Photo by Mario Mürner

Castiglione del Bosco Vacation Rentals

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Oct 19 - Oct 20
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Oct 24 - Oct 26
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Oct 31 - Nov 2

Vacation Rentals in Castiglione del Bosco

View from room
Abbadia Sicille Relais
Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (160)
"It was too cold for the swimming pool as it is mid October, there were people using the hot tub, but I have one in my room and the sauna so why bother it was so wonderful and the staff was super. Christina was the most wonderful ball."
United States
Christine
$72 nightly
The price is $83
Nov 2 - Nov 3
Total with taxes and fees
Abbadia Sicille Relais
Quadruple Room, City View | 1 bedroom, desk, iron/ironing board, free WiFi
Al Mercato B&B
Al Mercato B&B
9.0 out of 10, Wonderful, (91)
"Nice area and clean property "
United States
heeman
$80 nightly
The price is $92
Nov 12 - Nov 13
Total with taxes and fees
Al Mercato B&B
Breakfast, lunch, dinner served; local cuisine
Hotel San Gregorio
Hotel San Gregorio
3.0 star property
9.4 out of 10, Exceptional, (130)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
$122 nightly
The price is $141
Nov 4 - Nov 5
Total with taxes and fees
Hotel San Gregorio
Bar (on property)
Il Battistero Siena - Residenza d'Epoca
Il Battistero Siena - Residenza d'Epoca
9.6 out of 10, Exceptional, (186)
"Great location and friendly staff. "
United States
Parissa
$144 nightly
The price is $163
Nov 3 - Nov 4
Total with taxes and fees
Il Battistero Siena - Residenza d'Epoca
32-inch Smart TV with digital channels, TV, streaming services
B&B Il Corso
B&B Il Corso
9.8 out of 10, Exceptional, (183)
"great location, faciilties at hotel good"
United Kingdom
tracey
$95 nightly
The price is $109
Nov 9 - Nov 10
Total with taxes and fees
B&B Il Corso
Exterior
PALAZZO DEL PAPA
PALAZZO DEL PAPA
9.6 out of 10, Exceptional, (95)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
$157 nightly
The price is $178
Nov 5 - Nov 6
Total with taxes and fees
PALAZZO DEL PAPA
Outdoor pool, pool umbrellas, sun loungers
Villa Curina Resort
Villa Curina Resort
9.6 out of 10, Exceptional, (63)
"We had a truly AMAZING experience. So much so that our 18 year old said she wanted to come back and get married there!! Wonderful people, atmosphere, food, and wine Thank you Andrea for the suggestions). "
United States
Amy
$187 nightly
The price is $215
Oct 24 - Oct 25
Total with taxes and fees
Villa Curina Resort
Seasonal outdoor pool, pool umbrellas
Borgo San Lorenzo a Linari
Borgo San Lorenzo a Linari
8.6 out of 10, Excellent, (98)
"Such a pleasant stay and the staff was incredible. "
United States
Monica
Borgo San Lorenzo a Linari
Premium bedding, down comforters, minibar, in-room safe
La Locanda di San Francesco
La Locanda di San Francesco
9.8 out of 10, Exceptional, (125)
"Beautiful property nestled at the top of montepulciano. Very helpful owner Luca and unmatched hospitality! "
United States
Alizeh
$174 nightly
The price is $197
Nov 2 - Nov 3
Total with taxes and fees
La Locanda di San Francesco
Exterior
Meublé Il Riccio
Meublé Il Riccio
9.6 out of 10, Exceptional, (80)
"Excellent location and hospitality…"
United States
Yeh Tsong
Meublé Il Riccio
Birthday party area
Siena Vip
Siena Vip
9.2 out of 10, Wonderful, (407)
"Super clean super close to everything."
United States
Ramon
Siena Vip
Deluxe Double Room | View from room
Affitacamere Maria Gabriella
Affitacamere Maria Gabriella
9.8 out of 10, Exceptional, (49)
"Beautiful place and area with very good restaurants close by! We stayed in the cottage and it was well equipped with everything you need! "
United States
Ann Sofi
Affitacamere Maria Gabriella
Front of property - evening/night
Casanova - Panoramic Rooms and Suites
Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (75)
"Fantastic place"
United States
Clifford
Casanova - Panoramic Rooms and Suites
Restaurant
B&B Dei Rossi
B&B Dei Rossi
8.0 out of 10, Very Good, (17)
"Wonderful stay. Large room, shared kitchen and great location to shops and restaurants. A lot of stairs, but it comes with a beautiful view. "
Canada
Alana
$69 nightly
The price is $80
Nov 3 - Nov 4
Total with taxes and fees
B&B Dei Rossi
Lobby
Residenza Fabroni
Residenza Fabroni
8.8 out of 10, Excellent, (90)
"We had a wonderful stay, the staff was extremely friendly and helpful. Restaurants and shops were right at our doorstep."
Canada
Nicole
$90 nightly
The price is $104
Oct 21 - Oct 22
Total with taxes and fees
Residenza Fabroni
Panoramic Suite, City View | View from room
Residenza d'Epoca Palazzo Borghesi
Residenza d'Epoca Palazzo Borghesi
9.6 out of 10, Exceptional, (115)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
$183 nightly
The price is $207
Nov 16 - Nov 17
Total with taxes and fees
Residenza d'Epoca Palazzo Borghesi
Family Room | 1 bedroom, Egyptian cotton sheets, premium bedding, down comforters
Piazza Paradiso Accomodation
Piazza Paradiso Accomodation
9.2 out of 10, Wonderful, (155)
"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
Bar (on property)
Exclusive Stone Tower.
Exclusive Stone Tower.
9.8 out of 10, Exceptional, (6)
"The tower was a perfect place for our trip to Tuscany! It had a ton of space with a full kitchen and living room. The town it is located in is fantastic. There is a small grocery store, a pizza place, and a fantastic restaurant where two people can get a delicious meal and drinks for about €30 all within walking distance. You can easily drive from the tower to Siena, Florence, Montalcino, Montepulciano, and I'm sure many other places that we didn't have time to get to. Sauro was a great host and...
United States
Michael G.
$166 nightly
The price is $168
Nov 17 - Nov 18
Total with taxes and fees
Exclusive Stone Tower.
Aerial view
Bosco della Spina
Bosco della Spina
9.6 out of 10, Exceptional, (166)
"We enjoyed the scenery and service! Clean and comfortable. "
United States
Sanaz
$80 nightly
The price is $98
Nov 2 - Nov 3
Total with taxes and fees
Bosco della Spina
Superior Double Room, 1 Queen Bed, Private Bathroom, City View | View from room
B&B Palazzo del Magnifico
B&B Palazzo del Magnifico
9.8 out of 10, Exceptional, (62)
"Excellent host and location!"
United States
Kimberly
$99 nightly
The price is $114
Nov 3 - Nov 4
Total with taxes and fees
B&B Palazzo del Magnifico
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 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 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.

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 a coffee maker. 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.