Villastrada Vacation Rentals from $61: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Villastrada vacation rentals

A bakery display with various pastries and desserts.

1. La Piccola Locanda

Chiusi

autumn

$118 nightly

Oct 30 - Oct 31

Total with taxes and fees

A nighttime view of a building with a staircase leading to a door, surrounded by greenery and a well-lit pathway.

2. Borgo Dolciano

Chiusi

Carla

$147 nightly

Oct 30 - Oct 31

Total with taxes and fees

A patio area with outdoor seating, potted plants, and a view of the landscape.

3. Affitacamere Maria Gabriella

Pienza

Janine und Thomas

$117 nightly

Nov 4 - Nov 5

Total with taxes and fees

A rustic brick building with a mural, a clock, and various potted plants.

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

Casamaggiore

"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...

Anna

$96 nightly

Nov 29 - Nov 30

Total with taxes and fees

5. Casale dell'Assiolo

Castiglione del Lago

Emma

$108 nightly

Nov 6 - Nov 7

Total with taxes and fees

A view through a glass door into a patio area with a white chair, a table, and a banner advertising a boutique hotel.

6. Boutique Apartment Eleganza

Chiusi Scalo

Ryan W.

$95 nightly

Nov 2 - Nov 3

Total with taxes and fees

An interior courtyard with stone columns, arches, and a mosaic.

7. Meublé Il Riccio

Montepulciano

Christopher

$147 nightly

Nov 6 - Nov 7

Total with taxes and fees

A bedroom with a bed, a TV, a wardrobe, and a view of a garden.

8. Boutique Apartment Natura

Chiusi

Shelley

$86 nightly

Oct 30 - Oct 31

Total with taxes and fees

A terrace with a table set for dining, overlooking a scenic landscape with a castle in the distance.

9. FonteLiving

San Casciano dei Bagni

Dauray

$74 nightly

Nov 15 - Nov 16

Total with taxes and fees

A crowded restaurant with brick walls and multiple tables and chairs.

10. La Locanda di San Francesco

Montepulciano

Colin

$147 nightly

Nov 26 - Nov 27

Total with taxes and fees

A building with two open doors, each with a sign above. There are potted plants outside and a sign on the wall to the left.

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

Città della Pieve

Waseemuddin S.

$148 nightly

Nov 3 - Nov 4

Total with taxes and fees

12. montorio

Montepulciano

Joseph

$114 nightly

Oct 31 - Nov 1

Total with taxes and fees

An arched doorway leading to a building with a wooden door and a staircase.

13. Residenza Fabroni

Montepulciano

Marc

$95 nightly

Nov 8 - Nov 9

Total with taxes and fees

An interior with stone walls, a fireplace, and seating areas.

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

Fabro Scalo

Telly

$148 nightly

Nov 2 - Nov 3

Total with taxes and fees

A narrow alleyway with buildings on either side, string lights hanging above, and a sign reading "ROOMS".

15. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Shelly

$102 nightly

Nov 29 - Nov 30

Total with taxes and fees

A narrow street with old brick buildings, a wooden door, and potted plants.

16. Le Coin des Murs—Panicale Historic Center

Panicale

$92 nightly

Oct 30 - Oct 31

Total with taxes and fees

A brick building with a covered porch, steps leading up to a seating area with two chairs.

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

Sarteano

$129 nightly

Nov 4 - Nov 5

Total with taxes and fees

A terrace with a table set for breakfast, overlooking a scenic landscape.

18. Delcorto Suites

Montepulciano

Denise

$170 nightly

Oct 31 - Nov 1

Total with taxes and fees

A table set outdoors with breakfast items including bread, a cup, and a glass of juice.

19. Hotel San Gregorio

Pienza

Michael

$136 nightly

Nov 8 - Nov 9

Total with taxes and fees

An outdoor seating area with tables and chairs, surrounded by palm trees and a view of the sea.

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

Panicale

$221 nightly

Nov 2 - Nov 3

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Apartments

Aparthotels

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Villastrada Hotel Reviews

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."

Poggio Paradiso Resort & Spa

10/10 Excellent

"Our stay at Poggio Paradiso was as lovely as we could've imagined. The staff was very attentive to every need and it felt like we were at home throughout our time on the property. The location and views are amazing and the restaurant on site was delicious for both the complimentary breakfast and convenient dinners. Would absolutely stay here again!"

Relais Cloister Pienza

10/10 Excellent

"An Incredible Terrace with the Most Amazing Views! ⭐⭐⭐⭐⭐ The hotel is beautifully restored and in a fantastic location in Pienza, just off Piazza Pio II. Our room was spotlessly clean, comfortable, with good bedding and a lovely large bathroom. The room itself was simple but very comfortable and had everything we needed. However, the absolute highlight of this hotel is the terrace. The views across the Val d’Orcia are quite simply out of this world! You could sit there for hours just taking it all in. We honestly think it must be the best spot in the whole of Pienza to enjoy those incredible Tuscan views. The staff were attentive and welcoming, and breakfast was also good. We would highly recommend staying here, especially for the terrace. If you want to experience the beauty of Tuscany from a truly breathtaking viewpoint, this is the place to stay!"

Find out more about Villastrada

Everything you need to know about Villastrada vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Villastrada vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Villastrada vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Villastrada vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Villastrada. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Villastrada in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $61 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Villastrada rentals

At Expedia, we put the best Villastrada vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Villastrada rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Villastrada vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Villastrada. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

Room 1

Check prices for these dates

Our top choices for Villastrada vacation rentals

1. La Piccola Locanda

2. Borgo Dolciano

3. Affitacamere Maria Gabriella

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

5. Casale dell'Assiolo

6. Boutique Apartment Eleganza

7. Meublé Il Riccio

8. Boutique Apartment Natura

9. FonteLiving

10. La Locanda di San Francesco

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

12. montorio

13. Residenza Fabroni

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

15. Bed & Breakfast Vicolo dell'Oste

16. Le Coin des Murs—Panicale Historic Center

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

18. Delcorto Suites

19. Hotel San Gregorio

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

Find vacation rentals that suit your style

Top Villastrada Hotel Reviews

Hotel Corsignano

Monastero di Cortona Hotel & Spa

Nuovo Etruria Resort

Poggio Paradiso Resort & Spa

Fonteverde Thermal Spa Resort Tuscany

Hotel San Gregorio

Relais Cloister Pienza

Hotel Villa Ricci

La Collina Hotel

Find out more about Villastrada

Frequently asked questions