Cumberland County Holidays from AU$2,412

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Your Cumberland County Holiday

When adventure calls, answer it with a tailor-made holiday 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 holiday to the second you come back home, Expedia will take care of you every step of the way.

Top destinations in Cumberland County

Portland Head Light featuring rocky coastline, general coastal views and a lighthouse
FlightsFlightsHotelsHotels

Portland

Portland

The Latest Cumberland County Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Rangeley Lake Resort a Ramada by Wyndham

Rangeley Lake Resort a Ramada by Wyndham

2.5 out of 5
per person
26 Sept - 30 Sept
found 1 day ago
Return direct flight included
Sydney (SYD) to Augusta (AUG)
9.4/10 Exceptional! (59 reviews)
I was pleasantly surprised by how nice the cabin was! I read the positive reviews and felt comfortable staying there but didn’t realize how spacious and homey the cabin would feel! The beds were super comfortable, having a washer and dryer in the cabin was a pleasant surprise, and the quietness of the entire resort area was fantastic. Super spread out. Renting canoes, kayaks, and paddle boards was really easy. The cabin got a little warm during the day but the three box fans were a big help.

Reviewed on 16 Jul. 2025

Cliff House Maine

Cliff House Maine

4.5 out of 5
per person
26 Sept - 30 Sept
found 1 day ago
Return direct flight included
Sydney (SYD) to Portland (PWM)
9.4/10 Exceptional! (1,008 reviews)
everything very clean, wonderful place.

Reviewed on 19 Jul. 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
per person
26 Sept - 30 Sept
found 1 day ago
Return direct flight included
Sydney (SYD) to Portland (PWM)
9.2/10 Wonderful! (1,523 reviews)
Excellent location and walking distance to stores, restaurants and waterfront trail. We loved the courtyard where you can eat a meal. Breakfast at on-site restaurant was very good. The snack and beverage stations on every floor were great, too.

Reviewed on 20 Jul. 2025

Kennebunkport Captains Collection

Kennebunkport Captains Collection

4.5 out of 5
per person
26 Sept - 30 Sept
found 1 day ago
Return direct flight included
Sydney (SYD) to Portland (PWM)
9.4/10 Exceptional! (591 reviews)
The team made the stay for us. Really nice, genuine and people. Special mention for the way breakfast is served and a shout out for the breakfast sandwiches and baked eggs! Great location for an easy walk into town and for longer walks along the coast.

Reviewed on 17 Jul. 2025

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
per person
26 Sept - 30 Sept
found 1 day ago
Return direct flight included
Sydney (SYD) to Portland (PWM)
9.4/10 Exceptional! (1,338 reviews)
Always a nice stay here. We had a hard travel day and the staff made every effort to make us feel more comfortable. Great location and easy valet parking. Friendly staff.

Reviewed on 20 Jul. 2025

Cumberland County Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Top Sights
Higgins Beach, Sebago Lake and Sebago Lake State Park

Our pick of the best 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 AU$259 per night from 27 July to 28 July
AU$259
27 July - 28 July
includes taxes & fees
7.8/10 Good! (1,013 reviews)
"."

Reviewed on 19 Jul. 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 AU$263 per night from 28 July to 29 July
AU$263
28 July - 29 July
includes taxes & fees
7.6/10 Good! (1,044 reviews)
"Staff was wonderful!"

Reviewed on 20 Jul. 2025

Ramada Plaza by Wyndham Portland
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 AU$497 per night from 17 Aug to 18 Aug
AU$497
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"The hotel was very nice. Our room was elegant and quiet. The hotel lobby and front entrance are not ADA friendly. Lots of stairs and no ramps when you first enter the building. When we exited off of the highway and into Portland there were a lot of homeless people and graffiti on the buildings. Being ..."

Reviewed on 19 Jul. 2025

The Westin Portland Harborview
See all 2,244 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 Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

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beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Cumberland County holiday package cost?
Custom build your Cumberland County holiday package from an affordable AU$2,412. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.