
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.
LocationFamilyCleanliness
5.0 out of 5 average rating, 18 reviews
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.
LocationFamilyDecor
4.95 out of 5 average rating, 100 reviews
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.
ValueFamilyBeach
5.0 out of 5 average rating, 58 reviews
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.
FamilyLocationQuiet
4.97 out of 5 average rating, 119 reviews
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.
ValueLocationHiking
4.89 out of 5 average rating, 1010 reviews
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.
FamilyValueComfort
4.86 out of 5 average rating, 1005 reviews
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.
LocationFamilyBeach
4.94 out of 5 average rating, 48 reviews
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.
FamilyLocationParking
5.0 out of 5 average rating, 10 reviews
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.
FamilyLocationCheck-in
4.98 out of 5 average rating, 130 reviews
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!
FamilyLocationSleep quality
4.95 out of 5 average rating, 22 reviews
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.
FamilyLocationQuiet
5.0 out of 5 average rating, 17 reviews
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.
LocationFamilyAccuracy
5.0 out of 5 average rating, 13 reviewsPopular amenities for Cupramontana house rentals
House rentals with a pool

Laura's Country House
LocationFamilyAmenities
4.97 out of 5 average rating, 75 reviews
GrazieSole Agriturismo exclusive whole house
FamilyLocationNearby
5.0 out of 5 average rating, 8 reviews
Stone Villa: view, pool, bbq, a/c ensuite bedrooms
ValueLocationAccuracy
4.99 out of 5 average rating, 73 reviews
Almifiole
FamilyLocationKitchen
5.0 out of 5 average rating, 21 reviews
Sunset Breath
LocationFamilyDecor
4.93 out of 5 average rating, 14 reviews
Tenuta Sant'Apollinare
FamilyValueCleanliness
4.96 out of 5 average rating, 51 reviews
Villa, 5 minutes from downtown Fano
LocationBathroomGetting around
5.0 out of 5 average rating, 11 reviews
Farmhouse with pool Fano-Urbino
FamilyLocationHospitality
4.96 out of 5 average rating, 23 reviewsWeekly house rentals

The cottage in nature
ValueLocationIndoor spaces
4.77 out of 5 average rating, 35 reviews
Lucy's House | Wellness Cave & Panoramic Views
LocationFamilyCheckout
4.96 out of 5 average rating, 25 reviews
The View House
LocationNearbyIndoor spaces
5.0 out of 5 average rating, 3 reviews
Montana House in Stone-Garden-Panorama-Jacuzzi
ValueLocationHospitality
4.96 out of 5 average rating, 45 reviews
CasaLu
LocationConditionGetting around
5.0 out of 5 average rating, 13 reviews
Genga Terme Retreat | Cozy 1 BR Apt. near Frasassi
LocationValueComfort
4.85 out of 5 average rating, 20 reviews
Elegant apartment by the sea, air conditioning, Wi-Fi, parking
FamilyValueHiking
4.86 out of 5 average rating, 44 reviews
The Abbot's Garden close to Spello / Assisi
LocationFamilyCheck-in
4.99 out of 5 average rating, 82 reviewsPrivate house rentals

[Calende] Parking & Basilica, 2 Min. Walk
FamilyLocationCleanliness
5.0 out of 5 average rating, 13 reviews
Farmhouse in the hills 10 minutes from the sea of Senigallia
FamilyLocationBeach
5.0 out of 5 average rating, 46 reviews
Between the hills and the adriatic coast
FamilyValueCondition
4.88 out of 5 average rating, 49 reviews
The B&B La Spiga
ValueLocationKitchen
5.0 out of 5 average rating, 24 reviews
Casa Bettini
FamilyValueOutdoor spaces
5.0 out of 5 average rating, 15 reviews
Exclusive luxury farmhouse with infinity pool
FamilyLocationBathroom
4.94 out of 5 average rating, 18 reviews
Rustic hillside stone
LocationOutdoor spacesNearby
4.88 out of 5 average rating, 17 reviews
Bottega -Rustico -Fantastic view /Natural pond
FamilyLocationCondition
4.88 out of 5 average rating, 52 reviewsDestinations to explore
- Riviera del Conero
- Misano World Circuit
- Senigallia Beach
- Basilica of St Francis
- Palacongressi Della Riviera Di Rimini
- Frasassi Caves
- Sibillini Mountains National Park
- Spiaggia Urbani
- Furlo Gorge Nature Reserve
- Sibillini Mountains
- Oltremare
- Shrine of the Holy House
- Fiabilandia
- 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





