Downtown Portland Holidays

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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 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.

Find hotels in Old Port

Top hotels in Downtown Portland

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 S$283 per night from 5 May to 6 May
S$283
per night
5 May - 6 May
9/10 Wonderful! (1,172 reviews)
"It was nice to be right in the walkable area, and the rooms were lovely and comfortable. They had snacks, coffee, and water available on each floor, which was a nice touch!"

Reviewed on 29 Apr,2024

Portland Harbor Hotel
Canopy by Hilton Portland Waterfront
Canopy by Hilton Portland Waterfront
4 out of 5
9 Center Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is S$292 per night from 14 May to 15 May
S$292
per night
14 May - 15 May
9.2/10 Wonderful! (637 reviews)
"Enjoyed my stay!"

Reviewed on 27 Apr,2024

Canopy by Hilton Portland Waterfront
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
The price is S$299 per night from 12 May to 13 May
S$299
per night
12 May - 13 May
9.2/10 Wonderful! (1,073 reviews)
"In the heart of Old Port. We loved waking up and being able to walk along the waterfront, shop around, and grab a bite to eat in walking distance. We came for a weekend getaway to see a comedy show. Such a beautiful place. We will be back for sure!"

Reviewed on 2 May,2024

Portland Regency Hotel & Spa
See all 2,115 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.

Popular places to visit

Image for State Theatre

State Theatre

The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.

State Theatre
Image for Portland Museum of Art

Portland Museum of Art

4/5(2 reviews)

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

Portland Museum of Art
Image for Wadsworth-Longfellow House

Wadsworth-Longfellow House

3.5/5(2 reviews)

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

Things to do

Image for Portland: Old Port Seafood Lovers Tour

Portland: Old Port Seafood Lovers Tour

S$195
Per adult
Portland: Old Port Seafood Lovers Tour
Image for A Walk Through Time Tour in Portland

A Walk Through Time Tour in Portland

S$66
Per adult
96% of travellers recommend
A Walk Through Time Tour in Portland
Image for Audio Guided Walking Tour from Old Port of Portland, Maine

Audio Guided Walking Tour from Old Port of Portland, Maine

S$9
Per adult
Audio Guided Walking Tour from Old Port of Portland, Maine
See all activities in Portland

More trip options

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