Photo by Smtunli

Search Holiday Rentals in Asciano

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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Asciano holiday rentals

Seasonal outdoor pool
Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo

Albergo Diffuso Borgo Santo
Asciano
The price is ฿8,091
฿9,084 total
includes taxes & fees
27 Dec - 28 Dec
Albergo Diffuso Borgo Santo
Exterior
PALAZZO DEL PAPA

PALAZZO DEL PAPA

PALAZZO DEL PAPA
Siena City Centre
9.6 out of 10, Exceptional, (96)
"Hamza was so wonderful and accommodating, would definitely stay here again!"
United States
Elise
The price is ฿5,015
฿5,664 total
includes taxes & fees
22 Dec - 23 Dec
PALAZZO DEL PAPA
Breakfast meal
B&B Il Corso

B&B Il Corso

B&B Il Corso
Siena City Centre
9.8 out of 10, Exceptional, (191)
"Safe, clean, close to all attractions"
Canada
Carlo
B&B Il Corso
Room amenity
Siena Vip

Siena Vip

Siena Vip
Siena City Centre
9.2 out of 10, Wonderful, (422)
"A great location!"
Canada
Cheryl
The price is ฿4,387
฿4,973 total
includes taxes & fees
4 Jan - 5 Jan 2026
Siena Vip
Suite | Premium bedding, Select Comfort beds, minibar, in-room safe
La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House

La Terrazza Sul Campo Rooming House
Siena City Centre
9.8 out of 10, Exceptional, (239)
"Huge room! Great location "
Canada
karen
La Terrazza Sul Campo Rooming House
Property entrance
Residenza Fabroni

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 ฿2,744
฿3,165 total
includes taxes & fees
13 Jan - 14 Jan 2026
Residenza Fabroni
Food court
La Locanda di San Francesco

La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (131)
"Great room-great staff-great location"
United States
Richard
The price is ฿5,617
฿6,326 total
includes taxes & fees
18 Jan - 19 Jan 2026
La Locanda di San Francesco
Lobby
Villa Cassia di Baccano

Villa Cassia di Baccano

Villa Cassia di Baccano
Loro Ciuffenna
9.4 out of 10, Exceptional, (23)
"The staff were great and the villa was amazing"
United States
Ralphvincent
The price is ฿4,529
฿4,982 total
includes taxes & fees
7 Jan - 8 Jan 2026
Villa Cassia di Baccano
Terrace/patio
Abbadia Sicille Relais

Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is ฿2,527
฿2,890 total
includes taxes & fees
6 Jan - 7 Jan 2026
Abbadia Sicille Relais
Suite Bernardo, Panoramica al terzo piano senza ascensore | Terrace/patio
PienzaLettings Suites

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 ฿2,464
฿2,858 total
includes taxes & fees
22 Dec - 23 Dec
PienzaLettings Suites
Panoramic Cottage, 1 Bedroom | Exterior
Affitacamere Maria Gabriella

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
Exterior
B&B Le Scalette di Piazza

B&B Le Scalette di Piazza

B&B Le Scalette di Piazza
Montalcino
9.4 out of 10, Exceptional, (90)
"Great location and excellent staff. "
Canada
Jacek
B&B Le Scalette di Piazza
Triple Room, Balcony, City View | Desk, iron/ironing board, free WiFi, bed sheets
Al Mercato B&B

Al Mercato B&B

Al Mercato B&B
Siena City Centre
9.0 out of 10, Wonderful, (96)
"Hotel is a one block from main square of the city also have a good restaurant around the corner "
United States
Guillermo
The price is ฿2,256
฿2,953 total
includes taxes & fees
15 Jan - 16 Jan 2026
Al Mercato B&B
Daily continental breakfast (EUR 20 per person)
Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi

Residenza d'Epoca Palazzo Borghesi
Siena City Centre
9.6 out of 10, Exceptional, (116)
"We enjoyed our stay here. Convenient, clean, central to city center, shops, and restaurants. We would stay here again."
United States
Linda
The price is ฿6,018
฿6,767 total
includes taxes & fees
6 Jan - 7 Jan 2026
Residenza d'Epoca Palazzo Borghesi
Property entrance
Il Tosco

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 ฿8,305
฿9,283 total
includes taxes & fees
22 Dec - 23 Dec
Il Tosco
Tasting room
Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca

Il Battistero Siena - Residenza d'Epoca
Siena City Centre
9.6 out of 10, Exceptional, (193)
"Great location and friendly staff. "
United States
Parissa
Il Battistero Siena - Residenza d'Epoca
City view
Regis Condo

Regis Condo

Regis Condo
Siena City Centre
9.4 out of 10, Exceptional, (65)
"This was one of our favorite stays in Italy. It was spacious, clean, and in a great part of the city."
United States
Ben
Regis Condo
Interior
Meublé Il Riccio

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
Superior Double Room, 1 Queen Bed, Private Bathroom, City View | Egyptian cotton sheets, premium bedding, down duvets, minibar
B&B Palazzo del Magnifico

B&B Palazzo del Magnifico

B&B Palazzo del Magnifico
Siena City Centre
9.8 out of 10, Exceptional, (63)
"Great location. Room spacious and clean. Personnel friendly and great service walkable to best historic places. Could find something better "
United States
Rodolfo
B&B Palazzo del Magnifico
Food and drink
Hotel San Gregorio

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 ฿6,302
฿7,152 total
includes taxes & fees
5 Jan - 6 Jan 2026
Hotel San Gregorio
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Asciano Hotel Reviews

Hotel Italia

Hotel Italia

10/10 Excellent
"Nice clean room. Close to train/bus station. Very good breakfast "
Krista 1-night trip
Posted 3 days ago
Hotel Italia

Find out more about Asciano

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

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

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

Frequently asked questions

Can I find a holiday rental in Asciano?

Yes, there are holiday rentals close to the most popular sights in Asciano, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the countryside in Asciano. Make sure you have time to check out the wineries and coffee shops during your trip.

What are some of the best holiday rentals that Asciano has to offer?

Borgo Argiano: This holiday home rental outside Asciano is located on a river, and has a balcony, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and an electric kettle. You can relax into your holiday with a garden and a library.

How many holiday rentals are there in Asciano?

Expedia has 21 holiday rentals for your stay in Asciano.

What can I see and do in Asciano?

While exploring the area, visit family-friendly sights like Siena Circuit, or get outside and enjoy nature at Val di Chiana. Other places in town to visit include Monte Oliveto Maggiore Abbey and Museo Cassioli.

What are holiday rentals like in Asciano?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Asciano. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for small groups.