Cumberland County Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Rob Gosse

  • Plan, book, travel with confidence

  • Better together

    Save up to £335 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

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

FlightsFlightsHotelsHotels

Portland

Portland

Top Cumberland County Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
Price was £1,735, price is now £1,120 per person
£1,120
per person
5 Jun - 10 Jun
found 18 hours ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (252 reviews)
Excellent experience- clean and very helpful staff

Reviewed on 9 Mar 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £2,751, price is now £1,619 per person
£1,619
per person
21 May - 26 May
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub.

Reviewed on 23 Mar 2026

enVision Hotel Boston Everett

enVision Hotel Boston Everett

2 out of 5
Save 100% on your flight
Price was £3,312, price is now £2,239 per person
£2,239
per person
11 Jun - 21 Jun
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.6/10 Excellent! (1,001 reviews)
Close to restaurant, plenty of parking, shopping area around.

Reviewed on 25 Mar 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £3,067, price is now £2,135 per person
£2,135
per person
21 May - 26 May
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (238 reviews)
The photos doesn’t give this place justice.

Reviewed on 24 Mar 2026

The Westin Waltham-Boston

The Westin Waltham-Boston

4 out of 5
Save 100% on your flight
Price was £2,715, price is now £1,893 per person
£1,893
per person
11 Jun - 21 Jun
found 15 hours ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
8.8/10 Excellent! (1,095 reviews)
Awesome breakfast views!

Reviewed on 13 Mar 2026

Cumberland County Essential Information

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

Top hotels in Cumberland County

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 £95 per night from 16 Apr to 17 Apr
£95
16 Apr - 17 Apr
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
I frequently stay at this property. It is a very clean property with kind and helpful staff and an excellent restaurant and spa. I was locked out of the next door parking garage and Dan (door man?) helped me get my car out. He ran out there in the freezing cold, called the garage mgmt and got me ...

Reviewed on 26 Mar 2026

The Westin Portland Harborview
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 £72 per night from 13 Apr to 14 Apr
£72
13 Apr - 14 Apr
includes taxes & fees
8/10 Very Good! (1,403 reviews)
Great rooms and nice staff

Reviewed on 26 Mar 2026

Clarion Hotel Portland Airport ME
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 £123 per night from 5 Apr to 6 Apr
£123
5 Apr - 6 Apr
includes taxes & fees
9.2/10 Wonderful! (1,761 reviews)
We paid a little extra for a room with a Courtyard view. What we got was a 2nd floor room as far as possible from the elevator and when I pulled back the curtains I was looking at a giant kitchen exhaust fan that gave us a constant deep buzz in the room. The hotel did not seem busy and this room ...

Reviewed on 27 Mar 2026

Portland Harbor Hotel
See all 2,190 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Cumberland County travel package cost?
Starting from only £1,120, a travel package is your portal to low-cost travel. Create your own Cumberland County adventure by choosing from our wide range of hotels, airfares and rental cars.
If I'm not able to travel, can I cancel my Cumberland County travel package?
If your travel plans in Cumberland County have been upended, it's comforting to know that it's possible to cancel your booking. If you made your booking within the last 24 hours, you may be able to receive a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose a fee. To find out more, check our Customer Service Portal.
How do I get a cheap travel package to Cumberland County?
Bundle your bookings with Expedia to save big on your next exciting adventure. With over 550 partner airlines and 1,000,000 hotel options worldwide, your Cumberland County holiday package can be tailored exactly to suit your budget. With all those extra dollars, why not throw in a few fun experiences and tours? It's an easy way to unlock even more savings. Your dream holiday in Cumberland County is closer than you thought!
Does Expedia offer Book Now, Pay Later Cumberland County holidays?
We sure do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in instalments. Simply choose the payment plan that suits you best during checkout and take the stress out of budgeting for your next trip. Remember to bundle your flights, car hire and accommodation with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: If paying small amounts each month is what works best for you, Klarna can help. Paying in convenient monthly instalments will make that dream holiday possible.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay off your trip in multiple transactions.
  • Low deposit holidays: Clicking the "book now" button is easier with this plan. Just put down a small deposit on your escape and then start packing your bags.

Where should I stay in Cumberland County?
You can't go wrong in Portland. Popular sights, such as Portland Head Light and University of Southern Maine, will keep you on the go in this exciting city.
What are the top hotels in Cumberland County?
When it comes to hotels in Portland, The Westin Portland Harborview and Portland Sheraton at Sable Oaks are two great options. If you're also visiting Bridgton, The Westin Portland Harborview and Portland Sheraton at Sable Oaks look forward to welcoming you.
How far in advance should I book my Cumberland County holiday?
While not all airlines release tickets early, you can normally compare international airfares on Expedia up to 12 months in advance. This is the time you'll bag some fantastic bargains. If you're booking last minute, you could still be in luck. Low prices occasionally become available only weeks prior to departure.
What does an Expedia Cumberland County travel package include?
Rental cars, flights and hotels — we've got them well covered. With Expedia, you can shape your Cumberland County package just the way you want. All you have to do is determine what you need. Once you've made your booking, you can add on extras like experiences and activities. The more you bundle, the bigger your savings!
What should I know before booking a Cumberland County travel package?
Whether it's adventure or relaxation you're seeking, a Cumberland County travel package lets you organise your escape your way. Plus, you'll score great discounts when you combine your accommodation with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Cumberland County Expedia travel package?
Yes, you're in charge. We have access to over 550 partner airlines around the world, so you can design your Cumberland County holiday according to your budget and needs.

* 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.