Farmhouse in green rolling fields surrounded by cypress trees in swirling mist

Best Italian countryside hotel holidays

View our selection of our best hotel holidays in the Italian countryside

Expressions Holidays consider these to be some of our best countryside hotel holidays in Italy. They offer tailor-made stays at luxury hotels on country estates amid rolling hills and farmland, luxurious hotels with views over vineyards and charming country houses near picturesque villages. The hotels featured all provide an excellent base from which to explore nearby towns and villages as well as enjoying the views and activities in the stunning surrounding countryside. These luxury hotels in the Italian countryside are ideal as long, leisurely, single-centre stays or as part of a bespoke, touring holiday, combining hotels within a region or more than one Italian region.

Our best Italian countryside hotel holidays include

● Travel arrangements with flights, transfers or car-hire as required
● Flexible durations and multi-centre stays
● Accommodation in personally-selected 4-or 5-star hotels

Included in all our holidays

● Concierge service
● Handcrafted helpful hints and local information provided with all our holidays
● Personal service by your sales consultant who looks after all aspects of your holiday
● Full financial protection with our ATOL (3076) for all holidays including a flight and our ABTOT for all non-air holidays

Call us on 01392 441245

Golden lion on front of the blue and gold of St Mark's Basilica in Venice

VENICE AND THE VENETO THROUGH THE ALPS BY RAIL TOUR

9-night holiday by train to Venice with two nights in Munich and scenic day-time journey through the Brenner into Italy. Three nights in Venice and three nights in the Veneto near Vicenza and one night in Zurich on the way back. From £3,060 per person.

Tuscany field with small white chapel flanked by cypress trees with mountains behind

TUSCANY TO THE AMALFI COAST FLY-DRIVE TOUR

12-night fly-drive touring holiday from Tuscany to the Amalfi Coast with stays in Chianti, Frascati and Positano. From £4,220 per person.

Palladian classical villa with round rooftop called La Rotonda near Vicenza

PALLADIO'S VENETO FLY-DRIVE TOURING HOLIDAY

9-night fly-drive touring holiday of Palladio’s Veneto, staying in Padua, Vicenza and Verona. From £1,740 per person.

EXPLORE SOUTHERN TUSCANY RAIL-DRIVE TOUR

8-night touring holiday by train and hire-car via Switzerland to Florence, Chianti, Cortona. Return with an overnight stop in northern Italy or Switzerland. From £3,050 per person.

Green hills with cypress trees and orange coloured farmhouse in Tuscany

FLORENCE AND TUSCANY BY RAIL TOUR

10-night rail and car touring holiday of Tuscany by train and car via Switzerland to Florence and the Chianti region. From £2,770 per person.

Ornate mural in white on grey stone of a wall in Florence

TUSCANY AND UMBRIA TOUR BY RAIL AND CAR

9-night touring holiday with an overnight stop each way, train to Florence return, then hire-car for touring and stays in Chianti and Umbria. From £2,610 per person.

Landscape of patchwork of green vineyards of Barolo in Piemonte

PIEMONTE AND BAROLO BY TRAIN HOLIDAY

7-night train holiday to Piemonte from London to Turin and back on day trains. Use of hire-car. One night in Turin and six nights in the Piemonte countryside near Barolo vineyards. From £1,990 per person.

Small colourful boats in harbour water with houses of red and ochre in Portofino

LIGURIA, PIEMONTE AND THE ITALIAN ALPS FLY-DRIVE TOUR

12-night fly-drive touring holiday from the Ligurian Riviera to the Italian Alps with stays in Santa Margherita, Piemonte and Cogne. From £4,070 per person.

Roman columns and stone arches around pool at Hadrian's Villa in Tivoli near Rome

THE HEART OF ITALY: TUSCANY, UMBRIA, AND LATIUM FLY-DRIVE TOUR

9-night fly-drive touring holiday exploring three regions at the Heart of Italy: Tuscany, Umbria and Latium, staying in Chianti, the Umbrian countryside and near Frascati. From £1,995 per person.

