Cumberland Holidays
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Cumberland Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Wells-Ogunquit-Kennebunk by IHG
Price was S$1,829, price is now S$1,743 per person
S$1,743
per person
15 Mar - 21 Mar
found 20 hours ago
Return direct flight included
Singapore (SIN) to Portland (PWM)
9.2/10 Wonderful! (562 reviews)
This hotel was the perfect location for our weekend visiting Kennebunkport for Christmas prelude and Ogunquit for Christmas by the Sea. The hotel staff was very friendly and the room was very clean. We enjoyed the complimentary breakfast and 24 hour coffee/tea bar. There was even space for gathering with friends to play cards! The only issue we had was learning the shower did not work when we went to take showers the first morning. We had to switch rooms and luckily there was one available nearby. It was an inconvenience and the front desk was very apologetic but it really was an annoyance. If not for that, the rating would have been excellent!
Reviewed on 20 Dec, 2025
InnSeason Resorts The Falls at Ogunquit
Price was S$1,930, price is now S$1,783 per person
S$1,783
per person
15 Mar - 21 Mar
found 20 hours ago
Return direct flight included
Singapore (SIN) to Portland (PWM)
9.4/10 Exceptional! (356 reviews)
Pool was fine; unfortunately sauna was not working.
Reviewed on 2 Dec, 2025
Top hotels in Cumberland
Clarion Hotel Portland Airport ME
1230 Congress St Portland ME
Fully refundableReserve now, pay when you stay
The price is S$114 per night from 11 Jan to 12 Jan
S$114
11 Jan - 12 Jan, 2026
includes taxes & fees
7.8/10 Good! (1,307 reviews)
The airport shuttle was very convenient and appreciated on an early and snowy Christmas Eve morning. Night and morning desk staff were very helpful and friendly.
Reviewed on 26 Dec, 2025
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is S$126 per night from 25 Jan to 26 Jan
S$126
25 Jan - 26 Jan, 2026
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Staff was so friendly and had great dining recommendations. Room was super clean. Hotel was quiet and located in a perfect spot around the corner from the comedy show we went to see. Everything was so nice and good luck to the ginger bread house decoration competitors! We hope our choice wins!
Reviewed on 22 Dec, 2025
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (1,552 reviews)
Everything, wonderful hotel. Can't wait to be back.
Reviewed on 25 Dec, 2025
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.
What to do in Cumberland
Portland Golden Adventure Puzzle Quest and Tour
S$12
per adult
Maine: Portland Smartphone-Based Walking Audio Tour
S$15
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
S$20
per traveller
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* 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.
