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Holiday houses in Castiglione dei Pepoli

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Top-rated holiday rentals in Castiglione dei Pepoli

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Apartment in Castiglione dei Pepoli
4.97 out of 5 average rating, 180 reviews

Simona Comfort & Relax Apartment

🏡 Welcome to Simona Comfort & Relax Your home in the Apennines, between Bologna and Florence. ✨ STRENGTHS: 🔑 Self Check-in: Arrival in total freedom 24 hours a day. 🚗 A1 in 8 min: "Badia" exit. Ideal stop between North and South in both directions. 🏥 Nobili Clinic: Only 2 minutes (10 minutes on foot), to be close to your loved ones in a welcoming environment. 🌲 Apennines: Stage of the Via Lana e Seta and 5km from the Suviana and Brasimone Lakes. 📍 Close to the center: Restaurants, bars and services within walking distance of home.

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Top Guest favourite
A bright living area showcases large glass doors leading to an outdoor terrace with scenic views. A colorful area rug lies on the wooden floor, complemented by a modern sofa and decorative artwork on the wall. Natural light fills the space, enhancing its openness.
Home in Vaiano
5.0 out of 5 average rating, 279 reviews

The MOONLIT & SUNNY COTTAGE near Florence

IL COLLE DI FALTUGNANO: immersed in an olive grove on a Tuscan hills and with an amazing view of the valley, the stone cottage has been remarkably recovered a few months ago, a caravanserai a few century ago. In a strategic position close to Florence and Mugello is a good base for exploring Tuscany and be independent at the same time with supermarkets and restaurants just a few minutes away. Close to a farmhouse you can buy fresh local organic ingredients such as bio vegetables, eggs or cheese.

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Top Guest favourite
The exterior of the cottage is surrounded by greenery, featuring a sunlit terrace with a dining table and umbrella. Potted plants add color to the entrance, while the rustic charm of the stone and tiled details enhances the natural setting.
Home in Vaiano
4.99 out of 5 average rating, 290 reviews

Tuscan cottages in an ancient villa with a garden

The Cottage is part of a property owned by the Bernocchi family, which was already on maps of the area in the 1500s and is located right on an ancient Roman road that crossed the Calvana Mountains. About 9 km from Prato and 20 km from Florence. The Cottage, open on three sides, is situated in a panoramic position surrounded by a private park, ideal for walking and sports. A real home fitted with kitchen, living room, bedroom and bathroom. Large outdoor spaces, garden, and botanical garden.

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Top Guest favourite
Villa in Pistoia
4.99 out of 5 average rating, 86 reviews

Church of the Vaioni

An ancient deconsecrated church dating back to the early 1900s, originally built as a private chapel of Villa Philipson. Chiesino Dei Vaioni has a loft structure with two double bedrooms on two separate mezzanines. Outside, there is a kitchen with a wood-burning oven, private gardens with a tree-lined avenue and an olive grove. The gates and internal stairs were built by the Antica Fonderia Michelucci. Chiesino Dei Vaioni is immersed in the Tuscan countryside just minutes from the city.

ValueFamilyAccuracy

Guest favourite
A charming stone chalet is surrounded by colorful autumn foliage, featuring wooden shutters and a balcony that overlooks the landscape. The vibrant leaves contrast with the earthy tones of the building, while the lush green lawn is scattered with fallen leaves.
Cabin in Monzuno
4.96 out of 5 average rating, 121 reviews

House with a view surrounded by nature_ 5

A cozy stone and wood chalet with amazing views of the Apennines, surrounded by nature with a large garden where you can relax and enjoy the spectacular sunsets. We will be happy to host you on the ground floor which is dedicated to the B&B. The warm and welcoming rooms have independent entrances and lead onto the garden. Fantastic location between Bologna and Florence, 10' from the motorway exit and 30' from Bologna airport. Don't miss the sunset, even better with a good glass of wine!

ValueFamilyView

Guest favourite
A bright hallway connects several rooms, featuring wooden doors that lead to inviting spaces. A white console table, adorned with a flower arrangement and books, adds a touch of decor. Natural light filters through a nearby window, enhancing the warm tones of the tiled floor.
Home in Castiglione dei Pepoli
4.91 out of 5 average rating, 338 reviews

House nestled in the Apennines

The house is near the path of the gods and the wool and silk roads. The 120 sqm house, consisting of a kitchen with dining room, bathroom, dining room, laundry room, 2 double bedrooms (with 4-door wardrobe), single bedroom (with 4-door wardrobe), laundry room and garden. Immersed in the green of the Emilian Tuscan Apennines, about 45 km from Bologna and Florence, with a breathtaking landscape and perfect for those who want to walk and get away from the weariness of the city.

