
Holiday rentals in Cupramontana
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Top-rated holiday rentals in Cupramontana
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Farmhouse in Nature
Country house that offers moments of tranquility in a serene atmosphere, we produce DOC wine and EVO Oil. The Marche region is full of wonders given by Mother Nature, the sea, the mountains, the valleys dotted with rivers, the gorges and the natural passes of the Apennines, or built by the wisdom of renowned artists. But the works created by the simple hand of the farmer certainly do not disfigure in the panorama that opens before your eyes. "...may your walk be light, traveler, and your heart light."

Villa degli Olivi
Nestled among the ancient olive trees, Villa degli Olivi offers a haven of serenity and sophistication and is a short stroll into the cobblestoned paths of Spello along a flat, tree lined lane. This recently renovated Villa offers modern luxury while maintaining its Italian roots. Offering 4 bedrooms, 3 full baths and the possibility for 2 additional guests with a sleeper sofa. A cozy studio apartment with full kitchen, bathroom, laundry and sleeper sofa is also available for an additional cost.

Penthouse BeachFront All Inclusive for Families
Luxury SeaFront Penthouse with a 360° Stunning View for Families and Large Groups of up to 10 People. ALL INCLUSIVE: • Private Beach in Front of the House: with 3 Umbrellas, 9 Sunbeds, and a Free Pool⛱️ • Super Breakfast at 2 Top Bars 🥐 • 2 Parking Spaces 🅿️ This 140m2 Super Loft is located in Fano's most central building: restaurants, bars, supermarkets, and shops, just 100 meters from the historic center. Furnished to the highest standards with the best Made in Italy products.

Wellness Grotto & Panoramic View | Casa di Lucy
• A unique retreat in the heart of Spello • Unwind in the private panoramic courtyard with hot tub, outdoor fireplace, and the silent Umbrian valley stretching out before you. Step inside, light the fireplace, and descend into your private wellness grotto: infrared sauna and chromotherapy hydromassage tub, for your exclusive use throughout your entire stay. No timetables, no other guests. Just you. 🫧 Full exclusive access to the wellness grotto is included with every booking 🫧

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.

The house in the old granary
The country farm, surrounded by olive trees and centuries-old oaks, will be all for you just 25 minutes from the sea and an hour from the Sassotetto ski slopes. Ideal for couples or families looking for relaxation, our house is immersed in a silence of yesteryear. You are a 10-minute drive from Macerata and half an hour from the beaches. The space will be at your exclusive disposal. We have a Home Theater with HiFi system. A wood-burning oven is available upon request.

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.

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 hot tub, 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.

Delicious Treats in Cupramontana
Delightful apartment in a beautiful 18th century building located in a quiet alley of the historic center. The completely renovated apartment with striking stone and brick vaults is very cool and is ideal for 6 travelers. Delightful holiday home in a beautiful 18th century building located in a quiet alley of the historic center. The fully renovated apartment with striking stone and brick ceilings is very cool and is ideal for 6 travelers.

Casetta Valentina Former barn
Casetta Valentina is a former barn inside the courtyard of the Casale del Gelso (an old farmhouse from the late 1800s) and located in the Marche countryside. Independent, it consists of an apartment of about 60 square meters. Very bright and panoramic, it has a terrace/solarium and a pleasant and beautiful private space. Newly renovated, it has all the comforts, harmonizing tradition with modern needs.

The Guest House of the Tavignano Estate
The Tavignano estate is located in the heart of the Marche region, within the famous DOC of Verdicchio dei Castelli di Jesi, between the valleys of the river Esino and the Musone on one side, and between the Apennines and the sea on the other side. From the highest promontory of the Estate dominates the manor house, which houses the barrique, the family house, and an elegant Guest House.
Popular amenities for Cupramontana holiday rentals
Other great holiday rentals in Cupramontana

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Loft with hot tub

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





