Skip to main content

A historic Masseria in the Valle d'Itria featuring a heated outdoor pool an indoor spa

Masseria La Contessina is a traditional country estate located in the historic Valle d’Itria region of Apulia. The property is characterised by its whitewashed walls and multiple stone Trulli structures with conical roofs, showcasing authentic regional craftsmanship.

Positioned within gated grounds surrounded by expansive countryside views, the estate offers a luxurious private rural retreat. It combines historical architectural elements with modern amenities, offering a cohesive layout that accommodates up to 10 guests across separate living spaces, ideal for families or groups seeking an outdoor-oriented holiday.

The outdoor areas are extensive and focused on open-air living, starting with a heated swimming pool surrounded by a wide stone-paved terrace with sun loungers and umbrellas. Adjacent to the pool is a stone-walled courtyard that houses an outdoor lounge area featuring a fire pit and built-in seating.

Dining facilities include a long wooden table under a timber-and-bamboo pergola, providing a shaded space for al fresco meals. This area is served by a dedicated outdoor kitchen built into a stone alcove, complete with a traditional wood-fired pizza oven and a barbecue. Families are well catered for, too, with a children’s playground and a trampoline for plenty of entertainment.

Inside, the estate features vaulted limestone ceilings, exposed stone walls, and polished stone flooring throughout. The primary living spaces include a sitting area with a white curved sofa positioned next to large arched glass doors that overlook the courtyard. A separate seating nook contains wooden benches and an open fireplace with a prominent copper chimney. The dining room centres on a round glass-topped table supported by a tree-trunk base beneath exposed ceiling beams.

An indoor spa facility built into the stone architecture comprises a jacuzzi with a relaxing waterfall feature and an emotional shower for a rejuvenating wellness experience.

The five bedrooms are split between the main villa and independent suites. The main villa contains two king-size bedrooms with en-suite bathrooms, one featuring a standalone bathtub, and a twin room with an en-suite shower room. Two additional independent queen-size suites are accessed externally from the courtyard, each offering an en-suite bathroom and direct terrace access. This versatile configuration ensures privacy across the estate.

Overall, Masseria La Contessina is a refined country home that balances Apulian heritage with modern comfort.

Highlights

Heated Swimming Pool

Heated Swimming Pool

Spa Facilities

Spa Facilities

Countryside Views

Countryside Views

Services

Included

Available extras

Enhance Your Stay with Personalised Services

After booking, your dedicated concierge will craft the perfect experience — tailored to your preferences. From everyday essentials to exclusive experiences, our curated add-ons elevate every villa stay.

Essential

Essential

Signature

Signature

Prestige

Prestige

Features

Indoor

Outdoor

Bedrooms

This property comfortably accommodates up to 10 guests in its 5 bedrooms.

MAIN VILLA
Bedroom 1 – king-size bed, en-suite bathroom with dual vanity & bathtub
Bedroom 2 – king-size bed, en-suite bathroom with shower
Bedroom 3 – twin beds (converted to 1 x king-size on request) and en-suite bathroom with shower

INDEPENDENT SUITES
Bedroom 4 – queen-size bed, en-suite bathroom with bathtub & separate shower, and terrace access (Nb. Room accessed externally only)
Bedroom 5 – queen-size bed, en-suite bathroom with shower, and terrace access (Nb. Room accessed externally only)

Location

Disclaimer: the location on the map may be approximate due to privacy reasons.

About the area

Masseria La Contessina is located in the heart of Apulia’s Valle d’Itria, serving as a serene gateway to the region’s charm. The historic centre of Martina Franca is just a short drive away, offering a hub of quaint boutiques and authentic local dining.

Within 30 minutes, guests can reach the enchanting, white-washed towns of Ceglie Messapica, Cisternino, Locorotondo, Ostuni, and Alberobello. For a deeper dive into Salento’s history, the “Florence of the South,” Lecce, is an easy day trip. Visitors can spend the afternoon wandering through Baroque streetscapes before settling into a traditional wine bar for a chilled glass of local rosé.

For those who love the outdoors, the surrounding countryside is perfect for hiking, cycling, or even a round of golf.