Turquoise pond with jets of water from fountains with terraced stone landscape and trees at Villa d'Este Tivoli near Rome

TUSCANY TO THE ALBAN HILLS NEAR ROME FLY-DRIVE TOUR

10-night fly-drive touring holiday from Tuscany through Umbria to Latium with stays in the Chianti region, Orvieto and near Frascati. From £2,595 per person.

ROMANTIC INTERLUDES ITALIAN FLY-DRIVE TOUR

9-night fly-drive touring holiday from the Ligurian Riviera, to Tuscany staying in Chianti and on the coast. From £3,940 per person.

Shleves with wine bottles in Barbaresco Piemonte

WINE TOUR OF PIEMONTE

4-night wine tour of Piemonte for a small group accompanied by an experienced wine and food expert, staying in a hotel with Michelin-starred restaurant, including visits and wine-tasting. From £3,920 per person.

Village of Barolo in middle of rows of green vineyards in Piemonte

VINEYARDS OF BAROLO AND BRUNELLO FLY-DRIVE TOUR

8-night fly-drive touring holiday including stays near Alba in Piemonte and Montalcino in Tuscany, with time to explore the vineyards of Barolo and Brunello. From about £2,890 per person.

Lanscape with gently sloping vineyards and dry hills in the distance in Sicily

WINE TOUR OF SICILY

7-night wine tour of Sicily for a small group accompanied by an experienced wine and food expert, staying in 4 different places, including visits and wine-tasting. From £3,980 per person.

Side of the Greek theatre in Taormina with umbrella pine tree and pink bougainvillaea in terraces of the town

SPLENDID SICILY: THE ISLAND OF SICILY FLY-DRIVE TOUR

12-night fly-drive touring holiday from Taormina to Palermo, staying at Taormina, Siracusa-Ortigia, Ragusa, Agrigento and Palermo. Choice of accommodation. From £2,830 per person.

GARDENS OF TUSCANY TOUR

6-night garden tour of Tuscany for small groups of up to 14 people in Chianti and Lucca areas reflecting the diversity of Tuscan villas and their gardens. From about £3,230 per person.

Outline against sky of the towers and houses of the Tuscan town of San Gimignano

WINE TOUR OF TUSCANY

4-night wine tour of Tuscany, in particular Chianti and Brunello, for a small group accompanied by an experienced wine and food expert, staying in Radda-in-Chianti, including visits and wine-tasting. From £3,450 per person.

Winding road through green fields lined with cypress trees in Tuscany and red poppy

TUSCANY BY CAR SELF-DRIVE TOUR

13-night self-drive holiday to Tuscany for a week’s stay with overnight stops in France, Italy and Switzerland both ways. From about £2,460 per person.

Scattered tall cypress trees lining track through fields in Tuscany

UNDER THE TUSCAN SUN TUSCANY IN DEPTH FLY-DRIVE TOUR

14-night fly-drive touring holiday including Lucca, Florence, Chianti, Cortona, Montalcino and the Maremma. From £4,220 per person.

Cluster of tall cypress trees together in middle of green rolling Tuscan fields

TUSCANY BY TRAIN HOLIDAY

9-night holiday by train and car to Tuscany with rail travel on Eurostar and overnight stops each way with 7 nights in the Chianti region of Tuscany with a hire-car. Stay 4-star charming hotel. From £2,740 per person.

ITALIAN LAKES AND PIEMONTE TWO-CENTRE HOLIDAY

8-night two-centre fly-drive holiday combining Lake Como and Piemonte staying in two luxurious and charming hotels. From £3,200 per person.

TRUFFLE HUNTING HOLIDAY IN PIEMONTE

4-night truffle-hunting holiday to Piemonte including a half-day truffle hunt and staying at a 4-star hotel with Michelin-starred restaurant in vineyards near Alba. From £2,650 per person.

Bottles and glasses of wine on table for tasting

WINE-TASTING HOLIDAY IN PIEMONTE

4-night holiday to Piemonte including a wine-tasting and a half-day visit with local guide to the village of Barolo, with transfers included. You stay at a 4-star hotel with Michelin-starred restaurant in vineyards near Alba and we include a hire-car so that you can explore on your own too. From £1,990 per person.

