Vacations Close To Inland Woods and Trails
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Inland Woods and Trails Flight + Hotel packages
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Portland Regency Hotel & Spa
Downtown Portland
Price was $1,180, price is now $1,020 per person
$1,020
per person
Dec 28 - Jan 2
found 23 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Favorite hotel in old port. Great location for walking the whole area. Staff is are all great. Valet parking always goes smoothly... there is a public lot a coulpeof blocks inland and to the right if you prefer self parking.
Excellent breakfast. Nice dinner lounge below and whiskey lounge in the evenings.
3rd time staying there and will many more times. Very well run hotel.
Reviewed on Nov 2, 2026
The Docent's Collection at 178 Middle Street
Downtown Portland
Price was $1,921, price is now $1,626 per person
$1,626
per person
Dec 28 - Jan 2
found 23 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
room was very modern, however some areas did not look well cleaned (edge if the bed had some dried white liquid). the surrounding area has nice shops but is very sketchy at night. did not feel comfortable with the parking situation. also at 6am sounded like maintenance or cleaning crew was constantly in and out of the elevator making tons of noise. was good for a night but wouldnt stay again.
Reviewed on Oct 27, 2026
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