
House vacation rentals in Cupramontana
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Top-rated house rentals in Cupramontana
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Charming detached country cottage
Charming cottage in the hamlet of Castellaro di S.S.Quirico (AN), in a rustic, simple and comfortable style. With its two bedrooms and two bathrooms, it can comfortably accommodate up to 5 people. Fenced garden for the relaxation of guests and their animal friends. Parking spaces in the courtyard. Very quiet and private location but only 6 minutes from the SS76 connecting Ancona and Perugia. It is located 15 minutes from the Frasassi Caves; 20 minutes from the towns of Jesi and Fabriano; 35 minutes from the beaches.
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An ancient Villa in Gubbio
The "Bishop" is part of a complex of 1300 d.c. and rebuilt by the Bishop Maria Cavalli.It was built on Mastro Giorgio Andreoli Properties, the Greatest ceramist painter of All Time . Place in front of the Episcopal palace and just beside the offices of the Curia, our wonderful place is in the Ancient Heart Center of Gubbio. Few steps From the monuments more representative of the city as the famous Palazzo dei Consoli, the Ducal Palace, the Cathedral and the best restaurants and craft shops.
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Farmhouse with garden and pool for exclusive use of wifi
Casale Nonno Dario is a typical Marche countryside home nestled in the hills of the Balcone delle Marche and a strategic position to enjoy the surrounding beauty from the sea to the mountains It is located in the hamlet of Castelletta and includes a living area with a lounge, kitchen and fireplace. Bathroom with shower. Sleeping area with 3 double bedrooms and the possibility of adding a crib and a cot. Large outdoor garden with swimming pool, umbrella, barbecue Free parking on the property.
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GrazieSole Agriturismo exclusive whole house
The GrazieSole farmhouse is a newly renovated 1900s farmhouse, in a characteristic style with original stone walls, exposed bricks and ceilings with wooden beams, it has a 12-metre swimming pool with breathtaking views and a wide panorama that extends from the Sibillini Mountains to the adjacent hillside villages. It is located in open countryside one kilometer from the center of the village of Penna S. Giovanni, in a sunny and quiet position, surrounded by a garden and large green spaces.
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All-Inclusive Sea Villa • 16 Guests • Beach&Center
⭐ ALL-INCLUSIVE LUXURY FOR GROUPS UP TO 16 🏖 Beach Resort + 🥐 Breakfast + 🅿️ Parking + 🫧 Jacuzzi + 🪴 Garden INCLUDED 📍 1 min walk to beach & historic centre ✨ This is not just a house — it’s a full experience. Stay in the heart of Fano, just 1 minute walk from both the beach and the historic centre. Perfect for families and large groups up to 16 guests who want space, privacy and everything already included. Everything is designed to give you maximum comfort with zero stress.
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A JUMP IN THE ANCIENT ASSISI PERFETTA LETIZIA HOME
In the heart of the ancient Roman city of Asisium, between the splendid theater and the suggestive forum, where narrow streets with enchanting gaps run between arches, flowered vases, intertwining staircases, gardens, stone walls, and a luxurious villa still stands. Inhabited since the dawn of time by a noble family, it is still today embellished by a marvelous and large garden with a breathtaking view of the imposing Rocca and the entire deep valley: this is our structure.
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The Colored House
"La Casa Colorata" is a structure from another time. Immersed in the typical countryside of the area where the hills, carpeted with fields of wheat, sunflowers and vineyards, envelop the eye without parsimony. You can experience authentic contact with nature, whose scents and sounds will accompany you at any time of day. The farmhouse is surrounded by various types of trees: mulberry trees, rose gardens, fruit trees and the historic passion for flowers of all kinds.
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The cottage in nature
The house is a small apartment converted from a Marche-style farmhouse. Traditional furnishings revisited in a modern way and the use of natural materials make it authentic, cozy and intimate. It is located on the ground floor, overlooking a large lawn with a view of the green hills. It has a kitchenette with a fridge, sink, two electric hobs and a microwave. A refuge where you can experience regenerating moments in a disruptive nature and discover a rich territory
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Casale del Menotre | Countryside Umbrian Retreat
Just minutes from Assisi, between Rasiglia, Spello, and the Menotre Waterfalls, the tourist rental welcomes you. After a day discovering Umbria, just relax in the hydromassage, hammock, deckchairs and BBQ area immersed in nature and the silence of the Umbrian landscape. The house has Wi-Fi, Smart TV with access to personal Netflix, air conditioning and 3 bedrooms, one of which has a private bathroom. Non-entrepreneurial tourist rental without additional services.
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Dimora nel Borgo - A Relaxing Home
The “Dimora nel Borgo” is a cozy home in the medieval historic center of Maiolati Spontini. It offers a relaxed and comfortable atmosphere, thanks to the recent and careful renovation, and the quiet and peaceful surrounding environment, inside a courtyard of yesteryear. A few meters from the house there are always free parking spaces available, there are no ZTL restrictions regarding the historic center. The house is complete with all amenities.
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Apartment for 4 pers. with pool, min stay 5 nights
Peace, space, and panoramic views Escape the crowds in this peaceful little paradise. Enjoy our panoramic pool with comfortable sun loungers and relaxed hammocks on the large terrace. While you’ll find complete privacy here, the medieval village of Poggio Cupro is just a few minutes' walk away. For cozy restaurants, bars, and shops, a 5-minute drive (2 km) takes you to Cupramontana. The perfect home base for discovering authentic Italy!
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Casa Raggia
Welcome to your oasis of tranquility! This beautiful modern wooden semi-detached house, surrounded by the countryside, is the ideal retreat for those who want to relax in nature without sacrificing comfort and design. Made with natural and eco-friendly materials, the house is furnished with taste and attention to detail, offering a welcoming, bright, and contemporary environment.
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Popular amenities for Cupramontana house rentals
House rentals with a pool

Stone Villa: view, pool, bbq, a/c ensuite bedrooms
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Almifiole
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Country House with Pool and Garden
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Villa, 5 minutes from downtown Fano
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Tenuta Sant'Apollinare
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Laura's Country House
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Casa Magica - House with private Pool, Marche
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Farmhouse with pool Fano-Urbino
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Weekly house rentals

Montana House in Stone-Garden-Panorama-Jacuzzi
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Agriturismo Borgobo' independent orange house
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The View House
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CasaLu
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Lucy's House | Wellness Cave & Panoramic Views
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Casa Flavia
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Nido Visone Apartment
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CASA DE NONNA PEPPA farmhouse all to yourself
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Private house rentals

PalmHouse Cristian
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House in the hills with sea view, 3 km from the beach
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Casa dei Valli – Duchy of Urbino
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Genga Terme Retreat | Cozy 1 BR Apt. near Frasassi
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Exclusive luxury farmhouse with infinity pool
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Ca'Mi House - Stone farmhouse
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Casale Sotto le Stelle
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The Bookhouse home B&B
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Destinations to explore
- Riviera del Conero
- Misano World Circuit
- Senigallia Beach
- Palacongressi Della Riviera Di Rimini
- Basilica of St Francis
- Frasassi Caves
- Sibillini Mountains National Park
- Spiaggia Urbani
- Sibillini Mountains
- Furlo Gorge Nature Reserve
- Shrine of the Holy House
- Fiabilandia
- Oltremare
- Parco Naturale del Monte San Bartolo
- Sirolo
- Mount Subasio
- Tennis Riviera Del Conero
- Gola del Furlo
- Castello di Gradara
- Rocca Roveresca
- Spiaggia della Torre
- Fonti Del Clitunno
- Rocca Maggiore
- Cattedrale di San Rufino





