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

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 116 Rentals in Castellina In Chianti
loading...
Sort by
From
$4,459
Per Week
1 / 22
8 Bedrooms, 7 Bathrooms, Sleeps 16
Details Make Enquiry
From
$3,330
Per Week
1 / 16
5 Bedrooms, 5 Bathrooms, Sleeps 11
Details Make Enquiry
From
$3,786
Per Week
1 / 18
6 Bedrooms, 6 Bathrooms, Sleeps 14
Details Make Enquiry
From
$1,562
Per Week
1 / 16
Payment Protection
5 Bedrooms, 3 Bathrooms, Sleeps 9
Details Make Enquiry
Amenities & Details
  • Parking
  • Washer
  • Pool
  • Dishwasher
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Characteristic and small group of farmhouses made up of 3 units set 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.). The 3 structures has... View all property information
Make Enquiry
From
$1,208
Per Week
1 / 17
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 7
Details Make Enquiry
Amenities & Details
  • Parking
  • Grill
  • Dishwasher
  • Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Characteristic and small group of farmhouses set 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.). The 3 structures has been restored and... View all property information
Make Enquiry
From
$960
Per Week
1 / 22
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Washer
  • Parking
  • Deck
  • Garden
  • Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Casa Sibilla A is an apartment in the characteristic style of the Tuscan countryside. It sleeps four people. It is appoximately 60 square meters (645 square feet). It features a shared swimming pool, a shared garden and winter heating. You will be approximately 700 meters (770 yards) from San... View all property information
Make Enquiry
From
$1,139
Per Week
1 / 18
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 7
Details Make Enquiry
Amenities & Details
  • Grill
  • Dishwasher
  • Parking
  • Washer
  • Satellite TV
  • Private Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Stone-built farmhouse (150 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
Make Enquiry
From
$3,094
Per Week
1 / 30
Payment Protection
5 Bedrooms, 5 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Private Pool
  • Parking
  • Dishwasher
  • Grill
  • Air Conditioning
  • Satellite TV
  • Central Heating
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • 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
Make Enquiry
From
$3,094
Per Week
1 / 34
Payment Protection
5 Bedrooms, 7 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Internet Access
  • Parking
  • Grill
  • Air Conditioning
  • Satellite TV
  • Central Heating
  • Private Pool
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Large stone-built farmhouse (480 m2) completely restored farmhouse, situated inside a large property which covers an area of about 460 hectares near Castellina in Chianti in a peaceful and panoramic position amidst the vineyards and gently rolling hills of Chianti Classico (350 m a.s.l.) between... View all property information
Make Enquiry
Enquire for rates
1 / 18
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 3
Details Make Enquiry
Amenities & Details
  • Wi-Fi
  • Refrigerator
  • Washer
  • TV
  • Dishwasher
  • Microwave
  • Grill
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • Smoking allowed
  • Elder access
  • 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
Make Enquiry
Get the List
From
$363
Per Week
1 / 11
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Grill
  • Parking
  • Washer
  • Pool
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Characteristic and small group of farmhouses made up of 3 units set 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.). The 3 structures has... View all property information
Make Enquiry
From
$960
Per Week
1 / 24
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Pool
  • Garden
  • Deck
  • Parking
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Casa Sibilla B is a characteristic apartment surrounded by the vegetation. It sleeps four people. It is appoximately 60 square meters (645 square feet). It features a shared swimming pool, a shared garden and winter heating. You will be roughly 3 km (1.8 miles) from San Donato in Poggio , where... View all property information
Make Enquiry
From
$4,448
Per Week
1 / 24
8 Bedrooms, 7 Bathrooms, Sleeps 16
Details Make Enquiry
Amenities & Details
  • Washer
  • Private Outdoor...
  • Number Of Bedrooms
  • Internet Access
  • Satellite TV
  • Double Beds:(5)
  • Wi-Fi
  • Single Beds:(6)
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Charming country house in Chianti is the idyllic solution for exciting escapes in Italy. The property comprises of 5 double beds and 6 single beds, so it can comfortably host a party of 16 people. There are also 7 bathrooms to allow for comfort and privacy. There is a stunning swimming pool... View all property information
Make Enquiry
From
$702
Per Night
1 / 16
Payment Protection
4 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Refrigerator
  • Dishwasher
  • Private Pool
  • Garden
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Villa Gaiole features all the comforts and a wonderful panoramic Tuscan Villa in Chianti between Siena and Florence, with private pool, air conditioning, total privacy, and a lovely park. Additional amenities include: heating. View all property information
Make Enquiry
Enquire for rates
1 / 24
Payment Protection
2 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Terrace
  • Refrigerator
  • Fax
  • Satellite TV
  • Washer
  • DVD Player
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • 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. Entry is directly into the main living room, complete with a wood burning fireplace, a large comfortable... View all property information
Make Enquiry
Enquire for rates
1 / 16
Payment Protection
9 Bedrooms, 10 Bathrooms, Sleeps 16
Details Make Enquiry
Go to map view
Book Online(51)
Use filters to find the best results!

Suitability

  • Wheelchair access (8)
  • Elder access (39)
  • Suitable for children (70)
  • Pet friendly (37)
  • Smoking allowed (22)

Amenities

  • All pools (84)
  • Parking (67)
  • Grill (65)
  • Garden (59)
  • Other outdoor space (53)
  • View all amenities