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.
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?

 

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 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 Aug 11 to Aug 12
CA $208
CA $231 total
Aug 11 - Aug 12
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 1,854 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.
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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 $858 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.