Cumberland County Vacations & Trips from ￥171,574

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    Save up to ￥45,448 when you book a flight and hotel together*

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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 Lenox Hotel Boston

The Lenox Hotel Boston

4.5 out of 5
Back Bay
Price was ￥237,796, price is now ￥171,574 per person
￥171,574
per person
Feb 19 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (1,218 reviews)
Was a last-minute booking because of work being done on my apartment. Lovely hotel, helpful staff. Only "negative" is the coffee, which is truly ghastly---both at the morning coffee station and in the restaurant. Otherwise, a great overnight JS

Reviewed on Dec 19, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was ￥518,006, price is now ￥298,152 per person
￥298,152
per person
Feb 19 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
Everything was wonderful including a delicious breakfast. We will definitely return.

Reviewed on Dec 17, 2025

The Charles Hotel

The Charles Hotel

4 out of 5
West Cambridge
Price was ￥371,173, price is now ￥252,120 per person
￥252,120
per person
Feb 19 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.4/10 Exceptional! (1,003 reviews)
We love the Charles Hotel. From its helpful and friendly staff, spotless and well appointed rooms, and excellent on-site restaurants. It is the perfect place for a winter getaway.

Reviewed on Dec 14, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
Price was ￥418,090, price is now ￥284,254 per person
￥284,254
per person
Feb 19 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (181 reviews)
It was ok noting like the one overseas.

Reviewed on Dec 7, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
Price was ￥326,948, price is now ￥226,253 per person
￥226,253
per person
Feb 19 - Feb 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (482 reviews)
Phenomenon phenomenon will definitely will be back

Reviewed on Nov 26, 2025

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 ￥14,040 per night from Jan 5 to Jan 6
￥14,040
￥15,533 total
Jan 5 - Jan 6, 2026
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
Helpful staff

Reviewed on Dec 17, 2025

The Westin Portland Harborview
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 ￥13,642 per night from Dec 22 to Dec 23
￥13,642
￥21,112 total
Dec 22 - Dec 23
includes taxes & fees
9.2/10 Wonderful! (1,716 reviews)
The staff were amazing, the room was clean, and the valet parking was hassle free.

Reviewed on Dec 17, 2025

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! (1,550 reviews)
The location was perfect. It was very close to shopping, restaurants and the waterfront. The room was nice and clean. The hot tub was closed for several days for cleaning so we could not use which was a major bummer as we really really wanted to use it. Staff super friendly. Valet parking for $35 ...

Reviewed on Dec 17, 2025

Get rates
Portland Regency Hotel & Spa
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 vacation package cost?
Custom build your Cumberland County vacation package from an affordable ￥171,574. 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.