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Montecastelli Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Montecastelli vacation rentals

A stone building with a sloped roof, a covered porch, and a small garden area.

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

Apartment 'Glicine ad Antico Casale '700' with Shared Pool & Wi-Fi
Umbertide
$312 nightly
The price is $312
Nov 6 - Nov 7
Total with taxes and fees
Apartment 'Glicine ad Antico Casale '700' with Shared Pool & Wi-Fi
A modern kitchen with a central island, built-in appliances, and a dining area with a table and chairs.

2. The cyclist. Cycle your way to your perfect getaway!

The cyclist. Cycle your way to your perfect getaway!
Parlesca
$96 nightly
The price is $96
Nov 6 - Nov 7
Total with taxes and fees
The cyclist. Cycle your way to your perfect getaway!
A stone building with a balcony and a small garden area with plants.

3. L'Antica Sosta

L'Antica Sosta
Corciano
9.4 out of 10, Exceptional, (3 reviews)
"Molto accoglienti e gentili "
Italy
Valentina
$57 nightly
The price is $63
Nov 8 - Nov 9
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.

4. 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
$345 nightly
The price is $345
Nov 6 - Nov 7
Total with taxes and fees
Apartment 'Lavanda ad Antico Casale '700' with Shared Pool & Wi-Fi
An outdoor patio with a wooden table and chairs, surrounded by stone walls and a large shade sail.

5. Country House 'Casale San Pietro' with Mountain View, Private Terrace and Wi-Fi

Country House 'Casale San Pietro' with Mountain View, Private Terrace and Wi-Fi
Città di Castello
$811 nightly
The price is $815
Nov 8 - Nov 9
Total with taxes and fees
Country House 'Casale San Pietro' with Mountain View, Private Terrace and Wi-Fi
A dining table set outdoors with a view of the sunset over a body of water.

6. La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!

La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!
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.
$134 nightly
The price is $138
Nov 8 - Nov 9
Total with taxes and fees
La Perla del Lago Vacation Home - All the comforts of home with a view of the lake!
A narrow pathway leading to a building with a tree in the center, surrounded by greenery.

7. LANDLORD ALBACHIARA

LANDLORD ALBACHIARA
Ramazzano - Le Pulci
10.0 out of 10, Exceptional, (1 review)
"Ottimo appartamento, molto pulito e confortevole"
Italy
Fabio
$94 nightly
The price is $98
Nov 6 - Nov 7
Total with taxes and fees
LANDLORD ALBACHIARA
A courtyard with a pool, stone benches, and a view of a hill.

8. TH Perugia - Castello di Monterone

TH Perugia - Castello di Monterone
Perugia
9.8 out of 10, Exceptional, (328 reviews)
"Beautiful garden, beautiful view, easy parking and tasty restaurant."
Canada
Sandro
$210 nightly
The price is $239
Nov 18 - Nov 19
Total with taxes and fees
TH Perugia - Castello di Monterone
A courtyard with a stone pathway, potted plants, and a building with multiple windows and a door.

9. 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
$303 nightly
The price is $303
Nov 7 - Nov 8
Total with taxes and fees
Elegant Countryside Retreat
A window with open shutters, a radiator below, and a potted plant with flowers.

10. Casa Esposito - Holidays in the Heart of Gubbio, Medieval Umbria

Casa Esposito - Holidays in the Heart of Gubbio, Medieval Umbria
Gubbio
10.0 out of 10, Exceptional, (1 review)
"Wir , eine Familie mit 2 Kindern (16 und 8 Jahre) waren leider nur 1 Woche in Gubbio. Es ist eine großartige mittelalterliche italienische Stadt. Voller Leben, viele Sehenswürdigkeiten für Kinder und Erwachsene. Die Wohnung liegt mitten in der eindrucksvollen, lebendigen, authentischen Altstadt von Gubbio. Man ist direkt im Ort. Geschäfte, Cafés, Bars, Gelaterias, Restaurants....alles um die Ecke. Supermärkte, viele Sehenswürdigkeiten, Natur... alles zu Fuß erreichbar. Auch kulturell war einiges...
Germany
Stephan H.
$182 nightly
The price is $182
Nov 27 - Nov 28
Total with taxes and fees
Casa Esposito - Holidays in the Heart of Gubbio, Medieval Umbria
Exterior detail

11. Home of the Sun

Home of the Sun
Passignano sul Trasimeno
10.0 out of 10, Exceptional, (2 reviews)
"Highly Recommend!I couldn’t have asked for a better place to stay! The property was absolutely spotless, beautifully maintained, and incredibly comfortable. You can tell that a lot of care and attention goes into making sure guests have a wonderful experience.The host was fantastic—warm, welcoming, attentive, and genuinely committed to making sure everything was perfect. Communication was excellent, and I felt right at home throughout my stay.The location was another huge plus! Centrally located...
United States
Randell P.
$134 nightly
The price is $134
Nov 6 - Nov 7
Total with taxes and fees
Home of the Sun
A cozy breakfast setting with croissants, a coffee cup labeled "BOSS," and a vase of white flowers on a table.

