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

Cupramontana Vacation Rentals

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Our top choices for Cupramontana vacation rentals

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

3 bed - Sleeps 6 - Mountain View - Parking - Pets
Angeli di Rosora
The price is CA $114
CA $146 total
includes taxes & fees
Oct 4 - Oct 5
3 bed - Sleeps 6 - Mountain View - Parking - Pets

2. Casa Vacanze Merion

Casa Vacanze Merion
Arcevia
The price is CA $85
CA $94 total
includes taxes & fees
Oct 7 - Oct 8
Casa Vacanze Merion

3. Ospitalità Il Prato Jesi

Ospitalità Il Prato Jesi
Jesi
The price is CA $113
CA $193 total
includes taxes & fees
Sep 12 - Sep 13
Ospitalità Il Prato Jesi

4. 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 CA $130
CA $207 total
includes taxes & fees
Sep 7 - Sep 8
House in the medieval village Castelletta 700 mt height in the park Gola della Rossa

5. 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 CA $90
CA $99 total
includes taxes & fees
Oct 7 - Oct 8
Country House Federico I

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 CA $96
CA $125 total
includes taxes & fees
Sep 7 - Sep 8
Ravasio House located in the heart of the Marche region, among historic villages and unique views

7. 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 CA $92
CA $106 total
includes taxes & fees
Sep 14 - Sep 15
Rooms & Breakfast Centrale

8. casa grimaldi

casa grimaldi
Matelica
8.0 out of 10, Very good, (6 reviews)
"Rilassante viaggio nelle Marche con amici"
Italy
Maurilio
casa grimaldi

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 CA $96
CA $162 total
includes taxes & fees
Sep 21 - Sep 22
[La Casetta] Bilocale Centrale con Terrazza Parcheggio Gratuito Wifi PS4 Minipc

10. CASOLARE SANTILO' - CASOLARE SANTILO' - Esclusiva Movivillas

CASOLARE SANTILO' - CASOLARE SANTILO' - Esclusiva Movivillas
Poggio San Vicino
The price is CA $375
CA $1,115 total
includes taxes & fees
Sep 19 - Sep 20
CASOLARE SANTILO' - CASOLARE SANTILO' - Esclusiva Movivillas

11. 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 CA $225
CA $254 total
includes taxes & fees
Sep 14 - Sep 15
Small villa with a big garden and a big swimming pool - Sassoferrato

12. 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 CA $300
CA $648 total
includes taxes & fees
Sep 7 - Sep 8
Lovely villa in a peaceful area

13. 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 CA $145
CA $217 total
includes taxes & fees
Oct 1 - Oct 2
Inside the widespread village of Castelletta in the Gola della Rossa park.

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

SE246 – Senigallia, three-room apartment in an excellent location
Senigallia
The price is CA $72
CA $320 total
includes taxes & fees
Sep 12 - Sep 13
SE246 – Senigallia, three-room apartment in an excellent location

15. 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 CA $310
CA $340 total
includes taxes & fees
Sep 22 - Sep 23
Poggio Antico - Suites and Breakfast

16. SE275 – Senigallia, four-room apartment in the hills with parking space

SE275 – Senigallia, four-room apartment in the hills with parking space
Senigallia
The price is CA $55
CA $372 total
includes taxes & fees
Sep 12 - Sep 13
SE275 – Senigallia, four-room apartment in the hills with parking space

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 CA $99
CA $108 total
includes taxes & fees
Sep 15 - Sep 16
La Dimora del Borgo

18. La casa sulle mura in Borgo Loretello

La casa sulle mura in Borgo Loretello
Loretello
The price is CA $247
CA $247 total
includes taxes & fees
Oct 2 - Oct 3
La casa sulle mura in Borgo Loretello

19. SE055 -Montemarciano, huge three-room apartment with sea view

SE055 -Montemarciano, huge three-room apartment with sea view
Montemarciano
The price is CA $66
CA $310 total
includes taxes & fees
Sep 12 - Sep 13
SE055 -Montemarciano, huge three-room apartment with sea view

20. SE005 - Senigallia, three-room apartment on the sea with beach

SE005 - Senigallia, three-room apartment on the sea with beach
Senigallia
The price is CA $61
CA $330 total
includes taxes & fees
Sep 12 - Sep 13
SE005 - Senigallia, three-room apartment on the sea with beach
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a vacation rental in Cupramontana?

Yes, we offer vacation rentals near top local attractions in Cupramontana, or you can go with a more remote 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 vacation home rentals that Cupramontana has to offer?

Villa Gens Camuria: This vacation home rental outside of Cupramontana is located next to a golf course and has an outdoor pool, a terrace, and a barbecue grill 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 vacation with amenities like a garden.

How many vacation rentals will I find in Cupramontana?

With 11 Expedia vacation rentals, you're sure 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 a family-friendly sight such as Paradise Playcenter. Hermitage of the White Friars and Colonnara are other places to visit while you're in town.

What are vacation rentals like in Cupramontana?

Vacation rentals are privately owned properties where you can stay for several days or longer in Cupramontana. Vacation rentals offer amenities such as WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a family trip or a small group gathering.