Cumberland County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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 Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was CA $1,008, price is now CA $536 per person
CA $536
per person
Nov 1 - Nov 3
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St

2 out of 5
Back Bay
Price was CA $2,417, price is now CA $1,572 per person
CA $1,572
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (139 reviews)
Clean. Great location.

Reviewed on Jul. 31, 2025

Maverick Suites at 400 Columbus Ave

Maverick Suites at 400 Columbus Ave

2 out of 5
South End
Price was CA $2,281, price is now CA $1,491 per person
CA $1,491
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (118 reviews)
Property is located in a very nice area. No frill, what they advertise, you get.

Reviewed on May 23, 2025

Maverick Suites at 89 Marion

Maverick Suites at 89 Marion

2 out of 5
Coolidge Corner South Side
Price was CA $1,950, price is now CA $1,289 per person
CA $1,289
per person
Oct 25 - Nov 1
found 3 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.4/10 Very Good! (247 reviews)
We stayed here for a few days while visiting Boston, once at the beginning of our trip and once at the end and found it very convenient to hop on the train and walk to lots of shops and restaurants. The first room was on the third floor and was very small but was fine for two people. It was clean and had everything we needed. Our second room was in the basement and much larger and again, very clean and well-appointed. We did have some noise from the room above us but it wasn't a big issue. They provide earplugs in each room which was great. I will plan to stay here again the next time I am in town visiting and would recommend this location for anyone staying in Brookline.

Reviewed on Jul. 16, 2025

Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Price was CA $1,563, price is now CA $1,038 per person
CA $1,038
per person
Oct 5 - Oct 10
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (162 reviews)
Phil’s property is immaculate and the rooms are very clean and will all required amenities. Phil’s hospitality is also top notch and it will be my place to stay in my future cape cod visits!!

Reviewed on Aug. 20, 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 $210 per night from Aug 26 to Aug 27
CA $210
CA $233 total
Aug 26 - Aug 27
includes taxes & fees
7.8/10 Good! (1,018 reviews)
"The hotel definitely needs a facelift but it was fine for a brief one night stay. The bed was comfortable. When the elevator got stuck on the 5th floor while we waited in the lobby, the front desk clerk was quick to walk up the 5 flights to address the situation."

Reviewed on Aug. 17, 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 $176 per night from Sep 2 to Sep 3
CA $176
CA $195 total
Sep 2 - Sep 3
includes taxes & fees
7.8/10 Good! (1,043 reviews)
"The hotel was good enough for the time being (felt safe, clean, etc) but was overall just an okay property."

Reviewed on Aug. 20, 2025

Ramada Plaza by Wyndham Portland
La Quinta Inn & Suites by Wyndham Portland

La Quinta Inn & Suites by Wyndham Portland

3 out of 5
340 Park Ave, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $198 per night from Sep 1 to Sep 2
CA $198
CA $219 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (2,215 reviews)
"Nice and clean"

Reviewed on Aug. 20, 2025

La Quinta Inn & Suites by Wyndham Portland
See all 2,194 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 $536. 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.