Calzolaro Vacation Rentals from CA $227: Short-Term Rentals for 2026

Q: What are some of the best vacation home rentals in Calzolaro?

Holiday Home in Umbria with Pool : This vacation home rental near Calzolaro offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

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Our top choices for Calzolaro vacation rentals

1. iConic Wellness Resort

Arezzo

Rheymarie

CA $127 total

includes taxes & fees

Oct 25 - Oct 26

An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

2. B&B Piccolo Hotel

Cortona Old Town

mansoor

CA $227 total

includes taxes & fees

Nov 2 - Nov 3

A stone building with a balcony and a small garden area with plants.

3. L'Antica Sosta

Corciano

Valentina

CA $95 total

includes taxes & fees

Oct 6 - Oct 7

A narrow cobblestone street with a rustic stone building featuring a wooden door and arched window.

4. San Michele al Borgo

Castiglion Fiorentino

Vern

CA $212 total

includes taxes & fees

Oct 6 - Oct 7

A courtyard with a stone pathway, potted plants, and a building with multiple windows and a door.

5. Rustic Holiday Home in Citta di Castello With Swimming Pool

Città di Castello

CA $332 total

includes taxes & fees

Nov 4 - Nov 5

A building with a balcony, multiple windows, and a door.

6. Dolce Rosa Centro Storico

Sansepolcro

Sergio

CA $84 total

includes taxes & fees

Oct 12 - Oct 13

A narrow stone staircase leading up a hillside, flanked by buildings with wooden doors and windows, and hanging laundry.

7. Vicolo Della Scala Rooms - La Luna

Cortona Old Town

CA $159 total

includes taxes & fees

Oct 6 - Oct 7

A hotel room with a large bed, a desk, a chair, a small table, and a door leading to another room.

8. CASA AMBRA

Cortona Old Town

CA $485 total

includes taxes & fees

Oct 5 - Oct 6

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Top Calzolaro Hotel Reviews

Monastero di Cortona Hotel & Spa

10/10 Excellent

"5 star treatment, indoor pool is a charge to use and parking is rough. Overall excellent experience. Staff is great."

Hotel Priori Secret Garden

8/10 Good

"They shine in cleanliness. Provided a small fridge with water in the room and the air condition is good. Make sure you get the information on it and let them know the temperature you would prefer. Breakfast is excellent and the staff most attentive. My only dislike was the fact that the stairs up to the third floor are most convoluted. If you have difficulty climbing stairs, ask for the first floor."

Sina Brufani

10/10 Excellent

"Lovely elegant corner room in the front of the hotel, overlooking the valley; good breakfast; convenient location, helpful staff. An aside, needed to consult a medical dcotor for brief illness, hotel was very helpful in immediately contacting local physician who responded immediately and provided very help diagnosis (including a portable ultrasound) and consultation at an incredibly reasonable price."

Hotel Sant'Ercolano

8/10 Good

"The hotel is well situated very close to the mini metro where you can also easily take an elevator to the top of the historic centre or walk (lots of stairs); close to main points of interest and places to eat. While The Building is old, certainly my room had upgrades modern bathroom, very comfortable bed, and it was really clean apart from shower dispenser soap. There are no other amenities like shampoo and conditioner. I enjoyed my stay. If you were travelling casually, this is the place for you. I travelled alone and I felt very safe. However, some business travellers may need more amenities like a proper desk, etc.. staff was very hopeful"

A small cottage in authentic Tuscany. Serves 4

10/10 Excellent

"The host was very nice and met us at the property. She gave us a tour of the apartment and explained everything for us. She also provided some good snacks made by her mother and a bottle of wine. The location is perfect for visiting Cortana and many other small towns in the area. We had a wonderful time during our stay."

Find out more about Calzolaro

Everything you need to know about Calzolaro 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 Calzolaro vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... 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 Calzolaro vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Calzolaro vacation rentals: An excellent choice for every season

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

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Calzolaro vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Calzolaro vacation rentals we have selected for you start as low as CA $227 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Calzolaro rentals

At Expedia, we put the best Calzolaro 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 Calzolaro 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 Calzolaro 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 Calzolaro. 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 Calzolaro?

Yes, we have vacation rentals close to top local attractions in Calzolaro, or you can choose a more remote option if you're looking for a relaxing stay.

What are some of the best vacation home rentals in Calzolaro?

Holiday Home in Umbria with Pool: This vacation home rental near Calzolaro offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Calzolaro?

While exploring the area, visit family-friendly sights like Aboca Museum, or get outside and enjoy nature at Isola Maggiore. In the larger area, you’ll find Historic Town Montone and Civitella Ranieri Castle.

What’s a vacation rental in Calzolaro like?

Vacation rentals are private properties you can stay in for a long or short time in Calzolaro. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you to travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for family trips or small group gatherings.

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Check prices for these dates

Our top choices for Calzolaro vacation rentals

1. iConic Wellness Resort

2. B&B Piccolo Hotel

3. L'Antica Sosta

4. San Michele al Borgo

5. Rustic Holiday Home in Citta di Castello With Swimming Pool

6. Dolce Rosa Centro Storico

7. Vicolo Della Scala Rooms - La Luna

8. CASA AMBRA

9. Welchome suites

10. Maison Panorama

11. Tentazioni Raffinate - Luxury Suite

12. Casa Miramonti in Perugia

13. Vicolo Della Scala Rooms - Il Sole

14. Luxury Suite - Tentazioni Nascoste

15. Luxury Suite - Tentazioni Romantiche

Find vacation rentals that suit your style

Top Calzolaro Hotel Reviews

Monastero di Cortona Hotel & Spa

Hotel Sangallo Palace

Hotel Priori Secret Garden

Rosetta Hotel Perugia, Tapestry Collection by Hilton

Sina Brufani

Hotel Sant'Ercolano

Hotel Giò Wine e Jazz Area

A small cottage in authentic Tuscany. Serves 4

Relais Villa Baldelli

Find out more about Calzolaro

Frequently asked questions

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