Cumberland County Vacations & Trips from ￥290,060

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    Save up to ￥109,000 when you book a flight and hotel together*

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Top destinations in Cumberland County

FlightsFlightsHotelsHotels

Portland

Portland

The Latest Cumberland County Vacation Packages

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

Revere Hotel Boston Common

4 out of 5
Bay Village
Price was ￥354,378, price is now ￥290,060 per person
￥290,060
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9/10 Wonderful! (2,034 reviews)
Super friendly staff, great location, and very nice, quiet rooms.

Reviewed on Jun 10, 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was ￥603,187, price is now ￥392,924 per person
￥392,924
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,000 reviews)
Wonderful classic harbor front hotel. Very nice front desk. Would stay again

Reviewed on May 25, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Price was ￥472,958, price is now ￥369,037 per person
￥369,037
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.8/10 Excellent! (1,507 reviews)
It’s a great location and really good rooms. I liked the breakfast. One of the horrible things that happened was a guest created a very loud situation for an extended period of time. The hotel sided with the guest creating the situation. So if you need help or a problem resolved. The hotel point blank said they are not going to do anything about it and you are on your own. Very bizarre behavior by a hotel. Never really saw this before. Everything else was great. Clean rooms and everything was modern and nice.

Reviewed on Jun 8, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was ￥481,364, price is now ￥382,480 per person
￥382,480
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,006 reviews)
Well located and very well maintained property.

Reviewed on Jun 11, 2026

XV Beacon

XV Beacon

5 out of 5
Beacon Hill
Price was ￥503,660, price is now ￥413,130 per person
￥413,130
per person
Sep 2 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (391 reviews)
The location was fantastic for all things Boston! It was a very walkable location and such a comfortable room and a very friendly staff that was very helpful.

Reviewed on May 30, 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 refundable
The price is ￥19,041 per night from Jun 14 to Jun 15
￥19,041
￥21,068 total
Jun 14 - Jun 15
includes taxes & fees
8/10 Very Good! (1,491 reviews)
"Clean Property, rooms were spacious and comfortable. Easy 10 minute walk to Bissell Brewery and Thompson’s Point if you’re catching a show!"

Reviewed on Jun 10, 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
The price is ￥45,233 per night from Jun 14 to Jun 15
￥45,233
￥56,149 total
Jun 14 - Jun 15
includes taxes & fees
9.4/10 Exceptional! (1,784 reviews)
"Very accommodating, clean, great location and excellent food"

Reviewed on Jun 11, 2026

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
The price is ￥36,994 per night from Jun 14 to Jun 15
￥36,994
￥40,930 total
Jun 14 - Jun 15
includes taxes & fees
9.4/10 Exceptional! (1,687 reviews)
"Great accommodations right in the heart of the city. Friendly staff."

Reviewed on Jun 11, 2026

Portland Regency Hotel & Spa
See all 2,275 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 ￥290,060. 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.

Stay near popular Cumberland County attractions

Higgins Beach

4.4/5 (308 reviews)
At the mouth of the Spurwink River in Scarborough, take a stroll on the white sand or paddle a kayak over gentle waves.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.