
House vacation rentals in Cupramontana
Find and book unique houses on Airbnb
Top-rated house rentals in Cupramontana
Guests agree: these houses are highly rated for location, cleanliness, and more.

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.

Casa Annadelis with a view of Monte Nerone, Cagli
We are in Cerreto (a hamlet of Cagli), at the foot of Mount Nerone, in the central Apennines. From the top of the mountain you can enjoy a unique and absolutely relaxing view Possibility of CAI trails and routes 3 km from the Arch of Fondarca (Pieia). In Pianello you can find a grocery store, post office and other primary services, just 5 minutes by car. Gubbio 35 km away, Urbino 50 km away, the fantastic Furlo Gorge 20 km away. The ideal place to relax surrounded by nature among meadows, woods, rivers

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.

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.

Country Garden House: Tranquility in Spello Center
Located in the historic centre and near the famous Spello landmark, the Torri di Properzio, "La Bicicletta Rosa" provides three bedrooms, a balcony, terrace and a PRIVATE GARDEN for guests with stunning country views. Our light and spacious house is perfect for your holiday in Umbria--for a family or group of friends, or as a romantic getaway for a couple. The house is just a few minutes walk to the main squares with their many local restaurants, wine shops, and cafes.

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.

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 Home
• 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.

Agriturismo Borgobo' independent orange house
Borgobo' is inside the Rossa and Frasassi Gorge Park. It is a collection of small houses, alleys and steep meadows, a small village from the 17th century. The gaze of those in Borgobo' embraces glimpses of pristine landscapes caressed by the wind, where everything is in harmony in the wildest form. From the village, there are several paths that cross the Park.
Popular amenities for Cupramontana house rentals
House rentals with a pool

Almifiole

Sant 'Agelicahouse

Breath of Nature

Getaway to Umbria, Villa Claudia

Casa Ambrogi with jacuzzi hot tube

GrazieSole Agriturismo exclusive whole house

Laura's Country House

Farmhouse with pool Fano-Urbino
Weekly house rentals

Farmhouse in the hills 10 minutes from the sea of Senigallia

The little house in the hills

The cottage in nature

Casa Flavia

Nido Visone Apartment

CasaLu

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

Sorgiva
Private house rentals

Casa Cicetta Accommodation 1296

Casale Castro: Serrina Apartment

Between the hills and the adriatic coast

House of Olives

The Abbot's Garden close to Spello / Assisi

[Calende] Parking & Basilica, 2 Min. Walk

Oasi delle Gazze Holiday Home

Casa dei Valli – Duchy of Urbino
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





