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Calzolaro Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Calzolaro vacation rentals

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

1. L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
$59 nightly
The price is $65
Oct 15 - Oct 16
Total with taxes and fees
L'Antica Sosta
A stone building with a sloped roof, a covered porch, and a small garden area with potted plants.

2. Apartment 'Lavanda ad Antico Casale '700' with Shared Pool & Wi-Fi

Apartment 'Lavanda ad Antico Casale '700' with Shared Pool & Wi-Fi
Umbertide
8.0 out of 10, Very good, (1 review)
"Pros: Location in the mountains is superb, very friendly& supportive staff, fair price Cons: Only very small windows in the appartment, thus dark and nearly no chance for fresh cold air in the night. Due to the size of the location the pool was overcrowded and too less sun chairs. Photos better than reality."
United States
Anonymous traveler
$343 nightly
The price is $343
Oct 15 - Oct 16
Total with taxes and fees
Apartment 'Lavanda ad Antico Casale '700' with Shared Pool & Wi-Fi
A stone building with a sloped roof, a covered porch, and a small garden area.

3. Apartment 'Glicine ad Antico Casale '700' with Shared Pool & Wi-Fi

Apartment 'Glicine ad Antico Casale '700' with Shared Pool & Wi-Fi
Umbertide
$408 nightly
The price is $408
Oct 30 - Oct 31
Total with taxes and fees
Apartment 'Glicine ad Antico Casale '700' with Shared Pool & Wi-Fi
A courtyard with a stone pathway, potted plants, and a building with multiple windows and a door.

4. Elegant Countryside Retreat

Elegant Countryside Retreat
Città di Castello
9.4 out of 10, Exceptional, (29 reviews)
"Enjoyed evenings near that fireplace, really nice ambiance when winding down after excursions into town. Garden’s a good spot to chill if you want some fresh air as well."
United States
Anonymous traveler
$334 nightly
The price is $334
Oct 15 - Oct 16
Total with taxes and fees
Elegant Countryside Retreat
Holiday Home Exterior [summer]

5. Holiday Home in Umbria near Renaissance Castle

Holiday Home in Umbria near Renaissance Castle
Città di Castello
9.6 out of 10, Exceptional, (12 reviews)
"Good value overall considering included pool use and garden space. The location offered beautiful views that enhanced our relaxation throughout the stay."
United States
Anonymous traveler
$254 nightly
The price is $254
Oct 15 - Oct 16
Total with taxes and fees
Holiday Home in Umbria near Renaissance Castle
Exterior

6. Wohnung la Mimosa by Interhome

Wohnung la Mimosa by Interhome
Cortona
$228 nightly
The price is $233
Oct 24 - Oct 25
Total with taxes and fees
Wohnung la Mimosa by Interhome
A cozy living room with a wooden ceiling, a sofa, a dining table with chairs, a bookshelf, and a view through a window.

7. Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!

Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!
Castel Rigone
10.0 out of 10, Exceptional, (4 reviews)
"The place was amazing and as advertised! We enjoyed the area very much, the views are amazing! We shopped at the local market and enjoyed dinner in both nights we were there. If we are back in the area, we will stay here again! Saverio was very attentive and gracious. Check in and out couldn’t have been easier! "
United States
John L.
$141 nightly
The price is $145
Oct 25 - Oct 26
Total with taxes and fees
Vacation Home La Perla del Lago-All the comfort of your own home with a lake view!
A building with a balcony, multiple windows, and a door.

8. Dolce Rosa Centro Storico

Dolce Rosa Centro Storico
Sansepolcro
9.6 out of 10, Exceptional, (13 reviews)
"Ottimo rapporto qualità prezzo camera carina... un unico neo mancavano i tappi di vasca e bidet..."
Italy
Sergio
$56 nightly
The price is $61
Oct 23 - Oct 24
Total with taxes and fees
Dolce Rosa Centro Storico
A stone fireplace with a rustic mantel, a large vase, and a heart-shaped decoration on the wall.

9. The Garden Above the clouds

The Garden Above the clouds
Nuvole
$344 nightly
The price is $347
Nov 1 - Nov 2
Total with taxes and fees
The Garden Above the clouds
A table with food and drinks, a stone pillar, and a scenic view of hills and trees.

10. Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom

Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
Lisciano Niccone
10.0 out of 10, Exceptional, (1 review)
"Pros: The Quietness of the wonderful mornings, in the middle of Tuscan Woods. The clean and big pool with a view. The host, very friendly and engaged. a perfect vacation!"
United States
Anonymous traveler
$356 nightly
The price is $358
Oct 15 - Oct 16
Total with taxes and fees
Apartment 'Pugnano Alto – Castagna' with Panoramic View and Pool – 2 Bedrooms with Private Bathroom
Pool

11. iConic Wellness Resort

iConic Wellness Resort
Arezzo
8.8 out of 10, Excellent, (41 reviews)
"Beautiful and peaceful resort! Hope to return soon❤️"
United States
Rheymarie
$84 nightly
The price is $99
Oct 25 - Oct 26
Total with taxes and fees
iConic Wellness Resort
A courtyard with a stone pathway, potted plants, and a building with multiple windows and a door.

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

Rustic Holiday Home in Citta di Castello With Swimming Pool
Città di Castello
$212 nightly
The price is $234
Oct 16 - Oct 17
Total with taxes and fees
Rustic Holiday Home in Citta di Castello With Swimming Pool
A stone building with a balcony, outdoor seating, and a stone staircase.

13. Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi

Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi
lisciano niccone
10.0 out of 10, Exceptional, (2 reviews)
"Pros: Alles perfect in orde."
Netherlands
Anonymous traveler
$467 nightly
The price is $469
Oct 15 - Oct 16
Total with taxes and fees
Apartment "Pugnano Alto - Tartufo" with Shared Pool and Wi-Fi
A stone building with a balcony, outdoor seating, and a stone staircase.

14. Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi

Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi
lisciano niccone
$313 nightly
The price is $315
Oct 15 - Oct 16
Total with taxes and fees
Holiday Apartment 'Pugnano Alto - Tabacco' with Shared Pool, Private Terrace and Wi-Fi
A modern kitchen with a central island, built-in appliances, and a dining area with a table and chairs.

15. The Cyclist. Pedal your way to your ideal stay!

The Cyclist. Pedal your way to your ideal stay!
Parlesca
$110 nightly
The price is $110
Oct 15 - Oct 16
Total with taxes and fees
The Cyclist. Pedal your way to your ideal stay!
A narrow stone staircase leading up to a building with a red door, flanked by buildings with balconies and hanging laundry.

16. City / Village Apartment in Cortona with 1 bedrooms sleeps 2

City / Village Apartment in Cortona with 1 bedrooms sleeps 2
Cortona Old Town
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful location. Can't wait to go back."
United States
Dawn H.
$104 nightly
The price is $109
Oct 20 - Oct 21
Total with taxes and fees
City / Village Apartment in Cortona with 1 bedrooms sleeps 2
A modern apartment with a kitchen, dining area, living room, and a balcony.

17. Apartment 'Blu Trasimeno' with Private Garden, Wi-Fi and Air Conditioning

Apartment 'Blu Trasimeno' with Private Garden, Wi-Fi and Air Conditioning
Tuoro sul Trasimeno
10.0 out of 10, Exceptional, (1 review)
"Pros: Hervorragende Ausstattung der Küche. Sehr gute Kommunikation mit dem Gastgeber. Sehr sauber und liebevoll eingerichtet."
Germany
Anonymous traveler
$215 nightly
The price is $215
Oct 19 - Oct 20
Total with taxes and fees
Apartment 'Blu Trasimeno' with Private Garden, Wi-Fi and Air Conditioning
An upper floor view of a courtyard with stone walls, arched doorways, and seating areas with potted plants.

18. B&B Piccolo Hotel

B&B Piccolo Hotel
Cortona Old Town
9.2 out of 10, Wonderful, (25 reviews)
"This is such an amazing hotel in such an amazing place! "
United States
mansoor
$137 nightly
The price is $156
Oct 15 - Oct 16
Total with taxes and fees
B&B Piccolo Hotel
A stone building with a sloped roof, a covered porch, and a small garden area.

19. Apartment 'Magnolia Antico Casale '700' with Shared Pool and Wi-Fi

Apartment 'Magnolia Antico Casale '700' with Shared Pool and Wi-Fi
Umbertide
$571 nightly
The price is $571
Oct 30 - Oct 31
Total with taxes and fees
Apartment 'Magnolia Antico Casale '700' with Shared Pool and Wi-Fi
Exterior detail

20. Abode of the Sun

Abode of the Sun
Passignano sul Trasimeno
10.0 out of 10, Exceptional, (1 review)
"We had a great stay in Passignano. The apartments location was perfect to explore town"
United States
Ted M.
$141 nightly
The price is $141
Oct 15 - Oct 16
Total with taxes and fees
Abode of the Sun
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 Calzolaro Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"Frederico went above and beyond to transfer us to our villa and Giulio was a fantastic bartender"
lise 1-night trip
Posted 10 hours ago
Monastero di Cortona Hotel & Spa

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, 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 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 low season months. For more hustle and bustle, you may prefer to visit Calzolaro 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 $158 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 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.

Explore a world of travel with Expedia

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.