
House holiday rentals in Cupramontana
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Top-rated house rentals in Cupramontana
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Farmhouse in the hills 10 minutes from the sea of Senigallia
Our farmhouse was completely renovated in 2017 in the original Marche style. The house is bright and modern and equipped with all comforts. An outdoor garden offers sweeping views of the hills. The quiet and peaceful place will make you spend days of full relaxation! In the garden you will find Wendy, a friendly playful Labrador who will be adopted by you for the duration of your vacation, and some cats. NB Tourist tax: the municipality of Senigallia applies a tourist tax of 1 euro per day per person for those over 14 years of age, up to a maximum of 7 days of stay

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.

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.

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.

DREAM IN THE HEART OF 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.

Montana House in Stone-Garden-Panorama-Jacuzzi
House on two levels connected by an internal staircase, with independent entrances. On the ground floor there is a fully equipped kitchen, a living area, and a bathroom with a whirlpool bathtub. Upstairs you’ll find two bedrooms, including one with a double bed, a versatile room that can be used as a living room or bedroom, and a second bathroom. Three satellite TVs. Spacious, well-kept and comfortable interiors, ideal for couples, families or small groups looking to relax.

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.

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.

Wellness Cave & Panoramic Views | Lucy's House
• A unique retreat in the heart of Spello • Unwind in the private panoramic courtyard with an outdoor heated hot tub, open-air fireplace, and the silent Umbrian valley stretching out before you. Then descend into your private wellness grotto — infrared sauna and chromotherapy hydromassage tub — yours alone, with no timetables and no sharing, for your entire stay. 🫧 Full exclusive access to the wellness grotto is included with every booking 🫧

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!

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.

Borgobo' Farmhouse independent orange house
Borgobo' is located within the Gola della Rossa and Frasassi Park. It's a collection of small houses, narrow lanes and steep lawns—a little 17th-century village. The view from Borgobo’ takes in glimpses of unspoilt landscapes caressed by the wind, where everything is in harmony in its wildest form. Several trails leave from the village and run through the park.
Popular amenities for Cupramontana house rentals
House rentals with a pool

Country House with Pool and Garden

GrazieSole Agriturismo exclusive whole house

Laura's Country House

Breath of Nature

Farmhouse with pool Fano-Urbino

Stay in nature: Casa Kikenda Relais

Stone Villa: view, pool, bbq, a/c ensuite bedrooms

Almifiole
Weekly house rentals

Between the hills and the adriatic coast

The Pope's Caprice

The Colored House

CasaLu

Lulli's house. Relaxing on the Marche hills

The cottage in nature

Sorgiva

Casa Flavia
Private house rentals

Sweet hills

La Bellavista - Garden & View relax historic center

Spello Sant'Onofrio

House in the hills with sea view, 3 km from the beach

Casa dei Valli – Duchy of Urbino

Exclusive apartment by the sea, AC, Wi-Fi, parking

Views from the roof of Le Marche

Romantic suite in the village of Castelleone di Deruta.
Destinations to explore
- Riviera del Conero
- Misano World Circuit
- Senigallia Beach
- Frasassi Caves
- Basilica of St Francis
- Palacongressi Della Riviera Di Rimini
- Sibillini Mountains National Park
- Spiaggia Urbani
- Shrine of the Holy House
- Oltremare
- Fiabilandia
- Furlo Gorge Nature Reserve
- Sibillini Mountains
- Sirolo
- Tennis Riviera Del Conero
- Parco Naturale del Monte San Bartolo
- Mount Subasio
- Gola del Furlo
- Rocca Roveresca
- Castello di Gradara
- Rocca Maggiore
- Spiaggia della Torre
- Fonti Del Clitunno
- Cathedral of San Lorenzo





