Downtown Portland Holidays

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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.

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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$181 per night from 15 Mar to 16 Mar
NZ$181
15 Mar - 16 Mar
includes taxes & fees
8.8/10 Excellent! (1,001 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 2,272 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.

Discover the most popular places to visit in Downtown Portland

Portland featuring heritage elements

State Street Church

Portland’s history of religious tolerance finds its place in a Gothic Revival building at the city center, perfect for attending religious services while on vacation.

State Street Church
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

Port City Music Hall

You can make plans for a show at Port City Music Hall on your trip to Portland. Experience the area's entertainment choices and great live music.

Port City Music Hall

Activities

Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

NZ$28
per traveller
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
Self-Guided Driving & Walking Bundle of Portland Maine Tours

Portland Maine Self-Guided Driving & Walking Audio Tour Bundle

NZ$42
per adult
100% of travellers recommend
Portland Maine Self-Guided Driving & Walking Audio Tour Bundle
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

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

NZ$17
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.