Title: Castiglione della Valle Vacation Packages & Trips 2026 from CA $1,331 | Expedia.ca

[Hotels in Castiglione della Valle](https://expedia.ca/Castiglione-Della-Valle-Hotels.d3000028416.Travel-Guide-Hotels)[Vacation Rentals in Castiglione della Valle](https://expedia.ca/Castiglione-Della-Valle-Vacation-Rentals.d3000028416.Travel-Guide-VacationRentals)[Castiglione della Valle Car Rentals](https://expedia.ca/Car-Rentals-In-Castiglione-Della-Valle.d3000028416.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# Castiglione della Valle Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

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#### Your Castiglione della Valle Vacation

Book a Castiglione della Valle vacation package and you can focus on what matters — enjoying yourself. This means no more travel planning headaches, just more free time to immerse yourself in the best parts of this lively city, such as its rich history and spectacular views. Need some inspiration on what to see or do first during your trip to Castiglione della Valle? Head for famous attractions such as [Monte Vibiano Castle](https://www.expedia.ca/Monte-Vibiano-Castle-Marsciano.d6314971.Vacation-Attraction). Whoever you're taking time off with and whatever you plan to spend, your ultimate Castiglione della Valle vacation is only clicks away with Expedia.

## Top Castiglione della Valle Vacation Deals

Price found within the past 48 hours. Click for updated prices.

![Villa Borgo San Pietro](https://images.trvl-media.com/lodging/2000000/1680000/1677700/1677691/12bc3783_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Villa Borgo San Pietro

CA $1,331

per person

May 17 - May 23

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Perugia San Francesco d'Assisi – Umbria Intl. Airport (PEG)

9.2/10 Wonderful! (102 reviews)

Excellent staff. They went above and beyond. Someone in our party was ill and they suggested they would call a doctor and he would come to the resort. Within an hour the Dr arrived assessed situation provided prescription so our vacation was not disrupted. Excellent.

Reviewed on Oct 20, 2025

![Hotel San Michele](https://images.trvl-media.com/lodging/1000000/990000/984500/984435/cd5b1ca8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel San Michele

Cortona Old Town

CA $1,446

per person

May 17 - May 23

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Perugia San Francesco d'Assisi – Umbria Intl. Airport (PEG)

9/10 Wonderful! (273 reviews)

Very friendly and helpful staff. Nice rooms

Reviewed on Sep 7, 2025

![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/c358cc6c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Villa di Piazzano - Small Luxury Hotel of the World

CA $5,410

per person

May 15 - May 21

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Perugia San Francesco d'Assisi – Umbria Intl. Airport (PEG)

9.8/10 Exceptional! (228 reviews)

Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly

Reviewed on Nov 6, 2025

![Hotel Italia](https://images.trvl-media.com/lodging/2000000/1670000/1664000/1663916/22c9fd1e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Italia

Cortona Old Town

CA $1,521

per person

May 17 - May 23

found 11 hours ago

Roundtrip non-stop flight included

Toronto (YTO) to Perugia San Francesco d'Assisi – Umbria Intl. Airport (PEG)

9/10 Wonderful! (285 reviews)

The hotel amenities, comfort, hospitality are top notch. Should easily be a 4-star hotel!

Reviewed on Dec 7, 2025

![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

## 

The Annual Vacation Sale 

Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 

[Book now](https://expedia.ca/deals?rfrr=PKG_SPRING_PROMO_3000028416)

## Ready to book your vacation to Castiglione della Valle?

Choose your dates

## Castiglione della Valle Hotel Deals

![Precise Tale Poggio Alla Sala](https://images.trvl-media.com/lodging/91000000/90890000/90888700/90888666/8fbdd5cc_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Precise Tale Poggio Alla Sala

Via Poggio alla Sala 10 Montepulciano SI

CA $467

CA $524 total

Mar 20 - Mar 21

includes taxes & fees

9.4/10 Exceptional! (123 reviews)

Perfect escape

Fantastic hotel in an incredible setting. Staff were extremely helpful, attentive and understanding. The perfect location for a relaxing break and a centre for exploring Tuscany

Reviewed on Oct 27, 2025

[](https://expedia.ca/Hotel-Search?startDate=20%2F03%2F2026&endDate=21%2F03%2F2026&selected=90888666&PinnedHotelID=90888666&HadPinnedHotel=true&regionId=3000028416)

![TH Assisi - Hotel Cenacolo](https://images.trvl-media.com/lodging/4000000/3490000/3485400/3485400/c2e68b27_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

TH Assisi - Hotel Cenacolo

Viale Patrono d'Italia 70 Assisi PG

Fully refundableReserve now, pay when you stay

CA $140

CA $167 total

Mar 24 - Mar 25

includes taxes & fees

9.2/10 Wonderful! (643 reviews)

The hotel and staff were fantastic! It was incredibly convenient, right in the heart of everything. Even after my check-out, I was able to leave my car for a couple more hours without any problems. I highly recommend it!

Reviewed on Feb 20, 2026

[](https://expedia.ca/Hotel-Search?startDate=24%2F03%2F2026&endDate=25%2F03%2F2026&selected=3485400&PinnedHotelID=3485400&HadPinnedHotel=true&regionId=3000028416)

![Villa di Piazzano - Small Luxury Hotel of the World](https://images.trvl-media.com/lodging/1000000/980000/972000/971985/c358cc6c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Villa di Piazzano - Small Luxury Hotel of the World

Localita Piazzano, C.P. 6 Cortona AR

CA $942

CA $1,049 total

Apr 2 - Apr 3

includes taxes & fees

9.8/10 Exceptional! (228 reviews)

Room was wonderful, bathroom spacious and well appointed. Staff amazing and so friendly

Reviewed on Nov 6, 2025

[](https://expedia.ca/Hotel-Search?startDate=02%2F04%2F2026&endDate=03%2F04%2F2026&selected=971985&PinnedHotelID=971985&HadPinnedHotel=true&regionId=3000028416)

[See all 3,667 properties in Castiglione della Valle](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=04%2F03%2F2026&endDate=05%2F03%2F2026&regionId=3000028416)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

### What to do in Castiglione della Valle

![Perugia: Old Town Walking Tour, Piazza IV Novembre](https://mediaim.expedia.com/localexpert/44633641/00be2add-8f9a-4821-bf24-fede78faf06f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Perugia: Old Town Walking Tour, Piazza IV Novembre

CA $48

per adult

[](https://expedia.ca/things-to-do/perugia-old-town-walking-tour.a44633641.activity-details)

![Perugia: Chapter Museum Entry Ticket](https://mediaim.expedia.com/localexpert/48827216/b6c3a433-f3ea-4486-8939-4d2bf83cba47.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Perugia: Chapter Museum entry ticket

CA $13

per adult

[](https://expedia.ca/things-to-do/perugia-chapter-museum-entry-ticket.a48827216.activity-details)

![Umbria: guided tour to traditional oil mill + tasting](https://mediaim.expedia.com/localexpert/47926544/dbf189a5-003f-411f-a24a-84181fbe1a38.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Umbria: guided tour to traditional oil mill + tasting

CA $23

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/umbria-guided-tour-to-traditional-oil-mill-tasting.a47926544.activity-details)

[See all activities in Castiglione della Valle](https://expedia.ca/things-to-do/search?rid=3000028416)

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