Oak Grove Vacations from $395

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 Oak Grove Vacation

An easy way to experience this unique city is with a tailor-made Oak Grove vacation package. Base yourself in the neighborhood of Mississippi District, which is great for shopping, nightlife and bars and pubs or go someplace else — our package deals are all about you. You'll want to go sightseeing during your trip to Oak Grove. Drop by leading attractions such as Clackamas Town Center, Waverley Country Club and Milwaukie Farmers Market. A couple of clicks is all it takes to craft the perfect Oak Grove vacation on Expedia.

The Latest Oak Grove Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Skamania Lodge

Skamania Lodge

$395
per person
Sep 22 - Sep 24
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Portland (PDX)
9.2/10 Wonderful! (1,006 reviews)
My third time staying Escamilla Lodge. Can’t say enough. This place is wonderful for everything you want, activities, water, sightseeing, wildlife, etc. Had the opportunity to go with my grandkids and they absolutely loved it. The marked hiking trails are an added bonus where my five-year-old and three year-old grandchildren were able to easily maneuver the trails and got to see wildlife. What a wonderful experience. We will make it our fourth next year!

Reviewed on Aug 22, 2026

Bowline Hotel

Bowline Hotel

Save 100% on your flight
$1,005
per person
Oct 23 - Oct 30
found 17 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PDX)
9.4/10 Exceptional! (1,005 reviews)
Royal Canoe by Avantstay Walk to the Shore + Cozy Fireplace

Royal Canoe by Avantstay Walk to the Shore + Cozy Fireplace

Save 100% on your flight
$1,601
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Portland (PDX)
10/10 Exceptional! (3 reviews)
Great location! Everything was clean and nice. We loved it!

Reviewed on Jul 22, 2026

Beach Pines Bungalow by Avantstay Classic Cottage Steps to the Beach w/ Private Yard

Beach Pines Bungalow by Avantstay Classic Cottage Steps to the Beach w/ Private Yard

Save 100% on your flight
$1,466
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Portland (PDX)
10/10 Exceptional! (1 review)
We absolutely loved it. Can’t wait to go back!

Reviewed on Mar 23, 2026

Waves Hotel NYE Beach - Newport OR

Waves Hotel NYE Beach - Newport OR

$580
per person
Sep 27 - Oct 1
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Portland (PDX)
7.8/10 Good! (1,776 reviews)
It was a nice place for a weekend getaway. The room was spacious although dark. There are only two little lamps for light in the room. Upgrades to the bedding and towels would make the stay better. The staff was helpful and friendly.

Reviewed on Aug 22, 2026

Where to stay in Oak Grove

Find the best Oak Grove areas and neighborhoods for the activities you enjoy most. Learn more about Oak Grove
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.

Oak Grove Hotel Deals

The Paramount Hotel

The Paramount Hotel

808 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
$102 nightly
$119 total
Sep 8 - Sep 9
Total with taxes and fees
9.2/10 Wonderful! (3,649 reviews)
"Staff was friendly and helpful. Property was clean, nice, and conveniently located."

Reviewed on Aug 22, 2026

The Paramount Hotel
Oxford Suites Portland - Jantzen Beach

Oxford Suites Portland - Jantzen Beach

12226 N JANTZEN DRIVE Portland OR
Fully refundableReserve now, pay when you stay
$112 nightly
$129 total
Aug 26 - Aug 27
Total with taxes and fees
9/10 Wonderful! (1,707 reviews)
"I loved staying here, I was surprised by how many employees were working even late into the night! Most other places you can't find any employees! Such a nice stay! The gated parking felt extra safe as well!!"

Reviewed on Aug 22, 2026

Oxford Suites Portland - Jantzen Beach
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
Aug 30 - Aug 31
Total with taxes and fees
Hyatt Regency Portland at the Oregon Convention Center
See all 2,864 properties in Oak Grove
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 Oak Grove attractions

Bike N Hike

4.0/10 (1 review)
Enjoy a stop at Bike N Hike, an entertaining place to visit in Milwaukie. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
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.