Portland Vacation Packages

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Your Portland Vacation

When a break in the city is calling, answer it with a vacation package to Portland. The neighborhood of Parkside, which is great for festivals, markets and walking, makes a fantastic base for your adventures. Fill your free time with tours of Portland Head Light, University of Southern Maine and Portland Museum of Art, some of the top attractions you just have to see during your trip to Portland. Don't put off your visit to this destination any longer. Your perfect Portland vacation is just a few clicks away with Expedia.

Top Portland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
Nasons Corner
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
7.8/10 Good! (1,032 reviews)
Front desk was awesome! Very helpful and great in helping me. Overall however I would not say the room was worth $240 for one night. Sheets had stains as did the towels. The room had AC but had a funky smell to it. Again, the people and service were great! Quality of the room and hotel far below expectations based on the price. Would not stay there again.

Reviewed on Jul. 14, 2025

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
9.2/10 Wonderful! (1,523 reviews)
I was blown away by the Portland Harbor Hotel! I loved the backyard, it was beautiful and cozy and such a nice touch! We enjoyed a beautiful evening out there sipping wine. The rooms and lobby were beautiful as well, and the complimentary coffee and tea was such a nice touch. The staff was so friendly and attentive, and shared lots of tips about the area! I wish we stayed here longer!

Reviewed on Jul. 15, 2025

The McKernan Inn

The McKernan Inn

3 out of 5
Save 100% on your flight
per person
Sep 7 - Sep 12
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.2/10 Wonderful! (31 reviews)
Staff were very kind and attentive. Building had been upgraded and well maintained. It felt a little odd being on campus and being away from the trendy areas but loved the view of the harbor and supporting the hospitality students.

Reviewed on Jul. 12, 2025

The Docent's Collection

The Docent's Collection

3.5 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
9.6/10 Exceptional! (211 reviews)
Amazing room & exceptional service!

Reviewed on Jul. 15, 2025

Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Portland (PWM)
8.8/10 Excellent! (1,153 reviews)
Nice property. I would rate excellent except for over priced breakfast

Reviewed on Jul. 15, 2025

Where to stay in Portland

Find the best Portland areas and neighborhoods for the activities you enjoy most. Learn more about Portland
State Street Church

Downtown Portland

5 out of top 10 points of interest in this area
4.5/5(11 area reviews)

Downtown Portland is known for its captivating waterfront views, and with sights like Cross Insurance Arena and Maine College of Art, you won't get bored spending a day wandering around this part of Portland.

Find hotels in Downtown Portland

Ready to book your vacation to Portland?

 

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Portland Hotel Deals

Clarion Hotel Portland

Clarion Hotel Portland

2.5 out of 5
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $209 per night from Jul 20 to Jul 21
CA $209
CA $231 total
Jul 20 - Jul 21
includes taxes & fees
7.8/10 Good! (1,026 reviews)
"Closely located to airport and local attractions and great food options"

Reviewed on Jul. 14, 2025

Clarion Hotel Portland
Ramada Plaza by Wyndham Portland

Ramada Plaza by Wyndham Portland

3 out of 5
155 Riverside St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $212 per night from Jul 22 to Jul 23
CA $212
CA $235 total
Jul 22 - Jul 23
includes taxes & fees
7.6/10 Good! (1,032 reviews)
"Quick check in. The staff has been very helpful. I am on a motorcycle, it has been raining, they offered towels to dry the bike and found some towels i could take with me, as my seat is very soggy."

Reviewed on Jul. 10, 2025

Ramada Plaza by Wyndham Portland
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 $430 per night from Aug 14 to Aug 15
CA $430
CA $483 total
Aug 14 - Aug 15
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Nice hotel"

Reviewed on Jul. 6, 2025

The Westin Portland Harborview
See all 504 properties in 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

Discover the most popular places to visit in Portland

State Theatre showing street scenes as well as an individual female

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
Portland Museum of Art which includes interior views and art as well as a small group of people

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
East End Beach which includes a sandy beach and general coastal views as well as a small group of people

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

East End Beach

What to do in Portland

Portland Downtown Highlights: "The Golden Adventure" Exploration Game

Downtown Golden Adventure Quest Experience in Portland

CA $10
per adult
Downtown Golden Adventure Quest Experience in Portland
Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

CA $91
per adult
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sunset Lighthouse Cruise Tour from Casco Bay

Sunset Lighthouse Cruise Tour from Casco Bay

CA $77
per adult
90% of travellers recommend
Sunset Lighthouse Cruise Tour from Casco Bay
See all activities in Portland

Frequently asked questions

How much does a Portland vacation package cost?
Offering excellent value package deals from CA $798 on Expedia, you'll be surprised at how little a vacation to Portland costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Portland?
You can typically find reduced prices and greater availability in January, February and March. Explore our cheap Portland vacation packages and you could score some great off-season deals.
How many days is enough for Portland?
We'd suggest booking a Portland vacation for around 2 days. This will give you enough time to tick off popular sights including State Theatre and Portland Museum of Art, and also explore neighbourhoods like Downtown Portland and Old Port. You could even fit in a day trip or two outside of Portland.
Is it worth booking a vacation package to Portland?
During your Portland vacation, you can look forward to experiencing some top-notch walking trails and culture. Leave enough room in your itinerary to check out leading sights like Thompson's Point and State Theatre.
How to find the best Portland package deals?
Bagging a cheap Portland package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your maximum budget, add a few filters and see what's available. You can personalize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to view the most affordable Portland package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Portland vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging accommodations and flights individually. Better still, you can tailor your Portland trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Portland?
If you've got your Portland travel dates locked in, book as early as you can to snap up some unbeatable deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Portland?

  1. Pick the ideal time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Portland.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and food to activities and flights. Your hotel will likely be the biggest expense during your trip to Portland.
  3. Set the duration of your trip: Start by listing all the activities and sights you'd like to get to in Portland. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Portland vacation package.

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