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Cumberland Foreside Vacation Packages

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Cumberland Foreside Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Nautical Mile

Nautical Mile

2.5 out of 5
Price was $712, price is now $569 per person
$569
per person
Dec 9 - Dec 12
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this aparthotel in Wells. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Moody Beach and Footbridge Beach are located nearby.
I've stayed at the Nautical Mile many times! The rooms are perfect for a get-away! The pool is always ready to cool off in and the people, both working at the Nautical Mile and guests are very friendly.

Reviewed on Sep 8, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,294, price is now $1,026 per person
$1,026
per person
Dec 25 - Dec 30
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this hotel in Ogunquit. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Marginal Way and Ogunquit Beach are located nearby.

White Barn Inn & Spa, Auberge Collection

White Barn Inn & Spa, Auberge Collection

5 out of 5
Price was $2,367, price is now $2,013 per person
$2,013
per person
Dec 25 - Dec 30
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this luxury hotel in Kennebunk. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Dock Square and Kennebunkport Village Green are located nearby.

84 Main

84 Main

4 out of 5
Price was $1,026, price is now $873 per person
$873
per person
Dec 24 - Dec 27
found 1 day 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

Cape Arundel Inn and Resort

Cape Arundel Inn and Resort

3 out of 5
Price was $1,949, price is now $1,683 per person
$1,683
per person
Dec 25 - Dec 30
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Stay at this guesthouse in Kennebunkport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Dock Square and Colony Beach are located nearby.
A special hotel. Beautiful setting, unique one-of-kind inn. So very Maine coastal. Staff could not have been more appropriately available, helpful, kind. Lovely experience all around.

Reviewed on Oct 26, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Price was $1,898, price is now $1,652 per person
$1,652
per person
Dec 25 - Dec 30
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Every thing was great

Reviewed on Oct 27, 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Price was $681, price is now $596 per person
$596
per person
Jan 23 - Jan 25
found 23 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
Stay at this hotel in Portland. Enjoy free WiFi, parking (surcharge), and premium TV channels. Popular attractions State Theatre and Thompson's Point are located nearby.
The loft we stayed in was excellent. Well maintained, large and very clean. The kitchen was well equipped and spacious. Such an easy walk to lots of stores and restaurants. We utilized street parking as it was more of the off season but that was easy. The staff was very helpful during check-in.

Reviewed on Oct 30, 2026

Inn on Shore Road

Inn on Shore Road

2 out of 5
Price was $1,606, price is now $1,405 per person
$1,405
per person
Dec 25 - Dec 30
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
Book a stay at this spa guesthouse in Ogunquit. Enjoy free breakfast, free WiFi, and a full-service spa. Popular attractions Ogunquit Beach and Marginal Way are located nearby.
The homey feel, great beds and pillows. Rooms were spotless. The staff were friendly and morning breakfast perfect! I can’t wait to go back again! Happy customer Julie E

Reviewed on Oct 27, 2026

Cumberland Foreside Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Nautical Mile

Nautical Mile

2.5 out of 5
Price was $712, price is now $569 per person
$569
per person
Dec 9 - Dec 12
found 20 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
84 Main

84 Main

4 out of 5
Price was $1,026, price is now $873 per person
$873
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,032, price is now $883 per person
$883
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was $949, price is now $821 per person
$821
per person
Dec 10 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)

Cumberland Foreside Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $1,030, price is now $854 per person
$854
per person
Dec 25 - Dec 30
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was $1,294, price is now $1,026 per person
$1,026
per person
Dec 25 - Dec 30
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was $1,428, price is now $1,213 per person
$1,213
per person
Dec 25 - Dec 30
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
White Barn Inn & Spa, Auberge Collection

White Barn Inn & Spa, Auberge Collection

5 out of 5
Price was $2,367, price is now $2,013 per person
$2,013
per person
Dec 25 - Dec 30
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Delta
Tue, Dec 1 - Sat, Dec 5
JFK
John F. Kennedy Intl.
PWM
Portland Intl. Jetport
$207 Roundtrip, found 1 hour ago
$207
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Dec 1 from John F. Kennedy Intl. to Portland Intl. Jetport, returning Sat, Dec 5, priced at $207 found 1 hour ago
United
Sat, Dec 5 - Tue, Dec 15
EWR
Newark Liberty Intl. Airport
PWM
Portland Intl. Jetport
$207 Roundtrip, just found
$207
Roundtrip
just found
Select United flight, departing Sat, Dec 5 from Newark Liberty Intl. Airport to Portland Intl. Jetport, returning Tue, Dec 15, priced at $207 just found
American Airlines
Thu, Nov 26 - Wed, Dec 2
RDU
Raleigh - Durham Intl.
PWM
Portland Intl. Jetport
$210 Roundtrip, just found
$210
Roundtrip
just found
Select American Airlines flight, departing Thu, Nov 26 from Raleigh - Durham Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $210 just found
Breeze Airways
Wed, Nov 11 - Wed, Dec 2
MCO
Orlando Intl.
PWM
Portland Intl. Jetport
$214 Roundtrip, just found
$214
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Portland Intl. Jetport, returning Wed, Dec 2, priced at $214 just found