Cumberland County Vacations & Trips from ￥283,350

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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.
Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I made a mistake on my room type when I made the reservation, they hotel was extremely helpful in helping me get it corrected. The hotel is beautiful, the location/views are amazing, and the food at the hotel restaurant was outstanding.

Reviewed on Jul 23, 2025

The Whitney Hotel

The Whitney Hotel

4 out of 5
Beacon Hill
per person
Sep 11 - Sep 17
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Boston (BOS)
9.6/10 Exceptional! (413 reviews)
The air conditioning was not working properly. I mentioned it to front desk. They said that they have had other problems like this and that they would fix it but they never did. For the cost of staying at this hotel, there should not be any issues with the basics like air con. Also, it was very noisy; inconsiderate guests make lots of noise in the hallways well after midnight.

Reviewed on Jul 22, 2025

The Boxer

The Boxer

4 out of 5
West End
per person
Sep 15 - Sep 21
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
8.6/10 Excellent! (1,236 reviews)
This hotel is super cute. Our room was pretty tiny but the proximity to the TD Garden is what makes this the real winner. If you are super sensitive to noise the water running through the pipes is quite loud. It never woke me up but it was annoying when we were relaxing in our room. As far as noise goes, we never heard anyone in the hallway.

Reviewed on Jul 22, 2025

Mandarin Oriental, Boston

Mandarin Oriental, Boston

5 out of 5
Back Bay
per person
Oct 3 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.4/10 Exceptional! (349 reviews)
This experience from checking in to the quality of the room and the incredible concierge service that helped us with restaurants in our entire experience was unbelievable! It was probably the best experience I had with a luxury hotel in any city I visited. We will definitely be coming back!

Reviewed on Jul 20, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
per person
Sep 15 - Sep 21
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul 14, 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 ￥22,282 per night from Jul 29 to Jul 30
￥22,282
￥24,653 total
Jul 29 - Jul 30
includes taxes & fees
7.8/10 Good! (1,023 reviews)
"Excellent"

Reviewed on Jul 23, 2025

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 ￥22,126 per night from Aug 24 to Aug 25
￥22,126
￥24,480 total
Aug 24 - Aug 25
includes taxes & fees
7.6/10 Good! (1,048 reviews)
"Very nice"

Reviewed on Jul 21, 2025

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 ￥39,688 per night from Aug 25 to Aug 26
￥39,688
￥44,569 total
Aug 25 - Aug 26
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"The hotel was very nice. Our room was elegant and quiet. The hotel lobby and front entrance are not ADA friendly. Lots of stairs and no ramps when you first enter the building. When we exited off of the highway and into Portland there were a lot of homeless people and graffiti on the buildings. Being ..."

Reviewed on Jul 19, 2025

The Westin Portland Harborview
See all 2,246 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 ￥283,350. 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.