Montecastelli Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Montecastelli

Our top choices for Montecastelli holiday rentals

Castello di Monterone

9.8 out of 10, Exceptional, (290)
"It was almost as if we have the place to ourselves, magical building with excellent staff "
Castello di Monterone

Farmhouse in the hills with panoramic view and swimming pool

9.6 out of 10, Exceptional, (71)
"We‘ve spent two wonderful weeks with our two year old daughter and our dog. The house is beautifully located in the hills with no direct neighbours. The view is fantastic and we felt immediately at home in this beautiful house. We had a wonderful time and our hosts were just lovely. (We cannot say anything about the pool - except that it is huge - because we were there out of season in March when the pool was closed.)"
Farmhouse in the hills with panoramic view and swimming pool

Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

9.6 out of 10, Exceptional, (71)
"My husband and I loved our stay here! It was so close to town and the terrace was absolutely stunning. Would definitely stay here again! "
Sun-Soaked Private View Terrace in the Historical Centre of Cortona.

Villa Graziella, Romantic Perugia

9.6 out of 10, Exceptional, (7)
"Great place. Would stay here again."
The price is AU$342
includes taxes & fees
15 Sept - 16 Sept
Villa Graziella, Romantic Perugia

Tenuta Borgo San Michele

9.0 out of 10, Wonderful, (2)
"Très bon séjour : un bémol, le frigo se coupe en journée comme le reste du logement. C’est problématique avec des médicaments et des produits alimentaires !"
The price is AU$129
includes taxes & fees
3 Sept - 4 Sept
Tenuta Borgo San Michele

Welchome suites

9.8 out of 10, Exceptional, (7)
"The apartment was so nice and very reasonably priced. The bed was comfortable and I enjoyed the Sm"
The price is AU$207
includes taxes & fees
1 Sept - 2 Sept
Welchome suites

Luxury Cortona view hilltop Villa

10.0 out of 10, Exceptional, (48)
"The location and accommodations are perfect for a family. Nestled in the Italian countryside providing easy access to the nearby renaissance villages, art and landscapes and the people of Italy. The accommodations that Mieke has provided will only put a smile on your face."
Luxury Cortona view hilltop Villa

Beautiful renovated stone villa - private pool,park,air conditioning,smart tv

9.8 out of 10, Exceptional, (32)
"We love our stay st Ca de Santi. Everything was great and the property is really amazing. You feel the Tuscany atmosphere."
Beautiful renovated stone villa - private pool,park,air conditioning,smart tv

Camping Villaggio Cerquestra

3.0 star property
9.0 out of 10, Wonderful, (21)
"Staff molto cordiale e disponibile. "
The price is AU$99
includes taxes & fees
13 Sept - 14 Sept
Camping Villaggio Cerquestra

House with garden and panoramic view over Lake Trasimeno

9.8 out of 10, Exceptional, (46)
"Beautiful location, very handy for the lake (swimming, pedelos etc) and with some lovely restaurants and gelatos in the local town! Views from the property are amazing, it is very quiet and peaceful"
House with garden and panoramic view over Lake Trasimeno

Pretty Tuscan House next Anghiari, 8/14 guest,Pool, A.C WI.FI Family LAST WEEK

10.0 out of 10, Exceptional, (21)
"Fantastic maintained Villa with great layout for a big family. Beautiful surroundings. Staff easy to reach 24/7. Definatly a place to return to."
Pretty Tuscan House next Anghiari, 8/14 guest,Pool, A.C WI.FI Family LAST WEEK

Villa with swimming pool and garden- San Feliciano, Trasimeno lake

8.4 out of 10, Very good, (45)
"We had a great Family Holiday there. We enjoyed the pool so much and the nice terrasse, where we had all our meals and sat in the evenings to watch the Sunset on the lake. We liked the dogs visiting us and Massimo was always helpful."
Villa with swimming pool and garden- San Feliciano, Trasimeno lake

ancient villa with pool and park in total privacy

9.8 out of 10, Exceptional, (27)
"Nice place for a relaxing vacation. Perfect hub for trips to towns like Arezzo, Peruggia or Siena."
ancient villa with pool and park in total privacy