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Top Guest favourite
A landscape view reveals rolling hills in autumn hues, with vibrant foliage in shades of orange and gold. In the distance, a church steeple rises against a backdrop of mountains under a soft, cloudy sky, suggesting a serene and picturesque rural setting.
Apartment in Monzuno
4.96 out of 5 average rating, 280 reviews

Gorgeous One Bed Villa Overseeing the Apennines

Charming one-bedroom in Italian villa with a private terrace and brand-new air conditioning! Just a short walk from the famous Via degli Dei trail, this cozy retreat features a fully equipped kitchen, private bathroom, queen bed and breathtaking mountain views from your bedroom window. The friendly family below grows fruit and nuts and makes cakes, sauces and fresh pasta from scratch. Enjoy authentic countryside living with modern comfort and a warm, welcoming atmosphere!

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Top Guest favourite
Tower in Castiglione dei Pepoli
5.0 out of 5 average rating, 54 reviews

Ancient manor La Ploca

A charming studio apartment, perfect for couples looking for romance, solo travelers, or anyone who wants to break away from the routine and rediscover the beauty of nature and history. Nature, History and Relaxation in the Tuscan-Emilian Apennines. Experience the unique experience of staying in an authentic 14th-century manor, which belonged to the ancient family of the Counts Pepoli, immersed in a large park in Castiglione dei Pepoli, between Bologna and Florence.

LocationBathroomIndoor spaces

Guest favourite
Home in Scarperia e San Piero
4.92 out of 5 average rating, 12 reviews

Villa in Mugello, a stone's throw from the Autodromo

Independent villa with private road, 5 minutes from Scarperia and the Autodromo del Mugello. It has 5 double bedrooms and 3 bathrooms, ideal for groups and families. Infinity pool with breathtaking views of the hills, perfect for relaxing in total privacy. Comfort, tranquility and strategic location to make the most of Mugello. We would also like to inform you that there is an additional tourist tax, not included in the price, of 2 euros per person per night.

LocationFamilyCleanliness

Guest favourite
An inviting terrace is presented with a dining set, featuring a table adorned with candles and glasses. Soft lighting highlights the space against a backdrop of rolling hills under a twilight sky, while plants and decorative stones frame the area.
Holiday home in Montagnana
4.94 out of 5 average rating, 163 reviews

[Overlooking the hills] Green Hill Maranello

Style, light, silence and a breathtaking view of the hills. An exceptional flat just 10min from Maranello. The house, completely renovated and furnished with taste and attention, consists of: -Large living area with living room with sofa bed and fully equipped kitchen - Large panoramic terrace - Two elegant double bedrooms - Bathroom with shower Powerful wifi and private parking. An oasis of relaxation and nature, 10min drive from all city services!

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Top Guest favourite
Condo in Traversa
5.0 out of 5 average rating, 17 reviews

Anna's little house

Lovely renovated ground floor apartment, 2 bedrooms with 6 beds, kitchen, amenities, independent heating. Located in the town of Traversa - Firenzuola near the Via degli Dei, Strada Romana Flaminia Militare, Passo della Futa and near the naturalistic oasis of Covigliaio. Only 40 minutes from Florence and Bologna surrounded by nature and at the same time close to groceries, bars and restaurants Tourist tax €2 Please register: IT048018C2ZLAEZGCS

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Superhost
An outdoor space featuring a private pool surrounded by lush greenery. Lounge chairs are positioned along the poolside, and a gazebo provides shaded seating. The garden is well-maintained with colorful plants and a grassy area, creating an inviting environment for relaxation.
Villa in Castel di Casio
4.85 out of 5 average rating, 102 reviews

RelaisMor Villa with park in the Tuscan-Emilian Apennines

Bring the whole family and your friends to this great place with lots of space to have fun and relax surrounded by nature. Large garden and pine forest within walking distance of Lake Suviana, Rocchetta Mattei, the PORRETTA Thermal Baths and the medieval village of Castel di Casio. Available for overnight stays but also for events. Possibility of using the pool during the summer. Hot tub for a fee according to use.

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Popular amenities for Castiglione dei Pepoli holiday rentals