Homestead Vacations from $445

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

Your Homestead Vacation

Discover the unique personality of Homestead with a tailor-made Homestead vacation package. From its walking to its views and beyond, this neighborhood offers infinite possibilities for adventure and fun. Eager to do some sightseeing during your trip to Homestead? Be sure to stop by nearby attractions like Oregon Zoo, Portland State University and Portland Japanese Garden. No matter your travel goals or the size of your budget, booking your ideal Homestead vacation is a cinch with Expedia.

The Latest Homestead Vacation Packages

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

The Hotel Zags Portland

Downtown Portland
$445
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Portland (PDX)
8.6/10 Excellent! (1,207 reviews)
The Nines, a Luxury Collection Hotel, Portland

The Nines, a Luxury Collection Hotel, Portland

Downtown Portland
Save 100% on your flight
$629
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Portland (PDX)
9.2/10 Wonderful! (1,008 reviews)
Absolutely stunning luxury hotel. Staff very welcoming and made my stay feel so special. All staff went above and beyond to make my stay enjoyable. The service provided was exceptional. I would highly recommend this hotel and I plan to go back to this hotel in the very near future.

Reviewed on Aug 29, 2026

Sanctuary by the Sea by Avantstay Waterfront + Views

Sanctuary by the Sea by Avantstay Waterfront + Views

Save 100% on your flight
$2,509
per person
Oct 7 - Oct 12
found 1 day ago
Roundtrip flight included
Denver (DEN) to Portland (PDX)
No reviews
Kimpton Hotel Vintage Portland by IHG

Kimpton Hotel Vintage Portland by IHG

Downtown Portland
Save 100% on your flight
$1,477
per person
Nov 1 - Nov 8
found 1 day ago
Roundtrip flight included
Denver (DEN) to Portland (PDX)
9/10 Wonderful! (1,000 reviews)
I love Kimpton hotels. They have character and charm.

Reviewed on Aug 26, 2026

Portland's White House

Portland's White House

Northeast Portland
Save 100% on your flight
$1,146
per person
Nov 6 - Nov 13
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) to Portland (PDX)
No reviews

Where to stay in Homestead

Find the best Homestead areas and neighborhoods for the activities you enjoy most. Learn more about Homestead
Two people sitting on a blanket by a marina with boats docked in the background.

Downtown Portland

2 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.

A forested area with a stone structure, wooden benches, and a pathway leading to a central point.

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.

A street with a modern building featuring large murals, parked cars, and a café with outdoor seating.

Pearl District

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.

A dinosaur statue in front of a building with a glass facade and the letters 'OMS' on it.

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!

A cable car system, a cityscape with high-rise buildings, a river, and a mountain in the background.

Southwest Portland

3 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.

Homestead Hotel Deals

The Paramount Hotel

The Paramount Hotel

808 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
$113 nightly
$131 total
Sep 30 - Oct 1
Total with taxes and fees
9.2/10 Wonderful! (3,668 reviews)
"The room was nice, and roomy. The beds were fairly soft, but the plush pillows made it perfect. The bathroom tub had a brown film along the bottom that wiped out, and a hair on the floor. Overall, our room was nice."

Reviewed on Aug 31, 2026

The Paramount Hotel
Country Inn & Suites by Radisson, Portland International Airport, OR

Country Inn & Suites by Radisson, Portland International Airport, OR

7025 NE Alderwood Rd Portland OR
Fully refundable
$112 nightly
$130 total
Oct 1 - Oct 2
Total with taxes and fees
Country Inn & Suites by Radisson, Portland International Airport, OR
Hyatt Regency Portland at the Oregon Convention Center

Hyatt Regency Portland at the Oregon Convention Center

375 NE Holladay St Portland OR
Fully refundableReserve now, pay when you stay
$152 nightly
$176 total
Sep 13 - Sep 14
Total with taxes and fees
Hyatt Regency Portland at the Oregon Convention Center
See all 2,855 properties in Homestead
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 Homestead attractions

Terwilliger Boulevard Parkway

Explore the lovely green spaces of Terwilliger Boulevard Parkway and also enjoy the biking trails in Portland. Discover the area's acclaimed art scene and shops.
See properties

Marquam Nature Park

Explore the lovely green spaces of Marquam Nature Park and also enjoy the biking trails in Portland. Stroll along the riverfront or visit the shops in the area.
See properties

Sam Jackson Park

Explore the lovely green spaces of Sam Jackson Park and also enjoy the biking trails in Portland. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
See properties

Things to do

Portland: 2-hour Lunch Cruise on the Willamette River

Portland: 2-Hour Lunch Cruise Through Downtown

$88
per adult
98% of travellers recommend
Portland: 2-Hour Lunch Cruise Through Downtown
Portland: Willamette River 2.5-hour Dinner Cruise

Portland: Dinner Cruise on the Willamette River

$129
per adult
96% of travellers recommend
Portland: Dinner Cruise on the Willamette River
Picture 11 for Activity Portland: Champagne Brunch Cruise on Willamette River

Portland: Brunch Cruise on Willamette River

$105
per adult
92% of travellers recommend
Portland: Brunch Cruise on Willamette River
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.