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Villastrada Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Villastrada vacation rentals

A bakery display with various pastries and desserts.

1. La Piccola Locanda

La Piccola Locanda
Chiusi
8.0 out of 10, Very good, (14 reviews)
"Very homey and wonderful people! We loved the restaurant below."
United States
autumn
The price is ₩158,135
₩176,926 total
includes taxes & fees
Nov 1 - Nov 2
La Piccola Locanda
A rustic brick building with a mural, a clock, and various potted plants.

2. Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Casamaggiore
10.0 out of 10, Exceptional, (1 review)
"Stayed 2 nights in June 2026. Beautiful place with garden and private parking and outdoor terrace - all you can need in quite spacious studio condo. Comfy big bed, aircon and a ceiling fan, dining table with 4 chairs and a kitchenette if you want to cook your own dinners (full with cutlery and crockery, fridge and coffee machine). Clean private bathroom with shower, toilet and bidet. Host was very lovely too, we need an iron and we could borrow it with no fuss alongside ironing board. Very...
United Kingdom
Anna
The price is ₩110,840
₩144,254 total
includes taxes & fees
Nov 1 - Nov 2
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Terrace/patio

3. Casale dell'Assiolo

Casale dell'Assiolo
Castiglione del Lago
9.0 out of 10, Wonderful, (2 reviews)
"Super søde værter. Og rigtig fint værelse. Vi kommer igen"
Denmark
Emma
The price is ₩158,953
₩180,804 total
includes taxes & fees
Nov 5 - Nov 6
Casale dell'Assiolo
A crowded restaurant with brick walls and multiple tables and chairs.

4. La Locanda di San Francesco

La Locanda di San Francesco
Montepulciano
9.8 out of 10, Exceptional, (152 reviews)
"This place was great. Amazing view the room. Extremely friendly and helpful staff. This hotel made our trip - highly recommend"
Canada
Colin
The price is ₩200,298
₩226,283 total
includes taxes & fees
Nov 25 - Nov 26
La Locanda di San Francesco
A patio area with outdoor seating, potted plants, and a view of the landscape.

5. Affitacamere Maria Gabriella

Affitacamere Maria Gabriella
Pienza
9.8 out of 10, Exceptional, (74 reviews)
"A very pleasant and homey place to stay"
Germany
Janine und Thomas
The price is ₩144,331
₩195,833 total
includes taxes & fees
Nov 1 - Nov 2
Affitacamere Maria Gabriella
Exterior

6. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is ₩159,554
₩181,467 total
includes taxes & fees
Nov 11 - Nov 12
montorio
A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

7. Il Tosco

Il Tosco
Montepulciano
10.0 out of 10, Exceptional, (139 reviews)
"Excellent room, service and food. The best."
United States
Valerie
The price is ₩306,932
₩343,580 total
includes taxes & fees
Nov 6 - Nov 7
Il Tosco
An interior courtyard with stone columns, arches, and a mosaic.

8. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.8 out of 10, Exceptional, (121 reviews)
"What a gem! Absolutely loved the hotel and enjoyed our stay. Staff very friendly and helpful, and our room was outstanding. The view from our balcony was breathtaking. Top of our list!"
United States
Christopher
The price is ₩212,133
₩239,301 total
includes taxes & fees
Nov 1 - Nov 2
Meublé Il Riccio
A terrace with a table set for breakfast, overlooking a scenic landscape.

9. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (50 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is ₩228,178
₩256,951 total
includes taxes & fees
Nov 1 - Nov 2
Delcorto Suites
A terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

10. FonteLiving

FonteLiving
San Casciano dei Bagni
10.0 out of 10, Exceptional, (21 reviews)
"Fabulous apt., elegant, clean lines, quiet, pool and wonderful staff"
Italy
Dauray
The price is ₩108,400
₩122,217 total
includes taxes & fees
Nov 5 - Nov 6
FonteLiving
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

11. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (169 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is ₩182,247
₩209,404 total
includes taxes & fees
Nov 5 - Nov 6
Hotel San Gregorio
A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

12. L'Olmo

L'Olmo
Pienza
10.0 out of 10, Exceptional, (28 reviews)
"We were so comfortable and impressed with L'Olmo. Communication prior to our trip was perfect. We got there and the grounds were immaculate, the room was stunning, and the location was extremely convenient. The staff was very helpful. We loved staying here and can recommend it whole heartedly."
United States
Michelle
The price is ₩595,460
₩660,961 total
includes taxes & fees
Nov 2 - Nov 3
L'Olmo
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

13. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (144 reviews)
"Wonderful place - clean, comfortable, quiet with excellent hosts. Perfect location near everything in town including the parking. Can’t wait to return!"
United States
Shelly
The price is ₩140,067
₩160,029 total
includes taxes & fees
Nov 1 - Nov 2
Bed & Breakfast Vicolo dell'Oste
An arched doorway leading to a building with a wooden door and a staircase.