Heritage Tuscan Farmhouse with private swimming pool

10.0 out of 10, Exceptional, (48)
"Lovely old property with lots of history. Good size pool and lots or nice spots to sit around the house. Great restaurants not far away. Louise was an excellent host."
Heritage Tuscan Farmhouse with private swimming pool

Villa with wonderful view of Lake Trasimeno and large panoramic swimming pool

10.0 out of 10, Exceptional, (5)
"Amazing property with wonderful view of Lake Trasimino , 7 bedroom, 8 bathrooms, swimming pool, outside dining, great kitchen and several living rooms all with air conditioning. Shower gel annd tissues etc all provided. Adequately close to supermarkets. Sun beds were a bit tired/ broken."
Villa with wonderful view of Lake Trasimeno and large panoramic swimming pool

Agriturismo Nestore

9.8 out of 10, Exceptional, (6)
"Foi tudo bem. Lugar simples mas muito agradável. "
Agriturismo Nestore

Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.

9.4 out of 10, Exceptional, (12)
"Surrounding very nice and quiet. Accomodation very comfortable and huge garden. Large Shilling pool. Everything compiled to have a very nice stay."
Large stone manor with 8BR and 7BA, extended grounds, large fully-equipped pool.

Rustic Farmhouse for 8+2 person with Private Swimming Pool

9.8 out of 10, Exceptional, (36)
"We had a pleasant time at the nice old house. The place has a lot of space and even with a bunch of people there are enough littleS places to have a quiet time for themselves. Mauro was a very nice and helpful host, and his sister cooked Tuscan food for us - delicious!"
Rustic Farmhouse for 8+2 person with Private Swimming Pool

Il Rifugio, a farmhouse in Cortona with a panoramic view of Lake Trasimeno

10.0 out of 10, Exceptional, (1)
"Wir haben einen wunderschönen, erholsamen Urlaub in dieser liebevoll gestalteten Villa verbracht. Einziges Manko: die Handtücher wurden zwar gestellt, aber nie gewechselt. Ansonsten war es perfekt!!!"
Il Rifugio, a farmhouse in Cortona with a panoramic view of Lake Trasimeno

Casa Bacco - private house with a remarkable garden in the centre of Cortona

10.0 out of 10, Exceptional, (8)
"This is a lovely property. Plenty of room. Well equipped with everything you need. The courtyard is a beautiful place for breakfast in the morning and wine in the evening. The flowers planted in the courtyard are beautiful. Please be aware that you must be able to walk up steep hills to get to this property. Of course, pretty much anywhere you go in Cortona is a hill."
Casa Bacco - private house with a remarkable garden in the centre of Cortona
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Montecastelli Hotel Reviews

Find out more about Montecastelli

Find out more about Montecastelli

Everything you need to know about Montecastelli holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Montecastelli holiday rental for you. At Expedia, you can take your pick from private holiday 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 Montecastelli holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Montecastelli holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Montecastelli holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Montecastelli holiday rentals we have selected for you start as low as AU$99 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Montecastelli rentals

At Expedia, we put the best Montecastelli holiday 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 holiday.

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 holiday rental in Montecastelli?

Yes, there are holiday rentals close to the most popular sights in Montecastelli, or you can select a more secluded option if you're looking for a relaxing stay. Montecastelli is known for its spas and theme park. Make sure you have time to check out the cathedral and coffee shops during your trip.

What are some of the best holiday rentals that Montecastelli has to offer?

Agriturismo Nestore: This holiday home rental outside Montecastelli offers a garden, an arcade/games room and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and kitchenware.

What can I see and do in Montecastelli?

Explore the area and family-friendly sights such as Centro Turistico Sportivo Di Candeleto, or get out into nature at a spot like Tiber River. In the wider area, you’ll find Historic Town Montone and Civitella Ranieri Castle.

What’s a holiday rental in Montecastelli like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Montecastelli. Holiday rentals feature amenities such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy 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 standard hotel, which makes a holiday rental an attractive choice for a family trip.