Search Deals onPortland Vacation Packages
Portland Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
84 Main
Price was $692, price is now $488 per person
$488
per person
Feb 12 - Feb 17
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Stay at this condo in Kennebunk. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Dock Square and Kennebunk Free Library are located nearby.
Casco Bay Inn
Price was $692, price is now $498 per person
$498
per person
Feb 18 - Feb 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Freeport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions LL Bean Flagship Store and Eartha are located nearby.
The McKernan Inn
Price was $719, price is now $521 per person
$521
per person
Apr 2 - Apr 6
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this beach inn in South Portland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Fort Preble and Portland Harbor Museum are located nearby.
Cliff House Maine
Save 100% on your flight
Price was $1,359, price is now $999 per person
$999
per person
Feb 27 - Mar 2
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Portland (PWM)
Book a stay at this luxury resort in Cape Neddick. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Perkins Cove and Marginal Way are located nearby.
Portland Harbor Hotel
Price was $846, price is now $623 per person
$623
per person
Mar 30 - Apr 3
found 9 hours ago
Roundtrip flight included
Milwaukee (MKE) 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.
The Docent’s Collection – Thompson Block
Price was $896, price is now $706 per person
$706
per person
Mar 30 - Apr 3
found 9 hours ago
Roundtrip flight included
Milwaukee (MKE) 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.
Blind Tiger Portland - Danforth Street.
Price was $914, price is now $723 per person
$723
per person
Apr 2 - Apr 6
found 1 day 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.
Kennebunkport Captains Collection
Price was $1,102, price is now $887 per person
$887
per person
Feb 12 - Feb 17
found 19 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
Book a stay at this luxury hotel in Kennebunkport. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Dock Square and Kennebunkport Village Green are located nearby.
Portland Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Portland Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Tue, Feb 3 - Sat, Feb 7
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$194 Roundtrip, found 1 day ago
$194
Roundtrip
found 1 day ago
Wed, May 27 - Tue, Jun 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Tue, Feb 17 - Tue, Feb 24
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$204 Roundtrip, found 12 hours ago
$204
Roundtrip
found 12 hours ago
Tue, Jan 20 - Sat, Jan 24
DCA
Ronald Reagan Washington National
PWM
Portland Intl. Jetport
$219 Roundtrip, found 4 days ago
$219
Roundtrip
found 4 days ago
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