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.
Clackamas Inn & Suites
per person
Aug 14 - Aug 21
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PDX)
Book a stay at this business-friendly hotel in Clackamas. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Clackamas River and North Clackamas Aquatic Park are located nearby.
Hotel Lucia
Downtown Portland
Save 100% on your flight
per person
Aug 14 - Aug 21
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 Tom McCall Waterfront Park are located nearby.
The Royal Sonesta Portland Downtown
Downtown Portland
Save 100% on your flight
per person
Aug 14 - Aug 21
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PDX)
Stay at this 4.5-star luxury 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 Tom McCall Waterfront Park are located nearby.
The Hotel Zags Portland
Downtown Portland
per person
Aug 14 - Aug 21
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PDX)
Stay at this 4-star boutique hotel in Portland. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Moda Center and Tom McCall Waterfront Park are located nearby.
Hotel deLuxe
Downtown Portland
per person
Aug 14 - Aug 21
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 Tom McCall Waterfront Park are located nearby.
Dossier Hotel
Downtown Portland
Save 100% on your flight
per person
Aug 14 - Aug 21
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Portland (PDX)
Stay at this 4.5-star luxury hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Moda Center and Tom McCall Waterfront Park are located nearby.
Top Hotel Deals
The Hotel Salem
4370 Commercial St Se, Salem, OR
7.59 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 helpful staff ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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. ...
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 ...
Super 8 by Wyndham Woodburn
821 Evergreen Road, I-5 at Woodburn Exit 271, Woodburn, OR
24.21 km from Highland
Book a stay at this business-friendly motel in Woodburn. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Holiday Inn Express & Suites Salem North - Keizer by IHG
6150 Keizer Station Blvd. NE, Keizer, OR
6.12 km from Highland
Book a stay at this business-friendly hotel in Keizer. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Bridgeway Inn & Suites Sublimity
300 SW Sublimity Blvd, Sublimity, OR
23.77 km from Highland
Book a stay at this business-friendly motel in Sublimity. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
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.
Tue, Sep 30 - Sat, Oct 4
SFO
San Francisco Intl.
PDX
Portland Intl.
$137 Roundtrip, found 2 days ago
$137
Roundtrip
found 2 days ago
Sat, Jul 5 - Sat, Jul 19
ONT
Los Angeles - Ontario Intl.
PDX
Portland Intl.
$148 Roundtrip, found 2 days ago
$148
Roundtrip
found 2 days ago
Sat, Jul 5 - Thu, Jul 17
LAX
Los Angeles Intl.
PDX
Portland Intl.
$148 Roundtrip, found 2 days ago
$148
Roundtrip
found 2 days ago
Sun, Jul 13 - Mon, Aug 4
DEN
Denver Intl.
PDX
Portland Intl.
$148 Roundtrip, found 7 hours ago
$148
Roundtrip
found 7 hours ago
Best points of interest in Salem
- Silver Falls State Park Vacations
- Willamette Valley Vineyards Vacations
- Woodburn Premium Outlets Vacations
- Enchanted Forest Theme Park Vacations
- Evergreen Aviation and Space Museum Vacations
- Willamette University Vacations
- Oregon State Fairgrounds Pavilion Vacations
- Wings and Waves Waterpark Vacations
- Salem Riverfront Park Vacations
- Salem Hospital Vacations
More AARP Member Vacation Packages
- Las Vegas Vacations
- New York Vacations
- Orlando Vacations
- Los Angeles Vacations
- Miami Vacations
- San Francisco Vacations
- New Orleans Vacations
- Chicago Vacations
- Fort Lauderdale Vacations
- Boston Vacations
- Honolulu Vacations
- San Diego Vacations
- Washington Vacations
- Toronto Vacations
- Anaheim Vacations
- Atlanta Vacations
- Nashville Vacations
- Seattle Vacations
- Phoenix Vacations
- Myrtle Beach Vacations
- Vancouver Vacations
- Palm Springs Vacations
- Denver Vacations
- Tampa Vacations
- Niagara Falls Vacations
- San Antonio Vacations
- Atlantic City Vacations
- Philadelphia Vacations
- Austin Vacations
- Dallas Vacations