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

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

Portland

Portland

Top Cumberland County Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Moody
Price was £1,169, price is now £834 per person
£834
per person
14 Sept - 20 Sept
found 4 hours ago
Return direct flight included
London (LHR) to Portland (PWM)
9/10 Wonderful! (1,011 reviews)
This ida beautiful hotel close to all beaches, dining, and shopping in ogunquit and wells. It is unique because it sits on a hill. Everything was great. The only reason for 4 stars is all the stairs. Be sure you know where your room is located because you might end up dragging your stuff up and down some steep and lengthy stair cases.

Reviewed on 24 Jun 2026

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was £3,296, price is now £2,355 per person
£2,355
per person
17 Aug - 26 Aug
found 1 day ago
Return direct flight included
London (LGW) to Boston (BOS)
9.4/10 Exceptional! (661 reviews)
Incredible staff. This is an amazing location and the breakfast is great

Reviewed on 16 Jun 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £2,068, price is now £1,491 per person
£1,491
per person
30 Jul - 3 Aug
found 21 hours ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.8/10 Exceptional! (1,009 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on 15 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
Save 100% on your flight
Price was £2,181, price is now £1,581 per person
£1,581
per person
14 Sept - 20 Sept
found 4 hours ago
Return direct flight included
London (LHR) to Portland (PWM)
9.6/10 Exceptional! (335 reviews)
The apartment was great but parking is expensive

Reviewed on 24 Jun 2026

The Rockport House

The Rockport House

2 out of 5
Price was £1,752, price is now £1,285 per person
£1,285
per person
17 Aug - 26 Aug
found 1 day ago
Return direct flight included
London (LGW) to Boston (BOS)
9.4/10 Exceptional! (200 reviews)
We only stayed one night, but we were obsessed! The property was gorgeous and the rooms were so cute, clean, and the beds were cozy. We were disappointed we didn’t have more time and discussed booking it again for a whole weekend! It was dif type of check in than I was used to, but went so smoothly. Having a room with a keypad was extremely convenient too! We loved it!

Reviewed on 16 Jun 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

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 £262 per night from 5 Jul to 6 Jul
£262
5 Jul - 6 Jul
includes taxes & fees
9.4/10 Exceptional! (1,773 reviews)
"Iron broken. Construction outside."

Reviewed on 26 Jun 2026

Portland Harbor Hotel
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 £114 per night from 29 Jun to 30 Jun
£114
29 Jun - 30 Jun
includes taxes & fees
7.8/10 Good! (1,007 reviews)
"Smelliest Hotel I have ever stepped foot in. Even motels in the middle of nowhere smelled better. It smelled like a wet dog has barfed and ate thay barf then barfed again and rolled in it then rolled all over the hotel. The staff is great but that smell is horrific it wasn’t just the hallways it ..."

Reviewed on 25 Jun 2026

Ramada Plaza by Wyndham Portland
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 £230 per night from 5 Jul to 6 Jul
£230
5 Jul - 6 Jul
includes taxes & fees
9.4/10 Exceptional! (1,249 reviews)
"The air conditioning doesn’t stay on. The thermostat goes down to 64 but the temperature wouldn’t go below 69 which made it pretty warm to try and sleep."

Reviewed on 26 Jun 2026

Cambria Hotel Portland Downtown-Old Port
See all 2,316 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
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Family Friendly Holidays

Frequently asked questions

How much does a Cumberland County travel package cost?
Starting from only £834, 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.

Stay near popular Cumberland County attractions

A building with 'L.L. Bean Inc.' signage, a large boot sculpture, and outdoor seating.

LL Bean Flagship Store

9.2/5 (1,289 reviews)
During your visit to Freeport, you can enjoy retail therapy at LL Bean Flagship Store. Stroll along the area's waterfront or simply enjoy its seafood restaurants.
See properties

What to do in Cumberland County

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 County

* 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.