Villa Pippistrelli


A Hidden Country Estate

Just a few kilometres south of Siena, on the crest of the estate of Montesigliano, sits Villa Pippistrelli—an historic 17thC Tuscan Farmhouse. In the extensive woodland covering the Siena hills this elegantly restored farmhouse reaps the benefit of sweeping views across a verdant valley while also remaining close to city retreats (Siena, Florence, Pisa, Lucca, etc).

Interiors are a fusion of old world charm (wood-beams, classic fireplaces) and bright modern splashes (colourful fabrics, dramatic chandeliers, fully-equipped kitchens). Gingerly step outside toward the immaculate garden where you’ll drink in the Tuscan panorama from the infinity pool and side terrace that oh-so-casually shoulder the natural rocky environs. Later, the outdoor sitting area with a pergola smothered in bougainvillea provides the ideal location for a contemplative aperitif.

Spectacular Stays

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Who It’s For

Those who want to be tucked away in the privacy of a woodland (with exceptional landscape views from the Villa and infinity pool), but who also want to easily connect to the ancient walled towns, markets and vineyards of the region. This darling hamlet is perfect for large families and/or friends.

Luxury Villa
Verdant woodland, rolling hills of Siena
5 Luxury Suites

Comfortably sleeps 10

Corporate Retreats, Families, Friends
Call for price details

This villa is sold as part of part of a private B&R itinerary.


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Villa Pippistrelli

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Lodge selected by
Travel Expert:

Courtney Mundy

Favourite Feature The infinity pool is a definite highlight. A post-dinner dip with a glass of Chianti overlooking the Tuscan hills is the perfect end to your day.

Everything about our trip was memorable. Villa Pippistrelli, our guides, our truffle hunt and cooking lesson, the biking & hiking—so much great stuff. Our sightseeing in Rome was also well-organized and our guide was excellent.

—Pail McKinnell

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How to Get There

Villa Pippistrelli is located 15 minutes southwest of Siena. Your trip will likely begin in Florence. Most transatlantic flights to Italy fly into either Milan or Rome, and Florence is readily accessible by plane from either city.

By Plane and Car

Most direct flights from the US arrive to Rome which is approximately 2.5 hours from the Villa by car. If you fly into Florence your drive is closer to one hour. If you fly into Pisa or Bologna your drive will be approximately 2 hours.

By Train

Siena has a train station which connects to major cities and airports.

Activities & Amenities

While basking in the tranquil charms of the Villa and its attendant pool and gardens, you’ll want to keep in mind that pizza-making lessons, as well as water-colour painting are just a few of the other ways you can parse your time.

Villa Features

  • Daily cleaning
  • Air Conditioning
  • Wi-Fi
  • Satellite television & DVD Player

Additional Amenities

Villa Pippistrelli also comes complete with staff and services, including:

  • Personal chef for lunch and dinner*
  • Catering*
  • Childcare*
  • Extra cleaning services*
  • Central heating*
  • Land line*

In addition, you’ll have access to our talented team of Travel Advisors and Trip Designers who can help you coordinate, plan, build upon or expand your trip into an even grander journey.

*Additional cost


The Villa is a professionally restored farmhouse meant to amplify the charm of its many years while also boasting some modern upgrades and eclectic styling. The five rooms are spacious and allow for up to 10 people to sleep comfortably.

More Spectacular Stays

Tuscany is filled with properties that will immerse you in its vast landscape, incredible culture and envelop you in style and comfort. Here are a few of our favourites:

Stay at Villa Pippistrelli

Montestigliano, Tuscany Add a stay at one or more of the lodges below

Villa Origo

Siena, Tuscany

Built in three tiers on the slope of a hill, Villa Origo is a dreamy homestead with hilltop views as far as the eyes can see. It's bursting with old-world charm, showcasing gorgeous antique furniture and a beautiful library.

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Villa Cetinale

Sovicille, Tuscany

Welcome to your 17thC mansion with perfectly groomed gardens, touted amongst the best in Italy.

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Villa Laura

Cortona, Tuscany

Villa Laura is an airy hillside Cortona estate known as the life-changing home of Diane Lane in the movie Under the Tuscan Sun… its beautifully restored 17thC walls now house this incredible 5-star luxury retreat.

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More Trip Inspiration

Discover a few ways to weave Villa Pippistrelli into an even grander journey.

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