Vacation rentals in Castiglione della Valle

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Top-rated vacation rentals in Castiglione della Valle

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Guest favorite

Apartment in Monte Vibiano Vecchio

5.0 out of 5 average rating, 18 reviews

Penthouse Vineyard Views on Countryside Estate

Glorious Penthouse Apt on Luxury Countryside Estate offering high-end amenities and services in an idyllic Italian setting. A fresh breakfast greets you each morning as you slowly wake to find yourself immersed in ancient olive groves and vineyards. Soak in the breathtaking scenery poolside with sweeping views in every direction. The Estate's prime location allows you to discover the very best of Umbria and Tuscany. Live the Italian Dream when you book a stay at our Estate. Authenticity awaits!

Dec 24 – 31

R6,249 ZAR per night

Guest favorite

Condo in Mugnano

4.85 out of 5 average rating, 33 reviews

Idyllic Italian Escape Near Lake and City

A stylish, fully furnished second floor apartment positioned within a traditional 18th century converted building nestled in the heart of the charming village of Mugnano. Contemporary décor and styling blends well with feature-full period character providing spacious accommodation with modern facilities which comprise; a fitted kitchen diner with appliances, a generous sitting room with sofa bed which can also serve as a second bedroom, a comfortable double bedroom and a four-piece shower room

Jun 5 – 12

R994 ZAR per night

Guest favorite

Home in Orvieto

5.0 out of 5 average rating, 179 reviews

Vineyards Paradise

Amazing country house immersed in the vineyard of Cantina Lapone, viewing Orvieto. Recently restored, over 100 sm, organised on two floors. Ground floor is a single space with a big living room (with fireplace) and a spacious open kitchen. First floor with two bedrooms and two bathrooms: the main bedroom (looking at Orvieto) with a double bed and internal bathroom and a second one with a double bed and a bed sofa. Private garden and parking. Private pool (shared with another 4 guests house).

Dec 6 – 13

R6,620 ZAR per night

Guest favorite

Apartment in Montepulciano

4.97 out of 5 average rating, 330 reviews

A view from the top

A View From the Top is an apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 2 double rooms, 2 bathrooms with shower and a large kitchen-living room with a small terrace overlooking the hills From summer 2024 our wine tasting will be available in the new garden and we have a young private chef for cooking class at home ,not in the weekend. Guests will park close the apartment,in the street 50 mt away.

Jan 2 – 9

R3,018 ZAR per night

Guest favorite

Tower in Castiglione della Valle

4.95 out of 5 average rating, 39 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.

Oct 4 – 11

R1,687 ZAR per night

Guest favorite

Farm stay in Seggiano

4.98 out of 5 average rating, 193 reviews

Terra Delle Sidhe, Seggiano, Tuscany

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Nov 12 – 19

R2,083 ZAR per night

Superhost

Farm stay in Agello, Perugia

4.96 out of 5 average rating, 104 reviews

Residence of 300 (Tra Perugia and Lake Trasimeno)

Magnificent apartment located in a historic building of 300 Roman origin nestled in the heart of the Umbrian countryside, on a historic farm. The furnishings are renovated and comfortable. Spacious, bright, functional space with an all-Umbrian view, surrounded by vast vineyards, centuries-old olive groves, enchanting landscapes, large garden and other magnificent plants. 10 km from the historic centre of Perugia and 10 km from Lake Trasimeno.

Dec 21 – 28

R2,351 ZAR per night

Guest favorite

Apartment in Bagnoregio

4.99 out of 5 average rating, 351 reviews

L'Incanto di Civita (La Terrazza)

L'Incanto di Civita is located in the ancient village of Civita di Bagnoregio. Leaving the car at the parking lot, you will need to walk along the bridge, the only way to access our "tuff pearl". L'Incanto di Civita is located in the ancient hamlet of Civita di Bagnoregio. After leaving the car at the parking lot you will need to walk along the bridge, the only way to access our "tufo pearl".

Nov 17 – 24

R3,541 ZAR per night

Guest favorite

Apartment in Pietrafitta

4.91 out of 5 average rating, 11 reviews

Holiday home with pool and panoramic view

Colline di Rafael is a domain with 6 holiday homes with a shared swimming pool (6 x 14 metres) in the heart of Italy. On one side, you have a view of the nearby lake; on the other side, you have a view of the rolling hills with olive groves. The villages in the area are among the most beautiful in Italy. You can rent 1, several or all holiday homes together.

Sep 11 – 18

R2,229 ZAR per night

Guest favorite

Home in Assisi

4.82 out of 5 average rating, 231 reviews

Casa Spagnoli

Vintage residence in the historic center of Assisi, convenient for walking with free parking on site. The house includes a large dining room overlooking the Basilica of Santa Chiara, kitchen, two bedrooms with two private bathrooms equipped with a bathtub and shower. Equipped with Wi-Fi, television and heating.

Dec 9 – 16

R2,109 ZAR per night

Guest favorite

Home in Monticchiello

4.97 out of 5 average rating, 134 reviews

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

Mar 11 – 18

R6,057 ZAR per night

Guest favorite

Apartment in Monticchiello

4.99 out of 5 average rating, 296 reviews

Romantic Tower's dating 1200

The residence "Il Torrino" is a panoramic apartment obtained from the restauration of an ancient tower belonging to the boundaries of the medieval suburb Monticchiello. The apartment has an incredible view on the Val d'Orcia. You can't imagine ...

Jan 18 – 25

R4,746 ZAR per night