12. Italian Experience-Casa Miramonti

Italian Experience-Casa Miramonti
Perugia
$249 nightly
The price is $253
Nov 6 - Nov 7
Total with taxes and fees
Italian Experience-Casa Miramonti
A cozy breakfast setting with croissants, a coffee cup labeled "BOSS," and a vase of white flowers on a table.

13. Wonderful villa for 6 guests with WIFI, A/C, TV, balcony and panoramic view

Wonderful villa for 6 guests with WIFI, A/C, TV, balcony and panoramic view
Perugia
$258 nightly
The price is $263
Nov 8 - Nov 9
Total with taxes and fees
Wonderful villa for 6 guests with WIFI, A/C, TV, balcony and panoramic view
A courtyard with a stone pathway, potted plants, and a building with multiple windows and a door.

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

Rustic Holiday Home in Citta di Castello With Swimming Pool
Città di Castello
$225 nightly
The price is $242
Nov 7 - Nov 8
Total with taxes and fees
Rustic Holiday Home in Citta di Castello With Swimming Pool
A stone fireplace with a rustic mantel, a large vase, and a heart-shaped decoration on the wall.

15. The Garden Above the clouds

The Garden Above the clouds
Nuvole
$302 nightly
The price is $306
Nov 6 - Nov 7
Total with taxes and fees
The Garden Above the clouds
Holiday Home Exterior [summer]

16. 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
$249 nightly
The price is $249
Nov 7 - Nov 8
Total with taxes and fees
Holiday Home in Umbria near Renaissance Castle
A swimming pool with clear water reflecting trees and a stone building in the background.

17. Villa Graziella, Romantic Perugia

Villa Graziella, Romantic Perugia
La Valle
9.6 out of 10, Exceptional, (11 reviews)
"Great place. Would stay here again."
United States
Rob B.
$211 nightly
The price is $211
Nov 6 - Nov 7
Total with taxes and fees
Villa Graziella, Romantic Perugia
Exterior

18. Wohnung la Mimosa by Interhome

Wohnung la Mimosa by Interhome
Cortona
$236 nightly
The price is $242
Nov 27 - Nov 28
Total with taxes and fees
Wohnung la Mimosa by Interhome
A spiral staircase in a hallway with wooden flooring and a door leading to a room with a blue-tiled floor.

19. Apartment 'Posta Del Lago' with Lake View, Private Terrace and Wi-Fi

Apartment 'Posta Del Lago' with Lake View, Private Terrace and Wi-Fi
Passignano sul Trasimeno
10.0 out of 10, Exceptional, (2 reviews)
"Eine ausgesprochen angenehme Wohnung, sehr geräumig, ansprechend und zugleich praktisch eingerichtet, sehr sauber, superfreundliche, aber zurückhaltende Vermieter. Ein Ort, an den wir gerne zurückkehren werden."
Germany
Tobias W.
$213 nightly
The price is $216
Nov 8 - Nov 9
Total with taxes and fees
Apartment 'Posta Del Lago' with Lake View, Private Terrace and Wi-Fi
A modern kitchen with a wooden table, bar stools, a stone wall, and a TV mounted on the wall.

20. Historic Center B&B Luxury Apartment Suite Gubbio

Historic Center B&B Luxury Apartment Suite Gubbio
Gubbio
$185 nightly
The price is $185
Nov 8 - Nov 9
Total with taxes and fees
Historic Center B&B Luxury Apartment Suite Gubbio
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 Montecastelli Hotel Reviews

Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

10/10 Excellent
"The highlight was the experience at the bar with the entertaining bartenders! Great breakfast and service!"
Stephanie 4-night trip
Posted 3 days ago
Monastero di Cortona Hotel & Spa

Find out more about Montecastelli

Everything you need to know about Montecastelli 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 Montecastelli 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 Montecastelli vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Montecastelli vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Montecastelli. 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 Montecastelli 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 $154 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 Montecastelli rentals

At Expedia, we put the best Montecastelli 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 Montecastelli 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 Montecastelli 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 Montecastelli. 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 a vacation rental in Montecastelli?

Yes, you can find vacation rentals close to the most popular local attractions in Montecastelli, or you can select a more secluded option if you'd like a relaxing place to stay. Montecastelli is known for its spas and theme park. Make sure you have time to check out the cathedral and coffeehouses during your trip.

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

Holiday Home in Umbria with Pool: This vacation home rental near Montecastelli 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 Montecastelli?

While you're exploring the area, Tiber River and Isola Maggiore are a couple of picturesque spots to get outside and enjoy nature. In the larger area, you’ll find Historic Town Montone and Civitella Ranieri Castle.

What’s a vacation rental in Montecastelli like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Montecastelli. Vacation rentals provide amenities like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a vacation rental can offer a sense of privacy away from shared hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a small group gathering.