Cumberland Holidays from £1,418

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Your Cumberland Holiday

Say bye-bye to planning hassles and hello to a Cumberland holiday package. With everything organised before you go, you can focus on discovering this city, starting with Parkside, which is good for festivals, markets and walking. Not sure what to do or see first during your trip to Cumberland? Don't miss well-known attractions such as Twin Brook Recreation Area. Expedia can help you escape the everyday. Tailor your holiday to Cumberland to suit your style of travel, whatever that may be.

Top Cumberland Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
1802 House Bed and Breakfast

1802 House Bed and Breakfast

3.5 out of 5
Price was £1,603, price is now £1,418 per person
£1,418
per person
26 Sept - 30 Sept
found 4 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
9.8/10 Exceptional! (117 reviews)
Superb location. Easy and beautiful walk to downtown to avoid all the parking hassle there. Staff is out of this world and the breakfast, we want to go back just for that!!!

Reviewed on 29 Jun 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was £2,048, price is now £1,654 per person
£1,654
per person
26 Sept - 30 Sept
found 4 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
10/10 Exceptional! (5 reviews)
It was a spacious, clean, well thought out space with all the expected amenities. The location is ideal, and the hotel is truly a treasure.

Reviewed on 28 Jun 2026

The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was £1,636, price is now £1,454 per person
£1,454
per person
26 Sept - 30 Sept
found 4 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
9.6/10 Exceptional! (345 reviews)
The property is in a great location and at first seemed fine but after being there for a few days I noticed a few things - the sink in both the bathroom and the kitchen did not drain well (the bathroom sink actually took hours to drain), the faucet in the kitchen leaked and there living room was not cleaned thoroughly when we checked in. The bed was also very uncomfortable. I think this is a good place if you want to stay a day or so but not great for extended stay. They also do not provide house keeping on a daily basis. Overall disappointing exprience.

Reviewed on 5 Jul 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was £1,704, price is now £1,554 per person
£1,554
per person
26 Sept - 30 Sept
found 4 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
9.4/10 Exceptional! (1,775 reviews)
Only 4 rooms that were having A/C problems. Of course we had one the rooms. If the A/C isn’t working, why continue to reserve the rooms and not just fix the A/C??? Front desk attendant Dennecia was wonderful and was able to get us moved for our last night in Portland. She made the experience enjoyable. She did as much as she could. Just not sure why the hotel couldn’t fix the A/C in the rooms with KNOWN issues.

Reviewed on 8 Jul 2026

The Weldon Hotel

The Weldon Hotel

4.5 out of 5
Downtown Portland
Price was £1,775, price is now £1,628 per person
£1,628
per person
26 Sept - 30 Sept
found 4 hours ago
Return flight included
Aberdeen (ABZ) to Portland (PWM)
9.8/10 Exceptional! (101 reviews)
Spacious with plenty of room for my family of four. Excellent kitchen, washer and dryer and stellar location close to Waterfront district.

Reviewed on 5 Jul 2026

Cumberland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portland Intl. Jetport Airport (PWM)
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC

Top hotels in Cumberland

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med

3 out of 5
340 Park Ave Portland ME
Fully refundableReserve now, pay when you stay
The price is £132 per night from 13 Jul to 14 Jul
£132
13 Jul - 14 Jul
includes taxes & fees
8.6/10 Excellent! (2,193 reviews)
"Overall a fine place to stay but nothing special. Fridge was turned off when we arrived, coffee at breakfast was cold, and parking was a $10 daily charge. The humidity was also so bad the toilet bowl had constant condensation and dripped so much it created a puddle. The bed and pillows were comfortable ..."

Reviewed on 8 Jul 2026

La Quinta Inn & Suites by Wyndham Portland DT/Maine Med
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
The price is £326 per night from 12 Jul to 13 Jul
£326
12 Jul - 13 Jul
includes taxes & fees
9.4/10 Exceptional! (1,779 reviews)
"Only 4 rooms that were having A/C problems. Of course we had one the rooms. If the A/C isn’t working, why continue to reserve the rooms and not just fix the A/C??? Front desk attendant Dennecia was wonderful and was able to get us moved for our last night in Portland. She made the experience enjoyable. ..."

Reviewed on 8 Jul 2026

Portland Harbor Hotel
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
The price is £235 per night from 12 Jul to 13 Jul
£235
12 Jul - 13 Jul
includes taxes & fees
9.4/10 Exceptional! (1,258 reviews)
"Pros: The rooms are big and spacious. Clean rooms. Well maintained Good location. Central Part of downtown. Easy access to restaurants. Gym Good size gym . All necessary equipments available. Good weights range. Cons No smart TV, was hoping to relax and watch Netflix or HBO, or HDMI port to connect ..."

Reviewed on 7 Jul 2026

Cambria Hotel Portland Downtown-Old Port
See all 1,914 properties in Cumberland
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
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Beach Holidays
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Stay near popular Cumberland attractions

Greely Center for the Arts

Enjoy an outing to Greely Center for the Arts during your stay in Cumberland.
See properties

What to do in Cumberland

Portland Explorer: Cultural/Historical & 3 Lighthouses Tour

Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour

£68
per adult
100% of travellers recommend
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

£57
per adult
88% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

£13
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
See all activities in Cumberland

Frequently asked questions

How much does a Cumberland travel package cost?
Get set to book, because a getaway to Cumberland starts from just £1,418. When you combine your flights, hotels and car rentals into a package, you'll enjoy great deals.
If I'm not able to travel, can I cancel my Cumberland travel package?
If your travel plans in Cumberland have been upended, it's good to know that it's possible to cancel or amend your booking. If your booking was made less than 24 hours ago, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may charge a fee. To find out more, visit our Customer Service Portal.
How do I get a cheap travel package to Cumberland?
Browse and book everything all in one place with our Cumberland holiday packages. You'll find bargains on hotels, flights and more that'll keep your hip pocket happy and your adventurous side busy. And, with more than 550 partner airlines and 1,000,000 hotels across the globe to choose from, you have countless opportunities to mix and match your own way.
Does Expedia offer Book Now, Pay Later Cumberland holidays?
Your bank balance shouldn't stop you from taking a holiday, so Expedia has devised a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book a fantastic getaway without exhausting your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your escape. Check out these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If paying just a little each month works for you, choose this option at checkout.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your trip across multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan with Klarna.

Where should I stay in Cumberland?
If you plan to check out Twin Brook Recreation Area, give commuting a miss and stay close by. It's one of the top attractions in this neighbourhood.
What are the top hotels in Cumberland?
Peaceful Country Retreat, Minutes From Portland and Cabin - Rustic Charm Close To Portland are two of the most well-known hotels in Cumberland. Why not look up the facilities and rates at each and then decide?
How far in advance should I book my Cumberland holiday?
While not all air carriers release ticket prices early, you can usually start comparing international flights on Expedia up to 12 months in advance. This is the time when you'll nab some incredible deals. If you're booking late, you may still be in luck. Discounted prices occasionally emerge only weeks before departure.
What does an Expedia Cumberland travel package include?
It all comes down to what type of getaway you're contemplating. Cumberland travel deals can include car rentals, flights and hotels. You can mix and match to find the bundle that suits you. You can also add on activities and experiences after you've booked to score even bigger discounts.
What should I know before booking a Cumberland travel package?
Our prices are already low. However, you'll snap up even more bargains when you book your flights, hotels and car rentals together. With an Expedia travel package, you'll get transparent pricing and a great range of choice.
Can I choose my airline with a Cumberland Expedia travel package?
Most definitely. We offer more than 550 airlines across the globe, so you can design your Cumberland adventure according to your style and budget.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.