
Holiday houses in Castiglione della Valle
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Castiglione della Valle
Guests agree: these stays are highly rated for location, cleanliness and more.

Poggio Bicchieri Holiday Farm - Memoria apartment
Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!
FamilyValueCondition

Charming Tuscan Villa with View forFamily&Friends
The house is a typical podere of the late 1800, stone walls, chestnut beams, and hand-made tiles have all been kept; what has changed is the comfort behind them. The Host Fulvia lives in the ground-floor apt. and she's on hand throughout your stay without ever intruding — a rhythm that guests consistently single out. Total accommodation is 8 guests across 2 bdr and 2 bathrooms. Visit Montepulciano, Pienza, Bagni Vignoni and iconic Unesco sites in Val d'Orcia within short and easy driving away
FamilyLocationLong stay

La Perla del Lago Holiday home on Lake Trasimeno
La Perla del Lago:il tuo rifugio al Trasimeno Ritrova la tua armonia in questa oasi di pace assoluta. Lasciati incantare dalla nostra vista magica e dai tramonti che il Lago regala ogni sera. La Casa Vacanze La Perla del Lago domina lo specchio del Trasimeno. A 8 minuti trovi la superstrada per visitare borghi come Firenze, Perugia, Gubbio, Spoleto, Norcia e molti altri. Nel borgo avrai bar,ristoranti,market, farmacia, bancomat e aree bimbi;a 3 km sorge un'azzurra piscina per il relax estivo.
ValueFamilyParking

Exclusive 10 Acre Estate w/ Pool & Olive Grove!
Enchanting, exclusive 10acres estate on a hill, memorable sunsets; large pool framed by lavender&rosemary, open year-round. New air conditioning, Starlink internet. Very private&peaceful 2 floors, 4bedrooms, 4baths, jacuzzibathtub, 55inch smartTV, well-equipped kitchen, porch & pergola for alfresco dining, Weber barbecue, pizza oven, olive grove, fireplace; 20 min. to Orvieto,Todi,Amelia; 10 minutes drive to train station to Rome/Florence, 5min drive to shops in town. Grounds/pool caretaker
LocationFamilyNearby

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.
ValueLocationGetting around

Casa Dolce Toscana | Panoramic Suite with View
CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.
ValueFamilyBreakfast

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
LocationFamilyCheck-in

Casa Boschetto, villa with private pool
The rural house was built with ancient stone sourced locally in Umbria and offers a breath taking view overlooking the surrounding valley. The house encompasses a spacious living-room with two antique fire places, two kitchens, a recreation room, five bedrooms & four bathrooms. Outside there is a large swimming pool, dining area, a play house for children, multiple car-parking options and a 2 car fully enclosed garage. There are also a BBQ and a wood fire oven if you wish to cook outside.
FamilyLocationCheckout

Rural Tuscany | Family farmstay with restaurant
Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.
LocationValueSleep quality

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.
ValueLocationBathroom

Frankly welcoming for a fantastic stay
Loft ideale per per coppie, viaggiatori singoli o smart worker in cerca di tranquillità. Monolocale grande e nuovo, con balcone, tetto in legno e design moderno. Si trova al secondo piano di una casa curata ed abitata dalla famiglia che vi ospita. La cucina è completa di tutti gli elettrodomestici nuovi e di qualità. L'abitazione viene consegnata pulita ed igienizzata. Parcheggio gratuito all’interno della proprietà o lungo la via privata di accesso alla casa.
ValueLocationComfort

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.
FamilyLocationCondition
Popular amenities for Castiglione della Valle holiday rentals
Other great holiday rentals in Castiglione della Valle

Casa di Scoccia | Umbrian Farmhouse with Pool
LocationFamilyWalkability

Elegant historic Palazzo, views of Tuscan valley
ValueFamilyBreakfast

Villa Incanto – Todi
FamilyLocationAir conditioning

Sunset on the Lake – Passignano Centro Lake view
LocationAir conditioningCleanliness

Stone Farmhouse with Pool 1 - Italy
FamilyLocationIndoor spaces

Loft with pool surrounded by greenery
LocationFamilyIndoor spaces

Villa Amici Apartment
LocationSleep qualityAmenities
La Piazzetta - Cozy open space in the historic center of Montepulciano
LocationValueLong stay
Destinations to explore
- Lake Trasimeno
- Lake Bolsena
- Lake Vico
- Basilica of St Francis
- Frasassi Caves
- Centro Storico Orvieto
- Cascate del Mulino
- Sibillini Mountains National Park
- Mount Amiata
- Terme Dei Papi
- Villa Lante
- La Scarzuola
- Furlo Gorge Nature Reserve
- Avignonesi Winery Fattoria Le Capezzine
- Val di Chiana
- Mount Subasio
- Terme San Filippo
- Valdichiana Outlet Village
- Gola del Furlo
- Saturnia Thermal Park
- Abbey of Sant'Antimo
- Abbey of Monte Oliveto Maggiore
- Rocca Maggiore
- Spoleto Cathedral





