Cumberland Vacations from $420

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Your Cumberland Vacation

Say bye-bye to planning hassles and hello to a Cumberland vacation package. With everything organized before you go, you can focus on discovering this city, starting with Parkside, which is good for festivals, markets and walking. Not sure what to do or see first during your trip to Cumberland? Don't miss well-known attractions such as Twin Brook Recreation Area. Expedia can help you escape the everyday. Tailor your vacation to Cumberland to suit your style of travel, whatever that may be.

The Latest Cumberland vacation packages

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Save 100% on your flight
Price was $608, price is now $420 per person
$420
per person
May 23 - May 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9/10 Wonderful! (1,000 reviews)
The room was very clean!

Reviewed on Oct 31, 2025

84 Main

84 Main

4 out of 5
Save 100% on your flight
Price was $880, price is now $588 per person
$588
per person
Apr 20 - Apr 26
found 13 hours ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.8/10 Exceptional! (56 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.

Reviewed on Dec 29, 2025

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
Price was $1,683, price is now $1,154 per person
$1,154
per person
May 24 - May 30
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.8/10 Exceptional! (93 reviews)
Clean and comfortable. The gym was great.

Reviewed on Mar 6, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was $1,461, price is now $1,034 per person
$1,034
per person
May 24 - May 30
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Portland (PWM)
9.2/10 Wonderful! (1,766 reviews)
Everything was perfect

Reviewed on Mar 11, 2026

Cliff House Maine

Cliff House Maine

4.5 out of 5
Bald Head
Save 100% on your flight
Price was $1,214, price is now $907 per person
$907
per person
May 23 - May 25
found 1 day ago
Roundtrip flight included
New York (NYC) to Portland (PWM)
9.4/10 Exceptional! (1,005 reviews)
Great hotel with super nice views!

Reviewed on Mar 1, 2026

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Discover the most popular places to visit in Cumberland

Twin Brook Recreation Area

Explore the great outdoors at Twin Brook Recreation Area, a lovely green space in Cumberland Center. Stroll along the area's waterfront, or simply savor its top-notch restaurants.

Twin Brook Recreation Area

What to do in Cumberland

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

$17
per traveler
Portland Smartphone Audio Tour: Self-Guided Drive
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

$10
per traveler
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

$17
per traveler
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
See all activities in Cumberland

Cumberland 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 29 to Mar 30
$108 total
Mar 29 - Mar 30
Total with taxes and fees
8.8/10 Excellent! (1,009 reviews)
Just a great place to stay

Reviewed on Mar 10, 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! (1,403 reviews)
Breakfast doesn’t even start until 7. We had to leave before that. Many people stay for business and are gone by then. Also it was very cold and icy. The parking lot was pure ice and there was no salt or sand put down. We both almost landed on our faces and we had 2 children with us.

Reviewed on Mar 11, 2026

Clarion Hotel Portland Airport ME
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
$123 nightly
The price is $137 total per night from Mar 17 to Mar 18
$137 total
Mar 17 - Mar 18
Total with taxes and fees
9.4/10 Exceptional! (1,600 reviews)
This was an amazing hotel! We had a great relaxing time here. We are definitely planning to visit Portland again in the summer and this will be our go to place to stay!

Reviewed on Mar 11, 2026

Portland Regency Hotel & Spa
See all 1,803 properties in Cumberland
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 Vacation Packages

Cumberland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)

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Frequently asked questions

How much does a Cumberland vacation package cost?
You'll find cheap prices from $420 on Expedia for your Cumberland escape. However, a range of factors like the hotel choice, length of stay and season will determine how much your vacation to Cumberland costs.
What are the cheapest months to go to Cumberland?
If you'd like to book a cheap Cumberland vacation package, consider visiting in November, December and January. You'll generally find better prices on airfares and hotels during these months — perfect for travelers wishing to save money.
How many days is enough for Cumberland?
The ideal duration of your Cumberland vacation depends on what you'd like to see and do. Typically, a handful of days to a week will give you enough time to visit all the major sights and explore some hidden treasures along the way.
How to find the best Cumberland package deals?
Begin your search for a Cumberland package deal by entering your destination and preferred trip dates under our "Packages" tab. Then select some filters, like "Guest rating" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Cumberland package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Cumberland getaway off to a flying start.
Is it cheaper to book a Cumberland vacation as a package?
You can enjoy significant savings on your Cumberland retreat by booking a customized vacation package. Check the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Cumberland?
If you're considering a spur-of-the-moment Cumberland adventure, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Cumberland vacation packages?
Set off on your dream getaway to Cumberland with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait until the next payday — we've teamed up with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans mean you can spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's easy to budget for your trip and snap up bargains while they last.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.