Santiago Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Danielle Bartels
  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

    Plan, book, and manage your trip all in one place

Top Santiago Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Chiado 44

Chiado 44

Lisbon City Center
CA $1,052
per person
Nov 19 - Nov 25
found 7 hours ago
Roundtrip flight included
Montreal (YMQ) to Lisbon (LIS)
9.2/10 Wonderful! (507 reviews)
I think reviews should account for context. You shouldn’t expect a 4 star room in Paris to have the size of a 4 star room in Chicago for example. So, I’m accounting for the fact that Lisbon is an old city, with old plumbing, and inconsistent building standards. With that said, our room was a pretty blatant misrepresentation. The bed was not king size, the room a faint reflection of the photos. Both accompanied by a mold smelling motel 8 level bathroom. There is no shelving or drawer space. Not enough space to keep a suitcase open. No amenities, (facial tissue, shower cap, etc) The “towel rack” is a little ladder leaned against a wall. Definitely not 4 star level. The shower curtain was moldy, the hotel did change that the next day at least. However, it hangs so low that the new one was starting to smell moldy by the time we left. The location was wonderful and the breakfast good. The checkout was easy. We’ve stayed in rooms all over the world. Inconsistencies and disappointments are to be expected at times. They’ve never risen to the level where I’ve complained to the hotel before though. Other than changing the curtain and allowing us to cancel the rest of our reservation without penalty there wasn’t much they could do. It’s just a matter of misrepresentation. There are several other issues I’m not mentioning. You get the point.

Reviewed on Sep 27, 2026

Bacalhoeiros 125 Hotel

Bacalhoeiros 125 Hotel

Lisbon City Center
Save 100% on your flight
CA $1,096
per person
Nov 19 - Nov 25
found 7 hours ago
Roundtrip flight included
Montreal (YMQ) to Lisbon (LIS)
9.6/10 Exceptional! (143 reviews)
This is a very cute hotel. Leads on to the street which is very quaint. However We did not have hot water for the entire stay. Staff tried to help and no communication of the status of the situation until we inquired again. Pillows are so thin, which was not a good sleep

Reviewed on Sep 20, 2026

Pousada de Lisboa - Small Luxury Hotels Of The World

Pousada de Lisboa - Small Luxury Hotels Of The World

Lisbon City Center
Save 100% on your flight
CA $2,174
per person
Nov 8 - Nov 14
found 4 hours ago
Roundtrip flight included
Halifax (YHZ) to Lisbon (LIS)
9.6/10 Exceptional! (667 reviews)
The staff and facilities were outstanding. Hotel centrally located, easy to get everywhere in historic area. One of best overall hotels we have stayed at.

Reviewed on Sep 18, 2026

The Lumiares Hotel & Spa

The Lumiares Hotel & Spa

Lisbon City Center
Save 100% on your flight
CA $1,859
per person
Nov 16 - Nov 23
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Lisbon (LIS)
9.6/10 Exceptional! (375 reviews)
Excellent location

Reviewed on Sep 25, 2026

Masa Hotel 5 de Outubro

Masa Hotel 5 de Outubro

Lisbon City Center
CA $1,195
per person
Nov 15 - Nov 22
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Lisbon (LIS)
8.8/10 Excellent! (190 reviews)
A newish, basic tourist hotel in a good location. Nothing works with it. Nothing special about it. If you can get a good price, book it.

Reviewed on Sep 21, 2026

Santiago Beach Vacation

Chill out by the water's edge and feel the wind through your hair during your Santiago vacation. If you're a first-timer, why not pick up some seashells as a reminder of your trip to Santiago? Base yourself near Sesimbra Beach, a popular stretch of coast just 0.32 kilometres from the center. We also have value-for-money Santiago vacation packages closer to Praia da California, another terrific option.

