectacular views of the surrounding countryside. Ideal for families and groups of friends. See More

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    • Palazzo Leopoldo Radda In Chianti, Tuscany 14 rooms from £104

      Swimming Pool  -  Indoor heated pool, or use the outdoor pool for free at a sister property just 5 mins by car.
      Sights nearby  -  Great base for exploring all that Tuscany and the Chianti area has to offer
      Views  -  Stunning views from the terrace
      Restaurant  -  Traditional Tuscan cuisine
      Air conditioningSpaRestaurantSwimming PoolGardenPet friendlyViewsParking
      Recommended by  -  Sawdays

      A traditional hilltop hotel with an excellent terrace restaurant and spa. Bedrooms and suites have fireplaces, stone floors, killim rugs and wooden beams. Stunning valley views, indoor and outdoor pools, and cookery courses. Peaceful, serene, and rustic. See More

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    • Salvadonica San Casciano in Val di Pesa 19 rooms from £107

      Families  -  The generously proportioned family room with 2 adjoined ensuites, make this a comfortable choice for those travelling with kids
      Country Escape  -  A classic Tuscan stay hidden in the rolling Chianti hills, where life is slow and focused on good food and wine
      Cooking classes  -  Learn to cook traditional dishes with the resident chef
      Tennis  -  Play a game on the property's all-weather outdoor court
      Air conditioningTennisRestaurantSwimming PoolGardenParking

      A delightful farmhouse hotel amongst vineyards. Contemporary rooms and suites have rustic features; wrought-iron beds, frescoed walls, and exposed wooden beam ceilings. Pool, boules green, olive tree garden, tennis court and massages available. Excellent Tuscan cuisine. Romantic and very relaxing. See More

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    • Castello di Bibbione San Casciano in Val di Pesa 13 rooms from £113

      Country Escape  -  A rustic farmhouse set in the gorgeous Chianti hills.
      Swimming Pool  -  Outdoor pool.
      Full of character
      Views  -  Great views from hotel
      Swimming PoolGardenPet friendlyDisabled accessViewsParking

      A traditional Tuscan castle with gorgeous views of the Chianti region. Farmhouse-style apartments with high beamed ceilings, delightfully uneven white-washed walls and cast iron beds. An impressively proportioned infinity pool and bikes to potter around the surrounding countryside. Rural bliss. See More

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    • Castello di Fonterutoli Fonterutoli, Tuscany 12 rooms from £113

      Total relaxation  -  Beautiful weather, a lovely garden, walks through the quaint town and wonderful cuisine-what more could you ask for?
      Great walks  -  Head off to explore the stunning sourrounding Tuscan countryside and revel in the area's beauty
      Sights nearby  -  Check out the Torre del Mangia, Siena Cathedral or Piazza del Campo
      Full of character
      RestaurantGardenPet friendlyParking

      Castello di Fonterutoli is a medieval country house situated near Castellina in Chianti. Offering smart accommodation in a traditional setting, as well as a wonderful restaurant and knowledgeable sommeliers to take you through their wines. A quiet, charming and relaxing escape. See More

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    • Castelletto di Montebenichi Monte Benichi, Tuscany 9 rooms from £117

      Foodies  -  Plenty of opportunities for foodies from visits to vineyards and olive oil farms to cheese and truffle tasting
      Local exploring  -  The property provides the ideal base for exploring the glorious Chianti countrysde
      Great walks  -  Take long walks through the large private park near the castle that merges in with the gently sloping Tuscan hills
      Local markets  -  Visit the antiques fair in Arezzo (the largest in Italy)
      Air conditioningSwimming PoolGardenViewsParking

      A unique opportunity to stay in a historical hamlet in the Chianti hills. Apartments are utterly charming, filled with antiques and original features. The expansive grounds house a pool and command spectacular views of the surrounding region. The perfect Tuscan escape. See More

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    • Il Borgo di Vescine Radda in Chianti, Tuscany 26 rooms from £139

