Castiglione del Bosco Holiday Rentals

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Our top choices for Castiglione del Bosco holiday rentals

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (134 reviews)
"Super convenient location steps to the historic center. Possibly the only hotel with its own dedicated secure / covered parking. Well decorated and breakfast was great!"
Canada
Mark
Hotel San Gregorio

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (166 reviews)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is NZ$148
includes taxes & fees
1 Feb - 2 Feb
Abbadia Sicille Relais

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (424 reviews)
"Nice place!"
United States
Pavel
The price is NZ$256
includes taxes & fees
2 Mar - 3 Mar
Siena Vip

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (132 reviews)
"Great room-great staff-great location"
United States
Richard
The price is NZ$317
includes taxes & fees
16 Feb - 17 Feb
La Locanda di San Francesco

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (192 reviews)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (51 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
Affitacamere Maria Gabriella

Idolina Guest House

Idolina Guest House
Montalcino
9.4 out of 10, Exceptional, (105 reviews)
"The building is lovely - traditional Italian construction with big Chestnut beams in the ceiling. The owner/manager is very pleasant and helpful. Overall, a very nice place to stay. "
Canada
Carl
Idolina Guest House

PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (1 review)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is NZ$153
includes taxes & fees
2 Feb - 3 Feb
PienzaLettings Suites

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (196 reviews)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (87 reviews)
"Amazing room staff atmoshpehere, there is no other hotel my wife will stay at in the heart of the town."
United States
Michael.
Meublé Il Riccio

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (90 reviews)
"Great location and excellent staff. "
Canada
Jacek
B&B Le Scalette di Piazza

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (96 reviews)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is NZ$157
includes taxes & fees
1 Feb - 2 Feb
Residenza Fabroni

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (97 reviews)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is NZ$271
includes taxes & fees
23 Feb - 24 Feb
PALAZZO DEL PAPA

Casa di Campagna in Toscana

Casa di Campagna in Toscana
Sovicille
9.4 out of 10, Exceptional, (20 reviews)
"Fantastic experience with friendly hosts and an excellent breakfast! A little rustic here and there but all part of the charm!"
United Kingdom
Alasdair
Casa di Campagna in Toscana

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (128 reviews)
"Great hosts, central location "
United States
Alexander
Bed & Breakfast Vicolo dell'Oste

Domus il Palio B&B

Domus il Palio B&B
Ravacciano
9.2 out of 10, Wonderful, (82 reviews)
"Hotel clean comfortable. No elevator, no reception desk. "
United States
Karin
Domus il Palio B&B

Villa le Camelie Siena

Villa le Camelie Siena
Petriccio
8.6 out of 10, Excellent, (8 reviews)
"Personal people are very good. "
Switzerland
Wenjuan
The price is NZ$159
includes taxes & fees
31 Jan - 1 Feb
Villa le Camelie Siena

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti
Monteaperti
10.0 out of 10, Exceptional, (2 reviews)
"We loved this place. Modern cabin set in a rustic Tuscan setting. Beautiful property, very comfortable stay, and very attentive staff. Family owned and operated. Amazing restaurant just steps away. A perfect place for respite"
United States
Ian F.
The price is NZ$360
includes taxes & fees
8 Feb - 9 Feb
Cosy double room in pretty cottage with WiFi and AC in enchanting Monteaperti

Piazza Paradiso Accomodation

Piazza Paradiso Accomodation
Siena City Centre
9.2 out of 10, Wonderful, (155 reviews)
"What my girlfriend loved the most was the bathtub! We have been busy traveling the last week and a half and she was overjoyed with a chance to soak in a bath tub. Room was spacious and clean, the staff was helpful and friendly. The hotel was centrally located and within easy walking distance to Piazza del Campo. Looking forward to staying with Piazza Paradiso accommodation again. We will definitely recommend Piazza Paradiso to all our friends visiting Siena!"
United States
Niels G.
Piazza Paradiso Accomodation

Birbo Bike Hospitality

Birbo Bike Hospitality
Siena City Centre
8.0 out of 10, Very good, (17 reviews)
"Great location. Easier if travel light if you stay in top floors. Simple but clean. Good cost-benefit balance. "
United States
Carlos
Birbo Bike Hospitality
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

Everything you need to know about Castiglione del Bosco holiday rentals

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

Castiglione del Bosco holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Castiglione del Bosco holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Castiglione del Bosco holiday rentals we have selected for you start as low as NZ$142 per night. Entering your travel dates in the search wizard 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 holiday 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 holiday.

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 holiday rentals in Castiglione del Bosco?

Yes, there are holiday rentals close to the most popular sights in Castiglione del Bosco, or you can select a more secluded option if you're looking for a relaxing stay. Castiglione del Bosco is known for its restaurants.

What are some of the best holiday rentals that Castiglione del Bosco has to offer?

Beautiful stone house with garden and private pool.: This holiday home rental outside of Castiglione del Bosco is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of 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 wider area.

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

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Castiglione del Bosco. Holiday rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for small groups.