Photo by Mario Mürner

Search Vacation Homes in Castiglione del Bosco

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 570 Vacation Homes in Castiglione del Bosco with updated reviews, rates, and availability.

INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

9.8 out of 10, Exceptional, (66)
"The views from this house are fantastic! And the location is perfect - steps from the old town of Montepulciano. Communication with Erika, the host was great. She prepared us with lots of details and recommendations for things to do nearby. We had some questions during our stay and Erika was very responsive. There is so much to do in the area - I almost wished we had more time to hang out on the beautiful terraces!"
INDEPENDENT HOUSE LARGE TERRACES & SPECTACULAR VIEWS in CENTER W. PARKING

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

9.6 out of 10, Exceptional, (45)
"This property is several kilometers up a gravel road from Murlo, Italy. The road is okay but we got a little concerned after it had been raining for a while. The property is remote and near several hiking paths. It is great for people who want to get out and hike around the hills of Italy. The gardens are really nice. We would have spent more time outside if the weather had cooperated more. We went in the fall so it was getting a little cooler up in the hills. There was a nice fireplace that...
Farmhouse in the greenery of the Tuscany countryside with private pool and view

Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (21)
"We have just returned from a wonderful 10 night stay at Porcilia. The property was exactly as advertised and Francesca was a very welcoming and helpful host. The property was clean and well equipped. The pool was excellent and loved by all our party! The pool and the grounds were all very well maintained! We would highly recommend a stay at Porcilia!!"
Porcilaia tiny countryside property, shared pool, ideal base to discover Tuscany

Charming apartment in the Historic Center of Siena

10.0 out of 10, Exceptional, (16)
"This is a wonderful place. It was clean and spacious. It was well stocked. It even had bread and jam for us. It had a kitchen well-stocked with pots, pans, silverware and plates. The owner, Daniella, runs the clothing store in the same building and was very accessible and helpful. It is close by restaurants and shops and was even a nice sized Pam Local supermarket just a few doors away."
Charming apartment in the Historic Center of Siena

Beautiful stone house with garden and private pool.

9.6 out of 10, Exceptional, (58)
"Cottage is larger than described and outfitted nicely for a couple. We used the kitchen everyday for meals and while the bed was firm, it wasn’t bad. Directions to there were confusing. Basically, head to To"
Beautiful stone house with garden and private pool.

The House of Alice, charm and relaxation

9.6 out of 10, Exceptional, (55)
"Quaint apartment, with enough amenities for a great six day stay! The parking is a little tough, but the location and views are fabulous. The pellet stove needs to have directions for the renter when it is cooler weather. I would definitely say again. Francesco was great and helped me with a lot of questions!:)"
The price is AED 517
AED 720 total
includes taxes & fees
31 Mar - 1 Apr
The House of Alice, charm and relaxation

Detached villa with panoramic garden

9.8 out of 10, Exceptional, (52)
"We had a great stay at the house of Marisa and Paolo. Both were very welcoming, and we spent a perfect week in Chiusdino. The house provided everything we needed for our family of four. From the garden we had a beautiful view towards the hills. And the swimming pool was great to cool down and escape from the summer heat. Chiusdino provides a couple of good restaurants which are all in walking distance. We usually had our morning coffee in the bellavista bar, which rightfully has this name. For...
Detached villa with panoramic garden

A MAGICAL HOLIDAY IN TUSCANY

10.0 out of 10, Exceptional, (4)
"We had a fantastic stay for 2 nights. Perfectly located in the heart of the town. Comfortable rooms of lots of space. "
A MAGICAL HOLIDAY IN TUSCANY

Beautiful house on garden with shared pool just a few minutes Siena Tuscany

10.0 out of 10, Exceptional, (32)
"This is a fantastic place, with lots of space, a wonderful kitchen and amazing views. Wine tasting with Lorenzo was great and the wines are top notch. "
Beautiful house on garden with shared pool just a few minutes Siena Tuscany

Capanna, Typical Tuscan Farmhouse With Fruit Garden

10.0 out of 10, Exceptional, (67)
"Loved our stay the host was fantastic and the property is beyond beautiful. This is a type of place that has spectacular views and a magical atmosphere."
Capanna, Typical Tuscan Farmhouse With Fruit Garden

Exclusive Stone Tower.

9.6 out of 10, Exceptional, (5)
"The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and...
The price is AED 314
AED 553 total
includes taxes & fees
3 Apr - 4 Apr
Exclusive Stone Tower.

