Villastrada Vacation Rentals from $102: Search Short-Term Rentals

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Our top choices for Villastrada vacation rentals

1. La Piccola Locanda

Chiusi

autumn

$123 nightly

Sep 15 - Sep 16

Total with taxes and fees

2. Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany

Castiglione del Lago

Bin L.

$164 nightly

Sep 14 - Sep 15

Total with taxes and fees

3. Boutique Apartment Natura

Chiusi

Shelley

$83 nightly

Sep 14 - Sep 15

Total with taxes and fees

4. Villa on the Umbria-Tuscany border—for families and friends—with a private pool

Città della Pieve

Kim B.

$796 nightly

Oct 5 - Oct 6

Total with taxes and fees

5. Borgo Dolciano

Chiusi

Carla

$164 nightly

Sep 14 - Sep 15

Total with taxes and fees

6. La Locanda Di Cetona

Cetona

"We arrived quite late, but the staff were friendly, responsive, and very helpful with the self-check-in process. Their support made our arrival easy and stress-free. The room was charming, clean, and well cared for. We also really enjoyed the location and the atmosphere of this little town. Having a café just downstairs for breakfast was a nice bonus. We had a great stay and would be happy to return."

Ruby

$142 nightly

Sep 15 - Sep 16

Total with taxes and fees

7. Boutique Apartment Eleganza

Chiusi Scalo

Ryan W.

$85 nightly

Sep 20 - Sep 21

Total with taxes and fees

8. Villa San Biagio – Luxury with Lake View, Wi-Fi, and Air Conditioning

Città della Pieve

$2,305 nightly

Sep 14 - Sep 15

Total with taxes and fees

9. Affitacamere Maria Gabriella

Pienza

Christopher

$129 nightly

Oct 14 - Oct 15

Total with taxes and fees

10. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Shelly

$136 nightly

Oct 13 - Oct 14

Total with taxes and fees

11. Meublé Il Riccio

Montepulciano

Marlenne

$165 nightly

Sep 15 - Sep 16

Total with taxes and fees

12. La Locanda di San Francesco

Montepulciano

Isabelle

$195 nightly

Sep 27 - Sep 28

Total with taxes and fees

13. Spacious apartment with all amenities - short distance from Castiglione del Lago

Macchie

Lisa S.

$137 nightly

Sep 29 - Sep 30

Total with taxes and fees

14. Delcorto Suites

Montepulciano

Denise

$194 nightly

Oct 6 - Oct 7

Total with taxes and fees

15. Il Tosco

Montepulciano

Margaret

$299 nightly

Sep 24 - Sep 25

Total with taxes and fees

16. Boutique Apartment Family

Chiusi

Joseph M.

$88 nightly

Sep 14 - Sep 15

Total with taxes and fees

17. Residence al Lago

Contrada Fontivegge

Hananeh

$93 nightly

Sep 28 - Sep 29

Total with taxes and fees

18. Residenza Fabroni

Montepulciano

Nicholas

$89 nightly

Sep 22 - Sep 23

Total with taxes and fees

19. Gorgeously restored tranquil farmhouse

Castiglione Del Lago PG

John C.

$268 nightly

Oct 2 - Oct 3

Total with taxes and fees

20. L'Olmo

Pienza

Jennifer

$731 nightly

Sep 14 - Sep 15

Total with taxes and fees

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Top Villastrada Hotel Reviews

Hotel Corsignano

10/10 Excellent

"My husband and I had an absolutely wonderful experience at Hotel Corsignano. From beginning to end, the staff went above and beyond to make us feel welcome and cared for. When we arrived a little later than expected, they were genuinely concerned about us and even made sure to save a parking spot for us. That level of thoughtfulness and hospitality really stood out. The hotel was exceptionally clean and in a fantastic location, just a few steps from the historic center of Pienza. And the breakfast was wonderful, with plenty of delicious options to choose from. We truly felt welcomed and well taken care of throughout our stay. We would happily stay here again and highly recommend Hotel Corsignano!"

