Cumberland County Holidays

Photo by Rob Gosse

  • Plan, book, travel with confidence

  • Better together

    Save up to S$134 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Top destinations in Cumberland County

FlightsFlightsHotelsHotels

Portland

Portland
Rocky shores of the Maine Coast, Fort Williams Park, Cape Elizabeth, Maine, New England, USA
FlightsFlightsHotelsHotels

Cape Elizabeth

Cape Elizabeth

Cumberland County Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Club Quarters Hotel Faneuil Hall, Boston

Club Quarters Hotel Faneuil Hall, Boston

4 out of 5
Downtown Boston
Price was S$5,819, price is now S$4,328 per person
S$4,328
per person
22 Jun - 1 Jul
found 1 day ago
Return direct flight included
Singapore (SIN) to Boston (BOS)
9/10 Wonderful! (3,000 reviews)
Great location, easy to get to from the (free) shuttle to South Station. Easy check in, friendly staff. Reasonable restaurant attached in case you’re too tired to go out, and coffee places everywhere. Will stay there again

Reviewed on 11 Apr, 2026

Eurostars The Boxer

Eurostars The Boxer

4 out of 5
West End
Save 100% on your flight
Price was S$7,448, price is now S$4,883 per person
S$4,883
per person
22 Jun - 1 Jul
found 1 day ago
Return direct flight included
Singapore (SIN) to Boston (BOS)
8.8/10 Excellent! (1,426 reviews)
Everything advertised was correct and enjoyable relaxing.

Reviewed on 11 Apr, 2026

The Verb Hotel

The Verb Hotel

3.5 out of 5
Fenway–Kenmore
Save 100% on your flight
Price was S$7,738, price is now S$5,582 per person
S$5,582
per person
22 Jun - 1 Jul
found 1 day ago
Return direct flight included
Singapore (SIN) to Boston (BOS)
9.6/10 Exceptional! (2,028 reviews)
This is a one-of-a-kind place! The vibe was so cool and the staff so friendly. It felt like home rather than a hotel. The extra touches of a record player, pool-view rooms, and the amazing breakfast make this so unique. Highly recommend! Beware - parking on site costs extra $$.

Reviewed on 12 Apr, 2026

Hotel AKA Boston Common

Hotel AKA Boston Common

4 out of 5
Downtown Boston
Price was S$6,183, price is now S$4,608 per person
S$4,608
per person
22 Jun - 1 Jul
found 1 day ago
Return direct flight included
Singapore (SIN) to Boston (BOS)
9/10 Wonderful! (1,547 reviews)
Location was perfect

Reviewed on 12 Apr, 2026

Seaport Hotel Boston

Seaport Hotel Boston

4 out of 5
Seaport District
Price was S$6,674, price is now S$5,195 per person
S$5,195
per person
22 Jun - 1 Jul
found 1 day ago
Return direct flight included
Singapore (SIN) to Boston (BOS)
9.6/10 Exceptional! (4,116 reviews)
Breakfast was great Love the oatmeal

Reviewed on 12 Apr, 2026

Top hotels in Cumberland County

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 S$172 per night from 21 Apr to 22 Apr
S$172
21 Apr - 22 Apr
includes taxes & fees
8.8/10 Excellent! (1,013 reviews)
We enjoyed our stay. The only boy issue was a stain on the box spring, which staff took care of almost immediately. Would definitely stay again

Reviewed on 12 Apr, 2026

The Westin Portland Harborview
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is S$189 per night from 26 Apr to 27 Apr
S$189
26 Apr - 27 Apr
includes taxes & fees
9.4/10 Exceptional! (1,195 reviews)
Disappointed with Friday dinner. Ordered simple burgers and they were burnt. Staff great, though

Reviewed on 12 Apr, 2026

Cambria Hotel Portland Downtown-Old Port
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 S$220 per night from 26 Apr to 27 Apr
S$220
26 Apr - 27 Apr
includes taxes & fees
9.2/10 Wonderful! (1,769 reviews)
I had a wonderful stay at Portland Harbor Hotel and would absolutely recommend it! The location is perfect—right in the heart of the Old Port, making it easy to walk to shops, restaurants, and the waterfront. The staff was incredibly friendly and welcoming from the moment we arrived, always going ...

Reviewed on 12 Apr, 2026

Portland Harbor Hotel
See all 2,204 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 holiday package cost?
Custom build your Cumberland County holiday package from an affordable S$4,328. 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 holiday 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 Harbour Hotel and Casco Bay Hotel, Ascend Hotel Collection. Both are popular with travellers.
How far in advance should I book my Cumberland County holiday?
Travellers 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 holiday 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 holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.