Search Deals onWoolwich Vacation Packages
Woolwich Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Dormir
Price was $482, price is now $426 per person
$426
per person
Dec 18 - Dec 21
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this business-friendly hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Seacoast Adventure and Sebago Lake Basin are located nearby.
84 Main
Price was $1,030, price is now $871 per person
$871
per person
Dec 20 - Dec 23
found 24 hours ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
The property was very spacious, well equipped, and well taken care of. There was lots of natural light and a very large outdoor deck accessible from all bedrooms and the living room.
Reviewed on Jul 17, 2026
Portland Harbor Hotel
Price was $565, price is now $486 per person
$486
per person
Dec 18 - Dec 21
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) 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 State Theatre and Thompson's Point are located nearby.
Inn By The Sea
Price was $714, price is now $617 per person
$617
per person
Dec 18 - Dec 21
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury hotel in Cape Elizabeth. Enjoy free valet parking, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Crescent Beach State Park and Crescent Beach are located nearby.
Greenleaf Inn
Price was $1,151, price is now $1,000 per person
$1,000
per person
Dec 7 - Dec 11
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Augusta (AUG)
Stay at this hotel in Boothbay Harbor. Enjoy free WiFi, free parking, and a marina. Popular attractions Coastal Maine Botanical Gardens and Burnt Island Living Lighthouse are located nearby.
The Docent's Collection at 178 Middle Street
Price was $787, price is now $684 per person
$684
per person
Dec 18 - Dec 21
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and a 24-hour front desk. Popular attractions State Theatre and Thompson's Point are located nearby.
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
Kennebunkport Captains Collection
Price was $815, price is now $715 per person
$715
per person
Dec 18 - Dec 21
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Property was absolutely amazing. We fell in love with the area and our stay at the William Jefferds House was perfect. Love the breakfast and amenities in the house. We took advantage of the free bicycle use. Definitely on our list to return.
Reviewed on Nov 5, 2026
Harborline Hotel
Price was $488, price is now $440 per person
$440
per person
Dec 18 - Dec 21
found 8 hours ago
Roundtrip flight included
Atlanta (ATL) to Rockland (RKD)
Stay at this hotel in Rockland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Maine Lighthouse Museum and Project Puffin Visitor Center are located nearby.
Woolwich Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Woolwich 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.
Thu, Nov 12 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$231 Roundtrip, found 2 days ago
$231
Roundtrip
found 2 days ago
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$253 Roundtrip, found 3 hours ago
$253
Roundtrip
found 3 hours ago
Sat, Dec 5 - Tue, Dec 15
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$267 Roundtrip, found 3 hours ago
$267
Roundtrip
found 3 hours ago
Tue, Nov 10 - Wed, Nov 18
TPA
Tampa Intl.
PWM
Portland Intl. Jetport
$269 Roundtrip, found 11 hours ago
$269
Roundtrip
found 11 hours ago
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