Search Holiday Rentals in Villastrada

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Villastrada holiday rentals

La Locanda Di Cetona

La Locanda Di Cetona
Cetona
9.2 out of 10, Wonderful, (5)
"A lovely hotel and very welcoming staff. Cetona is a delight. "
Australia
Julian
La Locanda Di Cetona

Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (51)
"This property has a lovely view, great garden, attentive staff with good breakfast. Stayed in the cottage and the patio was very sunny and relaxing. "
United States
Lenise
Affitacamere Maria Gabriella

FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (5)
"Comfortable apartment in quiet block. Nicely furnished excellent housekeeping nice spacious bathrooms great view from the terrace."
United Kingdom
R
The price is ฿2,543
฿2,871 total
includes taxes & fees
17 Dec - 18 Dec
FonteLiving

Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (115)
"The staff was courteous, the food was amazing, and the location was great. We were very impressed"
United States
Joshua
The price is ฿8,355
฿9,339 total
includes taxes & fees
17 Dec - 18 Dec
Il Tosco

La Piccola Locanda

La Piccola Locanda
Chiusi
8.8 out of 10, Excellent, (8)
"This was a great place to stay for two nights in late October and to take out and back day trips by train to Siena and Florence on back-to-back days. Very close to the train station - very convenient. Breakfast in the restaurant in the morning was small, but good. Highly recommend this location! It's small, but serviced and supported very well by the staff at the restaurant. "
United States
Jeffery
La Piccola Locanda

Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (134)
"Such friendly staff, loved Pienza and the property was such a good location! "
United Kingdom
Bethan
The price is ฿6,465
฿7,333 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio

Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (32)
"Exceptional service great building felt like a Medici!"
United States
gaetano
The price is ฿6,308
฿7,086 total
includes taxes & fees
29 Dec - 30 Dec
Delcorto Suites

Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (128)
"Great hosts, central location "
United States
Alexander
The price is ฿3,700
฿4,218 total
includes taxes & fees
17 Dec - 18 Dec
Bed & Breakfast Vicolo dell'Oste

Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (25)
"Lovely restored Tuscan villa and farmhouse. Very comfortable stay. Felt that the people who run it do so with a lot of heart and style. Great value too. "
Canada
Carla
The price is ฿4,042
฿4,521 total
includes taxes & fees
17 Dec - 18 Dec
Borgo Dolciano

Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (86)
"Staff is great and many good restaurants in short walking distance."
United States
Mark
Meublé Il Riccio

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (130)
"Beautiful property nestled at the top of montepulciano. Very helpful owner Luca and unmatched hospitality! "
United States
Alizeh
The price is ฿5,858
฿6,592 total
includes taxes & fees
29 Dec - 30 Dec
La Locanda di San Francesco

TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (1)
"メイン通りの好立地。 客室は豪華でエレガント。 ウェルカムキットも良く、アメニティも良好。 次回も必ず利用したい。 スタッフの方、いろいろありがとうございました。"
Japan
keita
The price is ฿2,991
฿3,438 total
includes taxes & fees
12 Jan - 13 Jan 2026
TuscanyLettings Studio&Room

PienzaLettings Suites

PienzaLettings Suites
Pienza
10.0 out of 10, Exceptional, (1)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is ฿2,588
฿2,995 total
includes taxes & fees
13 Jan - 14 Jan 2026
PienzaLettings Suites

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (166)
The price is ฿2,303
฿2,644 total
includes taxes & fees
17 Dec - 18 Dec
Abbadia Sicille Relais

Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (24)
"Good house for one night. "
Germany
Heiner
The price is ฿2,684
฿3,027 total
includes taxes & fees
17 Dec - 18 Dec
Artisti del Cavallo Tourism

L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3)
"Molto accoglienti e gentili "
Italy
Valentina
The price is ฿2,198
฿2,418 total
includes taxes & fees
11 Jan - 12 Jan 2026
L'Antica Sosta

Poggiovalle Tenuta Italiana

Poggiovalle Tenuta Italiana
Fabro
9.6 out of 10, Exceptional, (5)
"Appartamenti confortevoli, servizi ottimi, ristorante con ottima qualità prezzo. Torneremo per usufruire delle piscine. "
Italy
stefano
The price is ฿4,343
฿8,481 total
includes taxes & fees
28 Dec - 29 Dec
Poggiovalle Tenuta Italiana

Bellarmino Boutique Apartments

Bellarmino Boutique Apartments
Montepulciano
6.0 out of 10, (1)
"Heat didnt work, it was FREEZING. Contact didnt seem to be local, seemed like they were managing remotely and couldnt or wouldnt send anyone to help. Nor did they really seem to care. Beautiful area though!"
United States
JON
The price is ฿3,145
฿3,608 total
includes taxes & fees
11 Jan - 12 Jan 2026
Bellarmino Boutique Apartments

Poggio del Sole

Poggio del Sole
Castiglione del Lago
8.0 out of 10, Very good, (4)
"El hotel no alcanzó el agua caliente y no se pudo bañar parte de la familia no contaba con suficientes amenidades "
Mexico
RAUL
Poggio del Sole

Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is ฿2,919
฿3,359 total
includes taxes & fees
6 Jan - 7 Jan 2026
Residenza Fabroni
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Villastrada Hotel Reviews

Find out more about Villastrada

Search for holiday rentals in Villastrada on Expedia! You can easily find your home rentals, villas, holiday apartments in Villastrada using one of the methods below:

  • View our selection of featured holiday rentals in Villastrada
  • Use the map to find apartments and other holiday homes in the Villastrada neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Villastrada while they last

Look no further and take a look at our great range of rental properties in Villastrada!

Frequently asked questions

Can I find holiday rentals in Villastrada?

Yes, there are holiday rentals close to the most popular sights in Villastrada, or you can select a more secluded option if you're looking for a relaxing stay.

What’s there to see and do in Villastrada?

Explore the area and family-friendly sights such as Centro Servizi Turistici Citta della Pieve, or get out into nature at a spot like Lake Trasimeno. In the wider area, you’ll find Labyrinth of Porsenna and Rocca del Leone.

What’s a holiday rental in Villastrada like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Villastrada. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for a small group gathering.