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.

Admiral Peary Inn

CA $1,236

per person

Jul 26 - Aug 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

8.8/10 Excellent! (51 reviews)

Good price, quiet property. They do state somewhere in their web page that they're no longer a bed and breakfast, it would be better to really put that up front, perhaps take the bed and breakfast sign down from inside the kitchen. It was nice to have tea and coffee, thank you. Surprising, but not totally unusual in this day and age to not see a single person from the property, that all contact was done via notes.

Reviewed on Jun 18, 2026

Portland Harbor Hotel

Downtown Portland

CA $2,380

per person

Jul 26 - Aug 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.4/10 Exceptional! (1,786 reviews)

Loved our stay and plan to stay again next time we visit. The room (suite garden view) was spacious, bright, very comfortable. We loved the snack/coffee bar on each floor, for grabbing and going and little treats at night to come back to, a very nice touch. Location is 10/10 and so walkable, overall a wonderful stay. Only hiccup I would say is the hefty daily amenity fee plus we were paying valet (about 45/day) which adds up! Otherwise a great value overall.

Reviewed on Jun 25, 2026

The Meadowmere Resort

CA $2,570

per person

Jul 26 - Aug 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

8.6/10 Excellent! (1,000 reviews)

Price was good for the amenities offered and location. Our room was just recently renovated.

Reviewed on Jun 22, 2026

Ogunquit River Inn & Suites

Moody

CA $2,168

per person

Jul 26 - Aug 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9/10 Wonderful! (1,011 reviews)

This ida beautiful hotel close to all beaches, dining, and shopping in ogunquit and wells. It is unique because it sits on a hill. Everything was great. The only reason for 4 stars is all the stairs. Be sure you know where your room is located because you might end up dragging your stuff up and down some steep and lengthy stair cases.

Reviewed on Jun 24, 2026

The Docent's Collection at 121 Middle Street

Downtown Portland

CA $3,155

per person

Jul 26 - Aug 2

found 1 day ago

Roundtrip non-stop flight included

Toronto (YTO) to Portland (PWM)

9.6/10 Exceptional! (335 reviews)

The apartment was great but parking is expensive

Reviewed on Jun 24, 2026

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

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.

Downtown Portland Hotel Deals

Portland Harbor Hotel

468 Fore Street Portland ME

Fully refundableReserve now, pay when you stay

CA $402

CA $500 total

Jul 5 - Jul 6

includes taxes & fees

9.4/10 Exceptional! (1,778 reviews)

"Loved our stay and plan to stay again next time we visit. The room (suite garden view) was spacious, bright, very comfortable. We loved the snack/coffee bar on each floor, for grabbing and going and little treats at night to come back to, a very nice touch. Location is 10/10 and so walkable, overall ..."

Reviewed on Jun 25, 2026

Cambria Hotel Portland Downtown-Old Port

25 HANCOCK STREET Portland ME

Fully refundable

CA $355

CA $431 total

Jul 5 - Jul 6

includes taxes & fees

9.4/10 Exceptional! (1,246 reviews)

"Love everything about this place. The Staffs, Cleanliness, and Location. All Amazing."

Reviewed on Jun 24, 2026

Portland Regency Hotel & Spa

20 Milk Street Portland ME

Fully refundableReserve now, pay when you stay

CA $336

CA $372 total

Jun 28 - Jun 29

includes taxes & fees

9.4/10 Exceptional! (1,682 reviews)

"Everything about our stay was great! Location was awesome with all the restaurants within walking distance. The staff were super accommodating and the friendliest we’d met !"

Reviewed on Jun 26, 2026

See all 2,455 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 CA $1,236, 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.