Castiglione d'Orcia Holiday Rentals from €95: Search Short-Term Rentals

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Holiday Rentals in Castiglione d'Orcia

Cozy living area with a high ceiling, exposed brickwork, and wooden beams, featuring a sofa, dining table, and kitchen with modern appliances.

"We stayed together with children and grandchildren and had a great stay. The house and grounds were beautiful and well kept and we had everything needed."

Relax by the serene pool surrounded by lush greenery and lounge under the shade of umbrellas.

"Excellent views and the property was overall lovely. The nearby town San Quirico d'Orcia also had a good selection of restaurants and was a nice place to stroll in the evening."

includes taxes & fees

21 Jul - 22 Jul

Surrounded by lush greenery and vineyards, this traditional complex offers a tranquil setting with a swimming pool and sun loungers.

"We enjoyed the scenery and service! Clean and comfortable. "

Enjoy dining under a shaded pergola surrounded by lush greenery and brick walls.

"Fabulous location just outside the entrance to the main part of town. Property is stylish in an olde worlde way, perfect for relaxation."

Relax in a serene outdoor space surrounded by lush greenery and tall trees, featuring a cozy fire pit and comfortable seating.

"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "

includes taxes & fees

20 Jul - 21 Jul

Relax by the pool surrounded by lush greenery and take in the breathtaking views of the surrounding mountains.

"Lovely villa, great host. We really enjoyed our stay. "

Relax by the pool surrounded by lounge chairs and lush greenery.

"Luigi was very helpful. We had a chef 3 nights that he helped facilitate. Beautiful location. "

Wander through historic streets lined with traditional stone buildings and arched doorways.

"The people here are authentic and welcoming! The building, rooms and facilities are gorgeous! One of our most beautiful stays in our many trips to Italy "

includes taxes & fees

26 Jul - 27 Jul

Relax by the serene pool with a soothing waterfall and beautifully manicured surroundings.

"Nice neighborhood with Sorano close by. No restaurant or bar open. Lack of bedsheets and towels for 3 people. The shower head was too heavy to stay in the shower head holder"

includes taxes & fees

20 Jul - 21 Jul

Stunning staircase with a grand, curved ceiling and elegant details.

"We loved staying here. Absolutely great communication, super room, lots of dining options. Highly recommend this place."

includes taxes & fees

24 Jul - 25 Jul

Relax by the serene pool surrounded by lush greenery and vibrant flowers.

"Exvellent Location close to all towns in Tuscany Good communication w Manager"

Standalone building surrounded by lush gardens and greenery.

"This is a charming house in a small town outside Cortona. Easily located near all the things you would want to see in the area. The host treated us like family and had homemade treats and wine waiting for our arrival. The house is perfectly suited for 4 people to stay and had a lot of charm. If you are looking to escape the hustle of daily life and relax this is the perfect location. "

Enjoy a spacious living area with a high ceiling, kitchen, dining table, and sofa, offering a view of the surrounding mountains.

"Loved everything about my stay"

includes taxes & fees

31 Jul - 1 Aug

Stroll through the historic garden, surrounded by vibrant blooms and accessed via a stone pathway.

"Located in a peaceful location, the house is charming and homey. The hosts are very kind and accommodating, and we had a wonderful stay. The view from the bedroom balcony is spectacular."

includes taxes & fees

20 Jul - 21 Jul

Relax by the serene pool surrounded by lush greenery and trees.

"Great property,only 30 mins from Siena, very peaceful large garden and large private pool. Just what we needed after doing 9 days touring Tuscan cities, highly recommend this property."

"Tolles Haus, wahnsinnig schöner Ausblick, super Urlaub"

Relax by the serene pool surrounded by lush greenery and comfortable lounge chairs.

"We had five wonderful days in beautiful Toscana! Great atmosphere, wonderful location of the hotel and very reasonably priced. Eating at their restaurant was quite pricy however. Breakfast ok but excellent croissants and coffee! One of the reasons we picked this hotel was the laundry service which was advertised on hotels.com. No laundry service was available. "

includes taxes & fees

20 Jul - 21 Jul

Relax by the serene pool surrounded by lush greenery and rolling hills.

"Wonderful garden, swimming pool and house, nice welcome by Marina."

Enjoy a panoramic view of the rolling hills and stone tower from the large arched window.

"Jacopo and his family were super friendly, the restaurant is the best in Montepulciano and the views are breathtaking. If we come back we will stay at Osteria del Borgo again without a doubt. "

includes taxes & fees

23 Jul - 24 Jul

Relax by the spacious outdoor pool surrounded by lush gardens and trees.

