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

FlightsFlightsHotelsHotels

Portland

Portland

Top Cumberland County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Price was CA $1,319, price is now CA $929 per person
CA $929
per person
Jun 28 - Jun 30
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff

Reviewed on Mar 9, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $3,893, price is now CA $2,142 per person
CA $2,142
per person
Jun 13 - Jun 16
found 4 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
clean room. friendly and helpful staff. good breakfast in reasonable price. hope they have a boutique store to sell Langham signature products, especially the home fragrance products.

Reviewed on Mar 29, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was CA $2,230, price is now CA $1,458 per person
CA $1,458
per person
Jun 13 - Jun 16
found 4 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
8.6/10 Excellent! (1,395 reviews)
Great hotel, in the middle of downtown, walking distance from td garden, friendly staff and great amenities, will be back for sure

Reviewed on Mar 30, 2026

Summer House Hotel

Summer House Hotel

2 out of 5
Price was CA $2,516, price is now CA $1,771 per person
CA $1,771
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
No reviews
The Westin Boston Seaport District

The Westin Boston Seaport District

4 out of 5
Seaport District
Price was CA $1,543, price is now CA $1,090 per person
CA $1,090
per person
Jun 13 - Jun 16
found 4 hours ago
Roundtrip flight included
Halifax (YHZ) to Boston (BOS)
9.2/10 Wonderful! (2,404 reviews)
Great hotel from start to finish. Highly recommend

Reviewed on Mar 22, 2026

Cumberland County Hotel Deals

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 $181 per night from May 3 to May 4
CA $181
CA $200 total
May 3 - May 4
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Breakfast was really good, free shuttle to town helped, the only problem was the bad was too small, but the rest was really good.

Reviewed on Mar 29, 2026

The Westin Portland Harborview
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 $119 per night from Apr 22 to Apr 23
CA $119
CA $132 total
Apr 22 - Apr 23
includes taxes & fees
8/10 Very Good! (1,405 reviews)
Everything was good except be nice if they didn’t charge for breakfast

Reviewed on Mar 31, 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 $144 per night from Apr 5 to Apr 6
CA $144
CA $197 total
Apr 5 - Apr 6
includes taxes & fees
9.4/10 Exceptional! (1,181 reviews)
Breakfast was excellent as was the room. We especially liked the room which was bright and airy and provided a view of the rooftop lounge. The decor and the layout of the room was very contemporary and a welcome change from the typical hotel room. Location was great, too!

Reviewed on Apr 2, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,205 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.
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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 $929. 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.