Downtown Portland Holidays

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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
Old Port featuring a bay or harbour

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.

Find hotels in Old Port

Top hotels in Downtown 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 S$142 per night from 16 Dec to 17 Dec
S$142
16 Dec - 17 Dec
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
Clean room. Staff corrected a booking issue promptly.

Reviewed on 9 Nov, 2025

The Westin Portland Harborview
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$216 per night from 4 Dec to 5 Dec
S$216
4 Dec - 5 Dec
includes taxes & fees
9.2/10 Wonderful! (1,667 reviews)
Wonderful property. Room was well-appointed and spotless. Hotel is an easy walk to a million restaurants.

Reviewed on 14 Nov, 2025

Portland Harbor Hotel
Holiday Inn Portland-By the Bay by IHG

Holiday Inn Portland-By the Bay by IHG

4 out of 5
88 Spring St Portland ME
Fully refundable
The price is S$120 per night from 1 Dec to 2 Dec
S$120
1 Dec - 2 Dec
includes taxes & fees
8.8/10 Excellent! (1,413 reviews)
Everything was exceptional no complaints

Reviewed on 20 Nov, 2025

Holiday Inn Portland-By the Bay by IHG
See all 2,279 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.

Popular places to visit

Charles Q. Clapp House which includes a house and heritage elements

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.

Charles Q. Clapp House

Things to do

Tour of Palace & Monument of Marrakech

Tour of Palace & Monument of Marrakech

S$51
per adult
Tour of Palace & Monument of Marrakech
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

S$22
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

S$13
per traveller
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
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.