Downtown Portland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Downtown Portland

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was CA $1,256, price is now CA $904 per person
CA $904
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
9/10 Wonderful! (1,000 reviews)
The room was very clean!

Reviewed on Oct 31, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,990, price is now CA $2,236 per person
CA $2,236
per person
Jun 11 - Jun 17
found 14 hours ago
Roundtrip flight included
Winnipeg (YWG) to Portland (PWM)
9.2/10 Wonderful! (1,776 reviews)
We could have moved right in and been happy for life. Flawless.

Reviewed on Mar 30, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $3,743, price is now CA $2,988 per person
CA $2,988
per person
Jun 11 - Jun 17
found 14 hours ago
Roundtrip flight included
Winnipeg (YWG) to Portland (PWM)
9.6/10 Exceptional! (175 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!

Reviewed on Mar 10, 2026

HomeAwhile

HomeAwhile

4 out of 5
Price was CA $1,438, price is now CA $1,168 per person
CA $1,168
per person
Jun 10 - Jun 16
found 14 hours ago
Roundtrip flight included
Winnipeg (YWG) to Portland (PWM)
No reviews
Brand new, clean, and affordable. Check in process is done via kiosk and the front desk is usually not occupied but it was easy.

Reviewed on Apr 2, 2026

Quality Inn & Suites South Portland

Quality Inn & Suites South Portland

2.5 out of 5
Sunset Park
Price was CA $1,393, price is now CA $1,155 per person
CA $1,155
per person
Jun 10 - Jun 16
found 14 hours ago
Roundtrip flight included
Winnipeg (YWG) to Portland (PWM)
6.6/10 (1,006 reviews)
Needs some repairs, regular maintenance. Fridge gasket falling off, not closing properly. Bathroom door wouldn’t close. Tub drain wouldn’t close. Had better, had worse. Mid.

Reviewed on Mar 8, 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

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 hotels 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 $194 per night from Apr 20 to Apr 21
CA $194
CA $214 total
Apr 20 - Apr 21
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Breakfast was really good, free shuttle to town helped, the only problem was the bad was too small, but the rest was really good.

Reviewed on Mar 29, 2026

The Westin Portland Harborview
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $158 per night from Apr 7 to Apr 8
CA $158
CA $212 total
Apr 7 - Apr 8
includes taxes & fees
9.4/10 Exceptional! (1,183 reviews)
Breakfast was excellent as was the room. We especially liked the room which was bright and airy and provided a view of the rooftop lounge. The decor and the layout of the room was very contemporary and a welcome change from the typical hotel room. Location was great, too!

Reviewed on Apr 2, 2026

Cambria Hotel Portland Downtown-Old Port
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 $164 per night from Apr 12 to Apr 13
CA $164
CA $235 total
Apr 12 - Apr 13
includes taxes & fees
9.2/10 Wonderful! (1,761 reviews)
.

Reviewed on Apr 3, 2026

Portland Harbor Hotel
See all 2,374 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Downtown Portland vacation package cost?
The most affordable Downtown Portland package is CA $904, 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

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
Portland Museum of Art

Portland Museum of Art

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

Things to do

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

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

CA $13
per traveller
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

CA $23
per traveller
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

CA $21
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
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.