Cumberland Foreside Vacations from $591

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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

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $936, price is now $591 per person
$591
per person
Apr 2 - Apr 7
found 18 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.2/10 Wonderful! (1,668 reviews)
Reduce noise from patrons near elevator and coffee area on second floor, very loud

Reviewed on Jan 10, 2026

The McKernan Inn

The McKernan Inn

3 out of 5
Price was $960, price is now $697 per person
$697
per person
Apr 2 - Apr 7
found 18 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9/10 Wonderful! (83 reviews)
Gorgeous grounds and venue with a beautiful oceanfront view. Plenty of parking as part of SMCC campus. Short drive to downtown Portland and lots of stores around in South Portland. Very unique experience, would stay again without hesitation!

Reviewed on Dec 27, 2025

The Docent’s Collection – Thompson Block

The Docent’s Collection – Thompson Block

3.5 out of 5
Downtown Portland
Price was $923, price is now $676 per person
$676
per person
Apr 2 - Apr 7
found 18 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.6/10 Exceptional! (249 reviews)
Room and amenities were great and ease of access to both the room and surrounding businesses is ideal.

Reviewed on Jan 10, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was $852, price is now $647 per person
$647
per person
Apr 2 - Apr 7
found 18 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.4/10 Exceptional! (1,512 reviews)
The location of this hotel was perfect in the old port district! Beautiful and simple hotel! The gym was great and staff was good! Would definitely stay again!

Reviewed on Jan 13, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was $1,275, price is now $986 per person
$986
per person
Apr 2 - Apr 7
found 18 hours ago
Roundtrip non-stop flight included
Denver (DEN) to Portland (PWM)
9.4/10 Exceptional! (288 reviews)
Room was ready early friendly staff and room is better than expected

Reviewed on Nov 16, 2025

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Cumberland Foreside Hotel Deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
$78 nightly
The price is $87 total per night from Jan 18 to Jan 19
$87 total
Jan 18 - Jan 19
Total with taxes and fees
8/10 Very Good! (1,322 reviews)
Very nice

Reviewed on Jan 11, 2026

Clarion Hotel Portland Airport ME
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
$98 nightly
The price is $108 total per night from Feb 8 to Feb 9
$108 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Room was clean and had all amenities.

Reviewed on Jan 6, 2026

The Westin Portland Harborview
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $147 total per night from Feb 3 to Feb 4
$147 total
Feb 3 - Feb 4
Total with taxes and fees
9.4/10 Exceptional! (1,573 reviews)
Room is awesome , love the hotel.

Reviewed on Jan 12, 2026

Portland Regency Hotel & Spa
See all 2,285 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 $591 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.