Cumberland County Vacations & Trips from ￥238,954

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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.
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Price was ￥265,211, price is now ￥238,954 per person
￥238,954
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.6/10 Excellent! (2,200 reviews)
Although room was compact, it was very nicely furnished. It is perfectly situated and within walking distant of all major attractions I wanted to see. It is also extremely close to the cruise line terminal. The Seaport area it a beautiful and vibrant location. Highly recommend

Reviewed on Aug 27, 2025

The Westin Copley Place, Boston, a Marriott Hotel

The Westin Copley Place, Boston, a Marriott Hotel

4 out of 5
Back Bay
Price was ￥426,063, price is now ￥372,760 per person
￥372,760
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.2/10 Wonderful! (1,329 reviews)
Nos encanta este hotel y siempre volvemos.

Reviewed on Aug 24, 2025

Global Luxury Suites Downtown Boston

Global Luxury Suites Downtown Boston

4 out of 5
Chinatown
Price was ￥291,271, price is now ￥257,240 per person
￥257,240
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8/10 Very Good! (588 reviews)
Overall is pretty good and the only thing that we don’t like it is the water volume of shower head just need to be way a lot more .please turn it up .

Reviewed on Aug 28, 2025

Fairmont Copley Plaza, Boston

Fairmont Copley Plaza, Boston

4.5 out of 5
Back Bay
Price was ￥331,322, price is now ￥294,542 per person
￥294,542
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
8.8/10 Excellent! (1,046 reviews)
A classic hotel - well situated- everything was very relaxed . They could benefit from having another bar or sports bar

Reviewed on Aug 25, 2025

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was ￥392,200, price is now ￥353,248 per person
￥353,248
per person
Nov 20 - Nov 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
Well appointed property, close to transit, downtown and highways. We had a lovely stay and look forward to returning soon.

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 ￥22,371 per night from Sep 2 to Sep 3
￥22,371
￥24,752 total
Sep 2 - Sep 3
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 ￥18,496 per night from Sep 1 to Sep 2
￥18,496
￥20,464 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 ￥32,347 per night from Sep 1 to Sep 2
￥32,347
￥36,326 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Clean and great staff, plenty of places to eat or go out that is very close walking distance to the hotel"

Reviewed on Aug 20, 2025

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 ￥238,954. 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.