7 nights from
$4,037 to $7,007
Casale Cipressi, Castellina in Chianti - Siena and Chianti
This is a great option for multi-generational families or friends who want to be spoilt. The beautifully kept Casale Cipressi impresses from the word go: its cypress-lined drive and a gleaming white stone sculpture announces that you are arriving somewhere special. There’s even a private helipad. A pleasant drive from the small hilltop commune of Castellina in Chianti, this purpose-built bolthole has commanding views across surrounding hills. It is well placed for days out in Siena, San Gimignano and Florence, but the temptation to simply chill out here will be strong.
The property exploits antique and contemporary natural materials – stone, terracotta, wood, rattan – beautifully, inside and out, while offering all the benefits of modern design. Organised on two floors, each with its own facilities, this is an ideal property for a group holiday that also allows individuals downtime. With five well-furnished terraces and loggia, including a delightful courtyard, gently sloping lawns, an outdoor fireplace for cooler evenings, ping-pong table and generous private pool, everyone, older and younger, will find their own favourite spots to colonise.
Ground Floor
Lounge-Diner
Sofa, two armchairs, two pouffes, coffee table, shelving, two antique stools, bench, armoire, table and chairs, fireplace, one door to wraparound terrace, two doors to courtyard
Kitchen
Fully equipped, doors to two terraces.
Bedroom 1
Four-poster double bed (cannot be converted to twins), two wardrobes, chair, bookshelves, door to terrace.
Bedroom 2
Double bed (cannot be converted to twins), wardrobe, chest of drawers, two doors to terrace.
Bedroom 3
Three-quarter bed, bookshelves, wardrobe, sideboard, door to garden.
Bathroom 2
Shower, sink, WC.
Bathroom 3
Shower, sink, WC.
Lower-Ground Floor
Lounge-Kitchen
Two sofas, four armchairs, coffee table, side table, table and chairs, dresser, fully equipped kitchen, range, two doors to terrace and garden.
Bedroom 4
Double bed (cannot be converted into twins), wardrobe, two benches, door to terrace.
En-suite Bathroom
Shower, sink, WC.
Bedroom 5
Twin beds (can be converted to a double), two wardrobes, two bedside tables, antique chest, desk and chair, bookshelves, door to garden.
Cloakroom
Sink, WC.
Our Thoughts
As pleasing as the interiors are, this property is designed to allow the views to puncture every room – so, even if you spend a lot of time here, you will be soaking up Chianti. Casale Cipressi’s beautiful furnishings, including on the wraparound loggia, invite a holiday of luxurious indolence. It will be difficult to choose between meals here or in the courtyard – although the latter’s professional barbecue will be a pull for some. Parents can keep an eye on children splashing in the pool from the cool of the loggia. Oh, and don’t forget the sauna, to complete your relaxation.
Notes
Five bedrooms. Three bathrooms, one en-suite. If you want the twin beds converted into a double, please specify when booking and note that parties must not exceed nine people, including infants. Two hours of maid service are included three times a week. A private helipad is available for your use. Pets are allowed, for a weekly charge, please discuss with your agent when booking. Firewood is available at an additional cost.
The standard time for all arrivals must be between 4pm and 7pm. In the event of a client’s late arrival, they must contact the villa owner on the number provided or check with your To Tuscany villas specialist. If you do not call you will not be able to enter the house.
There are no internal stairs at this property. To access either floor, one must go outside and use the exterior stairs.
The patio at the front faces East which allows for breakfast with a view of the sunrise.
There is an electric fence which prevents intrusions from wild animals.
Fire Place: open
Pool:
Length: 12 m
Width: 6 m
Depth: 1.35 - 1.5 m
Entrance: Roman steps
Opening times: May to mid Ocotober
Fenced: No
Furnished: Sunlounges
Cleansed: Chlorine
Distance from villa: immediately next to the house
There is a shower and a sauna nearby, and sunloungers on the adjacent lawn.
Facilities
To Tuscany Experiences
Save time and enjoy personalised services and experiences from the Tuscany experts, including private chefs, cooking courses, maid service, pre-arrival shopping, wine tastings and children's activities. With our unrivalled local knowledge, you can gain unique access to Tuscany's hidden treasures and make your trip to Tuscany an unforgettable experience. Click here for more info.
Review:
"Excellent concierge service!! Valentina Petri's recommendations and her eagerness to help with great advises were priceless. She responded super quickly to all our questions and her suggestions were highly appreciated."
Source: Trustpilot.com/Review/To-Tuscany.com
Villa rates
- 2022
House rules
The Security Deposit is €500 or equivalent in your own currency, cash payment is required on arrival. You will be reimbursed on check-out should no damage occur during your stay.
Tourist tax: 2,00 € per person, per night for the first 7 nights, some exemptions apply.
Children: Maximum number of guests includes infants.
Dog up to 30kg: 7 € daily charge per pet
Charged based on usage: Heating Villa
Arrival guide
Meet and greet
Arrival time is 16:00 - 19:00. Departure time is before 10:00.
Approach road: Unpaved, uneven, high clearance vehicle recommended
Parking: Private, onsite parking

1-929-445-5929 Toll Free
Layout (380 sqm)



















