Search Deals onOld Port Vacation Packages
Old Port Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Westin Portland Harborview
Downtown Portland
Price was $563, price is now $446 per person
$446
per person
Apr 16 - Apr 20
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions State Theatre and Portland Stage are located nearby.
The Docent’s Collection – Thompson Block
Downtown Portland
Price was $793, price is now $570 per person
$570
per person
Apr 16 - Apr 20
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Maine Sports Hall of Fame and Cathedral of the Immaculate Conception are located nearby.
The Weldon Hotel
Downtown Portland
Price was $774, price is now $573 per person
$573
per person
Apr 16 - Apr 20
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this luxury aparthotel in Portland. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Victoria Mansion and Charles Q. Clapp House are located nearby.
Portland Harbor Hotel
Downtown Portland
Price was $737, price is now $550 per person
$550
per person
Apr 16 - Apr 20
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Cross Insurance Arena and Fore Street Gallery are located nearby.
Blind Tiger Portland - Danforth Street.
West End
Save 100% on your flight
Price was $993, price is now $743 per person
$743
per person
Apr 16 - Apr 20
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Stay at this B&B in Portland. Enjoy free breakfast, free WiFi, and concierge services. Popular attractions Victoria Mansion and Portland Club are located nearby.
Portland Regency Hotel & Spa
Downtown Portland
Price was $677, price is now $528 per person
$528
per person
Apr 16 - Apr 20
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions N.W. Barrett Gallery and Fore Street Gallery are located nearby.
Inn By The Sea
Price was $982, price is now $776 per person
$776
per person
Apr 16 - Apr 20
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
Cambria Hotel Portland Downtown-Old Port
East Bayside
Price was $586, price is now $476 per person
$476
per person
Apr 16 - Apr 20
found 21 hours ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this business-friendly 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 Maine Jewish Museum and Maine Narrow Gauge Railroad Company and Museum are located nearby.
3-4 Night Vacations in Old Port
Price found within the past 48 hours. Click for updated prices.
5-7 Night Vacations in Old Port
Price found within the past 48 hours. Click for updated prices.
Cheap Hotel Deals in Old Port
Portland Harbor Hotel
468 Fore Street Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, 3 coffee shops/cafes, and breakfast (surcharge). Our guests praise the helpful staff ...
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Book a stay at this spa hotel in Portland. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Hyatt Place Portland Downtown - Old Port Square
433 Fore St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast ...
Save an average of 15% on thousands of hotels when you're signed in
Canopy by Hilton Portland Waterfront
9 Center Street Portland ME
Stay at this hotel in Portland. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
Hilton Garden Inn Portland Downtown Waterfront
65 Commercial St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
Courtyard Portland Downtown/Waterfront
321 Commercial St Portland ME
Book a stay at this business-friendly hotel in Portland. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
The Docent’s Collection – Thompson Block
121 Middle St. Portland ME
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions Maine Sports Hall of Fame and Cathedral of ...
The Docent's Collection - Boyd Block
178 Middle Street Portland ME
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and daily housekeeping. Popular attractions Fore Street Gallery and Maine Sports Hall of ...
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
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, May 27 - Fri, Jun 5
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$178 Roundtrip, found 2 hours ago
$178
Roundtrip
found 2 hours ago
Wed, Apr 15 - Mon, Apr 27
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$189 Roundtrip, found 1 hour ago
$189
Roundtrip
found 1 hour ago
Mon, Mar 9 - Sat, Mar 14
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$213 Roundtrip, found 4 days ago
$213
Roundtrip
found 4 days ago
Tue, Jun 2 - Wed, Jun 3
ATL
Hartsfield-Jackson Atlanta Intl.
PWM
Portland Intl. Jetport
$227 Roundtrip, found 16 hours ago
$227
Roundtrip
found 16 hours ago
Discover Other Travel Deals
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