Cumberland County Holidays

Photo by Rob Gosse

  • Plan, book, travel with confidence

  • Better together

    Save up to €185 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

    Plan, book, and manage your trip all in one place

Top destinations in Cumberland County

Portland Head Light which includes general coastal views, a lighthouse and rugged coastline
FlightsFlightsHotelsHotels

Portland

Portland

Top Flight + Hotel Deals in Cumberland County

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Boston/Cambridge

Hyatt Regency Boston/Cambridge

4 out of 5
MIT
Save 100% on your flight
Price was €1,729, price is now €1,137 per person
€1,137
per person
6 Apr - 16 Apr
found 20 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (2,215 reviews)
Convenient and clean. Love the glass atrium and the views of the Charles River.

Reviewed on 16 Jan 2026

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Save 100% on your flight
Price was €2,965, price is now €1,941 per person
€1,941
per person
6 Apr - 16 Apr
found 20 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
9/10 Wonderful! (1,094 reviews)
Everything about this hotel was excellent. The restaurant was awesome. Walking distance to great shopping

Reviewed on 20 Jan 2026

YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
Price was €2,046, price is now €1,370 per person
€1,370
per person
6 Apr - 16 Apr
found 20 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.6/10 Excellent! (2,315 reviews)
I very like staff very nice

Reviewed on 19 Jan 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was €1,924, price is now €1,342 per person
€1,342
per person
6 Apr - 16 Apr
found 20 hours ago
Return direct flight included
Dublin (DUB) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
Amazing hotel and staff that made my partner and I’s trip amazing!

Reviewed on 18 Jan 2026

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 €92 per night from 8 Feb to 9 Feb
€92
8 Feb - 9 Feb
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
What a great stay and great breakfast

Reviewed on 18 Jan 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 refundableReserve now, pay when you stay
The price is €74 per night from 27 Jan to 28 Jan
€74
27 Jan - 28 Jan
includes taxes & fees
8/10 Very Good! (1,328 reviews)
The pool was great!

Reviewed on 19 Jan 2026

Clarion Hotel Portland Airport ME
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4 out of 5
88 Spring St Portland ME
Fully refundable
The price is €74 per night from 29 Jan to 30 Jan
€74
29 Jan - 30 Jan
includes taxes & fees
8.8/10 Excellent! (1,470 reviews)
Location. We went to comedy show at State Theatre and was a 4 min. Walk. View from room was amazing for sunset, and the Breakfast was delicious!!

Reviewed on 20 Jan 2026

Holiday Inn Portland-By the Bay by IHG
See all 2,154 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.

Frequently asked questions

How much does a Cumberland County holiday package cost?
Custom build your Cumberland County holiday package from an affordable €1,137. 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.