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!

Oct 17 – 24

G$68,732 GYD per night

Guest favorite

Home in Orvieto

5.0 out of 5 average rating, 180 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).

Nov 19 – 26

G$72,820 GYD 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.

Jan 21 – 28

G$16,557 GYD 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.

Jan 18 – 25

G$22,911 GYD per night

Guest favorite

Home in San Feliciano

4.89 out of 5 average rating, 124 reviews

Casa dei 5 Sensi - Trasimeno view

Bioecological building in double class A, energy and environmental, consisting of two apartments, one on the ground floor and the other on the first floor. The one on the first floor is rented, consisting of independent entrance, kitchen/dining/living room,terrace, double bedroom and bathroom. 180 degree lake view, with pool and outdoor green space. The pool is private and is shared with the property. IF YOU CHOOSE IS BUSY, PLEASE CONTACT ME, WE WILL FIND A SOLUTION

May 24 – 31

G$25,382 GYD per night

Guest favorite

Home in San Quirico D'orcia

4.99 out of 5 average rating, 178 reviews

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni

Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

Apr 14 – 21

G$62,635 GYD per night

Guest favorite

Loft in Montepulciano

5.0 out of 5 average rating, 383 reviews

La Piazzetta - Cozy open space in the historic center of Montepulciano

Pour a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta flooring, stone walls. Then go out and take in the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana.

Jan 8 – 15

G$45,956 GYD per night

Guest favorite

Farm stay in Agello, Perugia

4.96 out of 5 average rating, 105 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.

Oct 30 – Nov 6

G$21,678 GYD per night

Guest favorite

Apartment in Bagnoregio

4.99 out of 5 average rating, 352 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

G$38,948 GYD 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.

Apr 9 – 16

G$24,521 GYD per night

Guest favorite

Apartment in Spello

4.97 out of 5 average rating, 133 reviews

Spello Nunnery Apartment

This beautiful 2bedroom- accomodation is located in the upper part of the historical centre of Spello in the second Nunnery dedicated in times to Saint Claire. Offering all comforts, services and a breathtaking outside space, it is perfect for who is searching for a reenergizing romantic base from which to explore the umbrian valley.

Jan 25 – Feb 1

G$23,305 GYD 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.

Jul 23 – 30

G$66,621 GYD per night