Rounds of bread and bowls of grain on table

COOKERY HOLIDAY IN SICILY

4-night cookery holiday in Sicily with hands-on cookery lessons and time to explore nearby Ragusa and Modica. From £1,490 per person.

Baglio Oneto aerial shot of hotel showing hotel buildings, pool and surrounding Sicilian countrysode

PAINTING HOLIDAY IN SICILY

4-night fly-drive luxury holiday to Sicily for local painting tuition. From about £1,180 per person.

Tuscan farmhouse surrounded by cypress trees standing in green field with mists

COOKERY AND WINE HOLIDAY IN TUSCANY

5-night Tuscan cookery and wine fly-drive luxury holiday based in the Chianti region. From about £2,490 per person.

Relais Villa Belpoggio Tuscany dining terrace outdoor breakfast table fruit toast

COOKERY HOLIDAY IN TUSCANY

4-night cookery holiday in Tuscany with hands-on cookery lessons with visits to local market, and pasta-making or a visit to an organic farm. From £1,860 per person.

FOOD AND WINE HOLIDAY IN TUSCANY’S CHIANTI

5-night food and wine luxury holiday at the 5-star Borgo San Felice, with Michelin-starred restaurant, in the Chianti classic region in Tuscany. Dinner with wine, wine-tasting and half-day cookery included. From £1,990 per person.

Stone carving of the emblem of the house of Medici on side of wall of building in florence

IN THE FOOTSTEPS OF THE MEDICIS HOLIDAY

4-night cultural break exploring the history of the Medici family in and around the city of Florence. You stay in a 5-star hotel on the River Arno just outside Florence and explore, with our guidance notes, in the city itself and by hire-car visiting the Medici villas. From £1,760 per person.

PAINTING HOLIDAY IN TUSCANY

6-night fly-drive luxury painting holiday in Tuscany’s Chianti countryside with three 3-hourly lessons from local painter included. From £1,990 per person.

TUSCAN COAST AND COUNTRYSIDE TWO CENTRE HOLIDAY

8-night two-centre fly-drive holiday combining the Tuscan coast and the countryside. Stay in two luxury hotels. From £2,770 per person.

TUSCANY AND UMBRIA FOOD AND WINE HOLIDAY

6-night fly-drive luxury holiday to Tuscany and Umbria for an authentic cookery and wine-tasting experience. From about £2,440 per person.

Hotel Borgo San Felice Tuscany courtyard bench flowers growing up wall

WINE-TASTING HOLIDAY IN CHIANTI

4-night wine-tasting holiday to Tuscany’s Chianti region including a wine-tasting of three regional wines at your hotel and an olive oil tasting. You stay at a 5-star hotel with Michelin-starred restaurant in amongst its own vineyards and we include a hire-car so that you can explore on your own too. From £1,920 per person.

Chef in whites holding strands of freshly made tagliolini

COOKERY HOLIDAY IN UMBRIA

4-night cookery holiday near Perugia in Umbria with hands-on cookery classes, wine-tasting and 2 dinners included. From £1,860 per person.

Bunch of olive leaves with olive oil in glass bottle Italy

OLIVE OIL TASTING HOLIDAY IN UMBRIA

4-night olive oil tasting and discovery holiday near Perugia in Umbria with hands-on cookery class, wine-tasting and 1 dinner included. From £1,650 per person.

IN THE FOOTSTEPS OF PALLADIO HOLIDAY

4-night holiday following in the work of the great High Renaissance architect Palladio, staying in a 4-star hotel at Vicenza and exploring the region with its Palladian villas by hire-car. From £1,090 per person.

LA MERIDIANA Liguria

A boutique, 5-star hotel with 25 rooms, golf course, pool and two restaurants in the countryside behind the Ligurian coast.

Villa Beccaris Piemonte windows shuttered windows traditional architecture

HOTEL VILLA BECCARIS Piemonte

A 4-star historic boutique hotel in the wine-town of Monforte d'Alba with 23 elegant rooms. Cosy bar and garden room for breakfasts. There are restaurants in the town within walking distance.

