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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 NT$3,840
NT$4,296 total
includes taxes & fees
Nov 2 - Nov 3
La Piccola Locanda
A nighttime view of a building with a staircase leading to a door, surrounded by greenery and a well-lit pathway.

2. Borgo Dolciano

Borgo Dolciano
Chiusi
9.0 out of 10, Wonderful, (26 reviews)
"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 NT$4,787
NT$5,338 total
includes taxes & fees
Oct 30 - Oct 31
Borgo Dolciano
A patio area with outdoor seating, potted plants, and a view of the landscape.

3. 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 NT$3,504
NT$4,755 total
includes taxes & fees
Nov 1 - Nov 2
Affitacamere Maria Gabriella
A rustic brick building with a mural, a clock, and various potted plants.

4. 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 NT$2,691
NT$3,503 total
includes taxes & fees
Oct 31 - Nov 1
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno
Terrace/patio

5. 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 NT$3,861
NT$4,391 total
includes taxes & fees
Nov 5 - Nov 6
Casale dell'Assiolo
An interior courtyard with stone columns, arches, and a mosaic.

6. Meublé Il Riccio

Meublé Il Riccio
Montepulciano
9.6 out of 10, Exceptional, (120 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 NT$5,151
NT$5,810 total
includes taxes & fees
Oct 30 - Oct 31
Meublé Il Riccio
A terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

7. 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 NT$2,633
NT$2,968 total
includes taxes & fees
Nov 5 - Nov 6
FonteLiving
A crowded restaurant with brick walls and multiple tables and chairs.

8. 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 NT$4,930
NT$5,568 total
includes taxes & fees
Nov 25 - Nov 26
La Locanda di San Francesco
Exterior

9. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is NT$3,698
NT$4,213 total
includes taxes & fees
Oct 31 - Nov 1
montorio
An arched doorway leading to a building with a wooden door and a staircase.

10. 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 NT$3,069
NT$3,521 total
includes taxes & fees
Nov 8 - Nov 9
Residenza Fabroni
A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

11. Bed & Breakfast Vicolo dell'Oste

Bed & Breakfast Vicolo dell'Oste
Montepulciano
9.6 out of 10, Exceptional, (143 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 NT$3,401
NT$3,885 total
includes taxes & fees
Nov 1 - Nov 2
Bed & Breakfast Vicolo dell'Oste
A terrace with a table set for breakfast, overlooking a scenic landscape.

12. Delcorto Suites

Delcorto Suites
Montepulciano
10.0 out of 10, Exceptional, (49 reviews)
"Room, location, staff - it was perfection. We can not wait to return."
United States
Denise
The price is NT$6,121
NT$6,878 total
includes taxes & fees
Nov 1 - Nov 2
Delcorto Suites
A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

13. Hotel San Gregorio

Hotel San Gregorio
3.0 star property
Pienza
9.4 out of 10, Exceptional, (168 reviews)
"Great location. Clean and quiet with good breakfast"
United States
Michael
The price is NT$4,425
NT$5,084 total
includes taxes & fees
Nov 5 - Nov 6
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.
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Top Villastrada Hotel Reviews

Hotel Corsignano

Hotel Corsignano

10/10 Excellent
"Excellent hotel. We had a superior room which was large and had a fabulous bathroom. The views over the valley were beautiful. The staff were really nice. We enjoyed chilling on the terrace solarium when we weren't exploring the lovely old town."
Susan 4-night trip
Posted 19 hours ago
Hotel Corsignano

Find out more about Villastrada

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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.