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

A lighthouse, a white house with a red roof, and rocky coastline at sunset.
FlightsFlightsHotelsHotels

Portland

Portland

Top Cumberland County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was CA $1,217, price is now CA $854 per person
CA $854
per person
Aug 18 - Aug 21
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9/10 Wonderful! (1,254 reviews)
The staff were all super kind and helpful. I really enjoyed the old school and glam aspect of the hotel but did lead to a few things. For example a gap under the door meant a bright light in the room which hinder sleep, room had slight smell of smoke and sound of water dripping. Great location, safe and clean.

Reviewed on Jul 12, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Price was CA $2,377, price is now CA $1,445 per person
CA $1,445
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great 👍

Reviewed on Jul 11, 2026

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $2,986, price is now CA $1,997 per person
CA $1,997
per person
Sep 23 - Sep 29
found 19 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) 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

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Price was CA $1,674, price is now CA $1,136 per person
CA $1,136
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on May 23, 2026

Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was CA $1,775, price is now CA $1,212 per person
CA $1,212
per person
Aug 21 - Aug 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
Clean room and very attentive staff! P

Reviewed on Jul 12, 2026

Cumberland County Hotel Deals

Clarion Hotel Portland Airport ME

Clarion Hotel Portland Airport ME

2.5 out of 5
1230 Congress St Portland ME
Fully refundable
The price is CA $203 per night from Jul 26 to Jul 27
CA $203
CA $225 total
Jul 26 - Jul 27
includes taxes & fees
8.2/10 Very good! (1,551 reviews)
"Could use an update"

Reviewed on Jul 12, 2026

Clarion Hotel Portland Airport ME
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $452 per night from Jul 26 to Jul 27
CA $452
CA $539 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (1,264 reviews)
"The room was perfect and spacious; the only downside was the view."

Reviewed on Jul 12, 2026

Cambria Hotel Portland Downtown-Old Port
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $559 per night from Jul 19 to Jul 20
CA $559
CA $673 total
Jul 19 - Jul 20
includes taxes & fees
9.4/10 Exceptional! (1,783 reviews)
"Our stay was great - the location of this hotel is perfect, the staff was friendly and our room was really nice. Every morning, there was a fully stocked pantry with snacks and drinks for guests on each floor. We had a great stay and would recommend this place highly!"

Reviewed on Jul 12, 2026

Portland Harbor Hotel
See all 2,320 properties in Cumberland County
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
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Frequently asked questions

How much does a Cumberland County vacation package cost?
Custom build your Cumberland County vacation package from an affordable CA $854. 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

A multi-story brick building with a large arched window and a sign that reads "STATE".

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.
See properties

What to do in Cumberland County

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

CA $109
per adult
88% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

CA $24
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
Portland, Maine: Hidden Histories Guided Walking Tour

Portland, Maine: Hidden Histories Guided Walking Tour

CA $77
per adult
Portland, Maine: Hidden Histories Guided Walking Tour
See all activities in Cumberland County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.