Cumberland Foreside Vacations from $494

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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.
Bourne's Ocean Acres Ogunquit

Bourne's Ocean Acres Ogunquit

2.5 out of 5
Price was $676, price is now $494 per person
$494
per person
Sep 4 - Sep 7
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9/10 Wonderful! (255 reviews)
We stayed here for 2 night, a family of four. The room was on the second floor, we had a problem with the toilet not flushing properly and they tried fixing it but it just broke after one time of use and my husband ended fixing it himself. Water pressure was not great and the beds weren't anything special. The property is definitely outdated and needs work. I would not recommend and would not stay again.

Reviewed on Jun 27, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Save 100% on your flight
Price was $1,151, price is now $670 per person
$670
per person
Sep 4 - Sep 7
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9/10 Wonderful! (1,017 reviews)
Room was spotless, staff is friendly and breakfast had lots of options. Convenient location between Wells and Ogunquit. Would stay here again.

Reviewed on Jun 30, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Save 100% on your flight
Price was $2,541, price is now $1,700 per person
$1,700
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Portland (PWM)
9.6/10 Exceptional! (185 reviews)
We were only there for 1 night, but the innkeeper made a great suggestion for dinner. Overall a great place and would stay again.

Reviewed on Jun 26, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Save 100% on your flight
Price was $1,199, price is now $816 per person
$816
per person
Sep 6 - Sep 11
found 1 day ago
Roundtrip non-stop flight included
Tampa (TPA) to Portland (PWM)
8.6/10 Excellent! (1,003 reviews)
Très propre, personnel gentille

Reviewed on Jul 1, 2026

InnSeason Resorts The Falls at Ogunquit

InnSeason Resorts The Falls at Ogunquit

2.5 out of 5
Save 100% on your flight
Price was $818, price is now $592 per person
$592
per person
Sep 4 - Sep 7
found 5 hours ago
Roundtrip flight included
Chicago (CHI) to Portland (PWM)
9.4/10 Exceptional! (396 reviews)
A nice property to stay at. The room was clean but definitely areas were overlooked,like the extra pillows in the closet had hair on them. The pool was immaculate which we loved.

Reviewed on Jun 27, 2026

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Cumberland Foreside Hotel Deals

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $165 total per night from Jul 5 to Jul 6
$165 total
Jul 5 - Jul 6
Total with taxes and fees
8.6/10 Excellent! (2,179 reviews)
"The rooms were a bit outdated and breakfast was very poor. They ran out things to eat so quickly that guests were waiting a long time to have food to eat. Staff was very nice!"

Reviewed on Jul 1, 2026

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
$331 nightly
The price is $366 total per night from Jul 5 to Jul 6
$366 total
Jul 5 - Jul 6
Total with taxes and fees
9.4/10 Exceptional! (1,776 reviews)
"Great room. Excellent location nice courtyard for food and drinks with firepit"

Reviewed on Jul 1, 2026

Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundableReserve now, pay when you stay
$266 nightly
The price is $294 total per night from Jul 5 to Jul 6
$294 total
Jul 5 - Jul 6
Total with taxes and fees
9.4/10 Exceptional! (1,255 reviews)
"Front desk and the other staff we encountered were friendly, thoughtful, and accommodating. Lovely experience for out-of-state visitors looking to explore the adventures of the Portland culinary landscape."

Reviewed on Jul 1, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,443 properties in Cumberland Foreside
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.

Find the Best Cumberland Foreside Vacation Packages

Cumberland Foreside Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Top Sights
State Theatre, East End Beach and Portland Museum of Art

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Frequently asked questions

How much does a Cumberland Foreside vacation package cost?
You'll find cheap prices from $494 on Expedia for your Cumberland Foreside getaway. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Cumberland Foreside costs.
What are the cheapest months to go to Cumberland Foreside?
November, December and January are the best times to search for cheap Cumberland Foreside vacation packages. Traveling in less busy periods means you can generally find lower prices on flights and accommodations.
How many days is enough for Cumberland Foreside?
The ideal length for your Cumberland Foreside vacation depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to check out all the major attractions and discover some hidden gems along the way.
How to find the best Cumberland Foreside package deals?
Start your search for a Cumberland Foreside package deal by entering your travel dates and destination under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Cumberland Foreside package deal straight away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Cumberland Foreside escape off to a flying start.
Is it cheaper to book a Cumberland Foreside vacation as a package?
You can enjoy significant savings on your Cumberland Foreside break by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Cumberland Foreside?
If you're planning a spontaneous Cumberland Foreside adventure, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find awesome deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Cumberland Foreside vacation packages?
Jet off on your perfect trip to Cumberland Foreside with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait until your next paycheck — we've partnered with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, it's easy to budget for your trip and snap up travel deals before they sell out.

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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.