Downtown Portland Holidays
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- The Docent's Collection at 178 Middle Street
Jul 13 - Jul 16The Docent's Collection at 178 Middle Street + Flight
Downtown Portland3 nights10/10 - Exceptional (23 reviews)"Beautiful, clean, modern room with modern amenities. Had everything you could need in an apartment even, and was so close to old for, everything was walking distance Staff with beyond friendly, helpful, assisting, and courteous. If I could give 6/5 stars instead I would have"Reviewed May 29, 2026Return • New York (LGA) - Portland (PWM)LGA - PWM • Direct PWM - LGA • Direct - Portland Harbor Hotel
Jul 13 - Jul 16Portland Harbor Hotel + Flight
Downtown Portland3 nights9.4/10 - Exceptional (1,757 reviews)"Staff was extremely gracious and helpful. From the valet to the front desk to the restaurant."Reviewed May 30, 2026Return • New York (LGA) - Portland (PWM)LGA - PWM • Direct PWM - LGA • Direct - Blind Tiger Portland - Danforth Street.
Jul 13 - Jul 16Blind Tiger Portland - Danforth Street. + Flight
West End3 nights9.6/10 - Exceptional (184 reviews)"The only real issue was the distance from all of the attractions and restaurants. "Reviewed May 15, 2026Return • New York (LGA) - Portland (PWM)LGA - PWM • Direct PWM - LGA • Direct - Inn By The Sea
Jul 13 - Jul 16Inn By The Sea + Flight
Cape Elizabeth3 nights9.6/10 - Exceptional (317 reviews)"Very nice place, very cclean and friendly."Reviewed May 30, 2026Return • New York (LGA) - Portland (PWM)LGA - PWM • Direct PWM - LGA • Direct - The Docent's Collection at 121 Middle Street
Jul 13 - Jul 16The Docent's Collection at 121 Middle Street + Flight
Downtown Portland3 nights9.6/10 - Exceptional (326 reviews)"The property is great. The amenities are quality- nothing is cheap… kitchen is stocked & utensils are not flimsy- bedding is nice. Some good touches like under mount lighting in the bathroom that comes on as you walk in- the temperature is easy to keep constant (which is rare in units) it’s very walkable and the parking is easy ($60 per night). Lots of good. The unit itself is very nice. My only complaint is that the furniture is stained and filthy… one chair had caked food and hair (a good..."Reviewed May 27, 2026Return • New York (LGA) - Portland (PWM)LGA - PWM • Direct PWM - LGA • DirectS$1,223S$991found 11 hours agoper traveller
Where to stay in Downtown Portland
Find the best Downtown Portland areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Portland
Old Port
5/5(5 area reviews)
Explore the cobblestone streets in Portland’s historic district, which combines a wealth of history with a thoroughly modern city experience.
Top hotels in Downtown Portland
Portland Harbor Hotel
468 Fore Street Portland ME
The price is S$402 per night from 7 Jun to 8 Jun
S$402
7 Jun - 8 Jun
includes taxes & fees
9.4/10 Exceptional! (1,757 reviews)
"Staff was extremely gracious and helpful. From the valet to the front desk to the restaurant."
Reviewed on 30 May, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is S$359 per night from 7 Jun to 8 Jun
S$359
7 Jun - 8 Jun
includes taxes & fees
9.4/10 Exceptional! (1,663 reviews)
"Portland Regency Inn and Spa is an amazing place to stay. It is centrally located in the Old Port area of Portland. The staff and amenities were incredible. Next time we visit Portland we will definitely stay again."
Reviewed on 30 May, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
The price is S$391 per night from 7 Jun to 8 Jun
S$391
7 Jun - 8 Jun
includes taxes & fees
9.4/10 Exceptional! (1,222 reviews)
"Room was well organized. Bed was comfortable. Breakfast was okay and on the expensive side. All in all enjoyed it."
Reviewed on 30 May, 2026
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
Popular places to visit
Charles Q. Clapp House
Demonstrating the wealth and artistic sensibilities of 19th-century Portland, this masterpiece of Greek Revival architecture is next to the Portland Museum of Art.
Things to do
Harbor Lights and Sights Cruise
S$68
per adult
90% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
S$19
per traveller
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour
S$115
per adult
100% of travellers recommend
* 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.