Search Deals onNew Gloucester Vacation Packages
New Gloucester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Kendall Inn
Price was $965, price is now $860 per person
$860
per person
Dec 31 - Jan 5
found 14 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this B&B in Freeport. Enjoy free breakfast, free WiFi, and free parking. Popular attractions LL Bean Flagship Store and Freeport Historical Society are located nearby.
Kennebunkport Captains Collection
Price was $1,485, price is now $1,201 per person
$1,201
per person
Dec 31 - Jan 5
found 19 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Inn By The Sea
Price was $1,401, price is now $1,194 per person
$1,194
per person
Dec 31 - Jan 5
found 19 hours ago
Roundtrip flight included
Dallas (DFW) 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.
Cliff House Maine
Price was $2,484, price is now $2,163 per person
$2,163
per person
Dec 28 - Jan 3
found 1 day ago
Roundtrip flight included
Raleigh (RDU) 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.
Canopy by Hilton Portland Waterfront
Price was $1,336, price is now $1,168 per person
$1,168
per person
Dec 31 - Jan 5
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Portland (PWM)
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. Popular attractions State Theatre and Thompson's Point are located nearby.
We highly enjoyed our stay here! Great restaurant downstairs, very clean, and helpful kind staff! Wish we could stay longer!
Reviewed on Nov 12, 2026
InnSeason Resorts The Falls at Ogunquit
Price was $1,044, price is now $923 per person
$923
per person
Dec 28 - Jan 3
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Portland (PWM)
Stay at this motel in Ogunquit. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Footbridge Beach and Ogunquit Beach are located nearby.
AWOL Kennebunkport
Price was $1,829, price is now $1,623 per person
$1,623
per person
Dec 28 - Jan 3
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Portland (PWM)
Stay at this 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.
Love Lark hotels. Afternoon cookies too!
Reviewed on Nov 12, 2026
The Beach House Inn
Price was $1,172, price is now $1,090 per person
$1,090
per person
Dec 28 - Jan 3
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to Portland (PWM)
Book a stay at this beach hotel in Kennebunk. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dock Square and Webhannet Golf Club are located nearby.
New Gloucester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
New Gloucester 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.
Mon, Feb 15 - Sat, Feb 20
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$224 Roundtrip, just found
$224
Roundtrip
just found
Wed, Feb 24 - Sat, Feb 27
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$256 Roundtrip, just found
$256
Roundtrip
just found
Sun, Feb 28 - Wed, Mar 10
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$267 Roundtrip, found 14 hours ago
$267
Roundtrip
found 14 hours ago
Sat, Dec 5 - Tue, Dec 8
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$277 Roundtrip, found 2 days ago
$277
Roundtrip
found 2 days ago
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