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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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Cupramontana vacation rentals

Standard Double Room, Microwave | Desk, WiFi (free)

1. Ospitalità Il Prato Jesi

Ospitalità Il Prato Jesi
Jesi
$103 nightly
The price is $112
Sep 5 - Sep 6
Total with taxes and fees
Ospitalità Il Prato Jesi
Outdoor spa tub

2. 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
$151 nightly
The price is $151
Aug 23 - Aug 24
Total with taxes and fees
House in the medieval village Castelletta 700 mt height in the park Gola della Rossa
Exterior

3. casa grimaldi

casa grimaldi
Matelica
8.0 out of 10, Very Good, (6 reviews)
"Rilassante viaggio nelle Marche con amici"
Italy
Maurilio
$119 nightly
The price is $131
Aug 29 - Aug 30
Total with taxes and fees
casa grimaldi
Interior

4. 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
$363 nightly
The price is $363
Aug 31 - Sep 1
Total with taxes and fees
The Bookhouse home B&B: Eco-Friendly Retreat in Nature near Jesi
Front of property

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
$67 nightly
The price is $73
Sep 22 - Sep 23
Total with taxes and fees
Country House Federico I
Outdoor dining

6. [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.
$114 nightly
The price is $118
Aug 29 - Aug 30
Total with taxes and fees
[La Casetta] Bilocale Centrale con Terrazza Parcheggio Gratuito Wifi PS4 Minipc
Interior

7. 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
$95 nightly
The price is $95
Aug 30 - Aug 31
Total with taxes and fees
Ravasio House located in the heart of the Marche region, among historic villages and unique views
Outdoor pool

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.
$186 nightly
The price is $186
Sep 16 - Sep 17
Total with taxes and fees
Small villa with a big garden and a big swimming pool - Sassoferrato
Lobby

9. 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
$61 nightly
The price is $70
Sep 21 - Sep 22
Total with taxes and fees
Rooms & Breakfast Centrale
Exterior

10. Borgo delle Rondini Relax Home

Borgo delle Rondini Relax Home
Genga
$191 nightly
The price is $210
Aug 28 - Aug 29
Total with taxes and fees
Borgo delle Rondini Relax Home
Outdoor spa tub

11. 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
$145 nightly
The price is $145
Sep 2 - Sep 3
Total with taxes and fees
House in the village of Castelletta at an altitude of 700 meters in the park Gola della Rossa
Outdoor dining

12. A house in nature, quiet and poetic, ideal for recharging your energy.

A house in nature, quiet and poetic, ideal for recharging your energy.
Marche
10.0 out of 10, Exceptional, (1 review)
$249 nightly
The price is $258
Aug 26 - Aug 27
Total with taxes and fees
A house in nature, quiet and poetic, ideal for recharging your energy.
Comfort Double Room, Courtyard View | Terrace/patio

13. 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
$64 nightly
The price is $71
Sep 17 - Sep 18
Total with taxes and fees
La Dimora del Borgo
Free daily buffet 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
$132 nightly
The price is $145
Sep 17 - Sep 18
Total with taxes and fees
Villa Coralia
Exterior detail

15. Not Just Valley - Chiaravalle

Not Just Valley - Chiaravalle
Chiaravalle
$146 nightly
The price is $146
Sep 16 - Sep 17
Total with taxes and fees
Not Just Valley - Chiaravalle
Living area

16. Apartment in the historic center with panoramic views

Apartment in the historic center with panoramic views
Monte San Vito
$152 nightly
The price is $152
Sep 16 - Sep 17
Total with taxes and fees
Apartment in the historic center with panoramic views
Outdoor pool

17. White Iron Room · Casa del Fattore, Villa Luzi

White Iron Room · Casa del Fattore, Villa Luzi
Treia
$251 nightly
The price is $251
Sep 5 - Sep 6
Total with taxes and fees
White Iron Room · Casa del Fattore, Villa Luzi
Exterior detail

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

SE055 -Montemarciano, huge three-room apartment with sea view
Montemarciano
$185 nightly
The price is $225
Sep 14 - Sep 15
Total with taxes and fees
SE055 -Montemarciano, huge three-room apartment with sea view
Apartment, City View | Living area | Flat-screen TV

19. Casa nel Vicolo - Duomo di Osimo

Casa nel Vicolo - Duomo di Osimo
Osimo
$171 nightly
The price is $178
Sep 1 - Sep 2
Total with taxes and fees
Casa nel Vicolo - Duomo di Osimo
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

EGO Hotel

EGO Hotel

10/10 Excellent
"Great hotel probably one of the best in Ancona. But few min from center."
Ralda 2-night trip
Posted 6 days ago
EGO Hotel

Find out more about Cupramontana

Everything you need to know about Cupramontana vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cupramontana vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cupramontana vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cupramontana in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $104 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cupramontana rentals

At Expedia, we put the best Cupramontana vacation 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 vacation.

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.

Explore a world of travel with Expedia

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 Coralia: This vacation home rental outside Cupramontana is located in a rural location and has a terrace, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and an electric kettle. You and your friends and family can relax into your vacation with amenities like a library. Our travelers also rate Idyllic artist's country house with pool & yoga room in a secluded location as a favorite home for rent in Cupramontana.

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.