Castiglione del Bosco Vacation Rentals

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Our top choices for Castiglione del Bosco vacation rentals

Casanova - Panoramic Rooms and Suites

Casanova - Panoramic Rooms and Suites
3.0 star property
San Quirico d'Orcia
9.2 out of 10, Wonderful, (79 reviews)
"Fantastic place"
United States
Clifford
The price is CA $268
CA $301 total
includes taxes & fees
May 10 - May 11
Casanova - Panoramic Rooms and Suites

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (171 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is CA $207
CA $233 total
includes taxes & fees
Apr 21 - Apr 22
Abbadia Sicille Relais

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (53 reviews)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
The price is CA $164
CA $221 total
includes taxes & fees
Apr 23 - Apr 24
Affitacamere Maria Gabriella

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 $139
CA $159 total
includes taxes & fees
Apr 22 - Apr 23
Il Pozzo di Sant'Andrea

La Dimora di Dida

La Dimora di Dida
Seggiano
The price is CA $102
CA $112 total
includes taxes & fees
Apr 18 - Apr 19
La Dimora di Dida

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (98 reviews)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is CA $138
CA $158 total
includes taxes & fees
Apr 28 - Apr 29
Residenza Fabroni

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (92 reviews)
"Great location, nice room, and great host!"
United States
Chris
The price is CA $167
CA $190 total
includes taxes & fees
May 3 - May 4
B&B Le Scalette di Piazza

Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
The price is CA $307
CA $345 total
includes taxes & fees
Apr 23 - Apr 24
Albergo Diffuso Borgo Santo

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (130 reviews)
"Loved this place ! Clean, modern, large rooms, perfect location and the owner kind and beyond attentive."
United States
Melissa
The price is CA $142
CA $163 total
includes taxes & fees
Apr 19 - Apr 20
Bed & Breakfast Vicolo dell'Oste

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (140 reviews)
"A wonderful hotel - great location, friendly staff, comfortable rooms. "
United States
beverly
The price is CA $300
CA $339 total
includes taxes & fees
May 7 - May 8
Hotel San Gregorio

Ca' Bianca Tuscany Relais

Ca' Bianca Tuscany Relais
Siena
10.0 out of 10, Exceptional, (43 reviews)
"Great time, perfect property and location."
United States
Christopher
The price is CA $337
CA $378 total
includes taxes & fees
Apr 17 - Apr 18
Ca' Bianca Tuscany Relais

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (91 reviews)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
The price is CA $219
CA $248 total
includes taxes & fees
Apr 22 - Apr 23
Meublé Il Riccio

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (199 reviews)
"Excellent location, rooms, staff."
United States
Mario Humberto
The price is CA $164
CA $187 total
includes taxes & fees
Apr 29 - Apr 30
B&B Il Corso

Luxury resort in the Tuscan countryside

Luxury resort in the Tuscan countryside
Trequanda
The price is CA $313
CA $349 total
includes taxes & fees
Apr 19 - Apr 20
Luxury resort in the Tuscan countryside

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (35 reviews)
"Wonderful "
United States
Rocio Q
The price is CA $249
CA $280 total
includes taxes & fees
Apr 17 - Apr 18
Delcorto Suites

L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (23 reviews)
"Absolutely first class and friendly Perfect location "
United States
Jennifer
The price is CA $650
CA $721 total
includes taxes & fees
Apr 19 - Apr 20
L'Olmo

Villa Curina Resort

Villa Curina Resort
Castelnuovo Berardenga
9.6 out of 10, Exceptional, (64 reviews)
"Great stay but can feel a bit captive to their restaurant for dinner. Min 2 courses mandatory per person and dessert doesn’t count "
Canada
Shelley
The price is CA $226
CA $262 total
includes taxes & fees
Apr 23 - Apr 24
Villa Curina Resort

Borgo Lucignanello Bandini

Borgo Lucignanello Bandini
Montalcino
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful stay "
United States
Marc
The price is CA $458
CA $520 total
includes taxes & fees
Apr 22 - Apr 23
Borgo Lucignanello Bandini

Idolina Guest House

Idolina Guest House
Montalcino
9.4 out of 10, Exceptional, (106 reviews)
"Excellent service, ideal location"
United Kingdom
Nigel
The price is CA $117
CA $141 total
includes taxes & fees
Apr 28 - Apr 29
Idolina Guest House

Dimora Santa Margherita - Relais di Charme

Dimora Santa Margherita - Relais di Charme
Cinigiano
7.8 out of 10, Good, (9 reviews)
"The place was great! Food from their was amazing but also a bit expensive. Poolarea was so beautiful and the view was amazing! Only negative thing is that the wine tasting is not in hotel, need to take own car drive for that. Also the last 2km was sand road, which was not that good shape."
Finland
Anonymous traveller
The price is CA $336
CA $373 total
includes taxes & fees
May 5 - May 6
Dimora Santa Margherita - Relais di Charme
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?

Beautiful stone house with garden and private pool.: This vacation home rental near Castiglione del Bosco is located in a rural location and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the garden in this rental home to help you unwind.

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.