
Cumberland Foreside Vacations from $613
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Your Cumberland Foreside Vacation
Lock in a Cumberland Foreside vacation package and get set to experience all this lively city has to offer. Consider basing yourself in the neighborhood of Parkside, which is good for festivals, markets and walking. Winslow Memorial Park, Gilsland Farm Audubon Center and Little John Island Preserve are just a few of the many attractions worth exploring during your trip to Cumberland Foreside. Stop daydreaming and start adventuring. Check out the multitude of options on Expedia today and put your Cumberland Foreside vacation plans into gear!
The Latest Cumberland Foreside vacation packages
Price found within the past 48 hours. Click for updated prices.

Portland Harbor Hotel
Downtown Portland
Save 100% on your flight
Price was $865, price is now $613 per person
$613
per person
Nov 3 - Nov 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.2/10 Wonderful! (1,552 reviews)
Beautiful hotel, great location
Reviewed on Aug 28, 2025

The Docent's Collection
Downtown Portland
Save 100% on your flight
Price was $1,114, price is now $740 per person
$740
per person
Nov 3 - Nov 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.6/10 Exceptional! (228 reviews)
Very modern and new condition. Digital key worked pretty well and convenient. Lots of good restaurants within walking distance. We enjoyed our stay.
Reviewed on Aug 25, 2025

Inn By The Sea
Save 100% on your flight
Price was $1,430, price is now $1,035 per person
$1,035
per person
Nov 3 - Nov 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (279 reviews)
We chose Inn by the Sea because it was advertised as a “pet-friendly” property with beach access for pets, which was a key factor in our decision. Unfortunately, our experience didn’t quite align with those expectations.
We arrived on a Sunday around noon and, as expected, our room wasn’t ready (check-in is at 4:00pm). However, unlike many hotels, we were not offered anything while we waited — no welcome drink, light refreshment, or even an early check-in estimate — despite having to wait the full four hours.
Once we checked in, we were told our assigned room was not pet-friendly, and we would be charged for any accidents — despite booking under the premise that this was a pet-friendly stay. Additionally, the restaurant only allows pets in the outdoor seating area, and the pool area is not pet-friendly at all. So while the hotel does accommodate pets in some areas, it’s misleading to call it fully pet-friendly when the main guest amenities are off-limits.
That said, the property is beautiful and most of the staff were friendly and professional, which we appreciated. But overall, if you’re traveling with a pet and hoping for a truly integrated experience, this may not be the best fit.
Reviewed on Aug 18, 2025

Kennebunkport Captains Collection
Save 100% on your flight
Price was $1,129, price is now $835 per person
$835
per person
Nov 3 - Nov 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Portland (PWM)
9.4/10 Exceptional! (609 reviews)
Walkable to downtown Kennebunkport shopping.
Reviewed on Aug 24, 2025

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View all tripsCumberland Foreside Hotel Deals

Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $168 total per night from Sep 2 to Sep 3
$168 total
Sep 2 - Sep 3
Total with taxes and fees

Days Inn by Wyndham Airport/Maine Mall
461 Maine Mall Rd, South Portland, ME
$116 nightly
The price is $127 total per night from Aug 31 to Sep 1
$127 total
Aug 31 - Sep 1
Total with taxes and fees
7.8/10 Good! (1,248 reviews)
"the breakfast was great"
Reviewed on Aug 25, 2025

Ramada Plaza by Wyndham Portland
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $134 total per night from Sep 1 to Sep 2
$134 total
Sep 1 - Sep 2
Total with taxes and fees
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.