Title: São Simão Trail Vacation Packages & Trips 2026 from CA $1,407 | Expedia.ca

[São Simão Trail Travel Guide](https://expedia.ca/Sao-Simao-Trail.dx760243295416180736)[Hotels in São Simão Trail](https://expedia.ca/Sao-Simao-Trail-Hotels.d760243295416180736.Travel-Guide-Hotels)[Vacation Rentals in São Simão Trail](https://expedia.ca/Sao-Simao-Trail-Vacation-Rentals.d760243295416180736.Travel-Guide-VacationRentals)[Flights to São Simão Trail](https://expedia.ca/Cheap-Flights-To-Sao-Simao-Trail.d760243295416180736.Travel-Guide-Flights)[São Simão Trail Car Rentals](https://expedia.ca/Car-Rentals-In-Sao-Simao-Trail.d760243295416180736.Car-Rental-Guide)

![](https://images.trvl-media.com/place/6358869/81c4a7c1-d6fb-429c-8f44-27a2c956e928.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# São Simão Trail Vacation Packages

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Photo by Diogo Matias

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## Top São Simão Trail Vacation Deals

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

![Vila Garden Guesthouse](https://images.trvl-media.com/lodging/16000000/15080000/15077800/15077744/de303813_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Vila Garden Guesthouse

Lisbon City Center

CA $1,407

per person

May 21 - May 27

found 5 hours ago

Roundtrip flight included

Montreal (YUL) to Lisbon (LIS)

9.4/10 Exceptional! (387 reviews)

Place was great. Very close to downtown and plenty of things to do around there. Very friendly staff. Heaters were only in the bedroom so it got a bit cold elsewhere, but tolerable. Definitely would stay again

Reviewed on Dec 20, 2025

![Eurostars Cascais](https://images.trvl-media.com/lodging/18000000/17420000/17410400/17410378/31b4235f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Eurostars Cascais

CA $1,563

per person

May 21 - May 27

found 1 day ago

Roundtrip flight included

Montreal (YUL) to Lisbon (LIS)

9.2/10 Wonderful! (791 reviews)

Clean, staff is very professional and friendly.

Reviewed on Feb 15, 2026

![Eurostars Das Letras](https://images.trvl-media.com/lodging/3000000/2060000/2059200/2059158/05a8d24e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Eurostars Das Letras

Lisbon City Center

CA $1,998

per person

May 21 - May 27

found 1 day ago

Roundtrip flight included

Montreal (YMQ) to Lisbon (LIS)

9/10 Wonderful! (1,001 reviews)

Room was perfect. Loved the complimentary apples in the lobby and gym areas.No complaints. Would stay there again if ever back in Lisbon.

Reviewed on Feb 27, 2026

![Eurostars Lisboa Baixa](https://images.trvl-media.com/lodging/89000000/88300000/88293800/88293770/53bb0399_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Eurostars Lisboa Baixa

Lisbon City Center

CA $1,990

per person

Apr 14 - Apr 19

found 1 day ago

Roundtrip non-stop flight included

Montreal (YUL) to Lisbon (LIS)

9.8/10 Exceptional! (217 reviews)

Good overall experience staying here. However, when I made my booking I accidentally booked an extra night. I realized my mistake immediately and got in touch with them minutes after making the booking. However, they were completely inflexible to a refund or change to my booking. I find this policy to be disappointing and when I told them that over email, they tried to blame it on Expedia when it clearly wasn't Expedia's fault. Only after multiple emails did they admit it was their own policy that was inflexible.

Reviewed on Feb 26, 2026

![Solar Do Castelo, a Lisbon Heritage Collection](https://images.trvl-media.com/lodging/1000000/880000/875100/875047/5e730592_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Solar Do Castelo, a Lisbon Heritage Collection

Lisbon City Center

CA $2,011

per person

May 21 - May 27

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Lisbon (LIS)

9.6/10 Exceptional! (1,001 reviews)

Fantastic hotel, with very friendly and helpful staff. Henri on reception went beyond the call of duty with his offer to give us a lift in the golf-buggy in the pouring rain. Our room was delightful; comfortable and clean, with a lovely view of the courtyard with its resident peacocks. The endless supply of delicious food and drink at breakfast and cakes and drinks throughout the afternoon and evening was a great source of pleasure to come back to. We would definitely recommend the hotel to others.

Reviewed on Feb 7, 2026

![](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_760243295416180736)

## Ready to book your vacation to São Simão Trail?

Choose your dates

## São Simão Trail Hotel Deals

![Convento da Serta Hotel](https://images.trvl-media.com/lodging/9000000/8730000/8720400/8720314/2b905004_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Convento da Serta Hotel

Alameda da Carvalha Serta 

Fully refundableReserve now, pay when you stay

CA $118

CA $126 total

Mar 5 - Mar 6

includes taxes & fees

9.8/10 Exceptional! (105 reviews)

This hotel is an oasis of calm and tranquillity. Rooms are bright and in good condition. The bed was comfortable and it was a pleasure to wake up to warm sunlight from the Juliet balcony. The location is great, with easy walking access to several restaurants in town. The staff are a credit to their ...

Reviewed on Sep 25, 2025

[](https://expedia.ca/Hotel-Search?startDate=05%2F03%2F2026&endDate=06%2F03%2F2026&selected=8720314&PinnedHotelID=8720314&HadPinnedHotel=true&regionId=760243295416180736)

![Belem Hotel](https://images.trvl-media.com/lodging/5000000/4280000/4274800/4274781/82802f6e_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Belem Hotel

Avenida Herois Do Ultramar 185 Pombal 

Fully refundableReserve now, pay when you stay

CA $134

CA $142 total

Feb 28 - Mar 1

includes taxes & fees

[](https://expedia.ca/Hotel-Search?startDate=28%2F02%2F2026&endDate=01%2F03%2F2026&selected=4274781&PinnedHotelID=4274781&HadPinnedHotel=true&regionId=760243295416180736)

![Bed and Breakfast Equitare Rural ](https://images.trvl-media.com/lodging/109000000/108170000/108164200/108164149/90a74c01_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Bed and Breakfast Equitare Rural 

Rua Eusébio Tamagnini Miranda do Corvo Coimbra

Fully refundableReserve now, pay when you stay

CA $107

CA $114 total

Mar 8 - Mar 9

includes taxes & fees

9.8/10 Exceptional! (23 reviews)

Nice and memorable stay

We enjoyed our stay. Clean and spacious. Kids also loved interacting with the animals.

Reviewed on Sep 2, 2025

[](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=108164149&PinnedHotelID=108164149&HadPinnedHotel=true&regionId=760243295416180736)

[See all 281 properties in São Simão Trail](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F02%2F2026&endDate=01%2F03%2F2026&regionId=760243295416180736)

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 São Simão Trail

![Rabaçal: Lagoa do Vento, Levada Risco and Levada 25 Fontes](https://mediaim.expedia.com/localexpert/48033752/c70cf300-5060-4d87-906d-9f0548f94b4a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Rabaçal: Lagoa do Vento, Levada Risco and Levada 25 Fontes

CA $97

per adult

[](https://expedia.ca/things-to-do/rabacal-lagoa-do-vento.a48033752.activity-details)

[See all activities in São Simão Trail](https://expedia.ca/things-to-do/search?rid=760243295416180736)

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\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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