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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Cupramontana vacation rentals

A bedroom with a bed, a wooden door, and a window.

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

3 bed - Sleeps 6 - Mountain View - Parking - Pets
Angeli di Rosora
$95 nightly
The price is $95
Oct 4 - Oct 5
Total with taxes and fees
3 bed - Sleeps 6 - Mountain View - Parking - Pets
A cozy living room with a fireplace, a bookshelf, a sofa, and a hanging plant.

2. 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
$268 nightly
The price is $268
Oct 7 - Oct 8
Total with taxes and fees
The Bookhouse home B&B: Eco-Friendly Retreat in Nature near Jesi
A rustic kitchen with stone walls, wooden beams, and a dining area with white chairs and a wooden table.

3. 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.
Lovely villa in a peaceful area
Two white plastic lounge chairs with floral cushions, positioned on a grassy area with trees and a brick wall in the background.

4. Casa Vacanze Merion

Casa Vacanze Merion
Arcevia
$57 nightly
The price is $63
Oct 9 - Oct 10
Total with taxes and fees
Casa Vacanze Merion
A swimming pool with a stone border, a metal ladder, and lounge chairs.

5. 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.
Small villa with a big garden and a big swimming pool - Sassoferrato
A person in a hot tub with a glass of wine, surrounded by a wooden deck and lush greenery in the background.

6. 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
$146 nightly
The price is $146
Oct 1 - Oct 2
Total with taxes and fees
House in the medieval village Castelletta 700 mt height in the park Gola della Rossa
A modern bedroom with a bed, a desk, and a chair.

7. Ospitalità Il Prato Jesi

Ospitalità Il Prato Jesi
Jesi
$100 nightly
The price is $109
Oct 31 - Nov 1
Total with taxes and fees
Ospitalità Il Prato Jesi
A stone building with a gated entrance, arched windows, and a small balcony.

8. 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
$59 nightly
The price is $65
Oct 14 - Oct 15
Total with taxes and fees
Country House Federico I
A coastal beach with clear blue waters, a rocky outcrop, and a mountainous backdrop.

9. 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
$212 nightly
The price is $234
Oct 4 - Oct 5
Total with taxes and fees
Poggio Antico - Suites and Breakfast
An open door leading to a balcony with a tiled floor and a view of a street.

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
$88 nightly
The price is $88
Oct 1 - Oct 2
Total with taxes and fees
Ravasio House located in the heart of the Marche region, among historic villages and unique views
A rooftop terrace with a circular stone planter, a paved area, and a view of distant mountains.

11. Borgo delle Rondini Relax Home

Borgo delle Rondini Relax Home
Genga
$185 nightly
The price is $204
Oct 2 - Oct 3
Total with taxes and fees
Borgo delle Rondini Relax Home
A small outdoor patio with a black table, a barbecue grill, and a tray with drinks and snacks.

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.
$111 nightly
The price is $115
Oct 7 - Oct 8
Total with taxes and fees
[La Casetta] Bilocale Centrale con Terrazza Parcheggio Gratuito Wifi PS4 Minipc
A spacious loft with a wooden dining table, a sofa, and a kitchen area.

13. 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
$109 nightly
The price is $109
Oct 1 - Oct 2
Total with taxes and fees
B&B The Treehouse – Wooden Apartment
An arched courtyard with a brick floor, a pergola, and a table with chairs.

14. 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
$63 nightly
The price is $70
Oct 11 - Oct 12
Total with taxes and fees
La Dimora del Borgo
An outdoor dining area with tables set for two, featuring woven placemats, white plates, and glassware.

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

Villa Elena: Your ideal holiday with an unforgettable view!
San Severino Marche
$325 nightly
The price is $397
Oct 7 - Oct 8
Total with taxes and fees
Villa Elena: Your ideal holiday with an unforgettable view!
A nighttime outdoor area with a tree, a hot tub, and a grassy platform with seating.

16. Holiday Home "Casa degli Ulivi" with Private Pool and Wi-Fi

Holiday Home "Casa degli Ulivi" with Private Pool and Wi-Fi
tolentino
10.0 out of 10, Exceptional, (2 reviews)
"Pros: La casa è super attrezzata di tutto quello che può servire, il giardino è molto grande e anche esso ben attrezzato di tutto; il panorama bello è la zona è tranquilla ottima per il relax; Jacuzzi top e in più è stato con noi per tutto il soggiorno il mitico Ugo, un cagnetto simpaticissimo che ha fatto compagnia ai nostri cagnetti. Cons: La piscina dovrebbe essere curata un po' di più."
Italy
Anonymous traveler
$368 nightly
The price is $368
Oct 1 - Oct 2
Total with taxes and fees
Holiday Home "Casa degli Ulivi" with Private Pool and Wi-Fi
A person in a hot tub with a glass of wine, surrounded by a wooden deck and lush greenery in the background.

17. 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
$141 nightly
The price is $141
Oct 7 - Oct 8
Total with taxes and fees
House in the village of Castelletta at an altitude of 700 meters in the park Gola della Rossa
A modern reception desk with a curved design, a laptop on top, and pendant lighting.

18. 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
$58 nightly
The price is $67
Oct 3 - Oct 4
Total with taxes and fees
Rooms & Breakfast Centrale
A person in a hot tub with a glass of wine, surrounded by a wooden deck and lush greenery in the background.

19. 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
$141 nightly
The price is $143
Oct 1 - Oct 2
Total with taxes and fees
Inside the widespread village of Castelletta in the Gola della Rossa park.
A dining area with wooden beams, white furniture, and large arched windows offering a view.

20. 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
$113 nightly
The price is $125
Oct 1 - Oct 2
Total with taxes and fees
Villa Coralia
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

G Hotel

G Hotel

8/10 Good
"Be aware there is no restaurant/bar/room service. We arrived after the nearby shops/cafes were closed. 🙁"
David 1-night trip
Posted 14 hours ago
G 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 $96 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 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 10 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.