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.
Hotel Ivy Boston Common

Hotel Ivy Boston Common

2.5 out of 5
Bay Village
Price was CA $1,871, price is now CA $1,239 per person
CA $1,239
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.4/10 Very Good! (1,451 reviews)
Very helpful and accommodating staff, free luggage storage is very convenient, hotel is located centrally among lots of restaurants/bars and just minutes walking to China Town. The room was exactly what we needed. Would definitely stay again!

Reviewed on May 27, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was CA $2,820, price is now CA $1,723 per person
CA $1,723
per person
Jun 27 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
9.8/10 Exceptional! (1,004 reviews)
Gorgeous property, excellent restaurants and the staff was very attentive and very kind....we'll definitely be back the next time we visit Boston! We loved our stay!

Reviewed on May 26, 2026

Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
West End
Price was CA $2,367, price is now CA $1,473 per person
CA $1,473
per person
Jul 30 - Aug 3
found 6 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Boston (BOS)
8.6/10 Excellent! (422 reviews)
Would definitely stay here again and again I loved it

Reviewed on May 27, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Price was CA $9,344, price is now CA $5,832 per person
CA $5,832
per person
Jul 11 - Jul 18
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
10/10 Exceptional! (9 reviews)
thanks u for very nice place and clean i really loved i will cominng back soon

Reviewed on May 8, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
Price was CA $2,602, price is now CA $1,712 per person
CA $1,712
per person
Aug 6 - Aug 9
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.4/10 Exceptional! (422 reviews)
The valet was fast and professional, the room was clean, the staff are very helpful. I would definitely stay again!

Reviewed on May 25, 2026

Cumberland County Hotel Deals

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 $295 per night from May 31 to Jun 1
CA $295
CA $379 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,769 reviews)
"An attractive city hotel with contemporary rooms and a lux feeling lobby area. Ed and pillow were very good; a/c was robust. Downside: The one working elevator to the guest rooms made transit up and downstairs slow."

Reviewed on May 25, 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $286 per night from May 31 to Jun 1
CA $286
CA $316 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,657 reviews)
"The place is wonderful. Just remember to get water from the lobby because it is not stocked in the rooms."

Reviewed on May 27, 2026

Portland Regency Hotel & Spa
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 $237 per night from May 31 to Jun 1
CA $237
CA $300 total
May 31 - Jun 1
includes taxes & fees
9.4/10 Exceptional! (1,223 reviews)
"We stay here every time we visit our daughter in Portland."

Reviewed on May 27, 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,246 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 $1,239. 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.