A historic stone building with a tower, a pathway leading to it, and a grassy area with scattered flowers.

Cupramontana Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Cupramontana holiday rentals

A person in a hot tub with a glass of wine, surrounded by a wooden deck and lush greenery in the background.

1. House in the medieval village of Castelletta, at an elevation of 700 meters, in the Gola della Rossa Park

House in the medieval village of Castelletta, at an elevation of 700 meters, in the Gola della Rossa Park
Castelletta
The price is AU$200
includes taxes & fees
11 Nov - 12 Nov
House in the medieval village of Castelletta, at an elevation of 700 meters, in the Gola della Rossa Park
Two white plastic lounge chairs with floral cushions, positioned on a grassy area with trees and a brick wall in the background.

2. Casa Vacanze Merion

Casa Vacanze Merion
Arcevia
10.0 out of 10, Exceptional, (1 review)
"La signora Mariagrazia davvero molto accogliente, mi ha offerto anche la visciola un vino fatto con le ciliegie. Appartamento immerso nella tranquillità dove si gode un bel panorama delle colline marchigiane. Vicino all’appartamento c’è un negozio di alimentari e un forno dove fanno una crostata che è uno spettacolo … 🔝 per tutto!"
Italy
Giovanni
The price is AU$111
includes taxes & fees
10 Dec - 11 Dec
Casa Vacanze Merion
A modern bedroom with a bed, a desk, and a chair.

3. Ospitalità Il Prato Jesi

Ospitalità Il Prato Jesi
Jesi
The price is AU$82
includes taxes & fees
10 Nov - 11 Nov
Ospitalità Il Prato Jesi
A person in a hot tub with a glass of wine, surrounded by a wooden deck and lush greenery in the background.

4. In the sprawling village of Castelletta in the Gola della Rossa Park.

In the sprawling village of Castelletta in the Gola della Rossa Park.
Castelletta
The price is AU$195
includes taxes & fees
10 Nov - 11 Nov
In the sprawling village of Castelletta in the Gola della Rossa Park.
A person in a hot tub with a glass of wine, surrounded by a wooden deck and lush greenery in the background.

5. House in the village of Castelletta, at an elevation of 700 meters, in the Gola della Rossa Park

House in the village of Castelletta, at an elevation of 700 meters, in the Gola della Rossa Park
Castelletta
The price is AU$192
includes taxes & fees
10 Nov - 11 Nov
House in the village of Castelletta, at an elevation of 700 meters, in the Gola della Rossa Park
An open door leading to a balcony with a tiled floor and a view of a street.

6. Ravasio House in the Heart of the Marche Region, Amid Historic Villages and Panoramic Views

Ravasio House in the Heart of the Marche Region, Amid Historic Villages and Panoramic Views
Montale
The price is AU$116
includes taxes & fees
10 Nov - 11 Nov
Ravasio House in the Heart of the Marche Region, Amid Historic Villages and Panoramic Views
Kitchen

7. Italian Experience-Movie Suite Jesi

Italian Experience-Movie Suite Jesi
Iesi
The price is AU$415
includes taxes & fees
11 Nov - 12 Nov
Italian Experience-Movie Suite Jesi
A modern reception desk with a curved design, a laptop on top, and pendant lighting.

8. Rooms & Breakfast Centrale

Rooms & Breakfast Centrale
Fabriano
10.0 out of 10, Exceptional, (3 reviews)
"CONSIGLIATISSIMO A TUTTE le persone che vogliono aver e che fare con un locatore capace di soddisfare il soggiorno perfetto … educato gentile sa ascoltare e se possibile risolvere qualsiasi quesito!!, la struttura è nuovissima completa di tutto il necessario la pulizia è estrema !! GRAZIE MILLE DEL PERFETTO SOGGIORNO CHE ABBIAMO TRASCORSO NELLA TUA STRUTTURA!!"
Italy
Max
The price is AU$108
includes taxes & fees
10 Nov - 11 Nov
Rooms & Breakfast Centrale
A small outdoor patio with a black table, a barbecue grill, and a tray with drinks and snacks.

9. [La Casetta] Bilocale Centrale con Terrazza Parcheggio Gratuito Wifi PS4 Minipc

[La Casetta] Bilocale Centrale con Terrazza Parcheggio Gratuito Wifi PS4 Minipc
Jesi
10.0 out of 10, Exceptional, (2 reviews)
"We were just passing through and were able to relax after the long drive. All the comforts and a very well-kept ambiance, including a small terrace, made our stay very pleasant. Communication with the owner and check-in went smoothly. Highly recommended!"
Germany
G. C.
The price is AU$154
includes taxes & fees
12 Nov - 13 Nov
[La Casetta] Bilocale Centrale con Terrazza Parcheggio Gratuito Wifi PS4 Minipc
A stone building with a gated entrance, arched windows, and a small balcony.

