Downtown Portland Holidays

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    Save up to S$1,300 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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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
A marina with boats docked, a wooden pier, and a red brick building with balconies.

Old Port

Explore the cobblestone streets in Portland’s historic district, which combines a wealth of history with a thoroughly modern city experience.

Find hotels in Old Port

Top hotels in Downtown Portland

Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
The price is S$419 per night from 26 Jul to 27 Jul
S$419
26 Jul - 27 Jul
includes taxes & fees
9.4/10 Exceptional! (1,269 reviews)
"Property is in a great location to walk around the Old Port area. Only bummer is the parking situation at the hotel is valet only."

Reviewed on 15 Jul, 2026

Cambria Hotel Portland Downtown-Old Port
Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
The price is S$562 per night from 26 Jul to 27 Jul
S$562
26 Jul - 27 Jul
includes taxes & fees
Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
The price is S$475 per night from 26 Jul to 27 Jul
S$475
26 Jul - 27 Jul
includes taxes & fees
9.4/10 Exceptional! (1,719 reviews)
"It's perfect to walk downtown/wharf area, no car needed. They provide shuttle service to and from airport which is a huge plus for me! It's a good place for a solo traveler to stay as well as there is a restaurant/bar on site so you don't have to go out at night alone if you had rather not...I would ..."

Reviewed on 15 Jul, 2026

Portland Regency Hotel & Spa
See all 2,433 properties in Downtown Portland
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 Downtown Portland holiday package cost?
The most affordable Downtown Portland package is , so your dream escape can become a reality — without spending a fortune. Combine flights, hotels and car rentals to build a package that fits you.
How do I get a cheap travel package to Downtown Portland?
Bundle your flights and hotels, add on extras such as tours, and save with a Downtown Portland holiday package. You won't just walk away with impressive discounts on your adventure — you'll have plenty of choice too. When you book with Expedia, you can choose from more than 550 airlines and 1,000,000 properties globally. Your next epic adventure begins right here, right now!
Where should I stay in Downtown Portland?
Take the leg work out of sightseeing by staying right around the corner from Downtown Portland's big attractions. University of Southern Maine and Portland Museum of Art are two of the best in this neighbourhood.
What are the top hotels in Downtown Portland?
Make a reservation at The Docents Collection. It's one of the neighbourhood's most sought-after properties. Another highly rated option in Downtown Portland is Canopy by Hilton Portland Waterfront.
How far in advance should I book my Downtown Portland holiday?
It's difficult to pick the perfect time for airfares, but we usually say the earlier, the better. Many international flights on Expedia become available to compare up to a year in advance. If you're unable to do so, don't worry. Bargain prices appear from time to time just weeks before departure dates.
What does an Expedia Downtown Portland travel package include?
You can select from any combination of hotels, rental cars and flights. Once you've made your booking, you can add the fun stuff like experiences and tours. Want to pick your fare class? That's also possible. The choice is yours when it comes to putting together your dream Downtown Portland getaway.
What should I know before booking a Downtown Portland travel package?
Our prices are always low. However, you'll snap up even more bargains if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll always get transparent pricing and a great range of choice.
Can I choose my airline with a Downtown Portland Expedia holiday package?
Yes — that's the beauty of an Expedia package. You're in control. We have more than 550 airline partners around the world, so you have lots of choice when arranging your Downtown Portland trip.
If I'm not able to travel, can I cancel my Downtown Portland holiday package?
Plans can change suddenly, so yes, you can. You may be able to cancel or amend your Downtown Portland holiday package at no cost within 24 hours of booking. For bookings older than that, you can still make changes, but your hotel, car rental company or airline may impose a charge. Want more information? Take a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.

Stay near popular Downtown Portland attractions

A multi-story brick building with a large arched window and a sign that reads "STATE".

State Theatre

8.8/10 (392 reviews)
The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.
See properties

Things to do

Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

S$100
per adult
88% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland Lighthouse Boat Cruise with Oysters & Prosecco

Portland Explorer: Boat Cruise with Oysters & Prosecco

S$177
per adult
Portland Explorer: Boat Cruise with Oysters & Prosecco
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

S$22
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
See all activities in Portland

* 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.