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Castiglione del Bosco Vacation Rentals

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Check prices for these dates

In two weeks
Sep 19 - Sep 21
In one month
Oct 3 - Oct 5
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30

Vacation Rentals in Castiglione del Bosco

Hotel San Gregorio
Breakfast, lunch, dinner served; local cuisine

Hotel San Gregorio

3.0 star property
9.4 out of 10, Exceptional, (124)
"Such friendly staff, loved Pienza and the property was such a good location! "
Hotel San Gregorio
Casanova - Panoramic Rooms and Suites
Front of property - evening/night

Casanova - Panoramic Rooms and Suites

3.0 star property
9.0 out of 10, Wonderful, (65)
"My fiancée and I enjoyed ourselves! It’s a beautiful place and I adored walking around in the nearby town. "
$173 nightly
The price is $196
Sep 7 - Sep 8
Total with taxes and fees
Casanova - Panoramic Rooms and Suites
ApartHotel Anghel
Lobby lounge

ApartHotel Anghel

8.4 out of 10, Very Good, (324)
"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."
ApartHotel Anghel
Residenza d'Epoca Palazzo Borghesi
Panoramic Suite, City View | View from room

Residenza d'Epoca Palazzo Borghesi

9.6 out of 10, Exceptional, (110)
"Beautiful, unique property in central Siena. Sonia at reception was excellent! "
$265 nightly
The price is $297
Oct 3 - Oct 4
Total with taxes and fees
Residenza d'Epoca Palazzo Borghesi
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Pool

Private and cozy retreat in Montalcino with private pool surrounded by vineyards

9.4 out of 10, Exceptional, (62)
"If you like a 360-degree view from the top of the hill, this is the place. Amazing views, out in the country with little traffic (more tractors than cars). Very private. We wanted to sit on the patio all day.The house is very comfortable and a good home base for sampling Brunello and visiting the Montalcino vineyards.Camilla was easy to communicate with before and during our stay."
Private and cozy retreat in Montalcino with private pool surrounded by vineyards
Bosco della Spina
Aerial view

Bosco della Spina

9.6 out of 10, Exceptional, (162)
"We enjoyed the scenery and service! Clean and comfortable. "
$102 nightly
The price is $122
Sep 30 - Oct 1
Total with taxes and fees
Bosco della Spina
Hilltop house in the heart of Tuscany with private pool
Outdoor dining

Hilltop house in the heart of Tuscany with private pool

9.8 out of 10, Exceptional, (90)
"Wonderful, quiet, beautiful. Everything you could want in country stay near a small village."
Hilltop house in the heart of Tuscany with private pool
Camping Siena Colleverde
Exterior

Camping Siena Colleverde

3.0 star property
8.2 out of 10, Very Good, (154)
"Safe, great proximity to Siena without being too close, nice pool."
Camping Siena Colleverde
Tuscasì Aparthotel
Royal Apartment | View from room

Tuscasì Aparthotel

9.2 out of 10, Wonderful, (19)
"Very clean and comfortable accommodations. Beautiful view of the countryside!"
$86 nightly
The price is $98
Sep 7 - Sep 8
Total with taxes and fees
Tuscasì Aparthotel
Villa in Montalcino, exclusive for you, stunning view!!!
Outdoor pool

Villa in Montalcino, exclusive for you, stunning view!!!

10.0 out of 10, Exceptional, (83)
"The villa is huge and well appointed with anything you could imagine There are two large dining rooms inside and several well appointed outside patio areas. The bucolic setting includes birds , roaming sheep down the hill meandering from field to field. Couldn’t be more restful! Also close enough to Siena , San gimingnano Assisi for day trips and even Florence Will definitely return. "
Villa in Montalcino, exclusive for you, stunning view!!!
Delcorto Suites
Interior

Delcorto Suites

10.0 out of 10, Exceptional, (25)
"Exceptional service great building felt like a Medici!"
$188 nightly
The price is $211
Sep 3 - Sep 4
Total with taxes and fees
Delcorto Suites
Il Battistero Siena - Residenza d'Epoca
Bar (on property)

Il Battistero Siena - Residenza d'Epoca

9.6 out of 10, Exceptional, (176)
"Excellent staffing, nice facility and great location"
$170 nightly
The price is $191
Sep 19 - Sep 20
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca
agriturismo la roggiola
Banquet hall

agriturismo la roggiola

9.6 out of 10, Exceptional, (108)
"Beautiful situation, close to Siena and Orcia valley. Three days very well spent, merci Simonetta !"
agriturismo la roggiola
Abbadia Sicille Relais
View from room

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 "
$149 nightly
The price is $168
Sep 7 - Sep 8
Total with taxes and fees
Abbadia Sicille Relais
The House of Alice, charm and relaxation
Exterior detail

The House of Alice, charm and relaxation

9.6 out of 10, Exceptional, (62)
"Unbelievable ambience and beauty of the region and the house. Francesco was super helpful. "
$270 nightly
The price is $275
Sep 3 - Sep 4
Total with taxes and fees
The House of Alice, charm and relaxation
Residenza Fabroni
Lobby

Residenza Fabroni

8.8 out of 10, Excellent, (89)
"We had a wonderful stay, the staff was extremely friendly and helpful. Restaurants and shops were right at our doorstep."
$90 nightly
The price is $104
Sep 4 - Sep 5
Total with taxes and fees
Residenza Fabroni
La Terrazza Sul Campo Rooming House
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe

La Terrazza Sul Campo Rooming House

9.8 out of 10, Exceptional, (231)
"Service was supreme. Decor was authentic Italian. Hard to beat the central location"
$126 nightly
The price is $143
Oct 1 - Oct 2
Total with taxes and fees
La Terrazza Sul Campo Rooming House
Il Tosco
Property entrance

Il Tosco

10.0 out of 10, Exceptional, (112)
"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 "
$252 nightly
The price is $282
Sep 5 - Sep 6
Total with taxes and fees
Il Tosco
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
Exterior

Tuscany romance. Rural charm between Montalcino and sea. Relax pur

9.6 out of 10, Exceptional, (38)
"The stay was very nice. It's a beautiful property and very photogenic! We all loved it, wish we had more time to spend and enjoy the house."
Tuscany romance. Rural charm between Montalcino and sea. Relax pur
panoramica casa con piscina privata
Pool

panoramica casa con piscina privata

7.0 out of 10, Good, (10)
"We had a lovely stay and the hosts were warm, accommodating and responsive. The location is incredible -- extensive views from both sides of the property; the hilltop village setting is out of a postcard with lovely little streets and nooks to explore; and the local shops, market days, restaurants provide everything needed locally. The property is adequate, a little rustic, but well suited to time outdoors by the lovely pool and as a springboard for day trips throughout amazing Tuscany....
$175 nightly
The price is $175
Sep 8 - Sep 9
Total with taxes and fees
panoramica casa con piscina privata
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

Find out more about Castiglione del Bosco

Everything you need to know about Castiglione del Bosco vacation rentals

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

Castiglione del Bosco vacation 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 low season months. For more hustle and bustle, you may prefer to visit Castiglione del Bosco in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $98 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

The House of Alice, charm and relaxation: This vacation home rental near Castiglione del Bosco is located in a rural location and has a fireplace, a terrace, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and kitchenware. Kick off your shoes and enjoy yourself with a garden and a selection of books.

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.