We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Homes near Castiglion del Bosco

Localita Castiglion del Bosco, 53024, Montalcino, Italy
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $1,088 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travellers to Montalcino are booking July dates now. Secure your holiday rental today, and have the perfect trip.
    All 99 Rentals in Montalcino
    Tuscany country apartment for 41 / 20
    (2)Excellent
    7.7 kilometres from Castiglion del Bosco
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Fornello di Sopra, luxury villa with private pool1 / 57
    (3)Excellent
    7.0 kilometres from Castiglion del Bosco
    4 Bedrooms, 5 Bathrooms, Sleeps 11 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Country house,Montalcino, Tuscany, TENUTA CANINA1 / 45
    (1)Excellent
    7.5 kilometres from Castiglion del Bosco
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Fonte Aulente Montalcino1 / 26
    (31)Excellent
    7.5 kilometres from Castiglion del Bosco
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Central Heating
    • Outdoor Dining Area
    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 August 2017
    This is a really gorgeous place to stay. The views could not be better, the garden is eclectic and the pool is warm and inviting. We were slightly unsure whether to book based...
    Reviewed 10 November 2016
    Our family thoroughly enjoyed this stay in Tuscany. My husband and I have been to Italy many times, but this is the first time we brought the kids with us. (Ages 3 and 6...
    See all reviews
    About this property
    Fonte Aulente is a Tuscan farmhouse from the 12th century recently restored and surrounded by beautiful garden-park, 2 km from the center of Montalcino, in a panoramic position with amazing views over the Tuscan hills. The apartment is a part of the old farmhouse, with its own entrance. The...
    View all property information
    Location Information
    Montalcino, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Cozy Collection of Villas in Tuscany1 / 30
    (51)Excellent
    6.4 kilometres from Castiglion del Bosco
    14 Bedrooms, 14 Bathrooms, Sleeps 26 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Mountain Views
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 October 2017
    We loved our villa, the property, our host and the region. The property was amazing. Wine, olives, lavender and lots of property. Located about 10-15 kilometers from...
    Reviewed 29 March 2017
    Matteo was a great host. Our stay was very enjoyable. The setting is as beautiful as all the pics! The cellar was terrific to see and the wine - even better!!
    See all reviews
    About this property
    PLEASE NOTE: THE PROPERTY IS DIVIDED INTO EIGHT SELF CONTAINED APARTMENTS, EACH SLEEPING 2-4 PEOPLE. THIS LISTING IS FOR A SINGLE APARTMENT. IF YOU CANNOT FIND YOUR DESIRED AVAILABILITY, PLEASE CONTACT US AND WE WILL TRY TO FIND A SUITABLE ARRANGEMENT. RATES VARY ACCORDING TO APARTMENT SIZE AND...
    View all property information
    Location Information
    Montalcino, Province of Siena
    Holiday Rental House - 14 Bedrooms, 14 Bathrooms, Sleeps 26
    Make Enquiry
    Fienile farmhouse in the  Borgo Castelrotto1 / 21
    (2)Excellent
    4.2 kilometres from Castiglion del Bosco
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Porch
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    If you want to go and visit Tuscany them you absolutely have to stay in the Val d'orcia or the Orcia Valley to see the real side of this incredible region, away from the...
    See all reviews
    About this property
    This charming and cosy two level recently renovated hay-loft/ farmhouse is perfect for families with children, or couples who want to get away from it all! A perfect get-away from it all immersed in the rolling hills of the Orcia valley where you can discover the Real Tuscany by staying on our...
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Affittacamere Caliani1 / 15
    (1)Very good
    7.6 kilometres from Castiglion del Bosco
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Private Room - 1 Bedroom, 2 Bathrooms, Sleeps 2
    Make Enquiry
    Casanova farmhouse in the Borgo Castelrotto1 / 25
    (6)Excellent
    5.0 kilometres from Castiglion del Bosco
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Housekeeping Included
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 September 2017
    This is a wonderful place, very private in the Tuscan countryside with fantastic views. We spent three nights here while attending our daughter's wedding nearby, and we loved...
    Reviewed 30 March 2017
    We all loved this Tuscan farmhouse and its proximity to the medieval towns such as Pienza, Siena and Montalcino makes all the difference. Yet, if you want to come back and spend...