Monastero di Cortona Hotel & Spa

10/10 Excellent

"Truly a stunning boutique hotel that sits in the perfect place within the walled village of Cortana, Really enjoyed my 3 nights here mid trip. The staff have been trained exceptionally well. Zero pretention, impeccable service. The calm ( so quiet), amenities such as the spa and pool area, the breakfast and restaurants, and staff ( mgt, Eleanora, Matteo, Spa leads), attention to details, views from my window, coupled with the energy of the hotel are stand outs. Do treat yourself to a couple massages or treatments. Very fair pricing, and after all the walking and travel, so worth it. I had a massage my first day and my last, that were sandwiched between two other stays in Tuscany, SO glad I did. Tips: Little micro laundry place right at the bottom of the hill that was perfect to do my laundry for my last leg of my vacation. Day trip to Arezzo was so easy and amazing. Attended mass at 6pm on Sunday at a beautiful church above Cortana at the highest elevation. Lovely. They even have a little gift shop in the church. And the first weekend of the month there is a massive antiques fair in the Grand Piazza. 500 vendors. Recommend. There are other stunning boutique hotels within Cortano. Honestly feel this is your best pick. In off seasons this hotel may consider becoming a school of sorts for family businesses in the area, to act as a training academy of sorts for younger generation family members to ensure success."

Villa Tiberini Wine Relais

10/10 Excellent

"Villa Tiberini is a beautiful place! The chef, staff and owners are wonderful people. The apartment was clean, had all of the necessities and thoughtful touches to make the experience welcoming and comfortable. The shower water pressure and pillow top bed were an extra treat! Breakfast was delicious and we loved the wine. We thoroughly enjoyed our time and would highly recommend this stay for anyone looking to get away from the buzz of tourist destinations. The actual winery is about a 10 minute drive away. We enjoyed our time lounging by the pool and exploring nearby towns by car."

Il Falconiere - Relais e Chateaux

10/10 Excellent

"Il Falconiere treats you as a true guest. Welcoming, courteous and professional were all staff members. Food truly excellent and with the Michelin star, you will enjoy a sumptuous meal, ample portions, amuse bouche at meal's start with a surprise dessert tray with little bites. All staff you interact with are well trained and genuinely friendly and still professional. Our room was in the origjnal residence and had a modern bathroom, lovely size bedroom, anti room with a second desk. In the salon, upon entering the suite, you will find "gifts" left for guests with seating if wishing to entertain. Our group, 4 persons, were very impressed with accommodations, meals and courteous staff. Of course, owner and chef, Silvia Baracchi, too was gracious coming to tables in the evening, welcoming guests and if passed anyone during day, always smiled a buon giorno to one and all. A delightful experience and wonderful to share with good friends."

Precise Tale Poggio Alla Sala

10/10 Excellent

"Incredible stay in a beautiful location. The staff were amazing and the hospitality was top tier. We will most definitely be back. The recommendations given were brilliant and the room was stunning along with the rest of the hotel. We didn’t dine in the restaurant but our breakfast each morning was also wonderful."

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 $102 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?

Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!: This vacation home rental outside of Villastrada is located in a rural location and has an outdoor pool, a patio, and air-conditioning to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

What’s there to see and do in Villastrada?

Explore the area and family-friendly sights such as Centro Servizi Turistici Citta della Pieve, or get out into nature at a spot like Lake Trasimeno. In the larger area, you’ll find Terme Sant'Elena and Isola Maggiore.

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. Casa Roda – Your Home by Lake Trasimeno, Between Umbria and Tuscany

3. Boutique Apartment Natura

4. Villa on the Umbria-Tuscany border—for families and friends—with a private pool

5. Borgo Dolciano

6. La Locanda Di Cetona

7. Boutique Apartment Eleganza

8. Villa San Biagio – Luxury with Lake View, Wi-Fi, and Air Conditioning

9. Affitacamere Maria Gabriella

10. Bed & Breakfast Vicolo dell'Oste

11. Meublé Il Riccio

12. La Locanda di San Francesco

13. Spacious apartment with all amenities - short distance from Castiglione del Lago

14. Delcorto Suites

15. Il Tosco

16. Boutique Apartment Family

17. Residence al Lago

18. Residenza Fabroni

19. Gorgeously restored tranquil farmhouse

20. L'Olmo

Find vacation rentals that suit your style

Top Villastrada Hotel Reviews

Hotel Corsignano

Monastero di Cortona Hotel & Spa

Relais Villa Grazianella - UNA Esperienze

Villa Tiberini Wine Relais

Il Falconiere - Relais e Chateaux

Nuovo Etruria Resort

Fonteverde Thermal Spa Resort Tuscany

Precise Tale Poggio Alla Sala

Villa di Piazzano - Small Luxury Hotel of the World

Find out more about Villastrada

Frequently asked questions