      Cooking classes  -  Tuscan cooking courses at the hotel
      Sights nearby  -  Siena is just 20 km away
      Great walks  -  Walk the local wineries
      Tennis  -  On site
      Air conditioningTennisRestaurantSwimming PoolGardenPet friendlyDisabled accessViewsParking
      Recommended by  -  Fodors

      This stunning little hotel comprises a series of medieval stone buildings with tiled roofs connected by cobbled paths. Bedrooms have high ceilings and terracotta tiled floors. The restaurant serves traditional Tuscan and Chianti cuisine paired with local wines. A quiet spot with glorious views. See More

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    • Relais Vignale Radda in Chianti, Tuscany 42 rooms from £154

      Restaurant  -  The restaurant specialises in traditional Tuscan cuisine
      Views  -  Glorious views over the surrounding area
      Great walks  -  Walking tours around Radda in Chianti
      Cooking classes  -  Tuscan Cooking School
      Air conditioningRestaurantGardenViewsParking
      Recommended by  -  Fodors

      18th century country house which has been sympathetically restored and now offers traditional rooms and suites with terra-cotta floors and exposed wooden beams. Lovely outdoor pool and terrace restaurant with glorious views of surrounding vineyards and olive trees. Stunning, remote and romantic. See More

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    • La Locanda Radda In Chianti, Tuscany 7 rooms from £191

      Views  -  Wonderful views over Volpaia
      Total relaxation
      Sights nearby  -  Perfect base for getting to the Chianti Classico area
      Cooking classes  -  Excllent cookery school in Volpaia
      Air conditioningRestaurantSwimming PoolGardenPet friendlyViewsParking
      Recommended by  -  Sawdays, CN Traveller

      A hilltop hotel full of character with magnificent views over vineyards, woodland and olive groves. Charming bedrooms in bold colours with private terraces. Delightful library and bar area and a sparkling swimming pool. A rustic treat in peaceful surroundings. See More

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    • Villa Bordoni Greve in Chianti, Tuscany 11 rooms from £195

      Great walks  -  Exploring the vineyards on foot is a romantic sunset scene.
      Cooking classes  -  Non residential and residential cooking courses.
      Swimming Pool  -  Outdoor pool with country landscape
      Views  -  Great views over the Chianti hills
      Air conditioningRestaurantSwimming PoolGardenDisabled accessViewsParkingNo pets
      Recommended by  -  Mr & Mrs Smith, Fodors

      Beautifully decorated country house with glorious views. A pretty pale blue facade and bedrooms that ooze traditional elegance - strong earthy colours, wooden beams, canopied beds and huge bath tubs. Excellent restaurant and cookery school. A popular choice with honeymooners and romantics. See More

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    • Vitigliano Relais & Spa Greve in Chianti, Tuscany 6 rooms from £564

      Country Escape  -  Vitigliano Relais & Spa enjoys a superb location amidst the rugged Tuscan countryside
      Romantic Break
      Total relaxation
      Great walks  -  Explore the numerous walking trails runiing through the surrounding countryside
      Air conditioningSpaRestaurantSwimming PoolGardenViewsParkingNo pets

      Set in the old village of Vitigliano's restored ruins, this luxurious property enjoys a hilltop location in prettyChianti. Boasting individually designed and incredibly spacious suites with bare stone walls and Persian rugs. Sample local cuisine in the exemplary restaurant and sip on regional wines. See More

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    • Villa Sassolini Montevarchi Arezzo, Tuscany 15 rooms from £154

      Restaurant  -  Regional cuisine produced from the ingredients of the finest local suppliers
      Local markets  -  Good for local colour.
      Air conditioningRestaurantSwimming PoolGardenParking
      Recommended by  -  Mr & Mrs Smith, Tablet, I Escape

      Stunning views, gourmet food, fabulous rooms and suites. A romantic and gastronomic Tuscan country escape in the hills of Chianti. Muted interiors exude understated luxury. Fantastic swimming pool and sunny terraces. A sophisticated Tuscan holiday. See More

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Written by Kat Parr Mackintosh

posted Monday, 4th April 2022