Villastrada Holiday Rentals from NZ$176: Search Short-Term Rentals

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Our top choices for Villastrada holiday rentals

A bakery display with various pastries and desserts.

1. La Piccola Locanda

Chiusi

autumn

includes taxes & fees

15 Sept - 16 Sept

A kitchen with a tiled backsplash and three hanging utensils.

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

Castiglione del Lago

Bin L.

includes taxes & fees

22 Sept - 23 Sept

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

3. Boutique Apartment Natura

Chiusi

Shelley

includes taxes & fees

24 Sept - 25 Sept

A terrace with a table and chairs, surrounded by greenery, overlooking a landscape with hills.

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

Città della Pieve

Kim B.

includes taxes & fees

5 Oct - 6 Oct

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

5. Borgo Dolciano

Chiusi

Carla

includes taxes & fees

14 Sept - 15 Sept

A large building with a cafe area, outdoor seating, and a covered patio.

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

includes taxes & fees

15 Sept - 16 Sept

A view through a glass door into a patio area with a white chair, a small table, and a banner advertising local attractions.

7. Boutique Apartment Eleganza

Chiusi Scalo

Ryan W.

includes taxes & fees

27 Sept - 28 Sept

A patio with outdoor furniture, a stone wall, and a view of a vineyard.

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

Città della Pieve

includes taxes & fees

27 Sept - 28 Sept

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

9. Affitacamere Maria Gabriella

Pienza

Young Rok

includes taxes & fees

4 Oct - 5 Oct

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

10. Bed & Breakfast Vicolo dell'Oste

Montepulciano

Shelly

includes taxes & fees

18 Sept - 19 Sept

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

11. Meublé Il Riccio

Montepulciano

Marlenne

includes taxes & fees

15 Sept - 16 Sept

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

12. La Locanda di San Francesco

Montepulciano

Isabelle

includes taxes & fees

8 Oct - 9 Oct

A two-story house with a patio area, outdoor seating, and a garden.

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

Macchie

Lisa S.

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

14. Delcorto Suites

Montepulciano

Denise

includes taxes & fees

6 Oct - 7 Oct

A narrow cobblestone street flanked by historic stone buildings with arched doorways and windows.

15. Il Tosco

Montepulciano

Margaret

includes taxes & fees

24 Sept - 25 Sept

A balcony with a red chair and table, a view of a residential building, and a wooden lattice partition.

16. Boutique Apartment Family

Chiusi

Joseph M.

includes taxes & fees

14 Sept - 15 Sept

A fountain with water cascading down a column, surrounded by greenery and a building in the background.

17. Residence al Lago

Contrada Fontivegge

Hananeh

includes taxes & fees

17 Sept - 18 Sept

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

18. Residenza Fabroni

Montepulciano

Nicholas

includes taxes & fees

22 Sept - 23 Sept

A thatched-roof pavilion overlooking a calm lake with distant mountains.

19. Gorgeously restored tranquil farmhouse

Castiglione Del Lago PG

John C.

includes taxes & fees

2 Oct - 3 Oct

A cozy outdoor seating area with stone walls and red foliage, featuring a table and chairs, and a door leading to a covered entrance.

20. L'Olmo

Pienza

Jennifer

includes taxes & fees

14 Sept - 15 Sept

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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

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?

Villa with private pool, air conditioning in Val d'Orcia. Very quiet place!!!: This holiday 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 that you can cook with friends or family. Make the most of 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 wider area, you’ll find Terme Sant'Elena and Isola Maggiore.

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.

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Check prices for these dates

Our top choices for Villastrada holiday 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 holiday 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

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