14. Residenza Fabroni

Residenza Fabroni
Montepulciano
8.8 out of 10, Excellent, (115 reviews)
"Very charming property in a fantastic location. The host was very responsive and we had a marvelous stay. Bear in mind this is a historic property and accordingly has some quirks. Those looking for modernity and perfect fixtures may not appreciate those quirks."
United States
Marc
The price is ₩126,670
₩145,292 total
includes taxes & fees
Nov 5 - Nov 6
Residenza Fabroni
A covered corridor with brick columns, potted plants, and a view of a lush landscape.

15. Abbadia Sicille Relais

Abbadia Sicille Relais
4.0 star property
Trequanda
8.8 out of 10, Excellent, (185 reviews)
"Great Historical location."
Canada
Robert
The price is ₩86,477
₩99,591 total
includes taxes & fees
Nov 26 - Nov 27
Abbadia Sicille Relais
A hotel entrance with an arched doorway, a sign with the name 'Albergo I Michele', and a potted plant to the right.

16. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.4 out of 10, Exceptional, (26 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
The price is ₩188,545
₩210,377 total
includes taxes & fees
Nov 4 - Nov 5
B&B Piccolo Hotel
A bedroom with a brick archway, a bed with white linens, a small table with a magazine, and a painting on the wall.

17. TuscanyLettings Studio&Room

TuscanyLettings Studio&Room
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Lugar maravilhoso, localização perfeita, super limpo e aconchegante."
Brazil
Lucas
The price is ₩116,924
₩134,572 total
includes taxes & fees
Nov 2 - Nov 3
TuscanyLettings Studio&Room
A stone building with a balcony and a small garden area with plants.

18. L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
The price is ₩86,819
₩95,501 total
includes taxes & fees
Nov 9 - Nov 10
L'Antica Sosta
A paved pathway lined with potted plants and neatly trimmed hedges, leading to a building with a red roof.

19. Artisti del Cavallo Tourism

Artisti del Cavallo Tourism
Foiano della Chiana
8.4 out of 10, Very good, (25 reviews)
"Good house for one night. "
Germany
Heiner
The price is ₩107,995
₩124,750 total
includes taxes & fees
Nov 1 - Nov 2
Artisti del Cavallo Tourism
A stone building with a wooden door, a staircase, and a small window with a metal grill.

20. Casa Gioia - Casa Olivieri

Casa Gioia - Casa Olivieri
Pienza
10.0 out of 10, Exceptional, (3 reviews)
"Good communication with management through WhatsApp. The taxi dropped us off one minute from the property. Very cozy top floor with only a few steps. The 2 bedroom unit is very comfortable, the kids enjoyed sleeping in the loft. Air conditioning worked very well. We had everything we needed, the location is wonderful. We really enjoyed our stay. Thank you!"
United States
Nancy
The price is ₩135,385
₩154,878 total
includes taxes & fees
Nov 3 - Nov 4
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.
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Top Villastrada Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Relaxing property!"
Natalie 5-night trip
Posted 9 hours ago
Monastero di Cortona Hotel & Spa

Find out more about Villastrada

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

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Frequently asked questions

Can I find vacation rentals in Villastrada?

Yes, we give you a choice of vacation rentals close to popular attractions in Villastrada, or you can go with a more remote option if you're looking for relaxation.

What’s there to see and do in Villastrada?

Explore the area and family-friendly sights such as Tavernelle Aquatic Park, or get out into nature at a spot like Chiusi Lake. In the larger area, you’ll find Lake Trasimeno and Terme Sant'Elena.

What’s a vacation rental in Villastrada like?

A vacation rental is a private property you can stay in for several days or longer in Villastrada. Vacation rentals feature extras such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive option for family gatherings.