Castiglione del Bosco Villas Rentals

A poolside area with lounge chairs and umbrellas, surrounded by a forested landscape.

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Our top choices for Castiglione del Bosco villas

1. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

Montalcino

$6,883 nightly

Sep 12 - Sep 13

Total with taxes and fees

2. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

Siena

$6,337 nightly

Sep 12 - Sep 13

Total with taxes and fees

3. Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi

Murlo

"Our stay at this property was absolutely excellent! The home was spotless, beautifully decorated, and even more spacious than the photos showed. Every amenity listed was fully functional, and the brand new swimming pool was amazing. The location was perfect— isolated peaceful and quiet, yet just a short drive from the Buonconvento .The host was wonderful to work with. Communication was lightning-fast, and the check-in and checkout instructions were crystal clear. They truly went above and beyond...

martina p.

$3,152 nightly

Sep 20 - Sep 21

Total with taxes and fees

4. Val d'Orcia Historic Farmhouse: 19th century dwelling with Pool and View. 10pl for groups

Montenero

$718 nightly

Sep 29 - Sep 30

Total with taxes and fees

5. Wp Relais Villa Vignalunga

CASTIGLIONE D'ORCIA (SI)

Chris S.

$1,174 nightly

Oct 11 - Oct 12

Total with taxes and fees

6. Il Poggio dell'Eremita

Sinalunga

Paul Q.

$180 nightly

Sep 15 - Sep 16

Total with taxes and fees

7. WPRELAIS BORGO VIGNALUNGA

Toscana

Jeremy F.

$1,689 nightly

Sep 24 - Sep 25

Total with taxes and fees

8. Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

San Quirico d'Orcia

$2,059 nightly

Sep 21 - Sep 22

Total with taxes and fees

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Top Castiglione del Bosco Hotel Reviews

Hotel Athena

10/10 Excellent

"We had a wonderful stay at Hotel Athena in Siena. The service was exceptional, the staff were warm, welcoming and genuinely helpful throughout our visit. The location was fantastic for exploring Siena, with everything within walking distance, while the hotel itself provided a comfortable and relaxing place to come back to after a day of exploring. We also loved the beautiful views from the terrace which was the perfect spot to unwind with a drink and take in the scenery. Sunset was especially beautiful and I would recommend calling the terrace staff themselves to reserve your seat. They are VERY busy up there so please exercise patience and kindness to the server and bartender as they work so hard to get your orders to you as quickly as possible. Self parking our car was a huge bonus as we rented a vehicle to explore Tuscany. A lovely hotel, a great location and wonderful service. We would happily stay here again when visiting Siena!"

Castello di Velona Resort Thermal SPA & Winery

8/10 Good

"Staying here was a wonderful and truly unique experience. The only reason I’m giving it 4 stars instead of 5 was because of the challenges we had with the air conditioning in our room. That said, the staff really did make an effort to find a workaround for us. While it wasn’t a perfect solution, it definitely helped, and we appreciated how responsive and accommodating they were. The hotel itself is an old castle, and that alone makes staying here such a special experience. The property is beautiful, incredibly charming, and very well maintained. You simply can’t replicate the character, history, and ambiance that come with staying in a property like this. The setting and surroundings are beautiful. It was definitely one of those experiences that felt uniquely Italian and added something special to our trip. My only recommendation would be to visit when the temperatures aren’t quite as hot. Given the age and historic nature of the property, I can appreciate that modernizing certain things like the air conditioning may not be as straightforward as it would be in a newer hotel. During cooler weather, I imagine our experience would have been close to perfect. Overall, we really enjoyed our stay and are glad we had the opportunity to experience such a beautiful and unique property. I would absolutely recommend it, just perhaps not during the hottest part of the summer!"

Find out more about Castiglione del Bosco

Castiglione del Bosco Villas information

Number of reviews	177
Accommodation	528 Villas
Lowest Price	$182
Highest Price	$6,883

Frequently asked questions

How much do villas in Castiglione del Bosco cost?

Rates for villas in Castiglione del Bosco range between $182 and $6,883 per night. Whatever your budget, you can find a place that fits the bill on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many villas are there in Castiglione del Bosco?

Pack your suitcase and pick from 528 villas in Castiglione del Bosco. For a family escape, a getaway with pals and everything in between, Expedia can help you find the right place in a few simple clicks.

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Montalcino Vacation Rentals

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Villas in Castiglione del Bosco

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Upfront pricing

Check prices for these dates

Our top choices for Castiglione del Bosco villas

1. VILLA BRUNELLO - Twelve Bedroom Villa, Sleeps 24

2. VILLA CHIGI - Seven Bedroom Villa, Sleeps 14

3. Villa 'Casa Alta Esclusiva' with Private Pool, Private Terrace and Wi-Fi

4. Val d'Orcia Historic Farmhouse: 19th century dwelling with Pool and View. 10pl for groups

5. Wp Relais Villa Vignalunga

6. Il Poggio dell'Eremita

7. WPRELAIS BORGO VIGNALUNGA

8. Villa "Podere Spagliarda" with Private Pool, Terrace & Wi-Fi

9. Villa 'In Antico Borgo Medievale' with Mountain View, Wi-Fi and Air Conditioning

10. Elegant ground floor villa of 93 m2 consisting of a large living room with sofas and fireplace, kitchen complete with dishwasher, microwave oven, electric oven, coffee machine, kettle, fridge and freezer.Indoor and outdoor dining area, a double bedroom w

11. Pet-Friendly Finca Olivos with Mountain View, Pool, Garden & Wi-Fi

12. Charming Tuscany Villa w/ Private Infinity Pool

13. Podere Manafiore - historical villa with swimming pool

14. Villa Falco-Cignella Resort Apartments in Tuscany

15. Red Heart - relax with those you love in Tuscany.

16. GuestHost - Porta Romana Elegant House with Private Parking!

17. Villa Cielo- Cignella Resort Tuscany Accommodation

18. '...a delicious farmhouse in the countryside where only the wind blows...'

19. VILLA ASCARA - Fifteen Bedroom Villa, Sleeps 30

20. Villa 'Tiberini - Casale Il Pecino' with panoramic Valdichiana view, private pool & Wi-Fi

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Top Castiglione del Bosco Hotel Reviews

Hotel Athena

Find out more about Castiglione del Bosco

Castiglione del Bosco Villas information

Frequently asked questions

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