"Amazing property. Very well run"

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Top Castiglione d'Orcia Hotel Reviews

Castello di Velona Resort Thermal SPA & Winery

10/10 Excellent

"We had the most amazing stay at Castello di Velona. The staff was top notch. The facilities are breathtaking. "

Agriturismo La Sovana

10/10 Excellent

"Friendly staff and great food! We had a Saturday dinner on arrival (pricier than weekday dinners but the pici pasta and florentina steaks were delicious) which was really a wonderful experience. The breakfast was tasty. Staff were always friendly. The property is great for walking around and so picturesque. "

Terme di Saturnia Natural Spa & Golf Resort - The Leading Hotels of the World

10/10 Excellent

"Overall, we had a fantastic stay. It was a wonderful way to celebrate my birthday. The food was pricey but delicious. They had a great spread for breakfast and we left every meal full and happy. We also had a couples massage that was wonderful. They really listened to our preferences and gave great massages (one deep tissue and one Swedish massage). 10/10 recommend coming here at least once. We hope to return!"

Rosewood Castiglion del Bosco

10/10 Excellent

"Peaceful, Relaxing Stay in Tuscany We had a great experience here. The setting is quiet and secluded—felt like a true escape from everyday life. The golf was excellent, the food was consistently good, and the service was friendly and professional. It is remote, which adds to the charm, but just a heads-up: if you need anything like Advil or small essentials, the nearest town is about 20 minutes away on a dirt road. Overall, everything was well done. We’d absolutely come back."

Find out more about Castiglione d'Orcia

Everything you need to know about Castiglione d'Orcia holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Castiglione d'Orcia holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Castiglione d'Orcia holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castiglione d'Orcia holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castiglione d'Orcia. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Castiglione d'Orcia holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Castiglione d'Orcia holiday rentals we have selected for you start as low as €95 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Castiglione d'Orcia rentals

At Expedia, we put the best Castiglione d'Orcia holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Castiglione d'Orcia rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Castiglione d'Orcia holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Castiglione d'Orcia. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there holiday rentals in Castiglione d'Orcia?

Yes, there are holiday rentals close to the most popular sights in Castiglione d'Orcia, or you can select a more secluded option if you're looking for a relaxing stay. Castiglione d'Orcia is known for its hot springs and spas. Make sure you have time to check out the riverfront while you're in the area.

What are some of the best holiday rentals that Castiglione d'Orcia has to offer?

Your dream home! In harmony with nature! Priv. Pool - fantastic views!: This holiday home rental outside of Castiglione d'Orcia is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of books so that you can immerse yourself in your holiday.

How many holiday rentals are there in Castiglione d'Orcia?

Choose from 32 Expedia holiday rentals in Castiglione d'Orcia for a memorable holiday.

What’s there to see and do in Castiglione d'Orcia?

Explore the area and family-friendly sights such as Parco Piscine Capenti Outdoor Pool, or get out into nature at a spot like Historic Centre of Pienza. While here, Baths of San Filippo and Valdorcia Terre Senesi are other places worth a visit.

What’s a holiday rental in Castiglione d'Orcia like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castiglione d'Orcia. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for a small group gathering.

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Holiday Rentals in Castiglione d'Orcia

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Holiday Rentals in Castiglione d'Orcia

Villa D'Orchia, luxury organic farm with private pool in Val D'orcia, Sleeps 15.

Casanova - Panoramic Rooms and Suites

Bosco della Spina

Hotel San Gregorio

Abbadia Sicille Relais

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

Villa in Montalcino, exclusive for you, stunning view!!!

Il Tosco

Villaggio Le Querce

Residenza Fabroni

Montalcino: Private villa in the heart of Tuscany, private pool,panoramic view!

Casina in authentic Tuscany

Corte Francigena

Il Poggio dell'Eremita

Gite Montemirello, with garden and swimming pool

Your dream home! In harmony with nature! Priv. Pool - fantastic views!

Borgo Dolciano

Farmhouse in the greenery of the Tuscany countryside with private pool and view

Osteria del Borgo

Historic Villa Ferrano has modern amenities, ideal for medium-sized events.

Top Castiglione d'Orcia Hotel Reviews

Castello di Velona Resort Thermal SPA & Winery

SI Montalcino Hotel

Agriturismo La Sovana

Precise Tale Poggio Alla Sala

Terme di Saturnia Natural Spa & Golf Resort - The Leading Hotels of the World

Hotel Villa Ricci

Albergo San Biagio

Rosewood Castiglion del Bosco

Hotel Panoramic

Find out more about Castiglione d'Orcia

Frequently asked questions