Downtown Portland Holidays

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Your Downtown Portland Holiday

Book your holiday package to Downtown Portland and get ready to enjoy its markets and more. Whether you're searching for adventure or relaxation, you'll find it in this appealing neighbourhood. Some popular nearby attractions to check out during your trip to Downtown Portland include Portland Museum of Art, University of Southern Maine and Victoria Mansion. Expedia is here to help put your travel plans into action. Book your perfect Downtown Portland holiday today.

Our guide on 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 showing a bay or harbour

Old Port

5/5(1 area review)

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

Our pick of the best Downtown Portland Hotel Deals

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 AU$396 per night from 1 Sept to 2 Sept
AU$396
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"The staff at front desk and staff at C2 restaurant were exceptional. The cleaning staff and valet were nice, but average service."

Reviewed on 16 Aug. 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 AU$527 per night from 1 Sept to 2 Sept
AU$527
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (1,545 reviews)
"The decor and private garden were nice, as was the self-service pantry on the 2nd floor. The destination fee was a little annoying on top of the proxy room rate, as the credit for the bar was not useful for one member of our party who does not drink. Very convenient to Old Port."

Reviewed on 17 Aug. 2025

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

Holiday Inn Portland-By the Bay by IHG

3 out of 5
88 Spring St, Portland, ME
Fully refundable
The price is AU$274 per night from 1 Sept to 2 Sept
AU$274
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (1,329 reviews)
"Overall, we enjoyed our stay. The restaurant and cleaning staff was very helpful and kind. Breakfast was good and had a nice variety. the location was walkable and very convenient. Parking was convenient and very reasonably priced. We wished the fridge in the room was larger and the microwave could’ve ..."

Reviewed on 16 Aug. 2025

Holiday Inn Portland-By the Bay by IHG
See all 2,416 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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.

Activities

Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

AU$103
per adult
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sunset Lighthouse Cruise Tour from Casco Bay

Sunset Lighthouse Cruise Tour from Casco Bay

AU$90
per adult
90% of travellers recommend
Sunset Lighthouse Cruise Tour from Casco Bay
Harbor Lights and Sights Cruise

Harbor Lights and Sights Cruise

AU$86
per adult
86% of travellers recommend
Harbor Lights and Sights Cruise
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.