Crestwood Vacations from $482

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Your Crestwood Vacation

Lock in a Crestwood vacation package and prepare to experience the highlights of this city. Consider staying in the neighborhood of Overlook, which is good for cycling, bars and pubs and dining. Make your trip to Crestwood even more fun and exciting by including some sightseeing. Oregon Zoo, Portland State University and Portland Japanese Garden are some of the most popular attractions you'll want to explore. Whoever you're going away with and whatever your bank balance, your dream Crestwood vacation is just clicks away with Expedia.

The Latest Crestwood Vacation Packages

Price found within the past 48 hours. Click for updated prices.
McMinnville Inn

McMinnville Inn

$482
per person
Oct 28 - Nov 2
found 7 hours ago
Roundtrip flight included
Los Angeles (LAX) to Portland (PDX)
8/10 Very Good! (1,001 reviews)
Property needs updating and breakfast was terrible

Reviewed on Sep 13, 2026

Heathman Hotel

Heathman Hotel

Downtown Portland
$633
per person
Oct 29 - Nov 5
found 1 day ago
Roundtrip flight included
Burbank (BUR) to Portland (PDX)
9.2/10 Wonderful! (1,070 reviews)
Pros: Very nicely appointed, rich decor; sizable and quiet bedrooms, comfortable beds; very convenient downtown location; excellent food at restaurant (though very limited selections while under renovation). Cons: While the staff was friendly and tried to be helpful, there were a lot of service glitches and delays at the hotel; had to request housekeeping multiple times and they forgot to replenish some toiletries multiple days; 4 housekeeping carts and a used food tray were left in the hallway on our floor for over 6 hours one day; the hotel manager did not seem proactive after we informed him; Restaurant seemed understaffed with brand new servers; many tables were not bussed even with only a few tables seated. Had to request silverware on 2 occasions after food was brought to table; Porters stationed at front doors stood there awkwardly, no offer to help with luggage or open a door. Again, everyone seemed brand new to their posts and in need of training, other than a couple of the check-in staff. We stayed at The Heathman Hotel last March during the library renovation and the staff seemed much better trained at that time. Things ran smoothly. We rated the hotel 5-stars then, now we have to give it 3-stars due to glitches/shortfalls in service.

Reviewed on Sep 14, 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

$1,950
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PDX)
10/10 Exceptional! (2 reviews)
We loved the location, size, style, and cleanliness. Had all the comforts of home. Would stay here again.

Reviewed on Aug 27, 2026

Grey Oak by Avantstay Surfers Retreat Walk to Cove Beach + Golf + Firepit

Grey Oak by Avantstay Surfers Retreat Walk to Cove Beach + Golf + Firepit

$1,983
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Portland (PDX)
10/10 Exceptional! (3 reviews)
5 stars, and if we could go higher, we would! This was one of the best family stays we have had so far. The beach was so close, and the town had so many great things to see and experience. The location was perfect and central enough that we could visit other beaches during the day and still be back home the same evening. The hosts were incredibly kind, and the managing agency stayed connected the whole time, so we never had to wonder about anything. The neighbourhood was quiet, the home was beautiful, and every little detail was appreciated, even the sandcastle building toys! We are so grateful for such a beautiful trip. Well done. We will be back!

Reviewed on May 19, 2026

Villa Manzanita by Avantstay Hot Tub, 1 Block to Beach/town, Chef's Kitchen

Villa Manzanita by Avantstay Hot Tub, 1 Block to Beach/town, Chef's Kitchen

Save 100% on your flight
$1,770
per person
Oct 14 - Oct 19
found 21 hours ago
Roundtrip non-stop flight included
Ontario Intl. Airport (ONT) to Portland (PDX)
10/10 Exceptional! (1 review)

Where to stay in Crestwood

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

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.

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

Northeast Portland

2 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

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.

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

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.

Crestwood Hotel Deals

The Paramount Hotel

The Paramount Hotel

808 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
$129 nightly
$150 total
Sep 20 - Sep 21
Total with taxes and fees
The Paramount Hotel
Heathman Hotel

Heathman Hotel

1001 SW Broadway Portland OR
Fully refundableReserve now, pay when you stay
$141 nightly
$164 total
Oct 11 - Oct 12
Total with taxes and fees
9.2/10 Wonderful! (1,087 reviews)
"Pros: Very nicely appointed, rich decor; sizable and quiet bedrooms, comfortable beds; very convenient downtown location; excellent food at restaurant (though very limited selections while under renovation). Cons: While the staff was friendly and tried to be helpful, there were a lot of service glitches ..."

Reviewed on Sep 14, 2026

Heathman 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
$108 nightly
$125 total
Oct 12 - Oct 13
Total with taxes and fees
Country Inn & Suites by Radisson, Portland International Airport, OR
See all 2,937 properties in Crestwood
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.

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
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
Full-Day Mount Hood & Multnomah Falls Tour

Full-Day Mount Hood & Multnomah Falls Tour

$140
per traveler
96% of travellers recommend
Full-Day Mount Hood & Multnomah Falls Tour
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.