Downtown Portland Holidays

Book a Hotel + Flight or Car together to unlock savings

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
An aerial view of a coastal city with dense urban development, a marina, and a large body of water.

Old Port

The ample dining options and captivating waterfront views are top of the list for many visitors to Old Port. A stop by Cross Insurance Arena or Casco Bay Lines Ferry Terminal might round out your trip.

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 NZ$202 per night from 6 Dec to 7 Dec
NZ$202
6 Dec - 7 Dec
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
"Perfectly situated in downtown Portland, near bars, restaurants, shops and galleries. Hotel is impeccably maintained and staff couldn’t be friendlier. Will be back!"

Reviewed on 8 Nov 2026

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 NZ$305 per night from 6 Dec to 7 Dec
NZ$305
6 Dec - 7 Dec
includes taxes & fees
9.2/10 Wonderful! (1,873 reviews)
"There is a $35 per day amenities charge to your room. You can use it for drinks, food at the hotel. But if you don't use it, they still charge you. It's a great hotel, great location. That charge was a surprise to me. They did tell me about it when I was checking in, but I don't remember seeing it ..."

Reviewed on 9 Nov 2026

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 NZ$183 per night from 8 Dec to 9 Dec
NZ$183
8 Dec - 9 Dec
includes taxes & fees
Holiday Inn Portland-By the Bay by IHG
See all 2,380 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.
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Activities

Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

NZ$30
per traveller
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

NZ$30
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

NZ$44
per adult
90% of travellers recommend
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle
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.