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Villastrada Holiday Rentals

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Check prices for these dates

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

Our top choices for Villastrada holiday 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 S$169
includes taxes & fees
29 Oct - 30 Oct
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 S$211
includes taxes & fees
30 Oct - 31 Oct
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 S$175
includes taxes & fees
3 Nov - 4 Nov
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 S$134
includes taxes & fees
27 Nov - 28 Nov
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 S$163
includes taxes & fees
5 Nov - 6 Nov
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 S$219
includes taxes & fees
1 Nov - 2 Nov
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 S$109
includes taxes & fees
29 Oct - 30 Oct
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 S$223
includes taxes & fees
25 Nov - 26 Nov
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 S$166
includes taxes & fees
29 Oct - 30 Oct
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 S$119
includes taxes & fees
29 Oct - 30 Oct
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 S$153
includes taxes & fees
1 Nov - 2 Nov
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 S$245
includes taxes & fees
29 Oct - 30 Oct
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 S$201
includes taxes & fees
9 Nov - 10 Nov
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 10 hours ago
Hotel Corsignano

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 Tavernelle Aquatic Park, or get out into nature at a spot like Chiusi Lake. In the wider area, you’ll find Lake Trasimeno and Terme Sant'Elena.

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.