RELAIS SAN MAURIZIO Piemonte

This is a luxurious 5-star boutique resort-style hotel in the vineyards of Piemonte located in a monastery dating from the 17th century. Luxurious rooms, service and outstanding gastronomy.

RELAIS SANT'UFFIZIO Piemonte

A delightful 4-star hotel, tastefully furnished, with a spa and a Michelin-starred restaurant in Asti's Monferrato wine-country. Wine-tasting and truffle-hunting arranged.

RELAIS VILLA D'AMELIA Piemonte

A delightful 4-star with 37 rooms and suites surrounded by hazlenut groves and vines not far from Alba. Restaurant has a Michelin star. Beautiful courtyard and gardens.

RELAIS VILLA MATILDE Piemonte

This handsome 18th century villa was a summer residence for an aristocratic family and is now a 4-star hotel with 43 rooms and suites. The converted stables house the hotel's restaurant. Spa, pool and tennis.

BAGLIO ONETO Marsala

A 5-star hotel on a wine estate amongst vineyards and olive groves in Marsala. An historic main residence with Sicilian-style bedrooms with balcony. Restaurant serves indoors and outside on a panoramic terrace in the summer.

EREMO DELLA GIUBILIANA Ragusa, Sicily

A boutique 5-star deluxe hotel set amidst a country estate not far from Ragusa, and with a history dating back to the 12th century. All manner of local excursions and authentic experiences can be arranged here.

GIARDINO DI COSTANZA LUXURY RESORT Mazaro del Vallo, Sicily

This is a resort-hotel in the Sicilian countryside a few miles from the sea, 5-star with 91 rooms with balcony or terrace. There is a pool, spa and private beach with free shuttle in the summer months.

Foresteria La Planeta Sicily pool by night

LA FORESTERIA PLANETA Menfi, Sicily

A small luxury 4-star hotel on a prestigious wine estate in southern Sicily. An authentic Sicilian experience. Wine-tasting, cooking, contemporary art. Cosy rooms and super food.

BELMOND CASTELLO DI CASOLE Tuscany

A supremely comfortable and luxurious 5-star hotel with 39 rooms set on a Tuscan country estate with rooms in a mediaeval castle and the estate buildings. Outstanding quality of surroundings and activities.

Borgo Pignano exterior of hotel building shown with lawn in front and vines growing up building

BORGO PIGNANO Tuscany

A delightful 4-star hotel with 14 luxury bedrooms in an 18th century villa as well as self-catering houses on an extensive estate in Tuscany with organic farmland, olives and vines. Lots of local experiences and activities on the estate.

BORGO SAN FELICE Tuscany

A 5-star hotel and Relais & Chateaux member occupying the hamlet of a wine estate with 30 rooms and 30 suites, Michelin-starred restaurant, wine shop and wine-tasting on-site. Swimming, cycling and walking.

BORGO SANTO PIETRO Tuscany

A sumptuously furnished, luxurious 5-star boutique hotel of just 20 rooms and suites located in a country estate about 20 miles from Siena. Michelin-starred restaurant, exquisite gardens, estate activities.

CASTEL MONASTERO Tuscany

Resplendent in its history from the Middle Ages, this fortified hamlet is now a 5-star resort-hotel with 74 rooms and suites in the Tuscan countryside near Siena. Hearty Tuscan cuisine and authentic local experiences.

Castello Banfi Tuscany exterior path way lined with shrubs and flowers

CASTELLO BANFI IL BORGO Tuscany

A luxurious boutique hotel with just 14 rooms and suites on a prestigious wine estate near Montalcino. Delightful gardens, swimming pool with vineyard views, restaurants and wine boutique.

Castello di Velona Tuscany exterior pool in foreground hotel in background

CASTELLO DI VELONA RESORT Tuscany

A 5-star luxury thermal spa and wine resort with 45 rooms located in a converted fortified settlement dating from the Middle Ages, perched on a hill overlooking Brunello vineyards.

