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Villastrada Holiday Rentals

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Our top choices for Villastrada holiday rentals

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 NZ$220
includes taxes & fees
31 Oct - 1 Nov
La Piccola Locanda

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 NZ$289
includes taxes & fees
30 Oct - 31 Oct
Borgo Dolciano

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 NZ$243
includes taxes & fees
12 Nov - 13 Nov
Affitacamere Maria Gabriella

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 NZ$188
includes taxes & fees
28 Nov - 29 Nov
Casa di Cristina - Tra Montepulciano e il Lago Trasimeno

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 NZ$224
includes taxes & fees
5 Nov - 6 Nov
Casale dell'Assiolo

6. Boutique Apartment Eleganza

Boutique Apartment Eleganza
Chiusi Scalo
9.6 out of 10, Exceptional, (5 reviews)
"Amazing apartment!So close to the train!"
United States
Ryan W.
The price is NZ$186
includes taxes & fees
29 Oct - 30 Oct
Boutique Apartment Eleganza

7. 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 NZ$300
includes taxes & fees
14 Nov - 15 Nov
Meublé Il Riccio

8. Boutique Apartment Natura

Boutique Apartment Natura
Chiusi
10.0 out of 10, Exceptional, (1 review)
"Great location and very clean!"
Canada
Shelley
The price is NZ$179
includes taxes & fees
29 Oct - 30 Oct
Boutique Apartment Natura

9. 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 NZ$150
includes taxes & fees
29 Oct - 30 Oct
FonteLiving

10. 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 NZ$302
includes taxes & fees
25 Nov - 26 Nov
La Locanda di San Francesco

11. 2 King Bed, 2 Full Bathroom Apartment in Città della Pieve, Umbria - Tuscany

2 King Bed, 2 Full Bathroom Apartment in Città della Pieve, Umbria - Tuscany
Città della Pieve
9.8 out of 10, Exceptional, (8 reviews)
"It's really a nice house in a beautiful small town. We enjoyed our stay. "
United States
Waseemuddin S.
The price is NZ$270
includes taxes & fees
3 Nov - 4 Nov
2 King Bed, 2 Full Bathroom Apartment in Città della Pieve, Umbria - Tuscany

12. montorio

montorio
Montepulciano
9.8 out of 10, Exceptional, (11 reviews)
"Amazing location, beautiful property"
United States
Joseph
The price is NZ$228
includes taxes & fees
29 Oct - 30 Oct
montorio

13. 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 NZ$163
includes taxes & fees
29 Oct - 30 Oct
Residenza Fabroni

14. Evelyn's home Fabro Scalo tra Umbria e Toscana

Evelyn's home Fabro Scalo tra Umbria e Toscana
Fabro Scalo
10.0 out of 10, Exceptional, (1 review)
"Alloggio bellissimo, con una notazione fuori dal comune (lavatrice e asciugatrice, tanto per dirne una). Proprietaria disponibile e bravissima. Davvero complimenti. Se torno in zona torno qui sicuramente. 💯💯💯"
Italy
Telly
The price is NZ$261
includes taxes & fees
29 Oct - 30 Oct
Evelyn's home Fabro Scalo tra Umbria e Toscana

15. 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 NZ$199
includes taxes & fees
3 Nov - 4 Nov
Bed & Breakfast Vicolo dell'Oste

16. Le Coin des Murs—Panicale Historic Center

Le Coin des Murs—Panicale Historic Center
Panicale
The price is NZ$176
includes taxes & fees
28 Nov - 29 Nov
Le Coin des Murs—Panicale Historic Center

17. Macadamia Tuscany House - Studio apartment surrounded by greenery, on the edge of the Val d'Orcia

Macadamia Tuscany House - Studio apartment surrounded by greenery, on the edge of the Val d'Orcia
Sarteano
The price is NZ$235
includes taxes & fees
4 Nov - 5 Nov
Macadamia Tuscany House - Studio apartment surrounded by greenery, on the edge of the Val d'Orcia

18. 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 NZ$336
includes taxes & fees
29 Oct - 30 Oct
Delcorto Suites

19. 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 NZ$289
includes taxes & fees
8 Nov - 9 Nov
Hotel San Gregorio

20. Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning

Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning
Panicale
The price is NZ$388
includes taxes & fees
2 Nov - 3 Nov
Holiday Home 'Il Forcone' with Shared Pool, Wi-Fi and Air Conditioning
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

Find out more about Villastrada

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Villastrada holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Villastrada. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Villastrada. Seeing all the best attractions is bound to make you fall in love with Villastrada. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Villastrada short-term rentals, that won’t be hard to do.

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

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome: This holiday home rental outside of Villastrada is located in a rural location, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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.