Photo by Mario Mürner

Castiglione del Bosco Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jul 25 - Jul 26
Tomorrow
Jul 26 - Jul 27
This weekend
Jul 25 - Jul 27
Next weekend
Aug 1 - Aug 3

Vacation Rentals in Castiglione del Bosco

Casanova - Panoramic Rooms and Suites
Relax by the serene pool surrounded by lush greenery and lounge under the shade of umbrellas.

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (62)
"My fiancée and I enjoyed ourselves! It’s a beautiful place and I adored walking around in the nearby town. "
The price is NT$5,579
NT$6,275 total
includes taxes & fees
Aug 25 - Aug 26
Casanova - Panoramic Rooms and Suites
Bosco della Spina
Surrounded by lush greenery and vineyards, this traditional complex offers a tranquil setting with a swimming pool and sun loungers.

Bosco della Spina

9.6 out of 10, Exceptional, (158)
"We enjoyed the scenery and service! Clean and comfortable. "
Bosco della Spina
ApartHotel Anghel
Relax in the stylish lobby with comfortable sofas, a glass coffee table, and a beautiful view of the surrounding area.

ApartHotel Anghel

8.2 out of 10, Very Good, (316)
"Hotel is close to Siena and the check-in person (Gabriela) was very friendly and helpful. Room is spacious, functional with easy parking in front of the building and just a 3 minute drive to garage in Siena old-town so very convenient to visit this beautiful city. Excellent value for the money."
The price is NT$2,990
NT$3,427 total
includes taxes & fees
Jul 26 - Jul 27
ApartHotel Anghel
Hotel San Gregorio
Enjoy dining under a shaded pergola surrounded by lush greenery and brick walls.

Hotel San Gregorio

3.0 star property
9.2 out of 10, Wonderful, (119)
"Fabulous location just outside the entrance to the main part of town. Property is stylish in an olde worlde way, perfect for relaxation."
The price is NT$8,237
NT$9,268 total
includes taxes & fees
Aug 8 - Aug 9
Hotel San Gregorio
Abbadia Sicille Relais
Relax in a serene outdoor space surrounded by lush greenery and tall trees, featuring a cozy fire pit and comfortable seating.

Abbadia Sicille Relais

4.0 star property
8.8 out of 10, Excellent, (159)
"An amazing place with a luxury feel. Comfy, welcoming and peacefully relaxing "
The price is NT$5,200
NT$5,824 total
includes taxes & fees
Jul 27 - Jul 28
Abbadia Sicille Relais
Il Battistero Siena - Residenza d'Epoca
Step into Il Battistero, a charming coffee shop with a welcoming atmosphere and a variety of beverages.

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (173)
"Excellent staffing, nice facility and great location"
The price is NT$4,570
NT$5,165 total
includes taxes & fees
Jul 29 - Jul 30
Il Battistero Siena - Residenza d'Epoca
Camping Siena Colleverde
Relax by the serene pool surrounded by lush greenery and well-maintained hedges.

Camping Siena Colleverde

3.0 star property
8.0 out of 10, Very Good, (151)
"Safe, great proximity to Siena without being too close, nice pool."
Camping Siena Colleverde
Regis Condo
Enjoy a compact kitchen with microwave, oven, and dishwasher, plus a dining area and cozy living space.

Regis Condo

9.4 out of 10, Exceptional, (63)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
Regis Condo
Il Tosco
Wander through historic streets lined with traditional stone buildings and arched doorways.

Il Tosco

10.0 out of 10, Exceptional, (111)
"The people here are authentic and welcoming! The building, rooms and facilities are gorgeous! One of our most beautiful stays in our many trips to Italy "
The price is NT$8,650
NT$9,653 total
includes taxes & fees
Jul 26 - Jul 27
Il Tosco
Tuscasì Aparthotel
Enjoy dining al fresco on this scenic outdoor terrace with a table set amidst a serene natural backdrop.

Tuscasì Aparthotel

9.4 out of 10, Exceptional, (18)
"Very clean and comfortable accommodations. Beautiful view of the countryside!"
The price is NT$2,487
NT$2,735 total
includes taxes & fees
Jul 26 - Jul 27
Tuscasì Aparthotel
Residenza Fabroni
Stunning staircase with a grand, curved ceiling and elegant details.

