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 Head Light which includes rocky coastline, general coastal views and a lighthouse
FlightsFlightsHotelsHotels

Portland

Portland

Top Cumberland County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Aug 29 - Sep 2
found 22 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I would rate this property quite high. Elegant and clean with extremely friendly staff. Great location and simply a lovely ambiance.

Reviewed on Jul. 21, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul. 14, 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
Save 100% on your flight
per person
Sep 7 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,008 reviews)
everything very clean, wonderful place.

Reviewed on Jul. 19, 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 2
found 2 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
It is a luxury hotel with nice view. The staff is very efficient and friendly. The price is reasonable.

Reviewed on Jul. 21, 2025

The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
per person
Aug 31 - Sep 5
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (31 reviews)
Staff were very kind and attentive. Building had been upgraded and well maintained. It felt a little odd being on campus and being away from the trendy areas but loved the view of the harbor and supporting the hospitality students.

Reviewed on Jul. 12, 2025

Cumberland County Hotel Deals

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 $209 per night from Jul 27 to Jul 28
CA $209
CA $231 total
Jul 27 - Jul 28
includes taxes & fees
7.8/10 Good! (1,013 reviews)
"."

Reviewed on Jul. 19, 2025

Clarion Hotel Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Jul 28 to Jul 29
CA $212
CA $235 total
Jul 28 - Jul 29
includes taxes & fees
7.6/10 Good! (1,041 reviews)
Good and clean
"Good location for us and very convenient to all the areas nearby that we had to go. We enjoyed the quiet and were able to easily and quickly get additional towels and supplies as we needed."

Reviewed on Jul. 14, 2025

Ramada Plaza by Wyndham Portland
The Westin Portland Harborview

The Westin Portland Harborview

4 out of 5
157 High St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $395 per night from Aug 17 to Aug 18
CA $395
CA $444 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"The hotel was very nice. Our room was elegant and quiet. The hotel lobby and front entrance are not ADA friendly. Lots of stairs and no ramps when you first enter the building. When we exited off of the highway and into Portland there were a lot of homeless people and graffiti on the buildings. Being ..."

Reviewed on Jul. 19, 2025

The Westin Portland Harborview
See all 2,244 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

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Cumberland County vacation package cost?
Custom build your Cumberland County vacation package from an affordable CA $1,087. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.