Cumberland County Vacation Packages
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Your Cumberland County Vacation
When adventure calls, answer it with a tailor-made vacation package to Cumberland County. Wherever your journey takes you and whatever you have planned, get set to discover a destination with so much to offer. With so many things to explore on a trip to Cumberland County, it can be hard to know where to start. Kick off your journey in Portland at Maine Mall and Thompson's Point — two popular attractions here. Another city to add to your itinerary is Brunswick. Don't miss Maine Street and LL Bean Flagship Store. From the instant you book your Cumberland County vacation to the second you come back home, Expedia will take care of you every step of the way.
Top vacation destinations in Cumberland County
Portland
Scarborough
South Portland
Freeport
Brunswick
Top Cumberland County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Boston Lodge and Suites
Dorchester
CA $811
per person
Oct 21 - Oct 23
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very good! (190 reviews)
Parking was not easy. It was advertised as free parming and the explanation made it seem simple enough but finding free street parking in the area is not easy and you co stantly have to move your vehicles.
Reviewed on May 19, 2026
Nantucket Inn
CA $1,689
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Boston (BOS)
9.2/10 Wonderful! (777 reviews)
20 min from Main Street but an hourly shuttle bus to and from main street was helpful. Near the airport but was not noisy. Room was not ready at 4:00PM checkin but staff was helpful in finding an alternate.
Reviewed on Aug 26, 2026
Cumberland County Hotel Deals
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
CA $152
CA $168 total
Sep 7 - Sep 8
includes taxes & fees
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
CA $152
CA $168 total
Sep 13 - Sep 14
includes taxes & fees
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
CA $348
CA $385 total
Aug 30 - Aug 31
includes taxes & fees
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.
Frequently asked questions
How much does a Cumberland County vacation package cost?
Custom build your Cumberland County vacation package from an affordable CA $811. Choose from any combination of flights, hotels and rental cars to put together the escape you've been dreaming about. Don't forget to add on a few experiences or activities!
How do I get a cheap travel package to Cumberland County?
Bundling your hotel and flight with Expedia won't just save precious time — it'll save you dollars too. A Cumberland County vacation package makes it a breeze to create the perfect trip. With more than 550 airlines across the world to select from, finding flights that fit your schedule won't be a hassle. Not only that, we've got over 1,000,000 properties globally to take your pick of. Now that's what you call choice. Whatever your budget, Expedia puts more of the world within your reach.
Where should I stay in Cumberland County?
If you've always wanted to explore Portland Head Light and University of Southern Maine, the city of Portland is calling your name.
What are the top hotels in Cumberland County?
The Westin Portland Harborview and La Quinta Inn & Suites by Wyndham Portland know how to make their guests feel at home in Portland. If your travel plans also include Bridgton, look up Portland Harbor Hotel and Casco Bay Hotel, Ascend Hotel Collection. Both are popular with travelers.
How far in advance should I book my Cumberland County vacation?
Travelers are usually able to compare international airfares on Expedia up to 12 months prior to departure. Booking late? With a little bit of luck, it's still possible to purchase an affordable ticket just weeks before your flight.
What does an Expedia Cumberland County travel package include?
Hotels, car rentals and flights — we bring you the best deals. All you have to do is figure out your preferred combination. After you've made your booking, you can add on the fun stuff like tours and experiences. Our travel packages make it easy to put together an unforgettable Cumberland County escape.
What should I know before booking a Cumberland County travel package?
An Expedia travel package can be customized for your budget and is a terrific way to make your hard-earned dollars stretch further. How little or much you include is totally up to you. Rental cars, hotels and flights — come up with a combination that suits your style.
Can I choose my airline with a Cumberland County Expedia vacation package?
Expedia offers access to more than 550 airline partners globally, so you certainly can. Just choose the airline you want and craft the perfect Cumberland County escape.
If I'm not able to travel, can I cancel my Cumberland County vacation package?
Yes, it's possible to cancel your Cumberland County booking if your travel plans have been upended. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to change or cancel free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to learn more.
Stay near popular Cumberland County attractions
LL Bean Flagship Store
9.2/10 (1,289 reviews)
During your trip to Freeport, you can enjoy retail therapy at LL Bean Flagship Store. Stroll along the area's waterfront or simply enjoy its seafood restaurants.
Portland Head Light
9.4/10 (928 reviews)
Look out across the Atlantic Ocean from Portland’s iconic white lighthouse, which has presided over the southern Maine coastline since the 18th century.
State Theatre
8.8/10 (392 reviews)
The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.
Higgins Beach
8.8/10 (308 reviews)
At the mouth of the Spurwink River in Scarborough, take a stroll on the white sand or paddle a kayak over gentle waves.
Maine Mall
8.4/10 (1,708 reviews)
You can do some window-shopping at Maine Mall during your visit to South Portland. Experience the area's entertainment choices and great live music.
Thompson's Point
8.8/10 (376 reviews)
Commune with nature and explore the great outdoors at Thompson's Point during your travels in Portland. Stroll along the waterfront or attend a sporting event in the area.
Cross Insurance Arena
8.6/10 (275 reviews)
Catch an event at Cross Insurance Arena during your trip to Portland. Stroll along the area's waterfront or experience its great live music.
What to do in Cumberland County
Sunset Windjammer Cruise Along the Coast of Portland Maine
CA $109
per adult
90% of travellers recommend
Morning Lighthouse Cruise Along the Coast of Portland Maine
CA $83
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
