Madison South Vacations from $285

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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.

The Latest Madison South Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Hotel Zags Portland

The Hotel Zags Portland

4 out of 5
Downtown Portland
Price was $421, price is now $285 per person
$285
per person
Feb 18 - Feb 22
found 11 hours ago
Roundtrip flight included
Burbank (BUR) to Portland (PDX)
8.6/10 Excellent! (1,008 reviews)
Although the staff is great, check in was great , the primary reason i booked the hotel was availability of EV charger but after reaching there, i realized that they just have 2 out which 1 was occupied and the other one was not working. So the whole point of booking a hotel with EV charging was moot. I could have stayed some place else with cheaper rates and similar amenities.

Reviewed on Nov 29, 2025

Mark Spencer Hotel

Mark Spencer Hotel

3 out of 5
Downtown Portland
Save 100% on your flight
Price was $518, price is now $298 per person
$298
per person
Feb 18 - Feb 22
found 11 hours ago
Roundtrip flight included
Burbank (BUR) to Portland (PDX)
9.2/10 Wonderful! (1,838 reviews)
Clean room, courteous & kind staff, well located, quiet rooms, comfortable bed, spacious room.

Reviewed on Nov 29, 2025

Black Walnut Inn & Vineyard

Black Walnut Inn & Vineyard

4 out of 5
Save 100% on your flight
Price was $1,419, price is now $853 per person
$853
per person
Jan 5 - Jan 9
found 2 hours ago
Roundtrip non-stop flight included
Orange County (SNA) to Portland (PDX)
10/10 Exceptional! (62 reviews)
Beautiful and Peaceful. Large room, wonderful sunrise views and amazing breakfasts. Friendly staff that respect your privacy and peace, so much that on a couple occasions I couldn’t find anyone. But if you want a quiet get away with a loved one, you’ll get it here.

Reviewed on Sep 26, 2025

Shilo Inn Suites Hotel - Warrenton

Shilo Inn Suites Hotel - Warrenton

2.5 out of 5
Save 100% on your flight
Price was $476, price is now $315 per person
$315
per person
Feb 18 - Feb 22
found 7 hours ago
Roundtrip flight included
Los Angeles (QLA) to Portland (PDX)
7.4/10 Good! (1,000 reviews)
no soap available for a shower. Phone in room does not work. Cable goes in and out. Staff was very courteous

Reviewed on Nov 28, 2025

Homewood Suites by Hilton Hillsboro/Beaverton

Homewood Suites by Hilton Hillsboro/Beaverton

3 out of 5
Five Oaks
Save 100% on your flight
Price was $491, price is now $336 per person
$336
per person
Feb 7 - Feb 11
found 21 hours ago
Roundtrip flight included
Los Angeles (QLA) to Portland (PDX)
9/10 Wonderful! (906 reviews)
Everything was clean and accessible. Nothing to add

Reviewed on Nov 24, 2025

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
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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 showing picnicing, boating and a bay or harbor

Downtown Portland

1 out of top 10 points of interest in this area
4.5/5(4,488 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

The Paramount Hotel

The Paramount Hotel

3.5 out of 5
808 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
$95 nightly
The price is $110 total per night from Dec 21 to Dec 22
$110 total
Dec 21 - Dec 22
Total with taxes and fees
9.2/10 Wonderful! (3,030 reviews)
friendly staff good food very nice rooms

Reviewed on Nov 25, 2025

The Paramount Hotel
Embassy Suites by Hilton Portland Airport

Embassy Suites by Hilton Portland Airport

3.5 out of 5
7900 Ne 82nd Ave Portland OR
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $129 total per night from Dec 7 to Dec 8
$129 total
Dec 7 - Dec 8
Total with taxes and fees
9/10 Wonderful! (2,103 reviews)
Friendly staff, fast check in, the room is very clean and roomy, we will return in the next travel trips.

Reviewed on Nov 26, 2025

Embassy Suites by Hilton Portland Airport
Embassy Suites by Hilton Portland Downtown

Embassy Suites by Hilton Portland Downtown

4 out of 5
319 SW Pine St Portland OR
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $131 total per night from Dec 21 to Dec 22
$131 total
Dec 21 - Dec 22
Total with taxes and fees
8.6/10 Excellent! (1,332 reviews)
Room was clean.. friendly staff will stay again

Reviewed on Nov 28, 2025

Embassy Suites by Hilton Portland Downtown
See all 2,772 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
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Discover the most popular places to visit in Madison South

The Grotto

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.

The Grotto

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 theater scene and shops.

Rose City Golf Course

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.

Hancock Park

Things to do

Half-Day Multnomah Falls & Gorge Waterfalls Tour

Half-Day Multnomah Falls & Gorge Waterfalls Tour

$85
per traveler
96% of travellers recommend
Half-Day Multnomah Falls & Gorge Waterfalls Tour
Portland: 2-hour Lunch Cruise on the Willamette River

Portland: 2-hour Lunch Cruise on the Willamette River

$87
per adult
98% of travellers recommend
Portland: 2-hour Lunch Cruise on the Willamette River
Portland: Willamette River 2.5-hour Dinner Cruise

Portland: Willamette River 2.5-hour Dinner Cruise

$127
per adult
96% of travellers recommend
Portland: Willamette River 2.5-hour Dinner Cruise
See all activities in Portland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.