Cumberland Foreside Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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!

Top Cumberland Foreside Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Inn at Diamond Cove

Inn at Diamond Cove

3.5 out of 5
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (177 reviews)
We had an amazing stay! What a gem of an experience - all of the staff was wonderful - Antonio at the lobby cafe was so kind and friendly and Kayla at concierge always went above and beyond!!

Reviewed on Jul. 20, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,008 reviews)
The oceanview was breathtaking, the morning sun was stunning

Reviewed on Jul. 22, 2025

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,338 reviews)
Charming and very welcoming staff. We were able to walk everywhere easily. Great location!

Reviewed on Jul. 23, 2025

Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
Downtown Portland
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Portland (PWM)
8.8/10 Excellent! (1,153 reviews)
Great location and wonderful customer service! Really quiet in the room so you can hear quite a bit outside, shower pressure wasn't great but bed was comfortable and room was clean. There was some construction going on that we weren't aware of but it wasn't a deal breaker. Love that they offer airport shuttle!

Reviewed on Jul. 22, 2025

Chebeague Island Inn

Chebeague Island Inn

4 out of 5
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (72 reviews)
Great place to go and relax for a few days.

Reviewed on Jul. 20, 2025

Ready to book your vacation to Cumberland Foreside?

 

Choose your dates

Cumberland Foreside Hotel Deals

Days Inn by Wyndham Airport/Maine Mall

Days Inn by Wyndham Airport/Maine Mall

2 out of 5
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Aug 24 to Aug 25
CA $150
CA $164 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,069 reviews)
Quiet, clean
"Good bed, clean, nice basic hotel. Only complaint was that the bathroom door stuck. There also was not much pressure for the cold water in the sink. Quiet even though it seemed full and was beside a busy road. Very close to the mall, dining, and turnpike."

Reviewed on Jul. 24, 2025

Days Inn by Wyndham Airport/Maine Mall
Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Jul 29 to Jul 30
CA $208
CA $231 total
Jul 29 - Jul 30
includes taxes & fees
7.8/10 Good! (1,023 reviews)
"Excellent"

Reviewed on Jul. 23, 2025

Clarion Hotel Portland
Comfort Inn Airport

Comfort Inn Airport

2.5 out of 5
90 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Jul 30 to Jul 31
CA $184
CA $200 total
Jul 30 - Jul 31
includes taxes & fees
8.4/10 Very Good! (1,416 reviews)
"Very handy (airport shuttle), reasonably priced hotel with friendly staff."

Reviewed on Jul. 23, 2025

Comfort Inn Airport
See all 2,413 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Cumberland Foreside vacation package cost?
You'll find cheap prices from CA $858 on Expedia for your Cumberland Foreside getaway. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Cumberland Foreside costs.
What are the cheapest months to go to Cumberland Foreside?
If you're looking to snag a cheap Cumberland Foreside vacation package, consider travelling in January, February and March. You'll typically find better prices on accommodations and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Cumberland Foreside?
We recommend planning a Cumberland Foreside vacation for a minimum of 2 days. This will allow you time to tick off key attractions including Gilsland Farm Audubon Centre and Mackworth Island State Park, as well as explore neighbourhoods like East Deering and Falmouth Foreside. You could even make time for a day trip (or two) outside of Cumberland Foreside.
How to find the best Cumberland Foreside package deals?
Begin your search for a Cumberland Foreside package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the ideal Cumberland Foreside package deal right away, just switch up your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Cumberland Foreside adventure off to a flying start.
Is it cheaper to book a Cumberland Foreside vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still get the freedom to create a customized Cumberland Foreside vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Cumberland Foreside?
If you've got your Cumberland Foreside vacation dates confirmed, book as early as you can to grab some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous getaways? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Cumberland Foreside?

  1. Choose when to get away: Check your calendar and pack your bags. Your preferred season and the activities on offer will also help you decide when to vacation in Cumberland Foreside.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and food to experiences and flights. Your hotel will probably be the largest expense during your trip to Cumberland Foreside.
  3. Determine how many days away: Start by listing all the attractions and activities you'd like to experience in Cumberland Foreside. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your airfare and accommodations: Once you've nailed down your dates and duration, lock in the perfect Cumberland Foreside vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.