Vacation rentals in Cupramontana

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Top-rated vacation rentals in Cupramontana

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Top guest favorite

A scenic view of rolling hills unfolds under a clear blue sky. Lush green fields contrast with earthy tones, while distant mountains provide a subtle backdrop. A tree branches gently frame the view, enhancing the peacefulness of the rural landscape.

Apartment in Castelplanio

4.88 out of 5 average rating, 40 reviews

Apartment near Jesi

The accommodation is part of the Agriturismo "Le Piagge" and offers possibilities for a relaxing vacation immersed in silence, in the flavors of the countryside with evocative views, in the Verdicchio wine area of the Castelli di Jesi, in the province of Ancona. With the horizon clear, to the east you can see the sea, to the south the Sibillini Mountains chain. It is easy to reach and allows you to move quickly to both seaside (Senigallia) and mountain resorts (Frasassi Caves).

Top guest favorite

A rustic farmhouse is set against a clear blue sky, surrounded by lush green grass and trees. The two-story structure features a mix of traditional stone and plaster walls, with multiple windows and a spacious outdoor area ideal for relaxation.

Home in Monte Roberto

4.96 out of 5 average rating, 28 reviews

The Colored House

"La Casa Colorata" is a structure from another time. Immersed in the typical countryside of the area where the hills, carpeted with fields of wheat, sunflowers and vineyards, envelop the eye without parsimony. You can experience authentic contact with nature, whose scents and sounds will accompany you at any time of day. The farmhouse is surrounded by various types of trees: mulberry trees, rose gardens, fruit trees and the historic passion for flowers of all kinds.

Top guest favorite

A vibrant sunset casts a warm glow over rolling hills, with clouds reflecting shades of orange and pink. The landscape features fields and distant trees, with a rustic building visible amidst the greenery, creating a serene scene in the countryside.

Barn in Serra De' conti

5 out of 5 average rating, 22 reviews

RosaClara Casetta

Casetta RosaClara is a former barn inside the courtyard of Casale del Gelso (ancient farmhouse of the late 1800s) located in the Marche countryside. Independent, it consists of two mini apartments of about 40 sqm each and communicating. Very bright and panoramic, it has a terrace/solarium and a pleasant and beautiful space, common to the two rooms, where you can relax and refresh. Newly renovated, it has all the amenities, harmonizing tradition with modern needs.

Top guest favorite

A charming wrought iron gate stands open, revealing a narrow stone pathway lined with potted plants. The archway above is made of light-colored stone, while a vibrant green door is visible in the background, inviting visitors into the historic setting.

Condo in Maiolati Spontini

5 out of 5 average rating, 12 reviews

Celeste Erard Guest House

Celèste Erard Guest House is the right starting point for visiting an entire region. The apartment is recently renovated and is located in the historic village of Maiolati Spontini. Sea, hills, mountains, sports, art, theatre, music, historic cities and a vast presence of wine cellars ensure different destinations every day within a half-hour drive. Among the main tourist attractions of the area there are also the natural wonders of the famous Frasassi Caves.

Superhost

The outdoor area features a serene swimming pool, complemented by a canopy umbrella and several lounge chairs. Cushions are placed along the poolside for added comfort, with lush greenery and rolling hills visible in the background under a clear blue sky.

Apartment in Belvedere Ostrense

House in nature with panoramic terrace and pool

The Pineta apartment, on the first floor, is a refined nest, designed for those seeking relaxation and style, overlooking a beautiful pine forest. It has a spacious bedroom, a modern bathroom, a large open space with a living room and an equipped kitchen, and an outdoor terrace perfect for breakfast in the sun or aperitifs at sunset. Ideal for 2-3 people. You can enjoy a shared swimming pool, perfect for cooling off on hot summer days, and a shared garden.

Superhost

A historic casa with a rustic exterior is surrounded by lush greenery and vibrant pink flowers. The structure features green shuttered windows and a prominent clock on the side. Dark clouds add a dramatic backdrop to the spacious garden area, which includes a seating area.

Home in Montecarotto

4.75 out of 5 average rating, 24 reviews

Casa Sole e Gatti, Room > Kassandra < with shower bath

One of three beautiful and bright Rooms in a historic house. The center of the small, pretty town of Montecarotto is within walking distance in 3 minutes. There you will find a bakery, a cafe bar, two small supermarkets, a butcher, a post office, a pharmacy, a tobacco shop, a hairdresser, a gas station, a bus stop as well as other small shops. Due to the elevated location of Montecarotto, a pleasant fresh breeze is also to be expected here in summer.

