Highland Vacation Packages for 2025
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Highland Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
OYO Woodland Hotel and Suites
per person
Sep 24 - Sep 28
found 2 hours ago
Roundtrip non-stop flight included
Chicago (MDW) to Portland (PDX)
Stay at this hotel in Woodland. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hulda Klager Lilac Gardens and Holland America Bulb Farms are located nearby.
Mark Spencer Hotel
Downtown Portland
per person
Sep 24 - Sep 28
found 2 hours ago
Roundtrip non-stop flight included
Chicago (MDW) to Portland (PDX)
Stay at this 3-star business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Moda Center and Powell's City of Books are located nearby.
OYO Hotel St. Helens, OR
per person
Sep 24 - Sep 28
found 2 hours ago
Roundtrip non-stop flight included
Chicago (MDW) to Portland (PDX)
Stay at this motel in St. Helens. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions McCormick Park and Columbia County Museum are located nearby.
Hotel Lucia
Downtown Portland
per person
Sep 24 - Sep 28
found 2 hours ago
Roundtrip non-stop flight included
Chicago (MDW) to Portland (PDX)
Stay at this 4-star boutique hotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Moda Center and Powell's City of Books are located nearby.
Woodlark Hotel Portland, a Tribute Portfolio Hotel
Downtown Portland
per person
Sep 24 - Sep 28
found 2 hours ago
Roundtrip non-stop flight included
Chicago (MDW) to Portland (PDX)
Stay at this 4-star hotel in Portland. Enjoy free WiFi, 2 bars/lounges, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Moda Center and Powell's City of Books are located nearby.
Hotel deLuxe
Downtown Portland
per person
Sep 24 - Sep 28
found 2 hours ago
Roundtrip non-stop flight included
Chicago (MDW) to Portland (PDX)
Book a stay at this boutique hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Moda Center and Powell's City of Books are located nearby.
Top Hotel Deals
The Hotel Salem
4370 Commercial St Se, Salem, OR
7.59 km from Highland
Stay at this 3-star business-friendly hotel in Salem. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Days Inn by Wyndham Black Bear
1600 Motor Ct Ne, Salem, OR
3.02 km from Highland
Stay at this hotel in Salem. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
The Independence
201 Osprey Lane, Independence, OR
17.18 km from Highland
Stay at this 3-star business-friendly hotel in Independence. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Oregon Garden Resort
895 W Main St, Silverton, OR
18.62 km from Highland
Stay at this 3-star spa hotel in Silverton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular ...
La Quinta Inn & Suites by Wyndham Salem OR
890 Hawthorne Avenue SE, Salem, OR
4.79 km from Highland
Stay at this 3-star business-friendly hotel in Salem. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Best Western Plus Mill Creek Inn
3125 Ryan Drive SE, Salem, OR
4.83 km from Highland
Book a stay at this business-friendly hotel in Salem. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Howard Johnson by Wyndham Salem
2250 Mission St Se, Salem, OR
3.89 km from Highland
Book a stay at this business-friendly hotel in Salem. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Holiday Inn Salem by IHG
3301 Market St Ne, Salem, OR
2.56 km from Highland
Stay at this 3-star business-friendly hotel in Salem. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Best Western McMinnville Inn
2035 SW Highway 99 W, McMinnville, OR
29.94 km from Highland
Book a stay at this business-friendly hotel in McMinnville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Comfort Suites Salem
630 Hawthorne Ave Se, Salem, OR
4.75 km from Highland
Book a stay at this business-friendly hotel in Salem. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
Red Lion Inn & Suites McMinnville
2535 N.E. Cumulus Avenue, McMinnville, OR
29.22 km from Highland
Book a stay at this business-friendly hotel in McMinnville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
La Quinta Inn & Suites by Wyndham Woodburn
120 Arney Road NE, Woodburn, OR
24.19 km from Highland
Stay at this 3-star business-friendly hotel in Woodburn. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Best Western Woodburn
2980 Tom Tennant Dr, Woodburn, OR
24.45 km from Highland
Book a stay at this business-friendly hotel in Woodburn. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Thu, Oct 16 - Sat, Oct 18
LAX
Los Angeles Intl.
PDX
Portland Intl.
$92 Roundtrip, found 6 days ago
$92
Roundtrip
found 6 days ago
Tue, Sep 9 - Tue, Sep 16
SFO
San Francisco Intl.
PDX
Portland Intl.
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
Wed, Oct 15 - Thu, Oct 23
LAX
Los Angeles Intl.
PDX
Portland Intl.
$153 Roundtrip, found 6 days ago
$153
Roundtrip
found 6 days ago
Tue, Sep 23 - Sat, Oct 4
DEN
Denver Intl.
PDX
Portland Intl.
$157 Roundtrip, found 6 days ago
$157
Roundtrip
found 6 days ago
Tue, Sep 23 - Sat, Oct 4
DEN
Denver Intl.
PDX
Portland Intl.
$167 Roundtrip, found 6 days ago
$167
Roundtrip
found 6 days ago
Best points of interest in Salem
- Silver Falls State Park Vacations
- Oregon State Fairgrounds Pavilion Vacations
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- Woodburn Premium Outlets Vacations
- Salem Riverfront Park Vacations
- Willamette University Vacations
- Wings and Waves Waterpark Vacations
- Willamette Valley Vineyards Vacations
- Evergreen Aviation and Space Museum Vacations
- Salem Hospital Vacations
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