Montecastelli Holidays from £343

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Your Montecastelli Holiday

Get ready to experience Montecastelli in your own style with a custom Montecastelli holiday package! Discovering the treasures of this lively city is made simpler with a base in a neighbourhood such as San Secondo, which is great for walking, among lots of other things. If a sightseeing tour is part of the programme during your trip to Montecastelli, look around popular attractions like Villa Valentina Resort e Spa, Civitella Ranieri Castle and Santa Croce Museum. Check out Expedia's wide range of travel options and book your ultimate holiday to Montecastelli today.

Top Montecastelli Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
International Hotel & Suite

International Hotel & Suite

4 out of 5
Save 100% on your flight
Price was £469, price is now £343 per person
£343
per person
7 Sept - 14 Sept
found 7 hours ago
Return flight included
Birmingham (BHX) to Ancona (AOI)
8.6/10 Excellent! (251 reviews)
We had a wonderful stay in one of the newly remodeled suites. It was more than enough space for us and our two young girls and we loved the soaking spa and balcony! Breakfast was a really nice addition and the customer service and friendly staff made it a very relaxing and enjoyable stay. Excellent location!

Reviewed on 19 Jul 2026

Hotel Relais Ducale

Hotel Relais Ducale

4 out of 5
Save 100% on your flight
Price was £501, price is now £357 per person
£357
per person
14 Oct - 21 Oct
found 1 day ago
Return flight included
London (LON) to Ancona (AOI)
8.8/10 Excellent! (281 reviews)
Nice hotel in Gubbio. Nice garden area and area at the front of the hotel. Staff were very hepful especially Barbara Gambini who emailed us about a purse we lost in Passignano. Thanks. Breakfast buffet with different options.

Reviewed on 19 Jun 2026

Posta Donini 1579 UNA Esperienze

Posta Donini 1579 UNA Esperienze

5 out of 5
Save 100% on your flight
Price was £499, price is now £359 per person
£359
per person
19 Sept - 23 Sept
found 1 day ago
Return flight included
Manchester (MAN) to Ancona (AOI)
9.2/10 Wonderful! (256 reviews)
Great place to stay lovely friendly staff excellent food and first class housekeeping.

Reviewed on 6 Jul 2026

Borgo Dei Conti Resort Relais & Chateaux

Borgo Dei Conti Resort Relais & Chateaux

5 out of 5
Save 100% on your flight
Price was £1,958, price is now £1,431 per person
£1,431
per person
19 Sept - 23 Sept
found 1 day ago
Return flight included
Manchester (MAN) to Ancona (AOI)
9/10 Wonderful! (16 reviews)
This property has the potential to be a 5 Star hotel/resort. The property and surrounding grounds are excellent. The rooms are modern and spacious. The problem, and it’s significant, is the food and beverage. We had the worst meal in Italy I’ve ever had in their “fine dining” restaurant w a family party of 18 which we set up in advance. It was awful, as was the service. We gave them another shot with just a party of three and it too was poor. The pool restaurant is much better so I advise you patronize the Osteria. They struggled w the basic cocktails- margaritas, martinis - and were very, very slow. This property needs management talent and a complete reset of its food and beverage strategy and service execution.

Reviewed on 9 Jul 2026

Sina Brufani

Sina Brufani

5 out of 5
Old Town Perugia
Save 100% on your flight
Price was £2,835, price is now £2,105 per person
£2,105
per person
12 Oct - 19 Oct
found 1 day ago
Return flight included
Birmingham (BHX) to Ancona (AOI)
9.2/10 Wonderful! (657 reviews)
Excellent location. Beautiful swimming pool in the basement among the Etruscan ruins. Friendly staff.

Reviewed on 21 Jul 2026

Montecastelli Essential Information

Language
Italian
Currency
Euros
Local Welcome
Ciao
Local Goodbye
Ciao
Closest Airport
Sant Egidio Airport (PEG)
Max Temp Winter
7ºC
Max Temp Summer
27ºC
Top Sights
Civitella Ranieri Castle, Church of Santa Maria della Reggia and Villa Valentina Resort e Spa

Top hotels in Montecastelli

Villa di Piazzano - Small Luxury Hotel of the World

Villa di Piazzano - Small Luxury Hotel of the World

5 out of 5
Localita Piazzano, C.P. 6 Cortona AR
The price is £538 per night from 26 Aug to 27 Aug
£538
26 Aug - 27 Aug
includes taxes & fees
9.8/10 Exceptional! (241 reviews)
"Very clean and very quiet"