    See all reviews
    About this property
    Are your looking for an ideal vacation spot to relax and enjoy the magnificently unspoilt Tuscan countryside in the Orcia valley while relaxing with a good book by the pool? Or do you prefer making cultural excursions to any of the numerous surrounding hill towns? well,, the Borgo Castelrotto at...
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    4.5 kilometres from Castiglion del Bosco
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Hot Tub
    • Balcony
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Central Heating
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Pari, Civitella Paganico
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    Fagianaia farmhouse at Borgo Castelrotto1 / 24
    (1)Excellent
    4.2 kilometres from Castiglion del Bosco
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Housekeeping Included
    • Cable/satellite TV
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If your looking for an ideal vacation spot to relax and enjoy the magnificently unspoilt Tuscan countryside while relaxing with a good book by the pool, or if your prefer making cultural excursions to any of the numerous surrounding hilltowns, Castelnuovo Tancredi is the place for families with...
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    Save time - get the best Montalcino rentals sent straight to your email!
    Get the List
    6.3 kilometres from Castiglion del Bosco
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Internet Access
    • Grill
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful stone-built villa rental accommodation (230 m2) situated approx. 500 m from the historical centre of Montalcino, ideal starting point for excursions to the spa resorts at Bagno Vignoni, the Orcia valley, Monte Amiata, the Maremma, Siena and the nearby wine producing estates for the...
    View all property information
    Location Information
    Montalcino, Province of Siena
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    Poggio Rubino, la casa di Idolina1 / 21
    (1)Very good
    6.5 kilometres from Castiglion del Bosco
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Montalcino, Province of Siena
    Private Room - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    6.3 kilometres from Castiglion del Bosco
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Grill
    • Central Heating
    • Wi-Fi
    • Mountain Views
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy winelovers' paradise in Montalcino from the beautifully renovated and spacious apartment - Casa Brunello di Montalcino - in the 17th century building with some nice original pieces, combining the traditional Tuscan countryside look with modern high-quality furniture and design. From the 30...
    View all property information
    Location Information
    Montalcino, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    7.7 kilometres from Castiglion del Bosco
    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Grill
    • Housekeeping Included
    • Central Heating
    • Porch
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Private Room - 6 Bedrooms, 6 Bathrooms, Sleeps 14
    Make Enquiry
    Romantica camera con piscina1 / 14
    (1)Excellent
    7.9 kilometres from Castiglion del Bosco
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2017
    We stayed at this wonderful property for a week, relaxing and enjoying the beautiful scenery! It is an amazing place, one of the best places for disconnecting from everyday life...
    See all reviews
    About this property
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    5.8 kilometres from Castiglion del Bosco
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Housekeeping Included
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This villa, located in Buonconvento, is ideal for 8 vacationers. It offers 4 bedrooms, a pool access, a furnished garden and a terrace. The lounge is perfect for unwinding after a day of exploration. Curl up on the comfortable sofa and enjoy a good book in front of the fireplace or take advantage...
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Enquiry
    6.5 kilometres from Castiglion del Bosco
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RECEPTIVE STRUCTURE. Casale Montebendico is a gracious, recently restored property. The property is located on the border of Val d’Orcia, area renown for the “Crete Cenesi” and the “Maremma”, a land which extends from the splendid countryside to the Tyrrhenian sea. Situated only a few kilometres...
    View all property information
    Location Information
    Montalcino, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    7.3 kilometres from Castiglion del Bosco
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Internet Access
    • Terrace
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4-room apartment 100 m2, on the upper ground floor. Spacious, renovated, beautiful and tasteful furnishings: living room with 1 double sofabed and satellite TV. Dining room. 2 double bedrooms, each room with shower/bidet/WC. Kitchenette (oven, dishwasher, 4 ceramic glass hob hotplates)....
    View all property information
    Location Information
    Montalcino, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    6.5 kilometres from Castiglion del Bosco
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Balcony
    • Cable/satellite TV
    • Mountain Views
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    RECEPTIVE STRUCTURE. Le Macine is a farmhouse which the owners finished renovating with great skill in 2011. It dates to the beginning of the 20th century and its name derives from the fact that along the entrance drive are present two antique millstones of an old oil mill. The renovation was...
