Cumberland Vacation Packages

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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.

Top Cumberland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
7.8/10 Good! (1,032 reviews)
Convenient location to highway

Reviewed on Jul. 27, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (1,523 reviews)
Excellent in a great location

Reviewed on Jul. 26, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
per person
Oct 17 - Oct 19
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

Canopy by Hilton Portland Waterfront

Canopy by Hilton Portland Waterfront

4 out of 5
Downtown Portland
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,004 reviews)
Nice place to stay. Great service.

Reviewed on Jul. 23, 2025

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
per person
Oct 1 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,338 reviews)
Great place to stay. Very walkable with lots of good restaurants

Reviewed on Jul. 28, 2025

Ready to book your vacation to Cumberland?

 

Choose your dates

Cumberland 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 27 to Aug 28
CA $150
CA $164 total
Aug 27 - Aug 28
includes taxes & fees
7.8/10 Good! (1,088 reviews)
"Staff was friendly and helpful"

Reviewed on Jul. 28, 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 Aug 27 to Aug 28
CA $208
CA $231 total
Aug 27 - Aug 28
includes taxes & fees
7.8/10 Good! (1,031 reviews)
"Everything about this hotel is lovely except the beds. The beds are horribly uncomfortable. Good location, plenty of parking, clean & well-kept. But they’ve been needing new mattresses. & for what i paid to stay there, i fully expected good sleep, which i didn’t get."

Reviewed on Jul. 27, 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 $205 per night from Jul 30 to Jul 31
CA $205
CA $223 total
Jul 30 - Jul 31
includes taxes & fees
8.4/10 Very Good! (1,420 reviews)
"Great economical stay in Portland area . Close to mall."

Reviewed on Jul. 26, 2025

Comfort Inn Airport
See all 1,859 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.
All Inclusive Vacations
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What to do in Cumberland

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

CA $91
per adult
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sunset Lighthouse Cruise Tour from Casco Bay

Sunset Lighthouse Cruise Tour from Casco Bay

CA $77
per adult
90% of travellers recommend
Sunset Lighthouse Cruise Tour from Casco Bay
Portland: Sightseeing Cruise to Portland Head Light

Portland: Sightseeing Cruise to Portland Head Light

CA $49
per adult
98% of travellers recommend
Portland: Sightseeing Cruise to Portland Head Light
See all activities in Cumberland

Frequently asked questions

How much does a Cumberland vacation package cost?
You can snap up a vacation package to this top destination from CA $1,077 on Expedia. But how much your vacation to Cumberland costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Cumberland?
To score cheap Cumberland vacation packages, plan your getaway outside of peak times such as school holidays. You'll generally find lower prices and better availability when it's less busy.
How many days is enough for Cumberland?
Usually, a handful of days is enough to check out the top attractions during your Cumberland vacation. But if you prefer to have some time to kick back or take day tours, think about extending your itinerary.
How to find the best Cumberland package deals?
Finding a cheap Cumberland package deal is a cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can tailor your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Cumberland package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Cumberland vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging hotels and flights individually. Better still, you can customize your Cumberland trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Cumberland?
Enjoy fantastic discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Cumberland vacation.
How to plan a trip to Cumberland?

  1. Pick your dates: What you want to do in Cumberland and your favourite season will help you decide when to travel.
  2. Calculate your budget: Ensure you have enough money to pay for everything from food and transportation to airfares and activities. Your accommodations will probably be the biggest expense during your trip to Cumberland.
  3. Determine how many days away: Start by compiling a list of the sights and activities you want to get to in Cumberland. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to find a Cumberland vacation package that brings all your bookings together.

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