Cumberland County Holidays

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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 showing a lighthouse, general coastal views and rugged coastline
FlightsFlightsHotelsHotels

Portland

Portland

Top Cumberland County Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Residence Inn Boston Dedham

Residence Inn Boston Dedham

3 out of 5
Price was £1,431, price is now £669 per person
£669
per person
26 Oct - 29 Oct
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
8.2/10 Very Good! (423 reviews)
Professional, friendly, helpful staff, especially Zorica, the breakfast hostess. Comfortable bed, the sofa not so much. We had a few minor issues in the room that were resolved quickly. AC was very loud, but we were certainly glad to have it with 90+ degree temperatures! The proximity to Legacy Place, with lots of shops/restaurants (including a Whole Foods) within walking distance is definitely a plus! There’s also a Costco nearby. This was our 2nd extended stay at this property and we would recommend it to others.

Reviewed on 25 Jul 2025

Boston Lodge and Suites

Boston Lodge and Suites

4 out of 5
Dorchester
Price was £1,722, price is now £681 per person
£681
per person
11 Nov - 18 Nov
found 7 hours ago
Return direct flight included
London (LON) to Boston (BOS)
8.4/10 Very Good! (186 reviews)
The Revolution Hotel

The Revolution Hotel

3.5 out of 5
South End
Price was £1,691, price is now £749 per person
£749
per person
26 Oct - 29 Oct
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
9/10 Wonderful! (2,140 reviews)
We had a separate bathroom out in the hall and they were impeccable the women were cleaning them day and night made me feel very good

Reviewed on 28 Aug 2025

Kimpton Marlowe Hotel by IHG

Kimpton Marlowe Hotel by IHG

4 out of 5
East Cambridge
Price was £1,748, price is now £890 per person
£890
per person
26 Oct - 29 Oct
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
9/10 Wonderful! (1,002 reviews)
Front desk guy was really nice when I talked about my moms recent brain surgery. He helped me through a tough moment by being empathetic. Very much appreciated.

Reviewed on 29 Aug 2025

Residence Inn by Marriott Boston Harbor on Tudor Wharf

Residence Inn by Marriott Boston Harbor on Tudor Wharf

3 out of 5
Charlestown
Price was £1,764, price is now £901 per person
£901
per person
26 Oct - 29 Oct
found 1 day ago
Return flight included
London (LHR) to Boston (BOS)
9/10 Wonderful! (1,002 reviews)
Liked breakfast. We could hear hallway noise.

Reviewed on 18 Aug 2025

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

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 £125 per night from 7 Sept to 8 Sept
£125
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (1,010 reviews)
"Consistent- we’ve chosen to stay many times both when we need Park and Fly and when going to local concerts at Thompson Point so we can walk over, and have the long drive home late at night. Clean, friendly and convenient. Price is reasonable."

Reviewed on 23 Aug 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 £103 per night from 1 Sept to 2 Sept
£103
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (1,053 reviews)
"-"

Reviewed on 27 Aug 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 £183 per night from 1 Sept to 2 Sept
£183
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Clean and great staff, plenty of places to eat or go out that is very close walking distance to the hotel"

Reviewed on 20 Aug 2025

The Westin Portland Harborview
See all 2,194 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.
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Frequently asked questions

How much does a Cumberland County travel package cost?
Starting from only £669, 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.