    View all property information
    Location Information
    Montalcino, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    6.7 kilometres from Castiglion del Bosco
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Washer
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This villa is set on a hill and overlooks the beautiful countryside as well as the nearby town of Montalcino. If you and your friends are looking for a quiet holiday in Tuscany, this vacation rental is certainly for you. Here you will be able to swim in a private swimming pool, enjoy homemade meals...
    View all property information
    Location Information
    Montalcino, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    5.5 kilometres from Castiglion del Bosco
    22 Bedrooms, 22 Bathrooms, Sleeps 44 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Borgo Finocchieto, in Buoncovento, Tuscany, part of *****************, Tuscany Villas & Italy Villa Rentals An entire village in the province of Siena has become an ideal holiday destination for large groups of friends who want to experience something truly historic. Borgo Finocchieto is located on...
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 22 Bedrooms, 22 Bathrooms, Sleeps 44
    Make Enquiry
    Beautifully restored farmhouse in Pari, Tuscany, f1 / 24
    (1)Excellent
    6.7 kilometres from Castiglion del Bosco
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Wi-Fi
    • DVD Player
    • Grill
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Central Heating
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Petriolo is a farmhouse carefully restored with great attention for the details and maintaining as much as possible the original characteristics of the building with tuscan cotto floors and wooden beamed ceilings. It is located on the hills on the border between Grosseto and Siena nestled in...
    View all property information
    Location Information
    Pari, Civitella Paganico
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    4.7 kilometres from Castiglion del Bosco
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Terrace
    • Private Garden
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Montalcino, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    B&B in centro storico Montalcino Val D'Orcia1 / 6
    (1)Excellent
    6.2 kilometres from Castiglion del Bosco
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping Included
    • Central Heating
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2016
    The room is so clean with self service breakfast that Gigliola and her husband provided. They r so kind,recommended the best restaurant and places to visit.
    See all reviews
    About this property
    Per chi ama trascorrere il proprio tempo libero o le vacanze a Montalcino e godersi lo stupendo paesaggio della Val D'orcia, il Bed and Breakfat Il Sogno del Musicista è il luogo ideale dove fermarsi. Il b&b ha tre ampie camere,con bagno privato, tv e connessione wi fi gratuita. Si trova nel...
    View all property information
    Location Information
    Montalcino, Province of Siena
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    6.5 kilometres from Castiglion del Bosco
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Private Garden
    • Housekeeping Included
    • Parking
    • Terrace
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Palazzina Cesira is a beautiful 13th Century residence with a refined and tranquil ambience. An elegant home, located in the historic center of Montalcino. It is a place where you will experience the style and atmosphere of times gone by. Palazzina Cesira offers an inviting and relaxed environment....
    View all property information
    Location Information
    Montalcino, Province of Siena
    Private Room - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    6.7 kilometres from Castiglion del Bosco
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Porch
    • Wi-Fi
    • Outdoor Dining Area
    • Private Garden
    • Mountain Views
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Montosoli is a sixteenth-century villa built on a design by famous Sienese architect Baldassare Peruzzi and is located near the town of Montalcino, in the countryside, among olive groves and vineyards. The place is steeped in history and art, architecture and even already present owners are...
    View all property information
    Location Information
    Montalcino, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    4.5 kilometres from Castiglion del Bosco
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Garden
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Parking
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Casale di Pari, Civitella Paganico
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Make Enquiry
    Villa Di Montesoli1 / 27
    (2)Excellent
    6.0 kilometres from Castiglion del Bosco
    9 Bedrooms, 10 Bathrooms, Sleeps 18 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2016
    We stayed here with a total of 16 adults for a week. I have rented about 6 villas in this part of Tuscany in the past 10 years, and this one was by far the best. It is very...
    Reviewed 16 July 2015
    Stayed for one week in July, we had a large group of 17 people. It was practically new and very clean. Although booked through a third party the owners were very accommodating...
    See all reviews
    About this property
    The original building was a typical Tuscan farm, and today it is a luxury holiday home in Tuscany. Besides the rooms in the typical Tuscan villa and the guesthouse, Villa Montesoli also offers luxury indoors and outdoors facilities: sophisticated architecture, completely restored in 2013, that...
