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.

Vacation Rentals in Castellina In Chianti, Italy

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    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}
    List your property
    Owner log in
    Payment Protection
    Use a credit card to book with our Payment Protection.Learn more
    Show Prices
    Update
    Price
    per night
    |||
    |||
    $0
    $219 Average
    $1,000+
    Bedrooms
    Any
    Amenities
    Any
    Sleeps
    Any
    View Map
    More filters
    loading...
    Travelers to Castellina In Chianti are booking October dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 30
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    1 / 20
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    Show Prices
    1 / 17
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Yard
    • Grill
    • Central Heating
    • Parking
    • Wi-Fi
    • Washer
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Bed places : 4<BR><BR>Three rooms, 60 square meters, with kitchen and TV, 2 double bedrooms (one with high window), a bathroom with shower. The apartment is at the first floor. On the ground floor there are tables, chairs and umbrellas for common use outdoors. It is possible to accommodate a +... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 30
    6 Bedrooms, 5 Bathrooms, Sleeps 11 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Stone built farmhouse (320 m2) situated inside a large property which covers an area of about 460 hectares near Castellina in Chianti. Peaceful and panoramic position amidst the vineyards and gently rolling hills of Chianti Classico (350 m a.s.l.). At guests’ disposal a private swimming pool... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 14
    Ricavo
    3 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Description: Notes for this villa All prices are per week for the accomodation only. Check-in between 4pm and 7pm on your arrival day (Saturday). Out of hour arrival needs to be arranged. Check-out by 10am on your departure day (the following Saturday). Please note that availability shown is... View all property information
    Location Information
    Ricavo, Castellina In Chianti
    1 / 18
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Villa Oratorio is a classic stone farmhouse going back to 1500. It started out as a chapel and in 1876 underwent its first transformation into a farmhouse. Today, thanks to a careful renovation, the house has been transformed into a lovely country residence. Villa Oratorio is part of the old... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 47
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Amenities & Details
    • Private Outdoor...
    • Grill
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful independent villa with swimming-pool situated near Castellina in Chianti, in the heart of the Chianti Classico area. This property was recovered by restoring the outbuilding of an ancient manor house. The restoration was very accurate and aimed to preserve the original architectural... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 30
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Parking
    • Grill
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    The villa in Chianti (400 m2) was built in the early 16th century as an ancient oratory. In 1876 it underwent its first transformation into a farmhouse and only today, thanks to a skilful restoration project that brought the structure back to its original beauty, a country villa rental has been... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 9
    8 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Beautiful restored farmhouse with swimming-pool situated in the heart of the Chianti Classico area, a few kilometers away from Castellina in Chianti. This property is quietly situated on a large 220-hectare farming estate producing excellent wines. Tastefully furnished, spacious and comfortable... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    1 / 31
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Sant Antimo was built in the early 16th century as an ancient oratory. In 1876 it underwent its first transformation into a farmhouse and only today, thanks to a skilful restoration project that brought the structure back to its original beauty, a country residence has been created. The house is... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 31
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Yard
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    This extraordinary villa welcomes up to 12 people in its ample common areas and bedrooms, and it has a wonderful garden and swimming pool. It is ideal for large families or groups of friends. This extraordinary villa welcomes up to 12 people in its ample common areas and bedrooms, and it has a... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 30
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    The villa in Chianti (400 m2) was built in the early 16th century as an ancient oratory. In 1876 it underwent its first transformation into a farmhouse and only today, thanks to a skilful restoration project that brought the structure back to its original beauty, a country villa rental has been... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 30
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    On request and to be paid for on location: domestic help (extra hours), cook. The guests can participate in a typical buffet dinner to taste the farm products that is organized every week (payment on location). Accommodation: Bedroom:- Double bed Bedroom:- Double bed Bathroom:- Toilet: Hot and cold... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 30
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    The Capanna Leopoldina, dating back to the first half of the 18th century as marked on the first Tuscan land register, has been completely restored and now offers 5 bedrooms and 5 bathrooms, while maintaining its typical Tuscan style with wood beamed ceilings and terracotta floors that are so... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 21
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    This beautiful independent villa has a private pool and is located in a scenic position, upon the Chianti Classico hills. This rental is surrounded by olive groves, vineyards and woods and the products of the estate (wine and olive oil) are available for clients to be purchased. This villa offers... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 18
    8 Bedrooms, 7 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool...
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    This large and attractive stone farmhouse dates back to 1800 and has recently been restored with care and taste in full respect of the original structure. It is comfortably furnished with quality items in rustic Tuscan style also comprising period pieces. Montornello is located on an ancient,... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 17
    11 Bedrooms, 8 Bathrooms, Sleeps 21 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    The Lilliano estate, an ancient fortified complex dating from the Middle Ages, extends over an area of around 460 hectares in a splendid, tranquil and panoramic position in the gently rolling hills of Chianti Classico, cloaked in vineyards, olive groves and fields of wheat protected by woods and... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 48
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
    Show Prices
    Amenities & Details
    • Internet Access
    • Satellite TV
    • DVD Player
    • Washer
    • Private Outdoor...
    • Secure Parking
    • Patio
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    RECEPTIVE STRUCTURE. Villa delle Upupe is located approximately 2 km from the borgo of Castellina in Chianti, in the hilly green countryside between Siena and Florence in the heart of Chianti Classico, a beautiful region famous throughout the world for its picture-postcard views and for the... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 10
    5 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Patio
    • Shared Yard
    • Central Heating
    • Outdoor Dining Area
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Apartment Cispiano<BR>A separate, spacious house unit for 5 people. Traditionally, Tuscan with large kitchen (and dishwasher) and with a fireplace, on the ground floor. A room with a double and single bed, and another room with a double bed. The bedrooms are on the upper floor and can be reached by... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    Get the List
    1 / 16
    9 Bedrooms, 5 Bathrooms, Sleeps 16 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Satellite TV
    • Wi-Fi
    • Private Yard
    • Air Conditioning
    • Grill
    • Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • DVD Player
    • Washer
    • Parking
    • Satellite TV
    • Wi-Fi
    • Central Heating
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Located between Florence and Siena, its undulating hills evoke the refined country life of antiquity while maintaining its beauty and balance. Along its extensive terrain, oak forests alternate with cypress, vineyards and centennial olive trees. Here, the best Tuscan wines and olive oils are... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 24
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool...
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Washer
    • Central Heating
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Sergio is a two storey ground floor apartment at the one end of the main building. It has a private furnished terrace that overlooks the olive groves, vineyards ande the picturesque countryside.<BR>Entry is directly into the main living room, complete with a wood burning fireplace, a large... View all property information
    Location Information
    Castellina In Chianti, Province of Siena
    1 / 23
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Grill
    • Washer
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Mountain Views
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Situated in a small hamlet around the Castellina region this villa looks out over the heart of the Chianti countryside. An elegant villa completely restored and renovated from an ancient farmhouse set in a private garden with swimming pool and stunning views overlooking the hills and valleys of... View all property information
    Location Information
    Castellina In Chianti, Province of Siena