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

Cupramontana Vacation Rentals

Q: 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.

Dates

November 2026

December 2026

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Our top choices for Cupramontana vacation rentals

A modern bedroom with a bed, a desk, and a chair.

1. Ospitalità Il Prato Jesi

Jesi

NT$2,119 total

includes taxes & fees

Nov 17 - Nov 18

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

2. Casa Vacanze Merion

Arcevia

Giovanni

NT$2,891 total

includes taxes & fees

Nov 8 - Nov 9

A stone building with a gated entrance, arched windows, and a small balcony.

3. Country House Federico I

Sassoferrato

Costantin

NT$2,383 total

includes taxes & fees

Nov 7 - Nov 8

A modern reception desk with a curved design, a laptop on top, and pendant lighting.

4. Rooms & Breakfast Centrale

Fabriano

Max

NT$2,509 total

includes taxes & fees

Nov 8 - Nov 9

An arched courtyard with a brick floor, a pergola, and a table with chairs.

5. La Dimora del Borgo

Montecassiano

"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!!"

Gabriel

NT$2,490 total

includes taxes & fees

Nov 12 - Nov 13

A dining area with wooden beams, white furniture, and large arched windows offering a view.

6. Villa Coralia

Osimo

David

NT$3,652 total

includes taxes & fees

Nov 8 - Nov 9

A modern living room with a sofa, black bean bag, and a wall with the text 'LIFE IS A BEAUTIFUL RIDE'.

7. Casa nel Vicolo - Duomo di Osimo

Osimo

NT$4,860 total

includes taxes & fees

Nov 15 - Nov 16

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Find vacation rentals that suit your style

Top Cupramontana Hotel Reviews

A poolside setting with a table set for two, including a cup and saucer, and a tray with a spoon and a cup.

Tuttaterra

Serra San Quirico

10/10 Excellent

My wife and I are traveling through Italy on our honeymoon. Over the past three weeks, we’ve stayed in a variety of hotels, B&Bs, agriturismos, and other accommodations. Without a doubt, this has been the best place we’ve stayed at during our trip. The atmosphere was warm and welcoming, the attention to detail was outstanding, and everything made us feel truly special. It was the perfect stop on our honeymoon.

Aivaras

A stone-walled room with modern black sofas and a wooden beam ceiling.

Relais Del Borgo Hotel e Spa

Staffolo

10/10 Excellent

William

A swimming pool with a white stone and a terracotta pot with red flowers.

Le MaRaClà Country House

Jesi

10/10 Excellent

Megan

A dining table with plates of food, cups of coffee, and a bowl of nuts.

Pineta Hotel

Monsano

10/10 Excellent

Renato

A dining area with a long table set for a meal, large windows with a view of greenery, and hanging pendant lights.

Frantoio L'Olinda

San Marcello

10/10 Excellent

Cathy

A large, multi-story building with a well-maintained lawn and a gated entrance.

Villa Miliani by Hannah Hotels Collection

Fabriano

10/10 Excellent

suk

A pool area with a rock formation, lounge chairs, and a table.

Hotel Le Grotte

Genga

10/10 Excellent

Zach

A dining table with a wine glass and a vase with a red rose, overlooking a historic stone building and greenery.

Hotel Terme di Frasassi

Genga

10/10 Excellent

Cathie

An outdoor patio with wooden furniture, potted plants, and a brick floor.

Boutique Hotel Residenza la Ceramica

Fabriano

10/10 Excellent

Amy

A view from a balcony with a wicker chair and a view of the sea and distant structures.

EGO Hotel

Ancona

10/10 Excellent

Anonymous traveler

Country House Federico I

Sassoferrato

10/10 Excellent

Stella, Antonio, and Giovanna all made for a great stay at Countryhouse Federico -- they were all very warm, welcoming, and helpful in answering questions about the town and its surroundings. I stayed in the downstairs suite, which including a large bathroom, bedroom, living room, and kitchen with gas stove and refridgerator. The house was on a direct line to the center of town, adjacent to San Francesco (one of the major churches), so finding the property was easy when I arrived. The house was...

Justin

A restaurant with white tables and chairs, a checkered floor, and a view of the sea.

Terrazza Marconi Hotel & Spamarine

Senigallia

10/10 Excellent

This is a beautiful hotel with outstanding service. The staff were always friendly and delighted Americans were staying. The food in the hotel restaurant for breakfast was excellent. And, for dinner tremendous! The section of beach included with our stay was very convenient and perfect. There are staff on the beach to serve you with towels and beverages. The beach is akin to a Florida beach with a gently sloping shoreline and soft sand with a section perfect for a morning run or walk. While many...

Terry

A person in a swimming pool with a view of the ocean.

Raffaello Hotel

Senigallia

10/10 Excellent

We found Raffaello to be a great hotel. Staff were eager to make our stay comfortable. The room was immaculate. The train station is a 10 minute walk from the hotel. From there multiple cities are easily accessible including Pesaro is a 20 minute ride. The train tracks run right past the hotel, however the rooms are well insulated with quadruple pain windows. If you leave the windows closed you're fine. Everything was fantastic, although I would have preferred a softer bed. (of note: the...

Anonymous traveler

Find out more about Cupramontana

Search for holiday rentals in Cupramontana on Expedia! You can easily find your home rentals, villas, holiday apartments in Cupramontana using one of the methods below:

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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.

Cupramontana Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Cupramontana vacation rentals

1. Ospitalità Il Prato Jesi

2. Casa Vacanze Merion

3. Country House Federico I

4. Rooms & Breakfast Centrale

5. La Dimora del Borgo

6. Villa Coralia

7. Casa nel Vicolo - Duomo di Osimo

Find vacation rentals that suit your style

Top Cupramontana Hotel Reviews

Tuttaterra

10/10 Excellent

Find out more about Cupramontana

Frequently Asked Questions

Can I find a vacation rental in Cupramontana?

What are some of the best vacation home rentals that Cupramontana has to offer?

How many vacation rentals will I find in Cupramontana?

What can I see and do in Cupramontana?

What are vacation rentals like in Cupramontana?