Villa location
Guest reviews: Casale Cipressi

Availability Guide
Mo | Tu | We | Th | Fr | Sa | Su |
1 | ||||||
2 | 3 | 4 | 5 | 6 | 7 | 8 |
9 | 10 | 11 | 12 | 13 | 14 | 15 |
16 | 17 | 18 | 19 | 20 | 21 | 22 |
23 | 24 | 25 | 26 | 27 | 28 | 29 |
30 | 31 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | 3 | 4 | 5 | ||
6 | 7 | 8 | 9 | 10 | 11 | 12 |
13 | 14 | 15 | 16 | 17 | 18 | 19 |
20 | 21 | 22 | 23 | 24 | 25 | 26 |
27 | 28 | 29 | 30 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | 3 | ||||
4 | 5 | 6 | 7 | 8 | 9 | 10 |
11 | 12 | 13 | 14 | 15 | 16 | 17 |
18 | 19 | 20 | 21 | 22 | 23 | 24 |
25 | 26 | 27 | 28 | 29 | 30 | 31 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | 3 | 4 | 5 | 6 | 7 |
8 | 9 | 10 | 11 | 12 | 13 | 14 |
15 | 16 | 17 | 18 | 19 | 20 | 21 |
22 | 23 | 24 | 25 | 26 | 27 | 28 |
29 | 30 | 31 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | 3 | 4 | |||
5 | 6 | 7 | 8 | 9 | 10 | 11 |
12 | 13 | 14 | 15 | 16 | 17 | 18 |
19 | 20 | 21 | 22 | 23 | 24 | 25 |
26 | 27 | 28 | 29 | 30 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | |||||
3 | 4 | 5 | 6 | 7 | 8 | 9 |
10 | 11 | 12 | 13 | 14 | 15 | 16 |
17 | 18 | 19 | 20 | 21 | 22 | 23 |
24 | 25 | 26 | 27 | 28 | 29 | 30 |
31 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | 3 | 4 | 5 | 6 | |
7 | 8 | 9 | 10 | 11 | 12 | 13 |
14 | 15 | 16 | 17 | 18 | 19 | 20 |
21 | 22 | 23 | 24 | 25 | 26 | 27 |
28 | 29 | 30 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | 3 | 4 | |||
5 | 6 | 7 | 8 | 9 | 10 | 11 |
12 | 13 | 14 | 15 | 16 | 17 | 18 |
19 | 20 | 21 | 22 | 23 | 24 | 25 |
26 | 27 | 28 | 29 | 30 | 31 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | ||||||
2 | 3 | 4 | 5 | 6 | 7 | 8 |
9 | 10 | 11 | 12 | 13 | 14 | 15 |
16 | 17 | 18 | 19 | 20 | 21 | 22 |
23 | 24 | 25 | 26 | 27 | 28 | 29 |
30 | 31 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | 3 | 4 | 5 | ||
6 | 7 | 8 | 9 | 10 | 11 | 12 |
13 | 14 | 15 | 16 | 17 | 18 | 19 |
20 | 21 | 22 | 23 | 24 | 25 | 26 |
27 | 28 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | 3 | 4 | 5 | ||
6 | 7 | 8 | 9 | 10 | 11 | 12 |
13 | 14 | 15 | 16 | 17 | 18 | 19 |
20 | 21 | 22 | 23 | 24 | 25 | 26 |
27 | 28 | 29 | 30 | 31 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | |||||
3 | 4 | 5 | 6 | 7 | 8 | 9 |
10 | 11 | 12 | 13 | 14 | 15 | 16 |
17 | 18 | 19 | 20 | 21 | 22 | 23 |
24 | 25 | 26 | 27 | 28 | 29 | 30 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | 3 | 4 | 5 | 6 | 7 |
8 | 9 | 10 | 11 | 12 | 13 | 14 |
15 | 16 | 17 | 18 | 19 | 20 | 21 |
22 | 23 | 24 | 25 | 26 | 27 | 28 |
29 | 30 | 31 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | 3 | 4 | |||
5 | 6 | 7 | 8 | 9 | 10 | 11 |
12 | 13 | 14 | 15 | 16 | 17 | 18 |
19 | 20 | 21 | 22 | 23 | 24 | 25 |
26 | 27 | 28 | 29 | 30 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | |||||
3 | 4 | 5 | 6 | 7 | 8 | 9 |
10 | 11 | 12 | 13 | 14 | 15 | 16 |
17 | 18 | 19 | 20 | 21 | 22 | 23 |
24 | 25 | 26 | 27 | 28 | 29 | 30 |
31 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | 3 | 4 | 5 | 6 | |
7 | 8 | 9 | 10 | 11 | 12 | 13 |
14 | 15 | 16 | 17 | 18 | 19 | 20 |
21 | 22 | 23 | 24 | 25 | 26 | 27 |
28 | 29 | 30 | 31 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | 3 | ||||
4 | 5 | 6 | 7 | 8 | 9 | 10 |
11 | 12 | 13 | 14 | 15 | 16 | 17 |
18 | 19 | 20 | 21 | 22 | 23 | 24 |
25 | 26 | 27 | 28 | 29 | 30 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | ||||||
2 | 3 | 4 | 5 | 6 | 7 | 8 |
9 | 10 | 11 | 12 | 13 | 14 | 15 |
16 | 17 | 18 | 19 | 20 | 21 | 22 |
23 | 24 | 25 | 26 | 27 | 28 | 29 |
30 | 31 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | 3 | 4 | 5 | ||
6 | 7 | 8 | 9 | 10 | 11 | 12 |
13 | 14 | 15 | 16 | 17 | 18 | 19 |
20 | 21 | 22 | 23 | 24 | 25 | 26 |
27 | 28 | 29 | 30 |
Mo | Tu | We | Th | Fr | Sa | Su |
1 | 2 | 3 | ||||
4 | 5 | 6 | 7 | 8 | 9 | 10 |
11 | 12 | 13 | 14 | 15 | 16 | 17 |
18 | 19 | 20 | 21 | 22 | 23 | 24 |
25 | 26 | 27 | 28 | 29 | 30 | 31 |