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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Our top choices for Cupramontana holiday rentals

1. 3 bed - Sleeps 6 - Mountain View - Parking - Pets

3 bed - Sleeps 6 - Mountain View - Parking - Pets
Angeli di Rosora
The price is NZ$182
includes taxes & fees
4 Oct - 5 Oct
3 bed - Sleeps 6 - Mountain View - Parking - Pets

2. Casa Vacanze Merion

Casa Vacanze Merion
Arcevia
The price is NZ$117
includes taxes & fees
23 Sept - 24 Sept
Casa Vacanze Merion

3. The Bookhouse home B&B: Eco-Friendly Retreat in Nature near Jesi

The Bookhouse home B&B: Eco-Friendly Retreat in Nature near Jesi
Castelplanio
The price is NZ$335
includes taxes & fees
28 Sept - 29 Sept
The Bookhouse home B&B: Eco-Friendly Retreat in Nature near Jesi

4. Lovely villa in a peaceful area

Lovely villa in a peaceful area
Genga
10.0 out of 10, Exceptional, (2 reviews)
"Super"
Germany
Matthias G.
The price is NZ$804
includes taxes & fees
18 Sept - 19 Sept
Lovely villa in a peaceful area

5. CASOLARE SANTILO' - CASOLARE SANTILO' - Esclusiva Movivillas

CASOLARE SANTILO' - CASOLARE SANTILO' - Esclusiva Movivillas
Poggio San Vicino
The price is NZ$1,376
includes taxes & fees
20 Sept - 21 Sept
CASOLARE SANTILO' - CASOLARE SANTILO' - Esclusiva Movivillas

6. Ospitalità Il Prato Jesi

Ospitalità Il Prato Jesi
Jesi
The price is NZ$264
includes taxes & fees
17 Sept - 18 Sept
Ospitalità Il Prato Jesi

7. House in the village of Castelletta at an altitude of 700 meters in the park Gola della Rossa

House in the village of Castelletta at an altitude of 700 meters in the park Gola della Rossa
Castelletta
The price is NZ$248
includes taxes & fees
16 Sept - 17 Sept
House in the village of Castelletta at an altitude of 700 meters in the park Gola della Rossa

8. Small villa with a big garden and a big swimming pool - Sassoferrato

Small villa with a big garden and a big swimming pool - Sassoferrato
Sassoferrato
10.0 out of 10, Exceptional, (51 reviews)
"We had a fantastic time enjoying the park, the surrounding and the swimming pool"
Italy
barbara s.
The price is NZ$315
includes taxes & fees
16 Sept - 17 Sept
Small villa with a big garden and a big swimming pool - Sassoferrato

9. Country House Federico I

Country House Federico I
Sassoferrato
9.6 out of 10, Exceptional, (17 reviews)
"Siamo stati benissimo tutto ok e la proprietaria non ci ha fatto mancare nulla. Consigliatissimo"
Italy
paolo
The price is NZ$124
includes taxes & fees
29 Sept - 30 Sept
Country House Federico I

10. Ravasio House located in the heart of the Marche region, among historic villages and unique views

Ravasio House located in the heart of the Marche region, among historic villages and unique views
Montale
The price is NZ$155
includes taxes & fees
16 Sept - 17 Sept
Ravasio House located in the heart of the Marche region, among historic villages and unique views

11. Poggio Antico - Suites and Breakfast

Poggio Antico - Suites and Breakfast
Monte San Vito
8.8 out of 10, Excellent, (3 reviews)
"Beautiful property and surroundings but it caters mainly to Germans. Reading materials in room was all in german as well as the majority of tv channels. Bring iron if you need one - rooms don’t have one one (which to me seems strange for a high end property). Also, breakfast was 19 euros per person per day - I would recommend including this in price of room. Way too expensive. "
United States
Paola
The price is NZ$419
includes taxes & fees
20 Sept - 21 Sept
Poggio Antico - Suites and Breakfast

12. [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 NZ$202
includes taxes & fees
21 Sept - 22 Sept
[La Casetta] Bilocale Centrale con Terrazza Parcheggio Gratuito Wifi PS4 Minipc

13. Borgo delle Rondini Relax Home

Borgo delle Rondini Relax Home
Genga
The price is NZ$359
includes taxes & fees
25 Sept - 26 Sept
Borgo delle Rondini Relax Home

14. La suite in piazza in Borgo Loretello

La suite in piazza in Borgo Loretello
Loretello
The price is NZ$330
includes taxes & fees
6 Oct - 7 Oct
La suite in piazza in Borgo Loretello

15. House in the medieval village Castelletta 700 mt height in the park Gola della Rossa

House in the medieval village Castelletta 700 mt height in the park Gola della Rossa
Castelletta
The price is NZ$258
includes taxes & fees
16 Sept - 17 Sept
House in the medieval village Castelletta 700 mt height in the park Gola della Rossa

16. La casa nel vicolo a Borgo Loretello

La casa nel vicolo a Borgo Loretello
Loretello
The price is NZ$306
includes taxes & fees
2 Oct - 3 Oct
La casa nel vicolo a Borgo Loretello

17. Rooms & Breakfast Centrale

Rooms & Breakfast Centrale
Fabriano
10.0 out of 10, Exceptional, (2 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 NZ$131
includes taxes & fees
27 Sept - 28 Sept
Rooms & Breakfast Centrale

18. B&B The Treehouse – Wooden Apartment

B&B The Treehouse – Wooden Apartment
Osimo
10.0 out of 10, Exceptional, (2 reviews)
"Eine ganz tolle Unterkunft, fast im Zentrum der Altstadt Osimo. Die Gastgeberin super nett, alles sehr sauber und auch das Frühstück sehr liebevoll. Wir waren zu viert als Familie, was echt super war. Für uns tatsächlich nur ein Zwischenstopp aber auch für einen längeren Aufenthalt sehr zu empfehlen."
Germany
Katrin
The price is NZ$192
includes taxes & fees
16 Sept - 17 Sept
B&B The Treehouse – Wooden Apartment

19. Villa Elena: Your ideal holiday with an unforgettable view!

Villa Elena: Your ideal holiday with an unforgettable view!
San Severino Marche
The price is NZ$698
includes taxes & fees
23 Sept - 24 Sept
Villa Elena: Your ideal holiday with an unforgettable view!

20. 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 NZ$131
includes taxes & fees
16 Sept - 17 Sept
La Dimora del Borgo
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

Find out more about Cupramontana

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cupramontana holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cupramontana. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cupramontana. Seeing all the best attractions is bound to make you fall in love with Cupramontana. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cupramontana short-term rentals, that won’t be hard to do.

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 11 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.