Downtown Portland Vacations

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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 harbor

Old Port

4.5/5(473 area reviews)

Cobblestone streets, 19th-century brick buildings, and fishing piers define this district, offering boutiques, restaurants, and bars. Explore Post Office Park, Tommy's Park with its large mural, and stroll the Eastern Promenade Trail to East End Beach.

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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 ₩131,497 per night from Jan 5 to Jan 6
₩131,497
₩145,489 total
Jan 5 - Jan 6, 2026
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
Helpful staff

Reviewed on Dec 17, 2025

The Westin Portland Harborview
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! (1,550 reviews)
The location was perfect. It was very close to shopping, restaurants and the waterfront. The room was nice and clean. The hot tub was closed for several days for cleaning so we could not use which was a major bummer as we really really wanted to use it. Staff super friendly. Valet parking for $35 ...

Reviewed on Dec 17, 2025

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Portland Regency Hotel & Spa
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 ₩134,503 per night from Dec 23 to Dec 24
₩134,503
₩205,181 total
Dec 23 - Dec 24
includes taxes & fees
9.2/10 Wonderful! (1,716 reviews)
The staff were amazing, the room was clean, and the valet parking was hassle free.

Reviewed on Dec 17, 2025

Portland Harbor Hotel
See all 2,293 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 vacation 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 vacation 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 neighborhood.
What are the top hotels in Downtown Portland?
Make a reservation at The Docents Collection. It's one of the neighborhood'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 vacation?
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 vacation 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 vacation package?
Plans can change suddenly, so yes, you can. You may be able to cancel or amend your Downtown Portland vacation 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.

Discover the most popular places to visit in Downtown Portland

Wadsworth-Longfellow House showing interior views, heritage elements and a house

Wadsworth-Longfellow House

As you tour this historic brick home, trace three generations of Maine family history and learn about the cultural and political impact of its family members.

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

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

Merrill Auditorium

You can enjoy a show at Merrill Auditorium during your trip to Portland. Stroll along the area's waterfront or experience its entertainment choices.

Merrill Auditorium
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.