Downtown Portland Holidays

Book a Hotel + Flight or Car together to unlock savings

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)

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.

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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 2.566.228 ₫ per night from 15 Mar to 16 Mar
2.566.228 ₫
2.839.274 ₫ total
15 Mar - 16 Mar
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
Location, clean rooms, pleasant staff

Reviewed on 23 Feb 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
9.2/10 Wonderful! (1,777 reviews)
Location was great, staff was friendly (especially adam at the front desk) but the bed was very uncomfortable, pillows were cheap and deflated, and the whole "resort fee" was very offputting. I would rather just be told a real rate when I book over getting an extra few hundred in charges. The 35$ ...

Reviewed on 23 Feb 2026

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Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (1,592 reviews)
The staff were Courteous

Reviewed on 25 Feb 2026

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Portland Regency Hotel & Spa
See all 2,244 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 1null000null000 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

State Theatre featuring street scenes as well as an individual female

State Theatre

You can get tickets for a performance at State Theatre during your stay in Portland. Experience the area's acclaimed theatre scene and great live music.

State Theatre
Portland Museum of Art featuring art and interior views as well as a small group of people

Portland Museum of Art

4/5(2 reviews)

You can spend time browsing the exhibits at Portland Museum of Art during your travels in Portland. Stroll along the area's waterfront or experience its entertainment choices.

Portland Museum of Art
MECA - Portland - building previously Porteous, Mitchell and Braun department store

Maine College of Art

You can spend time exploring the galleries in Maine College of Art during your trip to Portland. Experience the area's acclaimed theatre scene and great live music.

Maine College of Art