10. Country House Federico I

Country House Federico I
Sassoferrato
9.6 out of 10, Exceptional, (18 reviews)
"Ok"
Italy
Costantin
The price is AU$105
includes taxes & fees
10 Nov - 11 Nov
Country House Federico I
A hallway with a radiator, wooden doors, and a tiled floor.

11. Charming Holiday Apartment in Ostra

Charming Holiday Apartment in Ostra
Ostra
The price is AU$125
includes taxes & fees
10 Nov - 11 Nov
Charming Holiday Apartment in Ostra
A rustic room with exposed brick walls, a bed, a sofa, a small round table, and a fireplace.

12. La casa sulle mura in Borgo Loretello

La casa sulle mura in Borgo Loretello
Loretello
The price is AU$211
includes taxes & fees
11 Nov - 12 Nov
La casa sulle mura in Borgo Loretello
Inside other

13. Movie Suite Jesi by Interhome

Movie Suite Jesi by Interhome
Jesi
The price is AU$417
includes taxes & fees
12 Nov - 13 Nov
Movie Suite Jesi by Interhome
A swimming pool with water cascading from a fountain, surrounded by a wooden deck and a white building in the background.

14. Villa Coralia

Villa Coralia
Osimo
9.4 out of 10, Exceptional, (22 reviews)
"Outstanding location with pleasant staff. Incedible views to the surrounding countryside. "
Canada
David
The price is AU$175
includes taxes & fees
10 Nov - 11 Nov
Villa Coralia
A rustic building with a brick facade, a clock, and a staircase leading to a balcony.

15. La suite in piazza in Borgo Loretello

La suite in piazza in Borgo Loretello
Loretello
The price is AU$230
includes taxes & fees
10 Nov - 11 Nov
La suite in piazza in Borgo Loretello
A living room with a white sofa, a coffee table, a dining table with clear chairs, a chandelier, and exposed wooden beams.

16. Italian Experience - La Casa in Centro

Italian Experience - La Casa in Centro
Filottrano
The price is AU$283
includes taxes & fees
10 Nov - 11 Nov
Italian Experience - La Casa in Centro
An arched courtyard with a brick floor, a pergola, and a table with chairs.

17. La Dimora del Borgo

La Dimora del Borgo
Montecassiano
10.0 out of 10, Exceptional, (1 review)
"What a wonderful, hidden jewel! If you are looking for a true medieval experience with all the modern comforts THIS IS IT! Right off the bus stop, Montecassiano is a beautiful medieval village, with a historic piazza, typical italian bars to grab a breakfast or apperativo. For dinner, I highly recommend La Taverna San Nicola across the hotel with a fantastic wine selection and a unique presentation of popular polenta dish. Well worth the trip!!"
United States
Gabriel
The price is AU$110
includes taxes & fees
10 Nov - 11 Nov
La Dimora del Borgo
A modern building with a large spherical sculpture in the foreground, surrounded by a well-maintained lawn.

18. Villa Gens Camuria

Villa Gens Camuria
Camerano
9.6 out of 10, Exceptional, (57 reviews)
"Clean, friendly very accommodating pool excellent a great place to stay all year round."
United Kingdom
antonio
The price is AU$144
includes taxes & fees
15 Nov - 16 Nov
Villa Gens Camuria
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cupramontana Hotel Reviews

B&B HOTEL Fabriano Janus

B&B HOTEL Fabriano Janus

10/10 Excellent
"The best hotel in Fabriano if you're looking for a modern hotel in the heart of Fabriano. If you get a room on the upper levels you also get a wonderful view over the city."
Matthew 1-night trip
Posted 1 month ago
B&B HOTEL Fabriano Janus

Find out more about Cupramontana

Everything you need to know about Cupramontana holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cupramontana holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cupramontana holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cupramontana holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cupramontana. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cupramontana holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cupramontana holiday rentals we have selected for you start as low as AU$144 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cupramontana rentals

At Expedia, we put the best Cupramontana holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cupramontana rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cupramontana holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cupramontana. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Cupramontana?

Yes, there are holiday rentals close to the most popular sights in Cupramontana, or you can select a more secluded option if you're looking for a relaxing stay. Cupramontana is known for its festivals and churches. Make sure you have time to check out the wineries while you're in the area.

What are some of the best holiday rentals that Cupramontana has to offer?

Villa Gens Camuria: This holiday home rental outside of Cupramontana is located next to a golf course, and has an outdoor pool, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a full-sized fridge, a microwave and an espresso maker. You and your friends and family can relax into your holiday with amenities such as a garden.

How many holiday rentals will I find in Cupramontana?

With 10 Expedia holiday rentals, you're guaranteed to find just the right place for your Cupramontana stay.

What can I see and do in Cupramontana?

Explore the area and cultural attractions such as Teatro Comunale G. B. Pergolesi, or visit one of the family-friendly sights such as Paradise Playcenter. Hermitage of the White Friars and Colonnara are other places to visit while you're in town.

What are holiday rentals like in Cupramontana?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cupramontana. Holiday rentals offer amenities like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great choice for a family trip or a small group gathering.