Cumberland County Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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Top destinations in Cumberland County

A lighthouse, a white house with a red roof, and rocky coastline at sunset.
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Portland

Portland
A rocky coastline with waves crashing against the rocks and a distant island.
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Cape Elizabeth

Cape Elizabeth

Top hotels in Cumberland County

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 S$205 per night from 28 Jul to 29 Jul
S$205
28 Jul - 29 Jul
includes taxes & fees
8.2/10 Very good! (1,555 reviews)
"Love the hot tub although it obviously was not cleaned after closing between 10p-6a There were no towels available at 6:30 am The floor surface of the pool area needs attention. The pebble surface is loose and pulling up in some ares and pebbles are getting tracked int to pool. We enjoyed using the ..."

Reviewed on 13 Jul, 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 S$486 per night from 26 Jul to 27 Jul
S$486
26 Jul - 27 Jul
includes taxes & fees
9.4/10 Exceptional! (1,266 reviews)
"Very clean nice hotel and within walking distance to all shops and restaurants. We had breakfast one day and it was very good. The beds were comfy."

Reviewed on 13 Jul, 2026

Cambria Hotel Portland Downtown-Old Port
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 S$562 per night from 26 Jul to 27 Jul
S$562
26 Jul - 27 Jul
includes taxes & fees
9.4/10 Exceptional! (1,783 reviews)
"Our stay was great - the location of this hotel is perfect, the staff was friendly and our room was really nice. Every morning, there was a fully stocked pantry with snacks and drinks for guests on each floor. We had a great stay and would recommend this place highly!"

Reviewed on 12 Jul, 2026

Portland Harbor Hotel
See all 2,313 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.

Frequently asked questions

How much does a Cumberland County holiday package cost?
Custom build your Cumberland County holiday package from an affordable . 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

A multi-story brick building with a large arched window and a sign that reads "STATE".

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.
See properties

What to do in Cumberland County

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

S$100
per adult
88% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland Lighthouse Boat Cruise with Oysters & Prosecco

Portland Explorer: Boat Cruise with Oysters & Prosecco

S$177
per adult
Portland Explorer: Boat Cruise with Oysters & Prosecco
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

S$22
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
See all activities in Cumberland County

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.