Things You Should Know About Santiago

  • There's something magical about being close to the water. If staying within an easy stroll of a sunny shore is your idea of a blissful vacation, browse our Santiago beach hotels and see what's on offer.
  • Apartments such as Akisol Sesimbra Beach IV and Akisol Sesimbra Star are also very popular. Whether you're planning a family trip or a romantic escape with that special someone, you're sure to find something that suits your requirements.

Ready to book your vacation to Santiago?

Choose your dates

Santiago Hotel Deals

Four Points by Sheraton Sesimbra

Four Points by Sheraton Sesimbra

Rua 4 de Maio, 50 Sesimbra
Fully refundableReserve now, pay when you stay
CA $160
CA $169 total
Oct 12 - Oct 13
includes taxes & fees
9/10 Wonderful! (600 reviews)
"This is the 2nd time we have stayed here, rooms were clean and big, air conditioning good. The bathroom needs some maintenance. The walk to the ocean is a little far for some people and uphill but there is a free shuttle available"

Reviewed on Sep 22, 2026

Four Points by Sheraton Sesimbra
Ouro Rossio Hotel

Ouro Rossio Hotel

R. dos Sapateiros 213 Lisbon Lisboa
CA $217
CA $243 total
Oct 25 - Oct 26
includes taxes & fees
9.8/10 Exceptional! (97 reviews)
"Location, staff, cleanliness"

Reviewed on Sep 27, 2026

Ouro Rossio Hotel
My Story Hotel Tejo

My Story Hotel Tejo

Rua dos Condes de Monsanto 2 Lisbon Lisbon
My Story Hotel Tejo
See all 7,008 properties in Santiago
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.

Stay near popular Santiago attractions

Fortaleza de Santiago

9.4/10 (12 reviews)
You can learn about the history of Santiago with a stop at Fortaleza de Santiago. Wander the beautiful beaches and seaside in this quaint area.
See properties

What to do in Santiago

Hop-On Hop-Off Bus & Tramcar Tours

Hop-On Hop-Off Bus & Tramcar Tours

CA $61
per adult
82% of travellers recommend
Hop-On Hop-Off Bus & Tramcar Tours
Trolley in Lisbon

Hills Tramcar Hop-on Hop-off Tour

CA $32
per adult
80% of travellers recommend
Hills Tramcar Hop-on Hop-off Tour
Hop-On Hop-Off Boat Tour with Optional Bus Tour Combos

Lisbon Hop-On Hop-Off Packs

CA $40
per adult
Lisbon Hop-On Hop-Off Packs
See all activities in Santiago

Frequently asked questions

How much does a Santiago vacation package cost?
You can pick up a vacation package to this top destination from CA $1,052 on Expedia. But how much your vacation to Santiago costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Santiago?
November, December and January are great times to search for cheap Santiago vacation packages. Travelling in less busy months means you can typically find lower prices on flights and accommodations.
How many days is enough for Santiago?
To get the most out of your Santiago vacation, we suggest staying for 4 days. Divide your time between visiting Bicas Beach, Arrabida Life and other leading sights, as well as experiencing neighbourhoods like Zambujal and Caixas. If you've got some time to spare, include a day trip in your Santiago vacation itinerary.
How to find the best Santiago package deals?
Use Expedia's handy filters to find some of the best Santiago package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Santiago package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Santiago vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll usually snag a better deal than booking each component individually. And you'll still have the freedom to create a customized Santiago vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Santiago?
Enjoy amazing discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Santiago getaway.
How to plan a trip to Santiago?
  1. Choose your dates: The things you want to do in Santiago and your favourite season can help you decide when to go.
  2. Set your budget: Consider costs such as food, flights and transportation when working out how much to put aside for your trip to Santiago. Then, select a property that fits your budget, whether that's a wallet-friendly stay or a deluxe getaway.
  3. Decide how long to go away for: Now that you're up to speed on Santiago, you can work out the perfect length of your break. Pull together a draft itinerary and allocate enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a customized Santiago vacation package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.