COMO CASTELLO DEL NERO Tavarnelle, Tuscany

Historic, 5-star, castle-hotel with 50 rooms on a wine estate in Chianti, Tuscany. Spa, Michelin-starred restaurant, tennis, pool. Tuscan experiences and activities.

GROTTA GIUSTI Tuscany

This is a 4-star hotel and thermal resort situated in a 19th century villa, now with 64 rooms and suites. Bathrooms have running thermal water. Spectacular large thermal pool and grotto. Nutrition progammes.

HOTEL LE RENAIE Tuscany

A charming, family-run 3-star hotel in the countryside 3 km from San Gimignano with a great local restaurant, pretty garden and swimming pool. Tremendous value. Just 25 rooms.

HOTEL VILLA LA PRINCIPESSA Lucca

An historic 4-star villa hotel in countryside just 4 kms from Lucca. 41 rooms and suites, pool and restaurant. Historic botanical park surrounds the hotel.

Il Faconiere Tuscany exterior hotel front trees and potted plants

IL FALCONIERE Tuscany

A country boutique 4-star hotel, Relais & Chateaux member, with just 22 rooms in a villa and cottages. One Michelin-starred restaurant, own vineyard, cooking classes, spa.

Exterior of hotel and greenery with pool infront

L'ANDANA Tuscany

This 5-star hotel with just 33 rooms stands in a country estate, with Michelin-starred restaurant, a couple of miles from the sea. Golf, cycling and wine appreciation all possible.

PALAZZO LEOPOLDO Tuscany

A boutique hotel in an historic town mansion in the centre of Radda, 4-star hotel, with 46 rooms and suites furnished cosily and traditionally with lots of Tuscan features.

PARK HOTEL VILLA ARISTON Lido di Camaiore, Tuscany

A 4-star superior hotel in historic villa and park buildings in gardens about 50 metres from the seafront in Lido di Camaiore on the Tuscan coast.

View of the exterior of the Relais La Suvera with a stone building with arched window and greenery outside

RELAIS LA SUVERA Tuscany

A unique opportunity to stay in an Italian stately home, now a 5-star hotel with 36 rooms and sumptuous suites, historic ambience and fine dining. A living museum in the Tuscan countryside.

Exterior of hotel with white flowers infront, shutters on windows and wall lamps glowing

RELAIS VILLA BELPOGGIO Tuscany

An historic home from home historic residence, 4-star standard, with just 10 rooms and suites near Arezzo. Beautiful garden, views, pool and authentic cuisine served inside or on the terrace.

Large thermal pool with stone building behind

TERME DI SATURNIA Tuscany

An exclusie 5-star spa resort in southern Tuscany, with 124 rooms and a park of hot springs and thermal pools. Golf, tennis and cycling also available. A unique spa experience.

VILLA LA MASSA Tuscany

An historic villa on the banks of the River Arno just outside Florence, now a 5-star hotel with 41 delightful rooms and suites. Pool, restaurant and shuttle service to the centre of the city.

View of the exterior of the hotel with leafy vines growing over the front

VILLA LE BARONE Tuscany

This is a charming 4-star hotel with 28 rooms housed in a genuine Renaissance villa in the Chianti countryside, full of character and personal service. Traditional restaurant, cosy rooms and beautiful gardens with views.

Exterior of hotel showing yellow building, freshly trimmed hedges and trees

HOTEL VILLA DI MONTE SOLARE Umbria

An aristocratic, historic villa on a country estate, now a 4-star boutique hotel with 27 luxurious and authentically-furnished rooms and suites. Lots of local flavour from the olive groves, walks, cookery classes and local dishes.

Entrance to hotel with stone walk way, grass and trees on either side and building in the distance

VILLA DEL QUAR Veneto

An historic villa with a history from Roman times, a short distance from Verona and amongst the Amarone vineyards, this national monument is a boutique 5-star hotel with 25 rooms, restaurant, excellent wine list and pool.

VILLA MICHELANGELO Veneto

A Palladian-style country villa, now a 4-star hotel with 52 rooms, in parkland less than four miles from Vicenza. An atmospheric base for exploring Vicenza and Palladio's Veneto.