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

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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 £71
includes taxes & fees
4 Oct - 5 Oct
3 bed - Sleeps 6 - Mountain View - Parking - Pets

2. Inside the widespread village of Castelletta in the Gola della Rossa park.

Inside the widespread village of Castelletta in the Gola della Rossa park.
Castelletta
The price is £110
includes taxes & fees
4 Oct - 5 Oct
Inside the widespread village of Castelletta in the Gola della Rossa park.

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 £201
includes taxes & fees
6 Oct - 7 Oct
The Bookhouse home B&B: Eco-Friendly Retreat in Nature near Jesi

4. Ospitalità Il Prato Jesi

Ospitalità Il Prato Jesi
Jesi
The price is £90
includes taxes & fees
18 Oct - 19 Oct
Ospitalità Il Prato Jesi

5. Casa Vacanze Merion

Casa Vacanze Merion
Arcevia
The price is £48
includes taxes & fees
10 Oct - 11 Oct
Casa Vacanze Merion

6. 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 £69
includes taxes & fees
4 Oct - 5 Oct
Ravasio House located in the heart of the Marche region, among historic villages and unique views

7. 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 £113
includes taxes & fees
4 Oct - 5 Oct
House in the medieval village Castelletta 700 mt height in the park Gola della Rossa

8. [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 £89
includes taxes & fees
5 Oct - 6 Oct
[La Casetta] Bilocale Centrale con Terrazza Parcheggio Gratuito Wifi PS4 Minipc

9. 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 £108
includes taxes & fees
6 Oct - 7 Oct
House in the village of Castelletta at an altitude of 700 meters in the park Gola della Rossa

10. 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 £53
includes taxes & fees
18 Oct - 19 Oct
Country House Federico I

11. 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 £54
includes taxes & fees
10 Oct - 11 Oct
Rooms & Breakfast Centrale

12. Borgo delle Rondini Relax Home

Borgo delle Rondini Relax Home
Genga
The price is £153
includes taxes & fees
4 Oct - 5 Oct
Borgo delle Rondini Relax Home

13. 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 £178
includes taxes & fees
4 Oct - 5 Oct
Poggio Antico - Suites and Breakfast

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 £98
includes taxes & fees
4 Oct - 5 Oct
Villa Coralia

15. 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 £54
includes taxes & fees
9 Oct - 10 Oct
La Dimora del Borgo

16. Holiday Residence Belohorizonte

Holiday Residence Belohorizonte
Macerata
9.0 out of 10, Wonderful, (22 reviews)
"We stayed at multiple locations on this trip and this was our favorite by far Very cute apartment and the host was very friendly and responsive. Highly recommend it to anyone "
United States
Kelly
The price is £74
includes taxes & fees
4 Oct - 5 Oct
Holiday Residence Belohorizonte

17. SE143 - Senigallia, farmhouse surrounded by green hills

SE143 - Senigallia, farmhouse surrounded by green hills
Senigallia
8.0 out of 10, Very good, (1 review)
"Pro: Lage, Abgeschiedenheit, Ruhe, 2 schöne Schlafzimmer Zu verbessern: Sauberkeit (es sah so aus, als ob die letzte Reinigung bereits länger her war, wobei das Haus dazwischen nicht bewohnt wurde); Sonnenliegen wären schön; bei sehr heißem Wetter (wir hatten paar Tage mit mehr als 30 Grad) wäre eine Klimaanlage sehr wünschenswertAnmerkung: wir haben das 3. Zimmer nicht gebraucht. Wenn wir es aber getan hätten, dann gäbe es deutlich mehr zu bemängeln ( am wichtigsten Kellergeruch im Zimmer &...
Germany
Eugenia E.
The price is £204
includes taxes & fees
14 Oct - 15 Oct
SE143 - Senigallia, farmhouse surrounded by green hills

18. SE246 – Senigallia, three-room apartment in an excellent location

SE246 – Senigallia, three-room apartment in an excellent location
Senigallia
The price is £169
includes taxes & fees
4 Oct - 5 Oct
SE246 – Senigallia, three-room apartment in an excellent location

19. Villa Gens Camuria

Villa Gens Camuria
Camerano
9.6 out of 10, Exceptional, (55 reviews)
"Clean, friendly very accommodating pool excellent a great place to stay all year round."
United Kingdom
antonio
The price is £80
includes taxes & fees
9 Oct - 10 Oct
Villa Gens Camuria

20. SE235 - Senigallia, large three-room apartment with furnished courtyard

SE235 - Senigallia, large three-room apartment with furnished courtyard
Roncitelli
The price is £155
includes taxes & fees
4 Oct - 5 Oct
SE235 - Senigallia, large three-room apartment with furnished courtyard
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

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, apart-hotels, 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 favorite 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 depends 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 £74 per night. Entering your travel dates in the search wizard you might find 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.