Macciano Vacation Rentals

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
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Macciano vacation rentals

Seasonal outdoor pool, an infinity pool, pool umbrellas, sun loungers
FonteLiving

Townhouse in San Casciano dei Bagni

FonteLiving
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 P4,470
P5,055 total
includes taxes & fees
Jan 11 - Jan 12, 2026
FonteLiving
Exterior
Meublé Il Riccio

Townhouse in Montepulciano

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

Residence in Trequanda

Abbadia Sicille Relais
4.0 star property
8.8 out of 10, Excellent, (166)
"Room was beyond expectations. Helpful staff and overall great experience. "
United States
Robert
The price is P4,300
P4,938 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Abbadia Sicille Relais
Premium bedding, down comforters, minibar, in-room safe
La Locanda di San Francesco

Townhouse in Montepulciano

La Locanda di San Francesco
9.8 out of 10, Exceptional, (131)
"Great room-great staff-great location"
United States
Richard
The price is P10,562
P11,895 total
includes taxes & fees
Jan 18 - Jan 19, 2026
La Locanda di San Francesco
Lobby
Residenza Fabroni

Residence in Montepulciano

Residenza Fabroni
8.8 out of 10, Excellent, (94)
"gorgeous historical property, very attentive host, great location"
United States
Sarah
The price is P5,159
P5,952 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Residenza Fabroni
View from room
Affitacamere Maria Gabriella

Townhouse in Pienza

Affitacamere Maria Gabriella
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
1 bedroom, desk, laptop workspace, iron/ironing board
PienzaLettings Suites

Townhouse in Pienza

PienzaLettings Suites
10.0 out of 10, Exceptional, (1)
"Fantastic room in the city center, close to everything in Pienza"
Norway
Tom
The price is P5,031
P5,811 total
includes taxes & fees
Jan 6 - Jan 7, 2026
PienzaLettings Suites
Pillowtop beds, minibar, in-room safe, individually decorated
La Locanda Di Cetona

Townhouse in Cetona

La Locanda Di 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
Bar (on property)
La Piccola Locanda

Townhouse in Chiusi

La Piccola Locanda
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
Front of property - evening/night
Casanova - Panoramic Rooms and Suites

Residence in San Quirico d'Orcia

Casanova - Panoramic Rooms and Suites
3.0 star property
9.0 out of 10, Wonderful, (78)
"Fantastic place"
United States
Clifford
Casanova - Panoramic Rooms and Suites
Breakfast, lunch, dinner served; local cuisine
Hotel San Gregorio

Residence in Pienza

Hotel San Gregorio
3.0 star property
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 P11,026
P12,543 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Hotel San Gregorio
Outdoor pool, sun loungers
Borgo Dolciano

Aparthotel in Chiusi

Borgo Dolciano
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 P8,585
P9,582 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Borgo Dolciano
Exterior
Bed & Breakfast Vicolo dell'Oste

Townhouse in Montepulciano

Bed & Breakfast Vicolo dell'Oste
9.6 out of 10, Exceptional, (128)
"Great hosts, central location "
United States
Alexander
Bed & Breakfast Vicolo dell'Oste
Exterior
La Dimora di Dida

Residence in Seggiano

La Dimora di Dida
The price is P4,721
P5,193 total
includes taxes & fees
Jan 8 - Jan 9, 2026
La Dimora di Dida
Property entrance
Il Tosco

Residence in Montepulciano

Il Tosco
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 P19,807
P22,064 total
includes taxes & fees
Dec 31 - Jan 1, 2026
Il Tosco
Laptop workspace, iron/ironing board, free WiFi
TuscanyLettings Studio&Room

Townhouse in Pienza

TuscanyLettings Studio&Room
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 P5,590
P6,426 total
includes taxes & fees
Jan 11 - Jan 12, 2026
TuscanyLettings Studio&Room
Interior
Delcorto Suites

Residence in Montepulciano

Delcorto Suites
10.0 out of 10, Exceptional, (33)
"Exceptional service great building felt like a Medici!"
United States
gaetano
The price is P11,777
P13,232 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Delcorto Suites
Bar (on property)
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso

Townhouse in San Quirico d'Orcia

Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
9.0 out of 10, Wonderful, (46)
"Our stay was great. "
United States
Elena
Borgo San Quirico d'Orcia B&B - Capitano Collection - Albergo diffuso
Property grounds
Artisti del Cavallo Tourism

Villa in Foiano della Chiana

Artisti del Cavallo Tourism
8.4 out of 10, Very Good, (24)
"Good house for one night. "
Germany
Heiner
The price is P4,811
P5,430 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Artisti del Cavallo Tourism
Private kitchen
Casa Gioia - Casa Olivieri

Apartment in Pienza

Casa Gioia - Casa Olivieri
The price is P5,092
P5,878 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Casa Gioia - Casa Olivieri
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 Macciano Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Everything was perfect! Would like to give this Property a 6 Star rating. The staff made you feel like royalty!!"
Sabrina 4-night trip
Posted 12 days ago
Monastero di Cortona Hotel & Spa

Find out more about Macciano

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

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

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

Frequently asked questions

Can I find vacation rentals in Macciano?

Yes, you can find vacation rentals close to the most popular points of interest in Macciano, or you can go with a more secluded option if you'd like a relaxing place to stay. Macciano is known for its wineries and restaurants.

What’s there to see and do in Macciano?

While exploring the area, visit family-friendly sights like Centro Servizi Turistici Citta della Pieve, or get outside and enjoy nature at Piscine Termali Theia. Terme di Chianciano and Chiusi Lake are a couple of places you'll find in the larger area.

What’s a vacation rental in Macciano like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Macciano. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive choice for a small group gathering.