Cumberland County Vacations & Trips from ￥318,974

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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.
Hotel AKA Back Bay

Hotel AKA Back Bay

4.5 out of 5
Back Bay
Price was ￥437,150, price is now ￥318,974 per person
￥318,974
per person
Oct 7 - Oct 12
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (1,116 reviews)
Unbeatable location in back bay with access to rest, shopping, and train (T) stops. Safe elevators and neighborhood and walkable throughout back bay and to downtown Boston. Facilities in such historical building were impeccable and the staff superb. In-house bar and eating facilities were a plus. Wish bathroom was more updated and that at least a luggage rack be available.

Reviewed on Aug 29, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was ￥785,828, price is now ￥494,198 per person
￥494,198
per person
Oct 11 - Oct 17
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.8/10 Exceptional! (1,013 reviews)
Highly recommend! Beautiful and amazing service! Felt like 4 seasons or ritz service!

Reviewed on Aug 30, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was ￥613,523, price is now ￥401,610 per person
￥401,610
per person
Oct 7 - Oct 12
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (154 reviews)
I could not fault this hotel in any way. After long days out sightseeing and shopping it was great to get back and relax. This was our first time in Boston so we’re not sure which area was best to stay in. However the hotel’s location in Back Bay was excellent.

Reviewed on Aug 28, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was ￥577,994, price is now ￥420,398 per person
￥420,398
per person
Oct 7 - Oct 12
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (443 reviews)
Was a great looking hotel. Comfy beds. Updates decor. Strange that there was no cooler/fridge in the room though.

Reviewed on Aug 30, 2025

The Newbury Boston

The Newbury Boston

5 out of 5
Back Bay
Price was ￥500,586, price is now ￥364,956 per person
￥364,956
per person
Nov 20 - Nov 27
found 2 hours ago
Roundtrip non-stop flight included
Taipei (TPE) to Boston (BOS)
9.4/10 Exceptional! (490 reviews)
Love the Street Bar!

Reviewed on Aug 25, 2025

Cumberland County Hotel Deals

Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is ￥22,374 per night from Sep 4 to Sep 5
￥22,374
￥24,755 total
Sep 4 - Sep 5
includes taxes & fees
Clarion Hotel Portland
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 ￥17,999 per night from Sep 1 to Sep 2
￥17,999
￥19,914 total
Sep 1 - Sep 2
includes taxes & fees
Ramada Plaza by Wyndham Portland
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 ￥35,145 per night from Sep 1 to Sep 2
￥35,145
￥39,468 total
Sep 1 - Sep 2
includes taxes & fees
The Westin Portland Harborview
See all 2,194 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 ￥318,974. 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.