Chianti on the Hill
24 guests
-
12 bedrooms, 13 beds
12 bathrooms
6,997 sq/ft
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Perched on a hilltop in the Chianti countryside, this villa offers 360-degree views over the rolling hills that make it almost impossible to leave the terrace. The pool area is set up for long, unhurried days, with sun loungers, a pergola, and a poolside fridge – connected to the garden via an underground tunnel that keeps the whole outdoor setup feeling seamless. Inside, vaulted and beamed ceilings, terracotta floors, and restored fireplaces give the rooms a quiet grandeur. A separate ground-level cottage adds flexible accommodation and is fully wheelchair accessible. Fattoria Le Fonti winery and historic San Gimignano are just a short drive away.
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Do you have a question about this home or the local area?
What to expect
Highlights
Marvel at San Gimignano's medieval skyline of fourteen soaring stone towers
Swim out to rolling Tuscan hills stretching beyond the garden
Seat the whole group for a long alfresco lunch
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Home truths
Due to this home's location, we recommend hiring a car to get the most out of your stay. There are eight parking spaces on site – four sheltered and four uncovered. The approach road to the villa is unpaved, so a vehicle with reasonable ground clearance will make arrival more comfortable, especially after wet weather.
The pool is only open from the second Saturday in May until the last Saturday in September, so if you're visiting outside those dates you won't be able to use it. It's also 50 metres from the main villa, reached via a tunnel under the approach road.
The beds in bedrooms two, six, eight, and ten can be converted into twin beds on request – worth letting your host know in advance if you'd prefer that configuration.
While this home can accommodate two additional guests on a sofa bed in one of the living spaces, the maximum occupancy is 24 guests.
About this stay
Amenities
Outdoor seating
Laptop friendly workspace
Wi-fi
Air conditioning
Parking available
Washing machine
Dryer
Private outdoor pool
Bedrooms & bathrooms
12 bedrooms, 13 beds
12 bathrooms
Local guide
About Chianti
Chianti is a region situated in the heart of Tuscany, known for its picturesque rolling hills and sun-drenched landscape. Discover and enjoy locally produced wines while exploring the charming vineyards and family-owned wineries. You’ll find plenty of scenic towns and villages – from Montefioralle to Castellina, which are not to be missed. Here you can wander the narrow Medieval streets, and explore historic churches and impressive castles. Immerse yourself in the...
Explore the area
Local restaurants, cafes, museums, sites and activities, recommended by our community of hosts and travel experts
Sample Tuscan cuisine at Hotel Borgo di Cortefreda
Enjoy delicious food while taking in the breathtaking views of the Tuscany landscape at the Hotel Borgo di Cortefreda.
Enjoy the Americana at 1950 American Diner
Escape the typical Italian fare and indulge in a delicious burger and the best Oreo milkshake you've ever tasted. The happy and colourful ambience is perfect for families.
Taste Tuscan wines and delights at Tenuta Torciano
Indulge in a delightful wine-tasting experience at Tenuta Torciano. Sample exquisite wines, enjoy a scrumptious light lunch, and be amazed by the friendly and knowledgeable staff.
Explore the Sentierelsa Trail
A stunning walk along the river in Tuscany, perfect for hot weather. Enjoy the beautiful colours and landscapes.
Get around
Airport
Amerigo Vespucci
53 min
Pisa International
1 hr 28 min
Bologna Guglielmo Marconi
1 hr 46 min
Train station
Poggibonsi-S. Gimignano
10 min
Bus stop
Campomaggio
9 min
Local shops & services
Supermarket
7 min
Cafe
10 min
Pharmacy
26 min
Booking policies
House Rules
Children welcome (1-12 years)
Infants welcome (under 12 months)
No pets
No parties or events
No smoking
Good to know
Arrival time flexible
Arrange with the host
Departure time flexible
Arrange with the host
Air con
Wifi
Cancellation policy
Up until
60
days
Cancel at least 60 days before your check-in date for a full refund.
Not eligible for a refund once your check-in date is under 60 days away.
Host
This home is managed by Emily
This home is managed by a business on behalf of its owner. A member of their staff will be your point of contact before and during your stay. Emily and her team strive to give their guests the perfect Tuscan holiday. From their portfolio of incredible homes and villas to the tailor-made experiences they've curated, this professional team is all about Italian hospitality.
This home is nominated for the Plum Guide Award.
- Great hosts, not just great homes – We reject homes managed by hosts who don’t meet our standards of excellence.
The Plum Promise
- Every home scrutinised by experts, they have to meet our standards.
- Hosts we knowHigh-quality hosting, with track records of high-quality hosting.
- Impeccably clean, well maintained homes.
- Peace of mind in the rare event your host cancels.
- Rated ‘Excellent’ on Trustpilot, delivering exceptional service before, during and after your stay.