Cumberland County Vacations & Trips from ￥122,432

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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 Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Price was ￥166,763, price is now ￥122,432 per person
￥122,432
per person
May 4 - May 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (2,287 reviews)
Quality hotel. We enjoy our stay..

Reviewed on Mar 10, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was ￥315,162, price is now ￥192,660 per person
￥192,660
per person
May 4 - May 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
Outstanding. Definitely the best hotel I have ever stayed at and I've been all over the world. The hotel room was perfect but what shined was the impeccable service. The Boston Harbor Hotel had an amazing staff who were personable, always available and willing to assist in any way. Truly a gem.

Reviewed on Jan 25, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Save 100% on your flight
Price was ￥283,544, price is now ￥198,089 per person
￥198,089
per person
May 4 - May 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.6/10 Exceptional! (1,003 reviews)
Friendly staff, clean room

Reviewed on Feb 20, 2026

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Price was ￥966,118, price is now ￥684,181 per person
￥684,181
per person
May 11 - May 16
found 24 hours ago
Roundtrip flight included
Yonago (YGJ) to Boston (BOS)
9.6/10 Exceptional! (236 reviews)
The most perfect hotel and service I’ve ever experienced in my lifetime!

Reviewed on Feb 24, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was ￥469,648, price is now ￥350,549 per person
￥350,549
per person
May 16 - May 21
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.6/10 Excellent! (1,384 reviews)
Good location to T.D. Garden.

Reviewed on Mar 7, 2026

Cumberland County Hotel Deals

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 ￥15,470 per night from Apr 6 to Apr 7
￥15,470
￥17,116 total
Apr 6 - Apr 7
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
Just a great place to stay

Reviewed on Mar 10, 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 ￥12,185 per night from Mar 24 to Mar 25
￥12,185
￥13,482 total
Mar 24 - Mar 25
includes taxes & fees
8/10 Very Good! (1,400 reviews)
Great stay

Reviewed on Mar 9, 2026

Clarion Hotel Portland Airport ME
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! (1,598 reviews)
This is a wonderful hotel and deserves the very high rating that prior guests have given it. Excellent room, service, food, etc. My only regret is that the fitness room hours are the same as the spa (opening at 8 am and closing at 6 pm). At most hotels where we stay fitness centers are open 24 hours ...

Reviewed on Mar 10, 2026

Get rates
Portland Regency Hotel & Spa
See all 2,177 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 ￥122,432. 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.