Belvilla by OYO Oliveta

8.0 out of 10, Very Good, (2)
Belvilla by OYO Oliveta

Domus Nannini SPA - Belvedere Loggia - Palazzo Nannini

10.0 out of 10, Exceptional, (6)
"Great spot to stay when visiting Sienna. Grocery stores near by and lots of recommended restaurants. Our host was easy to get a hold of and his directions for entering were easy to follow as we ended up getting to the place late in the evening."
Domus Nannini SPA - Belvedere Loggia - Palazzo Nannini

Independent house in the hills of the Sienese countryside

10.0 out of 10, Exceptional, (73)
"The picture of the farmhouse doesn't do the location justice after you see it in person.. it's a spectacular view! We arrived on a beautiful sunny day and were warmly welcomed by our hosts. After getting a quick tour of where we would be staying for the next week, we were pleasantly surprised by the kind gesture of homemade olive oil and wine left for us to have. Thank you! The location of this property is perfect for visiting the Tuscany countryside. Not only did we visit Siena on a few...
Independent house in the hills of the Sienese countryside

The terrace overlooking the village, a restored Tuscan farmhouse.

The terrace overlooking the village, a restored Tuscan farmhouse.

Villa Banditello, secluded, panoramic view over Montepulciano valley.

10.0 out of 10, Exceptional, (23)
"This property and our stay was outstanding. Everything was exactly as we hoped. We had an absolutely wonderful stay. The villa is away from the city, but the town is easily accessible. You do need a car. The view from the property is like in a dream and we sat for many hours in the mornings and evenings taking it in. The home is spotless with everything we could possibly need. The owner is extremely helpful and assisted us with dinner reservations and our many questions. We even had wood...
Villa Banditello, secluded, panoramic view over Montepulciano valley.

A cozy nest for a pair

8.8 out of 10, Excellent, (3)
"Die Anfahrts Beschreibung zur Wohnung war etwas schwierig.Der Empfang durch Virginia war sehr freundlich, und die Einweiszng zur Wohnung war ausführlich. Die Lage der Wohnung ideal gleich neben einer wenig befahrenen Nebenstrasse. So gut wie keine Lärmbelästigung.Wunderschöner Garten mit toller Möbelausstattung. Die Küche klein ,aber alles vorhanden . was man zum kochen braucht. Alle Geräte funktionierten. Das Schlafzimmer sehr schön mit den Natursteinwänden, etwas klein , aber wir haben...
A cozy nest for a pair

Enchanting tuscan house, private garden, wellness, stunning views, easy to reach

10.0 out of 10, Exceptional, (19)
"This property in near everything we wanted to see yet far away from the busy tourist areas. Everything we wanted to see was a short drive away. At the end of the day we could retreat back to our villa and relax and get a good nights rest. Carine was a real sweetheart and very responsive. "
Enchanting tuscan house, private garden, wellness, stunning views, easy to reach

Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

10.0 out of 10, Exceptional, (10)
"Had a great time visiting the area. The home is beautiful. "
Legnaia countryside luxury property, shared pool, ideal base to discover Tuscany

Villa Le Tortore Tuscany private luxury pool relax

10.0 out of 10, Exceptional, (88)
"We had an amazing stay at this property. First, Thiago was a great host who was extremely helpful in all facets of the stay. The property is beautiful and really unique- it feels like you have your own Tuscan villa, but are still close to the town of Siena. It's a great compromise between staying in the actual city and in the country. The downside is that there is a decent walk to the town square (about 25 minutes) but it's very doable. There is a nice little grocery store/bar/cafe right down...
Villa Le Tortore Tuscany private luxury pool relax
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Castiglione del Bosco
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Castiglione del Bosco

Casanova - Panoramic Rooms and Suites

3.0 star property
9.2 out of 10, Wonderful, (43)
"It was a nice property- unfortunate what they charge to just swim"
The price is AED 647
AED 727 total
includes taxes & fees
1 Apr - 2 Apr
Casanova - Panoramic Rooms and Suites

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (111)
"Very nice staff, great service, super clean. Will stay again."
The price is AED 427
AED 493 total
includes taxes & fees
31 Mar - 1 Apr
Hotel San Gregorio

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (153)
"Fabulous property and staff. Rita was so helpful when our car had to be towed, we wouldn't have been able to continue our trip with out her and the other team members help. The people here are amazing."
The price is AED 543
AED 614 total
includes taxes & fees
31 Mar - 1 Apr
Il Battistero Siena - Residenza d'Epoca
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.