Enjoy a Classic Tuscan Hill Town holiday—now with AC!

Photo gallery for Enjoy a Classic Tuscan Hill Town holiday—now with AC!

An arched stone structure with benches and a view of a hilly landscape.
A building with a stone facade, a wooden door, and a sign reading "Il Conte Matto".
A dining table with plates, glasses, and a bottle, set in a room with a brick archway and a window with a view.
A kitchen counter with a plate of fruit, two cups, and a telephone.
A narrow cobblestone street flanked by historic buildings with exposed brick walls and green shutters.

Reviews

10 out of 10
Exceptional

Highlights

  • Made for relaxation
    Top-rated for comfort — guests feel right at home here.
  • Your private spa moment
    A rare find — soak and unwind in the jetted bathtub.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Balcony
  • Free Wi-Fi

Explore the area

View in a map
Trequanda, Tuscany
  • Place, The Saints Peter and Andrew Church
    ‪2 min walk‬
  • Place, Lake Trasimeno
    ‪39 min drive‬
  • Place, Fortress of Montalcino
    ‪49 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Second floor, Bedroom 1

1 Queen Bed

Second floor, Bedroom 2

1 Queen Bed

Third floor suite

1 Queen Bed

2 bathrooms

3rd floor suite, Bathroom

Soap · Towels provided · Bidet · Toilet · Shower only · Shampoo · Hair dryer

Second floor bathroom

Soap · Towels provided · Bathtub or shower · Bidet · Jetted bathtub · Shampoo · Hair dryer

Spaces

Kitchen
Balcony
Dining area

About this property

Enjoy a Classic Tuscan Hill Town holiday—now with AC!

Trequanda is a 14th century hilltop town in the heart of Tuscany, surrounded by vineyards, olive groves and lush greenery. Casa Trequanda offers an authentic Tuscan experience in a peaceful and picturesque setting, in the heart of the historical center of town. Trequanda has a regionally renown Zagat and Michelin Bib Gormand rated restaurant, Conte Matto, within a 4 minute walk and a unique and exceptional vegan restaurant, Ciriera, in the charming town square. We also have a traditional Italian pizzeria/restaurant, a pharmacy, local bar and a legitimate ATM. In the center of town in the piazza is a 14th century church in the old Romanesque style. Trequanda also has an excellent deli/butcher shop next to the pizzeria, Macelleria Ricci, that will vacuum pack guanciale and other goodies for your trip home. Their mortadella is the best in Tuscany and they are well stocked with wine, water, bread, olives and other goodies to enjoy with the sunset from your balcony but you will need to look up the open hours. On hot days, the community pool below the pizzeria is a great way to spend time with locals under the olive trees for a reasonable per day charge.

Trequanda is one of the famous "Cinque Sorelle" or Five Sister towns, a gateway to many day trips on scenic county roads. Other lovely renaissance hilltop towns, such as Montepulciano, Pienza, San Quirico, Cortona and Montalcino are just a short distance (around 30 minutes) away and make for an easy outing. Siena is 45 minutes away and Florence is 1-1/2 hours by car. San Gimignano and Assisi are also feasible day trips. At the end of the day, you can return to the tranquility of Trequanda. All around us are famous restaurants, including several In Monticchielo and Fondo, just outside of town.

Casa Trequanda has the upper two levels of a three-story flat located in the historic center of town. Middle Level: two bedrooms with queen beds, bathroom, full kitchen, living room and balcony. Upper Level: one large bedroom with queen bed, bathroom, sitting room, washer/dryer and microwave. Both units offer spectacular views of a beautiful Tuscan landscape with rolling hills. Enjoy the stunning sunsets from the 2nd floor balcony. Note that there are quite a few stairs leading to the 2nd and 3rd floors and no elevator. We have a very good cooling system in place for every bedroom for very hot days using portable AC units. We have our own client services person who speaks English and Italian fluently and lives nearby
Our prices include all fees. No hidden fees.

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House Rules

Check in after 2:00 PM
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
With adult supervision. Cot
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
Including balcony

Important information

You need to know

Property # 440247vb
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Trequanda

Trequanda is home to this apartment. The area's natural beauty can be seen at Historic Centre of Pienza and Val di Chiana, while Museo del Tartufo and Museo Cassioli are cultural highlights. Bosco della Ragnaia and RI Crea RE are also worth visiting. Take some time off to enjoy the winery tours in the area, or get some fresh air with adventures like ecotours, mountain biking and cycling nearby.
Map
Trequanda, Tuscany

What's nearby

  • The Saints Peter and Andrew Church - 2 min walk - 0.2 km
  • Lake Trasimeno - 39 min drive - 40.7 km
  • Fortress of Montalcino - 49 min drive - 37.5 km
  • Tenuta Greppo Franco Biondi Santi - 53 min drive - 39.7 km
  • Piazza del Campo - 64 min drive - 58.1 km

Getting around

  • Sinalunga Station - 17 min drive

Restaurants

  • ‪Bar L'Angolo - ‬8 min drive
  • ‪Pizzeria Paradiso - ‬4 min walk
  • ‪Menchetti - ‬23 min drive
  • ‪La Chiusa - ‬14 min drive
  • ‪LoScuro - ‬10 min drive

Frequently asked questions

Is Enjoy a Classic Tuscan Hill Town holiday—now with AC! pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Enjoy a Classic Tuscan Hill Town holiday—now with AC!?

As of 18 Aug 2026, prices found for a 1-night stay for 2 adults at Enjoy a Classic Tuscan Hill Town holiday—now with AC! on 20 Aug 2026 start from £392, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Enjoy a Classic Tuscan Hill Town holiday—now with AC!?

On-site parking is available at the property.

What time is check-in at Enjoy a Classic Tuscan Hill Town holiday—now with AC!?

Check-in begins at 2:00 PM.

What time is check-out at Enjoy a Classic Tuscan Hill Town holiday—now with AC!?

Checkout is at 11:00 AM.

Where is Enjoy a Classic Tuscan Hill Town holiday—now with AC! located?

Situated in Trequanda, this apartment building is steps away from Val di Chiana and The Saints Peter and Andrew Church. Monastery of Sant'Anna in Camprena and San Giovanni d'Asso Station are also within 9 miles (15 km).

About the host

Hosted by Indra Obeysekere

Host profile image
Partnership from the United States with management experience from other vacation rental asset in Mexico

Why they chose this property

This location is classic Tuscany, most easily identified with Italy and its rich culture and heritage. It is also centrally located and proximate to many other famous historic towns. You can come back at night make yourself a home cooked meal or walk down the street to one of two great family owned restaurants. For those seeking quiet and calm and more adventurous travelers, the perfect choice

What makes this property unique

Lovely views from all of the rooms, a balcony perfect for a glass of wine and the sunset. Furnished to be tasteful and comfortable in an open, uncluttered way. The bedrooms are great for siestas as the large windows bring the breezes in. The kitchen is modern and well equipped and both bathrooms on both floors are new.

Languages:

English, Italian
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