Downtown Portland Vacation Packages

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Top Holiday Package Deals in Downtown Portland

Price found within the past 48 hours. Click for updated prices.
River View Resort

River View Resort

2.5 out of 5
per person
Jul. 6 - Jul. 9
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (256 reviews)
This property was very clean with modern updates. The staff was kind and helpful, pool and hot tub were amazing. Highly recommend River View.

Reviewed on Mar. 11, 2024

Greenwood Manor Inn

Greenwood Manor Inn

3.5 out of 5
per person
Jul. 6 - Jul. 9
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
10/10 Exceptional! (2 reviews)
The Elizabeth Inn and Restaurant

The Elizabeth Inn and Restaurant

3 out of 5
per person
Jul. 6 - Jul. 9
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (26 reviews)
Stayed here to do some leaf looking. The staff was exceptionally helpful and made us feel right at home. The restaurant has great food and service as well. Room was very cozy although it could use shelf space in the bathroom and maybe an extra chair in the room. It was raining one afternoon so we checked out the Maine Mineral and Gem museum - very interesting visit. One of a number of nearby attractions. Hope to be back to the Elizabeth soon.

Reviewed on Oct. 9, 2023

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(7 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.

Find hotel + flight trips in Old Port

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 CA $239 per night from Jun. 2 to Jun. 3
CA $239
CA $272 total
includes taxes & fees
Jun 2 - Jun 3
8.4/10 Very Good! (1,053 reviews)
"The Westin is very conveniently located in downtown Portland. Great harbor view and wonderful staff."

Reviewed on May 4, 2024

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 CA $257 per night from May 19 to May 20
CA $257
CA $284 total
includes taxes & fees
May 19 - May 20
9/10 Wonderful! (1,185 reviews)
"Great place to stay and see the waterfront area of Portland"

Reviewed on May 15, 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 CA $339 per night from May 20 to May 21
CA $339
CA $374 total
includes taxes & fees
May 20 - May 21
9.2/10 Wonderful! (641 reviews)
"Wonderful place to stay. Spotlessly clean, great decor, exceptionally nice staff. Very good location."

Reviewed on May 10, 2024

Canopy by Hilton Portland Waterfront
See all 2,120 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.

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Frequently asked questions

How much does a Downtown Portland vacation package cost?
The most affordable Downtown Portland package is CA $1,237, 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

Image for State Theatre

State Theatre

4.5/5(5 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.

State Theatre
Image for Portland Museum of Art

Portland Museum of Art

5/5(5 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

4/5(1 review)

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

CA $198
Per adult
Portland: Old Port Seafood Lovers Tour
Image for Sunset Lighthouse Harbor Cruise from Portland's Old Port

Sunset Lighthouse Harbor Cruise from Portland's Old Port

CA $122
Per adult
Sunset Lighthouse Harbor Cruise from Portland's Old Port
Image for Portland, Maine: Old Port Brewery & Pub Walking Tour

Portland, Maine: Old Port Brewery & Pub Walking Tour

CA $121
Per adult
Portland, Maine: Old Port Brewery & Pub Walking Tour
See all activities in Portland

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