Cumberland Foreside Vacations from $376

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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.
The Wolfeboro Inn

The Wolfeboro Inn

3.5 out of 5
Save 100% on your flight
Price was $529, price is now $376 per person
$376
per person
May 1 - May 4
found 22 hours ago
Roundtrip flight included
Philadelphia (PHL) to Portland (PWM)
8.2/10 Very Good! (544 reviews)
We had a very nice room. We were given a free upgrade. Staff was very accommodating. Property is right in the center of town within walking distance of restaurants, shops, the lake and X-country skiing. We had a great time.

Reviewed on Mar 1, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,732, price is now $1,175 per person
$1,175
per person
May 23 - May 30
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.2/10 Wonderful! (1,765 reviews)
Nice place, clean room, courteous staff, NO FREE PARKING! :(

Reviewed on Feb 28, 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 $2,265, price is now $1,634 per person
$1,634
per person
May 23 - May 30
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The whole was cozy! Well curated style and knowledgeable staff.

Reviewed on Jan 5, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Save 100% on your flight
Price was $2,228, price is now $1,658 per person
$1,658
per person
May 23 - May 30
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.4/10 Exceptional! (300 reviews)
Inn by the Sea was an excellent place to stay. The front desk during check-in was 5 star and very helpful. Our room was clean, cozy and comfortable. The spa was wonderful and relaxing. The restaurant food was delicious, a lot of variety. I would recommend the Inn By The Sea to my friends and family.

Reviewed on Mar 1, 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $2,103, price is now $1,576 per person
$1,576
per person
May 23 - May 30
found 19 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Portland (PWM)
9.8/10 Exceptional! (86 reviews)
Location is excellent. Short walking distance to every good restaurant and shop. The property was very nice and clean. The kitchen is very well equipped. The gym is very good sized for the size of the apartment building with 13 units in it. The management’s communication was prompt and friendly and responded to all of our wishes. However, the place is advertised as a hotel, but don’t expect services as in a hotel. It resembles more a short term rental home - no cleaning service and no lobby. Otherwise everything was very nice in the apartment and we had a great time.

Reviewed on Jan 3, 2026

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Cumberland Foreside Hotel Deals

The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St Portland ME
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $108 total per night from Mar 22 to Mar 23
$108 total
Mar 22 - Mar 23
Total with taxes and fees
8.8/10 Excellent! (1,004 reviews)
The room was very clean, check in and out was easy, parking was affordable.

Reviewed on Mar 3, 2026

The Westin Portland Harborview
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
$77 nightly
The price is $85 total per night from Mar 24 to Mar 25
$85 total
Mar 24 - Mar 25
Total with taxes and fees
8/10 Very Good! (1,388 reviews)
I eventually had to leave this property in search of another hotel. This hotel, it left very much to be desired.The room I was in, I ended up being in four different rooms, because one particular staff person kept moving me.And I started getting very sick and asked the front desk if dogs had been ...

Reviewed on Mar 3, 2026

Clarion Hotel Portland Airport ME
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
$116 nightly
The price is $129 total per night from Mar 19 to Mar 20
$129 total
Mar 19 - Mar 20
Total with taxes and fees
9.4/10 Exceptional! (1,168 reviews)
Easy check in and friendly staff. Food was good room was big and with nice view.

Reviewed on Mar 2, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,261 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 $376 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.