Castiglione del Bosco Vacation Rentals

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Our top choices for Castiglione del Bosco vacation rentals

Tuscasì Aparthotel

Tuscasì Aparthotel
Sovicille
9.2 out of 10, Wonderful, (27 reviews)
"Newly built property featuring large modern accommodation. Safe and easy parking on property, excellent breakfast. "
United States
Sergey
The price is CA $121
CA $155 total
includes taxes & fees
Jul 4 - Jul 5
Tuscasì Aparthotel

La Dimora di Dida

La Dimora di Dida
Seggiano
The price is CA $103
CA $114 total
includes taxes & fees
Jun 18 - Jun 19
La Dimora di Dida

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (103 reviews)
"Staff was great, and they even scheduled transportation to and from the train station for us. Great location on the main strip of Montepluciano!"
United States
Nicholas
The price is CA $128
CA $147 total
includes taxes & fees
Jun 19 - Jun 20
Residenza Fabroni

Il Pozzo di Sant'Andrea

Il Pozzo di Sant'Andrea
Siena
9.8 out of 10, Exceptional, (16 reviews)
"Great host, lovely place near Siena"
United Kingdom
Prem
The price is CA $145
CA $166 total
includes taxes & fees
Jun 29 - Jun 30
Il Pozzo di Sant'Andrea

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (88 reviews)
"We loved our stay and wish we could have stayed longer. Our room was clean & comfortable. The view was AMAZING. We had breakfast included daily which was very good and had a bunch of gluten free options. Our bodies were tired after the hustle & bustle of Florence & Rome so we booked into the “light spa” and had the hot pools to ourselves. It was a short walk to town. We wish we could have stayed longer and plan to be back. "
Canada
Ron
The price is CA $262
CA $294 total
includes taxes & fees
Jun 11 - Jun 12
Casanova - Panoramic Rooms and Suites

La Coroncina Lodging

La Coroncina Lodging
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Fantastic place, and I highly recommend it."
United States
Hassan
The price is CA $204
CA $231 total
includes taxes & fees
Jun 8 - Jun 9
La Coroncina Lodging

RESIDENCE LECCIO

RESIDENCE LECCIO
Asciano
9.6 out of 10, Exceptional, (7 reviews)
"Very nice, affordable place in beautiful area"
United States
Corey
The price is CA $113
CA $132 total
includes taxes & fees
Jun 18 - Jun 19
RESIDENCE LECCIO

Bosco della Spina

Bosco della Spina
Murlo
9.6 out of 10, Exceptional, (172 reviews)
"Lovely stay! I would highly recommend this hotel. The indoor pool was just so enjoyable after a day out sightseeing. "
United Kingdom
Lizl
The price is CA $162
CA $191 total
includes taxes & fees
Jun 24 - Jun 25
Bosco della Spina

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (24 reviews)
"A wonderful stay. "
United States
Sally
The price is CA $184
CA $208 total
includes taxes & fees
Jun 16 - Jun 17
Casa di Campagna in Toscana

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (177 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is CA $277
CA $309 total
includes taxes & fees
Jun 8 - Jun 9
Abbadia Sicille Relais

Corte Francigena - Apartments

Corte Francigena - Apartments
Montalcino
9.8 out of 10, Exceptional, (6 reviews)
"Loved everything about my stay"
United States
Svetlana
The price is CA $236
CA $279 total
includes taxes & fees
Jun 21 - Jun 22
Corte Francigena - Apartments

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (142 reviews)
"Great location."
United States
James
The price is CA $202
CA $228 total
includes taxes & fees
Jun 11 - Jun 12
La Locanda di San Francesco

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (210 reviews)
"Friendly staff and good location."
Canada
Yongseok
The price is CA $198
CA $224 total
includes taxes & fees
Jun 24 - Jun 25
Il Battistero Siena - Residenza d'Epoca

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (103 reviews)
"Place is amazing and maintained perfectly."
United States
Dominic
The price is CA $230
CA $260 total
includes taxes & fees
Jun 12 - Jun 13
Meublé Il Riccio

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (91 reviews)
"Rooms were clean and spacious ! Happy there was a good blow dryer in the room and a heated towel rack. Staff were very friendly and helpful . Would stay again !"
Canada
Alissia
The price is CA $106
CA $123 total
includes taxes & fees
Jul 3 - Jul 4
Domus il Palio B&B

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (137 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is CA $189
CA $214 total
includes taxes & fees
Jun 25 - Jun 26
Bed & Breakfast Vicolo dell'Oste

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (203 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is CA $155
CA $177 total
includes taxes & fees
Jul 3 - Jul 4
B&B Il Corso

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (93 reviews)
"Great location, nice room, and great host!"
United States
Chris
The price is CA $200
CA $226 total
includes taxes & fees
Jun 30 - Jul 1
B&B Le Scalette di Piazza

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (145 reviews)
"Nice hotel - clean, good breakfast, perfect location. Would stay again!"
United States
Nancy
The price is CA $256
CA $291 total
includes taxes & fees
Jun 17 - Jun 18
Hotel San Gregorio

Villa Fontis Rapolano

Villa Fontis Rapolano
Rapolano Terme
The price is CA $127
CA $146 total
includes taxes & fees
Jun 7 - Jun 8
Villa Fontis Rapolano
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.
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Top Castiglione del Bosco Hotel Reviews

Find out more about Castiglione del Bosco

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Castiglione del Bosco. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 in the hills of the Sienese countryside: This vacation home rental near Castiglione del Bosco is located in a rural location and has a fireplace, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 Horti Leonini. 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.