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.
Hotel deLuxe
Downtown Portland
CA $805
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PDX)
8.6/10 Excellent! (1,109 reviews)
The staff at the front desk was very friendly. Our bartender at the Driftwood Room was attentive and we loved our waitress at Gracie’s for breakfast.
Reviewed on Sep 24, 2026
Schooner Landing
Agate Beach
CA $1,128
per person
Nov 8 - Nov 13
found 22 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
8.4/10 Very good! (78 reviews)
The staff we interacted with was very pleasant, friendly and helpful.
The property was really shabby. Siding needed to be pressure washed. Stair treads were very worn. The beach trail was not maintained. There was an accumulation of refuse at our front door.
The interior of our unit was very clean and comfortable, but very dated. The sliding door to the deck was in bad condition and wouldn’t slide easily.
I assume this is the reason the price was reasonable for the size of the unit.
Reviewed on Sep 19, 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
1 out of top 10 points of interest in this area
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.
Northeast Portland
1 out of top 10 points of interest in this area
Inner Northeast Portland boasts shopping areas like Lloyd District and Alberta Arts District, while the area near Burnside Bridge offers a lively nightlife with bars such as The Chesterfield and music venues like The Doug Fir Lounge.
Pearl District
1 out of top 10 points of interest in this area
Discover art galleries like Elizabeth Leach Gallery, dine at diverse restaurants, and unwind in public plazas such as Jamison Square. Easily navigate with the Portland Streetcar and explore nearby iconic Powell's City of Books.
Southeast Portland
Stretching from the Willamette River to Gresham, Southeast Portland boasts the scenic Mt. Tabor Park and the quirky Hawthorne district with its subculturally oriented shops. Don't miss exploring Reed College campus!
Southwest Portland
2 out of top 10 points of interest in this area
Downtown Portland boasts cultural, educational, and retail hotspots, with attractions like Tom McCall Waterfront Park, Portland Art Museum, and Pioneer Place mall. Enjoy pedestrian-friendly streets and unique residential areas in Southwest Portland.
Madison South Hotel Deals
The Paramount Hotel
808 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
CA $166
CA $193 total
Oct 14 - Oct 15
includes taxes & fees
9.2/10 Wonderful! (3,707 reviews)
"Beautiful hotel! Clean room, complimentary coffee bar downstairs and super friendly staff! Convenient and walking distance to most everything downtown."
Reviewed on Sep 23, 2026
Heathman Hotel
1001 SW Broadway Portland OR
Fully refundableReserve now, pay when you stay
CA $141
CA $213 total
Oct 18 - Oct 19
includes taxes & fees
9.2/10 Wonderful! (1,083 reviews)
"Truly convenient, well maintained hotel with a great staff - especially at the door. Overall efficient, secure, pleasant and up to date. Coffee SIP shop lobby a plus. However, we were surprised (and disappointed) to learn that you had to request housekeeping services (beds/towel changes/trash and ..."
Reviewed on Sep 23, 2026
Country Inn & Suites by Radisson, Portland International Airport, OR
7025 NE Alderwood Rd Portland OR
Fully refundable
CA $146
CA $171 total
Oct 25 - Oct 26
includes taxes & fees
8.8/10 Excellent! (3,240 reviews)
"Excellent facility at a very convenient location. Staff were friendly and helpful. Parking was easy. The room was clean and spacious. Highly recommended"
Reviewed on Sep 23, 2026
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.
Frequently asked questions
How much does a Madison South vacation package cost?
Our Madison South packages, which begin at just CA $780, 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.
Stay near popular Madison South attractions
The Grotto
6.0/10 (2 reviews)
You can learn about the history of Portland with a trip to The Grotto. Stroll along the area's riverfront or experience its entertainment choices.
Rose City Golf Course
Play a round of golf in Portland at Rose City Golf Course, and enjoy other activities such as biking. Discover the area's acclaimed art scene and shops.
Rocky Butte
Explore the great outdoors at Rocky Butte and enjoy the beautiful waterfalls during your trip to Portland. Wander around the area's picturesque gardens or experience its acclaimed art scene.
Glenhaven Park
Glenhaven Park is just one of the places to see in Portland, so why not enjoy the other things to explore during your travels? Discover the area's acclaimed art scene and shops.
Hancock Park
Hancock Park is just one of the places to see in Portland, so why not enjoy the other things to explore during your travels? Stroll along the riverfront or seek out the biking trails.
Joseph Wood Hill Park
After visiting Joseph Wood Hill Park, make a plan to see the other sights and activities in Portland. Wander the area's riverfront or simply enjoy one of its top-notch restaurants.
Things to do
Half-Day Multnomah Falls & Gorge Waterfalls Tour
CA $118
per traveller
96% of travellers recommend
Portland: 2-Hour Lunch Cruise Through Downtown
CA $122
per adult
98% of travellers recommend
Full-Day Mount Hood & Multnomah Falls Tour
CA $194
per traveller
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.