
Holiday rentals 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.

Under the sunset, Montepulciano
In 2023 my son Guglielmo and I decided to restore the old oratory of a church from the 1600s by creating a two floor apartment: upstairs we have 2 bedrooms equipped with AC and 2 en-suite bathrooms with shower; downstairs a spacious living room with stereo Available a table outside with great view and a nice garden 50 mt away where to have a private wine tasting for all the guests of our 4 apartments We can organize barbecue with paired wines after 7 pm. Large free parking area 100 mt away

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.

Casale Santa Barbara - Exclusive Apartment
At a glance: • Location: perfect entry door to the Val d’Orcia between Pienza (8,5 km) and Montepulciano (8,5 km). • Charming warm old stones Tuscan house – completely restored in 2016 • Big apartment (100m2), designed for 2 persons, completely independent, fully furnished, Tuscan style with modern equipment. • Exclusivity: we are living on the 1st floor; the ground floor is yours. You are our only guests. • Spacious private garden (+ 300m2) • Stunning view on the Tuscan hills.

La Perla del Lago Holiday home
Forget all your worries in this oasis of serenity. Let yourself be soothed by our amazing views and the sunsets that the lake offers us every evening La Perla del Lago Holiday Home overlooks Lake Trasimeno. 8 minutes away is the highway from which you can easily reach Florence, Perugia,Gubbio, Spoleto, Norcia and many others In the village there are bars, restaurants, food restaurants, ATM pharmacy,a small playground, 2 km away, a beautiful pool for the hottest days.

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.

La Dolce Agogia Cottage Panicale
A territory rich in history and traditions The will to share the love for simple but authentic things with others, making them feel part of our family. From all this comes "la Dolce agogia" If what you are looking for is a place to sleep immersed in the quiet of the Umbrian/Tuscan countryside while remaining in contact with the comforts of the city centre, La Dolce Agogia is the ideal location for your stay in the green heart of Italy.

Cottage surrounded by nature
"IL PODERACCIO" is a typical stone farmhouse located on the hills surrounding Lake Trasimeno, immersed in beautiful Mediterranean vegetation. The building is spread across two floors. The pool and garden frame the whole. The swimming pool is open from May 1st to October 15th. Please note that following the COVID 19 emergency, all the directives required by the legislation have been adopted for cleaning and sanitizing the house.

The Enchantment of Civita (The Terrace)
L'Incanto di Civita is located inside the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot, you will need to walk along the bridge, the only way to access our "tufo pearl". L'Incanto di Civita is located in the ancient village of Civita di Bagnoregio. After leaving your car at the parking lot you will need to walk along the bridge, the only way to access our "tufo pearl".

1 room apartments in farmhouse whit pool
At Borgo Solario we have 4 apartments of this type, with 1 bedroom. Those 4 apartments are on ground floor, in rustic tuscany style living room with furnished kitchenet, 1 bedroom, bathroom with shower and private and independent entry. The property has a 360° view over the valley and down to the Trasimeno lake. Garden with common pool in summer and play ground. MAX people 2, no kids under 12 years old.

Dreamy Countryside Apt on Organic Estate
Spacious and sunlit, L’Arco is our grand apartment on a year-round luxury countryside estate. Enjoy high-end amenities, vineyard views, and plenty of space to unwind. With a pool, olive groves, and easy access to Umbria and Tuscany, it’s the perfect base. We usually rent the full estate, so apartments like this are rarely available. If your dates are open, book now—your Italian escape awaits.

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...

House of Olives
Delightful semi-detached house immersed in the peace of the green Umbrian hills, just 15 minutes from the center of Perugia, and a short distance from the most beautiful Umbrian towns. Relaxation, intimacy, as well as being close to all amenities. My apartment is suitable for couples, solo adventurers, business travelers, families (with children)
Popular amenities for Castiglione della Valle holiday rentals
Other great holiday rentals in Castiglione della Valle

Hidden gem in Tuscany

Castiglione vacation home - 4 beds

Torre di Orlando - Medieval Tower 12th century

Palazzo di Bagnaia House of Scoccia

The Terrace of Victory

Luxury Tuscan countryside villa with pool/WiFi/AC

Agriturismo Via della Stella | Apartment Lecci

Exclusive panoramic villa with private pool
Destinations to explore
- Lake Trasimeno
- Lake Bolsena
- Frasassi Caves
- Lake Vico
- Avignonesi Winery Fattoria Le Capezzine
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Tenuta Le Velette
- Terme Dei Papi
- Villa Lante
- Basilica of St Francis
- Castiglion del Bosco Winery
- Cantina Colle Ciocco
- Furlo Gorge Nature Reserve
- Mount Subasio
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Casa Del Cioccolato Perugina
- Monte Prata Ski Area
- Abbey of Monte Oliveto Maggiore
- Madonna del Latte
- Podere Il Cocco
- Monti Sibillini national park
- Cantina de' Ricci
- Cantina Contucci
- Antonelli San Marco