Residenza Fabroni

8.8 out of 10, Excellent, (87)
"We loved staying here. Absolutely great communication, super room, lots of dining options. Highly recommend this place."
The price is NT$2,821
NT$3,241 total
includes taxes & fees
Jul 27 - Jul 28
Residenza Fabroni
Residenza d'Epoca Palazzo Borghesi
Enjoy a serene city view from the comfort of your room, where a beautifully set table invites you to a soothing tea experience.

Residenza d'Epoca Palazzo Borghesi

9.6 out of 10, Exceptional, (110)
"Beautiful, unique property in central Siena. Sonia at reception was excellent! "
The price is NT$5,388
NT$6,064 total
includes taxes & fees
Aug 2 - Aug 3
Residenza d'Epoca Palazzo Borghesi
Osteria del Borgo
Enjoy a panoramic view of the rolling hills and stone tower from the large arched window.

Osteria del Borgo

9.2 out of 10, Wonderful, (145)
"Jacopo and his family were super friendly, the restaurant is the best in Montepulciano and the views are breathtaking. If we come back we will stay at Osteria del Borgo again without a doubt. "
The price is NT$4,074
NT$4,620 total
includes taxes & fees
Jul 30 - Jul 31
Osteria del Borgo
Corte Francigena
Enjoy a spacious living area with a high ceiling, kitchen, dining table, and sofa, offering a view of the surrounding mountains.

Corte Francigena

10.0 out of 10, Exceptional, (5)
"Loved everything about my stay"
The price is NT$5,501
NT$6,464 total
includes taxes & fees
Jul 27 - Jul 28
Corte Francigena
La Terrazza Sul Campo Rooming House
Classic hotel room with a large bed, sitting area, and dining space.

La Terrazza Sul Campo Rooming House

9.8 out of 10, Exceptional, (229)
"Would 10/10 recommend this stay to a friend and would stay here again! Room was beautiful, location was perfect, and the staff is kind and helpful!"
La Terrazza Sul Campo Rooming House
Porta Pispini Residence
Relax in a stylish outdoor space with comfortable seating areas and a staircase leading to an upper level.

Porta Pispini Residence

2.0 star property
9.6 out of 10, Exceptional, (16)
"That’s not a hotel room, that’s small apartment with guest room and kitchen with washer and dishwasher Amazing window view Free parking Very clean 3 minutes walk from the city wall More than reasonable price "
Porta Pispini Residence
Borgo Il Poggiaccio
Relax by the serene pool surrounded by lush trees and comfortable lounge chairs.

Borgo Il Poggiaccio

8.8 out of 10, Excellent, (61)
"Great property for getting the Tuscan vibe. The restaurant and the pool are perfect for a relaxing vacation. We stayed four nights and were able to checkout nearby towns with ease."
Borgo Il Poggiaccio
Castello di Modanella
Stroll through the historic entrance, lined with lush greenery and soft lighting.

Castello di Modanella

7.6 out of 10, Good, (14)
"Property is closing and looks like it. Very unfortunate, I was there 30 years ago with fond memories! Obviously I should have done more homework!! Very sad."
Castello di Modanella
The Balcony Suite -Piazza del Campo View
Overlooking a historic square with a prominent clock tower, this property offers a glimpse into the city's rich heritage.

The Balcony Suite -Piazza del Campo View

9.0 out of 10, Wonderful, (12)
"Great view of Plaza del Campo"
The price is NT$6,842
NT$7,837 total
includes taxes & fees
Aug 3 - Aug 4
The Balcony Suite -Piazza del Campo View
Palazzo Piccolomini
Flat-screen TV

Palazzo Piccolomini

The price is NT$7,066
NT$7,910 total
includes taxes & fees
Jul 27 - Jul 28
Palazzo Piccolomini
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castiglione del Bosco Hotel Reviews

Hotel Athena

Hotel Athena

10/10 Excellent
"We have always loved Sienna . Love the history , the architecture . "
Leane 1-night trip
Posted 3 days ago
Hotel Athena

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’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 I Canaloni del Torrente Farma. 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.