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 9 Bedrooms, 10 Bathrooms, Sleeps 18
    Make Enquiry
    4.5 kilometres from Castiglion del Bosco
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Parking
    • Balcony
    • Grill
    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Casale di Pari, Civitella Paganico
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    4.3 kilometres from Castiglion del Bosco
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Shared Garden
    • Parking
    • Central Heating
    • Shared Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Casale di Pari, Civitella Paganico
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    6.6 kilometres from Castiglion del Bosco
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Housekeeping Included
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Murlo, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    6.1 kilometres from Castiglion del Bosco
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Central Heating
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Montalcino, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    7.9 kilometres from Castiglion del Bosco
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DEAR TRAVELER, PLEASE KINDLY NOTE: The rental price includes: final cleaning; electricity; linens; towels. Available for a fee, if desired:heating (when needed) EUR 75.00/week. Refundable security deposit paid cash upon arrival: EUR 200. Casa Prospero A is a pleasant and spacious apartment...
    View all property information
    Location Information
    Casal di Pari, Civitella Paganico
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    5.9 kilometres from Castiglion del Bosco
    9 Bedrooms, 10 Bathrooms, Sleeps 18 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Private Outdoor Pool (Unheated)
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Ombrone is set in the Crete Senesi and the Val d'Orcia countryside, south of Siena. Until a few years ago Villa Ombrone was the classic Tuscan farmhouse, it has been renovated in depth and equipped with all the comforts. It has in fact become a beautiful villa accommodation for rent with 9...
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 9 Bedrooms, 10 Bathrooms, Sleeps 18
    Make Enquiry
    Villa Di Montesoli1 / 32
    (1)Excellent
    6.0 kilometres from Castiglion del Bosco
    9 Bedrooms, 10 Bathrooms, Sleeps 18 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Grill
    • Washer
    • Sauna
    • Wi-Fi
    • Hot Tub
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 August 2014
    Just spent a week there with 18 friends, it was amazing! The farm manager pietro and his team really looked after us and the place is huge, is well maintained and has amazing...
    See all reviews
    About this property
    Make a romantic Tuscan getaway at Villa Di Montesoli. Though the spacious nine-bedroom property offers accommodations in both a main villa and guest house, its interiors feel traditional and intimate, and amenities like a spa area, jetted tub and billiards room are hotel-worthy perks. If you can...
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 9 Bedrooms, 10 Bathrooms, Sleeps 18
    Make Enquiry
    5.9 kilometres from Castiglion del Bosco
    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Grill
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Ombrone is set in the Crete Senesi and the Val d'Orcia countryside, south of Siena. Until a few years ago Villa Ombrone was the classic Tuscan farmhouse, it has been renovated in depth and equipped with all the comforts. It has in fact become a beautiful villa accommodation for rent with 9...
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
    Make Enquiry
    Farmhouse Rental in Tuscany, Montalcino - Villa Montalcino1 / 46
    (34)Very good
    6.3 kilometres from Castiglion del Bosco
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2014
    Outstanding location and home. It was great having a pool (even though it was above ground, fabric, four feet deep and had a manual cover you had to put back every time you...
    See all reviews
    About this property
    This beautiful villa for rent in Tuscany is in a great location - within walking distance of the town of Montalcino and is an ideal starting point for excursions around southern Tuscany. You'll love exploring Siena and the other surrounding towns, but you'll also want to spend plenty of time at...
    View all property information
    Location Information
    Montalcino, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    7.9 kilometres from Castiglion del Bosco
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:This property is a characteristic apartment surrounded by the greenery. It sleeps four people. It is approximately 100 square meters (1076 square feet). It features a shared swimming pool, a private garden, air conditioning (please read description below to check in which rooms...
    View all property information
    Location Information
    Pari, Civitella Paganico
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    7.2 kilometres from Castiglion del Bosco
    2 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Housekeeping Included
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our agriturismo offers its guests wellness and tranquility on the spacious sunning patio around the swimming pool in the park that surrounds the old convent. The Antica Grancia di Quercecchio agriturismo is the ideal place to spend your Tuscan holiday in peace and quiet among olive groves and...