Guest favorite

Vacation home in Agugliano

4.92 out of 5 average rating, 49 reviews

Room: in Villa Quercetti

Your perfect retreat in the Marche hills. A cozy and bright room in a wonderful villa. Located outside a small village near Ancona, not far from the sea, it is an oasis of relaxation and tranquility, excellent as a starting point to discover the best opportunities that the Marche territory offers: Urbino, Recanati, Loreto, Caves of Frasassi, in addition to the multiple attractions of the Adriatic Riviera, from Senigallia to Portonovo, Numana, Sirolo

Top guest favorite

A cozy bedroom features a spacious bed dressed in light blue bedding. A stone wall adds texture alongside warm wooden beams overhead. A minimalist closet and shelving unit are integrated into the design, while a comfortable armchair invites relaxation in the corner.

Home in Maiolati Spontini

4.97 out of 5 average rating, 93 reviews

Dimora nel Borgo - A Relaxing Home

The “Dimora nel Borgo” is a cozy home in the medieval historic center of Maiolati Spontini. It offers a relaxed and comfortable atmosphere, thanks to the recent and careful renovation, and the quiet and peaceful surrounding environment, inside a courtyard of yesteryear. A few meters from the house there are always free parking spaces available, there are no ZTL restrictions regarding the historic center. The house is complete with all amenities.

Top guest favorite

A dining area is shown, featuring a rectangular table surrounded by six chairs. A decorative tablecloth covers the table, which holds a bottle of water and a bowl of fruit. A carpet lies beneath the table, and warm-colored walls create a cozy ambiance.

Apartment in Cupramontana

4.82 out of 5 average rating, 39 reviews

Delicious Treats in Cupramontana

Delightful apartment in a beautiful 18th century building located in a quiet alley of the historic center. The completely renovated apartment with striking stone and brick vaults is very cool and is ideal for 6 travelers. Delightful holiday home in a beautiful 18th century building located in a quiet alley of the historic center. The fully renovated apartment with striking stone and brick ceilings is very cool and is ideal for 6 travelers.

Guest favorite

A charming stone farmhouse is set against a serene landscape, featuring large green shutters and expansive windows. A wooden deck with lounge chairs overlooks a natural swimming pool, surrounded by lush grasses and distant trees, creating a peaceful outdoor space.

Home in Iesi

4.92 out of 5 average rating, 12 reviews

Villa Corte degli Ulivi (Olive Court)

This stylish place to stay is perfect for group trips. You can experience staying in a typical Marche farmhouse completely renovated with the highest level finishes where the original materials have been harmoniously combined with the most modern solutions with an absolutely unique result. Privacy and silence dominate the surrounding environment, enhanced by the view that can be enjoyed with Mount San Vicino in the background.

Top guest favorite

A charming stone cottage is shown, featuring a sloped roof and large glass windows that provide panoramic views. Soft lighting accentuates the exterior, while the surrounding grassy area leads the eye to the distant hills.

Cabin in Cerreto d'Esi

4.99 out of 5 average rating, 129 reviews

Hillside chalet in stone and wood.

At the foot of Mount San Vicino, on a beautiful hill 420 meters above sea level, in complete tranquility and easily accessible, you can enjoy a beautiful 360-degree view, from the Sibillini Mountains to the Gola della Rossa. Easily reachable in 15 minutes Fabriano, in 20 minutes the beautiful caves of Frasassi, in 30 minutes Gubbio and in 60 minutes Senigallia or the Bay of Conero, in 20 minutes the ducal city of Camerino.

Guest favorite

A serene landscape showcases a rustic country house surrounded by lush greenery and rolling hills. The building features a traditional stone facade and terracotta roof, while the winding driveway is lined with tall cypress trees and olive groves, enhancing the tranquil setting.

Farm stay in Cingoli

4.97 out of 5 average rating, 75 reviews

The Guest House of the Tavignano Estate

The Tavignano estate is located in the heart of the Marche region, within the famous DOC of Verdicchio dei Castelli di Jesi, between the valleys of the river Esino and the Musone on one side, and between the Apennines and the sea on the other side. From the highest promontory of the Estate dominates the manor house, which houses the barrique, the family house, and an elegant Guest House.