Castiglione del Bosco Vacation Rentals from $102: Search Short-Term Rentals

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Our top choices for Castiglione del Bosco vacation rentals

Standard Double Room (La Piazza) | Desk, soundproofing, WiFi (free), bed sheets

1. B&B Le Scalette di Piazza

Montalcino

François

$129 nightly

Sep 14 - Sep 15

Total with taxes and fees

2. Idolina Guest House

Montalcino

Bradley

$134 nightly

Sep 28 - Sep 29

Total with taxes and fees

3. Bosco della Spina

Murlo

Lizl

$109 nightly

Oct 14 - Oct 15

Total with taxes and fees

4. Corte Francigena - Apartments

Montalcino

Ryan

$137 nightly

Oct 7 - Oct 8

Total with taxes and fees

5. Palazzo Saloni

Montalcino

BRIAN

$353 nightly

Sep 23 - Sep 24

Total with taxes and fees

6. Podere Belsogno-camera Lavanda

Montalcino

Johannes S.

$160 nightly

Sep 17 - Sep 18

Total with taxes and fees

7. Exclusive Stone Tower.

Casciano

Ryan C.

$155 nightly

Sep 14 - Sep 15

Total with taxes and fees

8. Casanova - Panoramic Rooms and Suites

San Quirico d'Orcia

Jarkko

$159 nightly

Oct 13 - Oct 14

Total with taxes and fees

9. Agritourism in val d'orcia

montalcino

$392 nightly

Sep 14 - Sep 15

Total with taxes and fees

Seasonal outdoor pool, open 7:30 AM to 7:30 PM, pool umbrellas

10. Podere Vesta

Asciano

Katerine

$172 nightly

Sep 17 - Sep 18

Total with taxes and fees

11. Affitacamere Maria Gabriella

Pienza

Christopher

$129 nightly

Oct 14 - Oct 15

Total with taxes and fees

Couples treatment rooms, sauna, hot tub, steam room, body treatments

12. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

San Quirico d'Orcia

Elena

$192 nightly

Sep 15 - Sep 16

Total with taxes and fees

Premium bedding, down comforters, pillowtop beds, desk

13. Tuscasì Aparthotel

Sovicille

Sergey

$93 nightly

Sep 27 - Sep 28

Total with taxes and fees

14. Il Borghetto - The House of Elba, rooftop panoramic terrace

Castelnuovo dell'Abate

$186 nightly

Oct 6 - Oct 7

Total with taxes and fees

15. La Dimora di Dida

Seggiano

$75 nightly

Sep 14 - Sep 15

Total with taxes and fees

16. Il Borghetto - La Ghibellina Townhouse, private apartment with balcony

Castelnuovo dell'abate

Matt D.

$176 nightly

Oct 4 - Oct 5

Total with taxes and fees

17. Apartment 'Casa Francesca' with Hills View & Courtyard

Montalcino

Angela B.

$368 nightly

Oct 1 - Oct 2

Total with taxes and fees

Monolocale Exclusive, vista città, secondo piano senza ascensore | Laptop workspace, iron/ironing board, WiFi (free)

18. TuscanyLettings Studio&Room

Pienza

Lucas

$113 nightly

Sep 14 - Sep 15

Total with taxes and fees

19. Abbadia Sicille Relais

Trequanda

Robert

$139 nightly

Oct 12 - Oct 13

Total with taxes and fees

20. Albergo Diffuso Borgo Santo

Asciano

David

$225 nightly

Oct 13 - Oct 14

Total with taxes and fees

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Top Castiglione del Bosco Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

10/10 Excellent

"Very warm and friendly service."

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

Everything you need to know about Castiglione del Bosco vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Castiglione del Bosco vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 del Bosco vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Castiglione del Bosco vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Castiglione del Bosco. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Castiglione del Bosco in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $102 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Castiglione del Bosco rentals

At Expedia, we put the best Castiglione del Bosco vacation 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 del Bosco 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 del Bosco vacation.

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 del Bosco. 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

Can I find vacation rentals in Castiglione del Bosco?

Yes, there are vacation rentals close to well known attractions in Castiglione del Bosco, or you can choose a more secluded option if you want a relaxing place to stay. Castiglione del Bosco is known for its restaurants.

What are some of the best vacation home rentals in Castiglione del Bosco?

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING: This vacation home rental near Castiglione del Bosco is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a terrace, a garden, and a selection of books so you can immerse yourself in your vacation.

What’s there to see and do in Castiglione del Bosco?

Explore the area and family-friendly sights such as Terme Petriolo, or get out into nature at a spot like Val di Merse. Castiglion del Bosco Winery and Fortress of Montalcino are a couple of places you'll find in the larger area.

What’s a vacation rental in Castiglione del Bosco like?

A vacation rental is a private property where you can stay for short or long periods in Castiglione del Bosco. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for a family trip.

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Check prices for these dates

Our top choices for Castiglione del Bosco vacation rentals

1. B&B Le Scalette di Piazza

2. Idolina Guest House

3. Bosco della Spina

4. Corte Francigena - Apartments

5. Palazzo Saloni

6. Podere Belsogno-camera Lavanda

7. Exclusive Stone Tower.

8. Casanova - Panoramic Rooms and Suites

9. Agritourism in val d'orcia

10. Podere Vesta

11. Affitacamere Maria Gabriella

12. Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

13. Tuscasì Aparthotel

14. Il Borghetto - The House of Elba, rooftop panoramic terrace

15. La Dimora di Dida

16. Il Borghetto - La Ghibellina Townhouse, private apartment with balcony

17. Apartment 'Casa Francesca' with Hills View & Courtyard

18. TuscanyLettings Studio&Room

19. Abbadia Sicille Relais

20. Albergo Diffuso Borgo Santo

Find vacation rentals that suit your style

Top Castiglione del Bosco Hotel Reviews

Castiglion del Bosco, A Rosewood Hotel

Palazzo Ravizza

Hotel Chiusarelli

Grand Hotel Continental Siena – Starhotels Collezione

Hotel Italia

Hotel Athena

Castello di Leonina Relais

NH Siena

Castello di Velona Resort Thermal SPA & Winery

Find out more about Castiglione del Bosco

Frequently asked questions

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