Madison South Vacation Packages

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Your Madison South Vacation

A great way to experience this interesting city is with a tailor-made Madison South vacation package. Base yourself in the neighborhood of Mississippi District, which is good for shopping, nightlife and bars and pubs or go someplace else — our package deals are all about you. A trip to Madison South is an ideal opportunity to take in the sights. Be sure to look around well-known attractions like Portland State University, Veterans Memorial Coliseum and Tom McCall Waterfront Park. Check out Expedia's wide range of travel options and start planning your ultimate vacation to Madison South today.

Top Holiday Package Deals in Madison South

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

KEX Portland

2 out of 5
Northeast Portland
Price was CA $640, price is now CA $511 per person
CA $511
per person
May 22 - May 25
found 13 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
9/10 Wonderful! (524 reviews)
The staff is great so is the vibe

Reviewed on Feb 23, 2026

The Nines, a Luxury Collection Hotel, Portland

The Nines, a Luxury Collection Hotel, Portland

5 out of 5
Downtown Portland
Price was CA $1,194, price is now CA $917 per person
CA $917
per person
May 21 - May 25
found 17 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Portland (PDX)
9/10 Wonderful! (1,002 reviews)
What’ a great find this was. The staff is so welcoming and friendly. The decor is chic. The bedding is luxurious. Very centrally located. You can’t go wrong with staying at The Nines.

Reviewed on Feb 2, 2026

Holiday Inn Portland West - Hillsboro by IHG

Holiday Inn Portland West - Hillsboro by IHG

3 out of 5
Tanasbourne
Price was CA $1,077, price is now CA $871 per person
CA $871
per person
May 15 - May 19
found 17 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Portland (PDX)
8.6/10 Excellent! (1,004 reviews)
All was in great ..clean, polite staff and good services... The restaurant's menu could improve with more selection.

Reviewed on Mar 2, 2026

Staybridge Suites Hillsboro North by IHG

Staybridge Suites Hillsboro North by IHG

3 out of 5
Price was CA $1,056, price is now CA $875 per person
CA $875
per person
May 15 - May 19
found 17 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Portland (PDX)
8.8/10 Excellent! (300 reviews)
Room was spotless. Staff was courteous.

Reviewed on Jan 30, 2026

Washington Plaza Apartments

Washington Plaza Apartments

3 out of 5
Downtown Portland
Price was CA $824, price is now CA $690 per person
CA $690
per person
May 21 - May 25
found 17 hours ago
Roundtrip non-stop flight included
Regina (YQR) to Portland (PDX)
8.2/10 Very Good! (356 reviews)
Clean room. Courteous staff

Reviewed on Feb 9, 2026

Where to stay in Madison South

Find the best Madison South areas and neighborhoods for the activities you enjoy most. Learn more about Madison South
Downtown Portland - South Waterfront which includes boating, a bay or harbour and picnicking

Downtown Portland

4.5/5(545 area reviews)

Explore the Portland Art Museum, Oregon Historical Society, and Tom McCall Waterfront Park in this central business district with high-rise buildings. Enjoy walkable streets, and easily access public transportation like MAX light rail and Portland Streetcar.

Find hotels in Downtown Portland

Madison South Hotel Deals

Park Lane Suites and Inn

Park Lane Suites and Inn

2.5 out of 5
809 SW King Avenue Portland OR
Fully refundable
The price is CA $108 per night from Mar 10 to Mar 11
CA $108
CA $126 total
Mar 10 - Mar 11
includes taxes & fees
8.8/10 Excellent! (1,651 reviews)
Every part of this stay was a pleasant experience. And it was a short drive to OHSU Hospital.

Reviewed on Mar 2, 2026

Park Lane Suites and Inn
The Paramount Hotel

The Paramount Hotel

3.5 out of 5
808 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Mar 8 to Mar 9
CA $128
CA $149 total
Mar 8 - Mar 9
includes taxes & fees
9.2/10 Wonderful! (3,230 reviews)
Staff was friendly. Room was comfy

Reviewed on Mar 3, 2026

The Paramount Hotel
Cambria Hotel Portland - Pearl District

Cambria Hotel Portland - Pearl District

3 out of 5
165 NW Park Ave Portland OR
Fully refundable
The price is CA $150 per night from Mar 25 to Mar 26
CA $150
CA $173 total
Mar 25 - Mar 26
includes taxes & fees
9.8/10 Exceptional! (305 reviews)
Great room, nice staff, clean gym.

Reviewed on Mar 3, 2026

Cambria Hotel Portland - Pearl District
See all 2,850 properties in Madison South
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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Madison South vacation package cost?
Our Madison South packages, which begin at just CA $511, are the best way to save precious money. Pick and choose your preferred hotels, flights and rental car to create a customized getaway.
How do I get a cheap travel package to Madison South?
Booking a Madison South vacation package with Expedia is a great way to save. We have access to more than 550 partner airlines and 1,000,000 properties across the globe. With such a broad range to choose from, you'll have no difficulty pulling together your next dream trip.
Where should I stay in Madison South?
Make sightseeing easy by staying just a stone's throw away from Madison South's terrific attractions. Oregon Zoo and Portland State University are two of the most popular.
What are the top hotels in Madison South?
Perfect Portland Location, Tiki Backyard Layout and Days Inn by Wyndham Portland Central are a couple of the most popular hotels in Madison South. Why not have a look at the amenities and facilities at each and then make up your mind?
How far in advance should I book my Madison South vacation?
Savvy travelers often book early. You can normally compare international airfares on Expedia up to a year before your intended flight. If you're booking last minute, there's no need to worry. Cheap prices occasionally become available just weeks before departure dates.
What does an Expedia Madison South travel package include?
Flights, hotels and a reliable car for your road trip adventures. Simply choose your favorite bundle and gain access to great discounts. Once you've made your booking, add on some sightseeing tours and watch your savings pile up. When it comes to organizing your Madison South escape, you're in control!
What should I know before booking a Madison South travel package?
A travel package can be tailored to your budget and is a terrific way to stretch your hard-earned dollars. How little or much you include is totally up to you. Hotels, rental cars and flights — decide on a combination that suits your plans.
Can I choose my airline with a Madison South Expedia vacation package?
You can. Expedia has access to more than 550 partner airlines worldwide, so select the carrier that's a good fit for your travel needs.
If I'm not able to travel, can I cancel my Madison South vacation package?
Don't stress if you're rethinking your Madison South vacation 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 airline, hotel or car rental company. We understand life can throw the occasional spanner in the works, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we're ready to help.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.