Cumberland County Vacations & Trips from ₩1,493,140

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Top destinations in Cumberland County

Portland Head Light showing rocky coastline, general coastal views and a sunset
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Portland

Portland

The Latest Cumberland County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Boston Hotel

The Boston Hotel

2 out of 5
Brighton
Save 100% on your flight
Price was ₩2,264,704, price is now ₩1,493,140 per person
₩1,493,140
per person
Apr 14 - Apr 20
found 1 hour ago
Roundtrip flight included
San Francisco (SFO) to Boston (BOS)
7.4/10 Good! (802 reviews)
Everyone was nice, the room was decent size and there were options. Water was HOT! I loved it

Reviewed on Feb 3, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was ₩7,720,248, price is now ₩4,516,700 per person
₩4,516,700
per person
Apr 14 - Apr 20
found 1 hour ago
Roundtrip flight included
San Francisco (SFO) to Boston (BOS)
9.6/10 Exceptional! (1,004 reviews)
Perfect service, quite classic luxury hotel. We had a perfect stay and look forward to our next stay. Thank you

Reviewed on Feb 3, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was ₩3,104,995, price is now ₩1,995,516 per person
₩1,995,516
per person
Apr 14 - Apr 20
found 1 hour ago
Roundtrip flight included
San Francisco (SFO) to Boston (BOS)
8.6/10 Excellent! (1,337 reviews)
Thank you for the cool corner suite on the 9th floor! We stayed over after attending a Bruins game. Short stay but nice place. Good location for our adventures. We’ll stay again if when we are back in Boston! Ty

Reviewed on Jan 29, 2026

Battery Wharf Hotel, Boston Waterfront

Battery Wharf Hotel, Boston Waterfront

4.5 out of 5
North End
Save 100% on your flight
Price was ₩2,956,780, price is now ₩1,974,185 per person
₩1,974,185
per person
Apr 14 - Apr 20
found 1 hour ago
Roundtrip flight included
San Francisco (SFO) to Boston (BOS)
8.6/10 Excellent! (1,728 reviews)
Another great stay at the Battery Wharf Hotel! Everything was wonderful - from the hot mulled cider in the lobby to the quiet and comfortable room to the friendly & helpful staff. I have to recognize (again) Emmanuel at the front desk who is incredibly kind, friendly and welcoming. Thank you, Battery Wharf! We’ll be back soon!

Reviewed on Jan 29, 2026

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
Price was ₩3,488,926, price is now ₩2,349,415 per person
₩2,349,415
per person
Apr 14 - Apr 20
found 1 hour ago
Roundtrip flight included
San Francisco (SFO) to Boston (BOS)
9.6/10 Exceptional! (3,386 reviews)
Didn’t get room update

Reviewed on Feb 4, 2026

Cumberland County Hotel Deals

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 ₩112,757 per night from Feb 16 to Feb 17
₩112,757
₩124,754 total
Feb 16 - Feb 17
includes taxes & fees
8/10 Very Good! (1,351 reviews)
Great location great staff everything functioned.

Reviewed on Feb 6, 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
9.2/10 Wonderful! (1,751 reviews)
Wonderful stay!

Reviewed on Feb 7, 2026

Get rates
Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (1,578 reviews)
The room was impeccable, the restaurant was delicious and perfect location

Reviewed on Jan 29, 2026

Get rates
Portland Regency Hotel & Spa
See all 2,152 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 vacation package cost?
Custom build your Cumberland County vacation package from an affordable ₩1,493,140. 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 vacation 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 Harbor Hotel and Casco Bay Hotel, Ascend Hotel Collection. Both are popular with travelers.
How far in advance should I book my Cumberland County vacation?
Travelers 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 vacation 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 vacation 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.