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Holiday houses in Castiglione della Valle

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Top-rated holiday rentals in Castiglione della Valle

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
Home in Perugia
4.98 out of 5 average rating, 193 reviews

La Perla del Lago Holiday home on Lake Trasimeno

La Perla del Lago: your refuge at Trasimeno ​Rediscover your harmony in this oasis of absolute peace. Let yourself be enchanted by our magical view and the sunsets that the lake offers every evening. The La Perla del Lago Holiday Home overlooks the mirror of Lake Trasimeno. 8 minutes away you will find the highway to visit towns such as Florence, Perugia, Gubbio, Spoleto, Norcia and many others. In the village, you will find bars, restaurants, a market, a pharmacy, an ATM, and children's play areas. There is a swimming pool 3 km away where you can relax in the summer.

Top Guest favourite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay in Ruscello
4.99 out of 5 average rating, 499 reviews

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Guest favourite
A historic villa is set against a clear blue sky, surrounded by manicured gardens. The building features bright yellow walls, classic architectural details, and large windows. Neatly trimmed hedge lines and sculpted greenery enhance the lush landscape, with vibrant red flowers adding a pop of color to the foreground.
Holiday home in Perugia
4.77 out of 5 average rating, 35 reviews

Historic Residence with Pool near Perugia

🏡 Historic Residence with Pool near Perugia 📍 Perfect for exploring Umbria, just minutes from Perugia, Assisi & Lake Trasimeno ✨ Elegant apartment inside the historic Palazzo di Bagnaia with antique furniture and original details 🛏️ 5 bedrooms • 🛁 2 bathrooms • Spacious interiors ideal for families and groups 🌳 Swimming pool, large private park and barbecue area surrounded by Umbrian countryside 💫 Historic charm, relaxation and authentic Italian atmosphere in a 17th-century residence

Top Guest favourite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano
4.97 out of 5 average rating, 225 reviews

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

Top Guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano
4.93 out of 5 average rating, 308 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Top Guest favourite
Tower in San Quirico d'Orcia
5 out of 5 average rating, 111 reviews

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Top Guest favourite
A spacious bedroom features a large, inviting bed adorned with a light blanket. Natural light floods through sheer curtains draped over a large window, revealing views of the lush valley outside. The rustic walls, made of tufo, add a unique character to the room.
Apartment in Civita
4.94 out of 5 average rating, 279 reviews

The Cellar (Palazzo Pallotti)

The apartment is two floors below the square, entirely dug into the tuff. Overlooking the valley, it is isolated from the noises of the street, quiet, private, and very welcoming. The tuff walls give it an ancient vibe to transport you to another time. It can be reached on foot, via a footbridge that takes you directly to the square where the property is located. It is perfect for short stays of complete relaxation, but with the fully equipped kitchen you can make the most of it.

Top Guest favourite
An aerial view captures the medieval borgo of Castiglione della Valle, where stone-roofed buildings are interspersed with winding paths. Soft lights illuminate the streets, highlighting the compact layout and the natural greenery surrounding the historical village.
Tower in Castiglione della Valle
4.94 out of 5 average rating, 52 reviews

Torre di Orlando - Medieval Tower 12th century

In the tranquillity of the village of Castiglione della Valle, adjacent to the walls of the historic centre, rises the Torre di Orlando, a medieval square tower dating back to 1100 AD. A plunge into the past, to discover the unique and rural rhythms of the Umbrian countryside, through the typical village streets, enveloped in mystical silence, to experience a regenerating and relaxing holiday, the Tower welcomes those who wish to be surrounded by areas of exclusive scenic value.

Top Guest favourite
A sunlit vineyard stretches across a gentle hillside, lined with rows of lush grapevines. In the background, an elegant historic mansion is framed by tall cypress trees against a clear blue sky, offering a picturesque glimpse into the surrounding Umbrian countryside.
Farm stay in Agello
4.97 out of 5 average rating, 130 reviews

Residenza del 300 (Between Perugia and Lake Trasimeno)

Magnificent apartment located in a historic 14th-century building of Roman origin nestled in the heart of the Umbrian countryside, on a historic farm. The furniture is renovated and comfortable. Large, bright, functional space with an all-Umbrian view, surrounded by the vast vineyard, centuries-old olive groves, enchanting landscapes, large garden and other magnificent plants. 10 km from the historic center of Perugia and 10 km from Lake Trasimeno.

Top Guest favourite
The bedroom features a spacious double bed adorned with soft linens and cushions, complemented by subtle bedside lamps. Exposed wooden beams highlight the ceiling, while natural light filters through a window, adding warmth to the serene, neutral color palette.
Apartment in Cortona
4.97 out of 5 average rating, 413 reviews

Cortona Shabby Chic House - independent & balcony-

Questo è un appartamento curato da una Superhost che vive Cortona ogni giorno. Il mio alloggio è situato in pieno centro storico a soli pochi passi dalle piazze e vie principali. Questo grazioso appartamento è di recente ristrutturazione e può ospitare fino a 3 persone. Appartamento indipendente con entrata singola tutto in un solo piano, con balcone. Arredato con cura, dotato di tutti i comfort per un totale relax

Top Guest favourite
A country house is nestled among the Umbrian hills, showcasing natural stone walls and a tiled roof. Lush gardens with vibrant flowers surround the entrance. The outdoor area is accentuated by a shaded seating space, enhancing the tranquil countryside ambiance.
Apartment in Cannara
4.98 out of 5 average rating, 60 reviews

Il Casale di Fiore - Large apartment in Umbria

The apartment is on the ground floor of a hillside farmhouse. It includes a large open space with kitchen and dining room, a bathroom, a double bedroom, a bedroom with a French bed and a garden. The apartment is on the ground floor of a big country house in the middle of Umbrian hills. It has a big open space with kitchen and dining room, 1 bathroom, 1 double bed, 1 small double bed and a garden.

Top Guest favourite
A charming stone cottage is set within a lush green landscape. The building features a rustic tiled roof and wooden shutters. Surrounding plants include flowering vines and a cactus in the foreground, creating a serene outdoor atmosphere.
Cabin in Massa Martana
4.95 out of 5 average rating, 233 reviews

Country Chalet and mini spa

A welcoming and comfortable nest, immersed in the bright colors of the Umbrian countryside, among roses and lavender, in the silent garden that frames it... Live a romantic dream: let yourself be enveloped by the warmth of the hot tub, under a starry sky and in the heart of the magic of our chalet. An oasis of tranquility, but well connected to all the major attractions of the region...

Popular amenities for Castiglione della Valle holiday rentals

  1. Airbnb
  2. Italy
  3. Umbria
  4. Perugia
  5. Castiglione della Valle