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Villastrada Vacation Rentals

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Our top choices for Villastrada vacation 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 CA $166
CA $185 total
includes taxes & fees
Nov 3 - Nov 4
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 CA $207
CA $230 total
includes taxes & fees
Oct 31 - Nov 1
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 CA $144
CA $197 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $114
CA $148 total
includes taxes & fees
Nov 22 - Nov 23
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 CA $157
CA $179 total
includes taxes & fees
Nov 15 - Nov 16
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 CA $133
CA $162 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $207
CA $234 total
includes taxes & fees
Nov 7 - Nov 8
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 CA $132
CA $161 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $106
CA $119 total
includes taxes & fees
Nov 5 - Nov 6
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 CA $206
CA $232 total
includes taxes & fees
Nov 26 - Nov 27
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 CA $102
CA $208 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $160
CA $182 total
includes taxes & fees
Oct 31 - Nov 1
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 CA $123
CA $142 total
includes taxes & fees
Nov 5 - Nov 6
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 CA $163
CA $207 total
includes taxes & fees
Nov 2 - Nov 3
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 CA $144
CA $165 total
includes taxes & fees
Nov 30 - Dec 1
Bed & Breakfast Vicolo dell'Oste

16. Le Coin des Murs—Panicale Historic Center

Le Coin des Murs—Panicale Historic Center
Panicale
The price is CA $101
CA $129 total
includes taxes & fees
Nov 1 - Nov 2
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 CA $123
CA $187 total
includes taxes & fees
Nov 5 - Nov 6
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 CA $238
CA $268 total
includes taxes & fees
Oct 31 - Nov 1
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 CA $191
CA $220 total
includes taxes & fees
Nov 5 - Nov 6
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 CA $233
CA $309 total
includes taxes & fees
Nov 2 - Nov 3
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 vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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 are some of the best vacation home rentals in Villastrada?

Tuscan villa pool spa Siena Montepulciano Perugia Pienza Florence 2 hours from Rome: This vacation home rental outside of Villastrada is located in a rural location and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a patio, a garden, and a selection of games so you can immerse yourself in your vacation.

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.