Reviewed on 15 Jul 2026

Villa di Piazzano - Small Luxury Hotel of the World
Monastero di Cortona Hotel & Spa

Monastero di Cortona Hotel & Spa

5 out of 5
Via del Salvatore Cortona AR
Fully refundableReserve now, pay when you stay
The price is £312 per night from 16 Aug to 17 Aug
£312
16 Aug - 17 Aug
includes taxes & fees
10/10 Exceptional! (298 reviews)
"Beautiful oasis in a beautiful town"

Reviewed on 25 Jul 2026

Monastero di Cortona Hotel & Spa
Il Falconiere - Relais e Chateaux

Il Falconiere - Relais e Chateaux

5 out of 5
Localita San Martino 370 Cortona AR
The price is £324 per night from 22 Aug to 23 Aug
£324
22 Aug - 23 Aug
includes taxes & fees
Il Falconiere - Relais e Chateaux
See all 3,097 properties in Montecastelli
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

What to do in Montecastelli

Perugia: Chapter Museum Entry Ticket

Perugia: Chapter Museum entry ticket

£7
per adult
Perugia: Chapter Museum entry ticket
Perugia: Old Town Walking Tour, Piazza IV Novembre

Perugia: Old Town Walking Tour, Piazza IV Novembre

£26
per adult
Perugia: Old Town Walking Tour, Piazza IV Novembre
Gubbio Express

Gubbio Express

£9
per adult
Gubbio Express
See all activities in Montecastelli

Frequently asked questions

How much does a Montecastelli travel package cost?
From as little as £343. Yes, you read that right. Our Montecastelli packages are the quickest way to stretch your budget further. Bundle your hotels, flights and rental car and get out and see this exciting destination.
If I'm not able to travel, can I cancel my Montecastelli travel package?
Don't worry if you're rethinking your Montecastelli travel package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We get that life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we're here to help.
How do I get a cheap travel package to Montecastelli?
Our Montecastelli travel packages offer plenty of savings for the savvy traveller. For the best deals, simply combine your hotel, flights and activities into a budget-friendly package. But impressive bargains are just the beginning of your next memorable adventure. Book with Expedia and and you'll have over 550 airlines and 1,000,000 properties throughout the world to choose from. Whatever your budget or style, there's a package here just for you.
Does Expedia offer Book Now, Pay Later Montecastelli holidays?
Expedia has teamed up with online lender Klarna to make booking your next break easier on your bank balance. Paying in instalments means you can spread the costs of your next dream escape, leaving you with more money to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find one that falls within your budget. Consider these flexible payment options:

  • Pay monthly holidays: If paying small amounts each month is what works best for you, Klarna can help. Paying in easy monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: If you'd prefer to pay off your escape across multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: When you want to grab an unbeatable deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you get what you want.

Where should I stay in Montecastelli?
Montecastelli boasts numerous fascinating places to explore, including Church of Santa Maria della Reggia. Stay somewhere close by and make sightseeing easier.
What are the top hotels in Montecastelli?
If it's your first visit to Montecastelli, reserve a room at Agriturismo Nestore or Agriturismo Goccia Di Luna. Both offer friendly service and are top options with lots of travellers.
How far in advance should I book my Montecastelli holiday?
It's hard to pick the best time for airfares, but we normally say the earlier, the better. Plenty of international journeys on Expedia become available up to 12 months in advance. If you're unable to do so, don't stress. Low prices occasionally appear just weeks before departure dates.
What does an Expedia Montecastelli travel package include?
Choose from a combination of flights, hotels and rental cars. Once you've made your booking, you can add activities and tours. Want to pick your airfare class? That's easily done too. The choice is all yours when it comes to planning your perfect Montecastelli escape.
What should I know before booking a Montecastelli travel package?
Bundling your bookings into a Montecastelli travel package is the easiest way to organise your trip. Not only that, you'll save when you combine your hotels, flights and car rentals. Once you've booked, why not add on a day tour or an activity?
Can I choose my airline with a Montecastelli Expedia travel package?
Yes, you're in control. Expedia has access to more than 550 partner airlines around the world, so you can tailor your Montecastelli trip according to your travel needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.