Cumberland County Holidays
- Plan, book, travel with confidence
- Better togetherSave up to €900 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Flight + Hotel Deals in Cumberland County
Price found within the past 48 hours. Click for updated prices.
Battery Wharf Hotel, Boston Waterfront
North End
€996
per person
1 Dec - 6 Dec
found 9 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,071 reviews)
The room and property met my expectations. Given the angle of the building to the water I didn't think there would be much of a view but we got lucky and even from the SE facing side of building 3 we could watch sailboats coming and going from the Boston channel.
Reviewed on 22 Oct 2026
Club Quarters Hotel Faneuil Hall, Boston
Downtown Boston
€963
per person
1 Dec - 6 Dec
found 2 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (3,468 reviews)
We arrived early so the front desk held our luggage and gave us good intructions on where we needed to go. They have a nice bar and have coffee and hot tea available 24/7 in the cozy lobby. Rooms were small but fine. The location was amazing! Minutes to the Freedom Trail and many other landmarks.
Reviewed on 23 Oct 2026
Top hotels in Cumberland County
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
€107
18 Nov - 19 Nov
includes taxes & fees
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundable
€82
1 Nov - 2 Nov
includes taxes & fees
8.2/10 Very good! (1,798 reviews)
"The hotel feels outdated but the room was spacious and the bed was comfortable."
Reviewed on 23 Oct 2026
Fireside Inn & Suites Portland
81 Riverside St Portland ME
Fully refundableReserve now, pay when you stay
€98
1 Nov - 2 Nov
includes taxes & fees
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.
Frequently asked questions
How much does a Cumberland County holiday package cost?
Custom build your Cumberland County holiday package from an affordable €514. 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 holiday 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 Harbour Hotel and Casco Bay Hotel, Ascend Hotel Collection. Both are popular with travellers.
How far in advance should I book my Cumberland County holiday?
Travellers 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 holiday 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 holiday 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
LL Bean Flagship Store
9.2/10 (1,289 reviews)
During your visit to Freeport, you can enjoy retail therapy at LL Bean Flagship Store. Stroll along the area's waterfront or simply enjoy its seafood restaurants.
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.
Portland Head Light
9.4/10 (928 reviews)
Look out across the Atlantic Ocean from Portland’s iconic white lighthouse, which has presided over the southern Maine coastline since the 18th century.
Bowdoin College
9.2/10 (248 reviews)
Experience the charm of the beautiful campus at this small-town college in Brunswick, Maine, once home to Longfellow, Hawthorne and Harriet Beecher Stowe.
Maine Mall
8.4/10 (1,708 reviews)
You can browse for the perfect souvenirs at Maine Mall during your stay in South Portland. Experience the area's great live music and entertainment choices.
Thompson's Point
8.8/10 (376 reviews)
Commune with nature and explore the great outdoors at Thompson's Point during your travels in Portland. Stroll along the waterfront or attend a sporting event in the area.
Cross Insurance Arena
8.6/10 (275 reviews)
Catch an event at Cross Insurance Arena during your trip to Portland. Stroll along the area's waterfront or experience its great live music.
What to do in Cumberland County
Afternoon Windjammer Cruise Along the Coast of Portland Maine
€61
per adult
96% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
€69
per adult
92% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
€15
per traveller
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