Distances

Frequently asked questions

Inclusions vary by property but generally cover accommodation, cleaning services, and basic utilities. Some villas may also include additional services such as concierge, breakfast, or a private chef. Full details can be found on each villa’s page. If a service is not included in the price, our concierge team can arrange it for you, ensuring a fully personalised stay. Let us know your preferences, and we’ll take care of the rest!
Booking is simple! If you have a specific villa in mind, click "Send Enquiry" on its page. If you're considering multiple options, click the heart icon to save your favorites and send one enquiry for all of them. Our team will check availability and send you a detailed offer within 24 hours. Need help choosing? We’re happy to assist!
Yes, a deposit is required at the time of booking, typically 30% of the total amount. The remaining balance is usually due 30 to 90 days before check-in, depending on the property. Some villas may have different payment schedules, which will be specified in the offer we send you.
We accept bank transfers and major credit cards. Payment details will be provided during the booking process.
Yes, we offer a wide range of services, including in-villa options like private chefs, chauffeurs, and spa treatments, as well as activities such as yacht charters, wine tastings, and guided tours. We can also arrange experiences for the rest of your holiday, even beyond your villa stay. After booking, your dedicated concierge will contact you to customise your itinerary.
Yes, most high-end villas require a minimum stay of 7 nights, usually starting from a Saturday. However, many properties offer flexibility during certain times of the year, except for peak seasons like summer and Christmas holidays, which typically have stricter requirements. A smaller number of properties accept shorter stays year-round. If you have specific dates in mind, please contact us for availability.

Have more questions?

Connect with our Villa Experts – we’ll handle the rest.

-

From EUR 9,875 to EUR 19,375 per week

Superb Service

5/5

"Thank you My Private Villas for the outstanding service. Paolo Macchiaroli goes above and beyond to accommodate all our needs, making for an exquisite vacation."

— Sir Anthony Hopkins

Why guests love our villas...

Wonderful vacation in an island paradise

5/5

"Excellent and very responsive service. They coordinated all aspects of our stay very efficiently. A great team to work with."

— Lynette

Top villa rental company

5/5

"Best villa rental company we have ever used. We found them to be easy to communicate with, expert, friendly and cooperative, to assure that our stay was enjoyable."

— Jim Long

Amazing

5/5

"Service was very excellent. Owners were very helpful and caring."

— Trusted Client

Servizio impeccabile, ci hanno organizzato la vacanza in ogni dettaglio.

5/5

"Cura del cliente ai massimi livelli. Assistenza h24, profonda conoscenza della proprietá e della destinazione. Hanno reso la vacanza indimenticabile. Saro’ sicuramente loro cliente a vita, assolutamente migliori di qualsiasi altro operatore di cui ho usufruito."

— Francesco

Wonderful to work with!

5/5

"Best company to schedule a vacation with! My family and friends were celebrating my 50th birthday in the south of France. My Private Villas helped me with the villa selection (it was stunning!), the chef and dinner party at the house. It was all fabulous! Couldn't have asked for a better celebration. We will definitely be using them again...possibly when our daughter graduates college in a few years!"

— Cristina March

First class operation!

5/5

"The attention to detail and ease of booking process was excellent. The customer support was 1st class. The on-site team at the villa was superb, and arranged anything we needed."

— Trusted Client

Best holiday ever!

5/5

"The house was outstanding and exactly as described. Furthermore Francesca provided a very friendly, proactive and highly efficient follow-up on all the details we requested to make this our best family holiday ever."

— Simon Coombe

Wonderful villa in spectacular surroundings!

5/5

"A very thorough approach to the process of advising on numerous points of detail raised by a 10 strong party whose ages ranged from 7 ti 69. Clear understanding of the facilities and services on offer and how they could be tailored to accommodate us all. Communications were clear and questions addressed promptly. Issue on arrival was dealt with promptly and to our satisfaction."

— Dennis

10/10 Company!

5/5

"Great service! They helped us throughout the whole process, even though it was very last minute. Francesca is wonderful, looking forward to working with her again: she made the whole experience 10 times better."

— Trusted Client

Explore similar properties