    View all property information
    Location Information
    Tavernelle, Montalcino
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 3
    Make Enquiry
    5.3 kilometres from Castiglion del Bosco
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:Typical farmhouse, 250 sq. m. with 4 double bedrooms, two of which include a double sofa bed, and 4 bathrooms, holding up to 10 persons. The property has a large garden with private swimming pool, and outdoor area perfect for meals, air conditioning, Wi-Fi and satellite TV. The...
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Make Enquiry
    4.9 kilometres from Castiglion del Bosco
    2 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Balcony
    • Terrace
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Montalcino, Province of Siena
    Condo/Apartment - 2 Bedrooms, 4 Bathrooms, Sleeps 6
    Make Enquiry
    7.1 kilometres from Castiglion del Bosco
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • DVD Player
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Santilaria farmhouse is situated on the top of a small hill in the middle of a large farm in the Crete Senesi. The landscape surrounding the property is characterized by the gentle rolling hills that alternate between farmed fields and small wood groves. Absolute peace and quiet and in the...
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    5.9 kilometres from Castiglion del Bosco
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Ombrone is set in the Crete Senesi and the Val d'Orcia countryside. Until a few years ago Villa Ombrone was the classic Tuscan farmhouse, it was has been renovated in depth and equipped with all the comforts. It has in fact become a beautiful villa rented in various ways depending on the...
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
    Make Enquiry
    5.9 kilometres from Castiglion del Bosco
    8 Bedrooms, 9 Bathrooms, Sleeps 16 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Central Heating
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:This property is set in the Crete Senesi and the Val d'Orcia countryside, south of Siena. Until a few years ago this property was the classic Tuscan farmhouse, it has been renovated in depth and equipped with all the comforts. It has in fact become a beautiful villa...
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 8 Bedrooms, 9 Bathrooms, Sleeps 16
    Make Enquiry
    Borgo Castelrotto at Castelnuovo Tancredi Wine Estate-your perfect holiday1 / 21
    (1)Excellent
    5.1 kilometres from Castiglion del Bosco
    10 Bedrooms, 8 Bathrooms, Sleeps 18 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Cable/satellite TV
    • Washer
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 September 2017
    This is a wonderful place, a very private compound in Tuscany consisting of three houses with room for 16 people and fantastic views over the surrounding countryside. We spent...
    See all reviews
    About this property
    Wonderful and exclusively yours-an antique and private hamlet, called a borgo in italian, immersed in the countryside of the Orcia Valley and dating back to the last century. Three farmhouses that have been recently restored and lovingly maintained so that you can savor the real flavor of Tuscany....
    View all property information
    Location Information
    Buonconvento, Province of Siena
    Holiday Rental House - 10 Bedrooms, 8 Bathrooms, Sleeps 18
    Make Enquiry
    7.9 kilometres from Castiglion del Bosco
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:This property is a welcoming apartment surrounded by meadows and by green hills. It sleeps four people. It is approximately 50 square meters (540 square feet). It features a shared swimming pool, a shared garden and winter heating. You will be roughly 6 km (3.7 miles) from Iesa...
    View all property information
    Location Information
    Pari, Civitella Paganico
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    6.1 kilometres from Castiglion del Bosco
    2 Bedrooms, 2 Bathrooms, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Grill
    • Parking
    • Central Heating
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Montalcino, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 3
    Make Enquiry
    6.1 kilometres from Castiglion del Bosco
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Washer
    • Central Heating
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Montalcino, Province of Siena
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    7.3 kilometres from Castiglion del Bosco
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Grill
    • Internet Access
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2-room apartment 60 m2, on the upper ground floor. Spacious, renovated, beautiful and tasteful furnishings: living/dining room with satellite TV. 1 double bedroom. Kitchenette (oven, X ceramic glass hob hotplates). Shower/bidet/WC. Air-conditioning (extra). Small terrace. Terrace furniture....
    View all property information
    Location Information
    Montalcino, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    6.7 kilometres from Castiglion del Bosco
    Studio, 5 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This large villa, characterized by its elegant country décor, has airy and spacious rooms. A beautiful, private swimming pool and green, sprawling lawns are ideal for taking in valley views. With both a main house and guest house, this property offers privacy, beauty, and modern conveniences....
    View all property information
    Location Information
    Montalcino, Province of Siena
    Holiday Rental House - 5 Bathrooms, Sleeps 12
    Make Enquiry
    1
    List your property
    Owner log in