Portland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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

The eclectic style and cultural experiences are just the beginning of the things Portland has going for it. Discover the sights and sounds of this city the way you want with a personalized Portland vacation package. A trip to Portland is an ideal opportunity to do a bit of sightseeing. Check out renowned attractions like Wesleyan University, Brownstone Exploration & Discovery Park and TPC River Highlands. Expedia can help you escape the everyday. Tailor your vacation to Portland to suit your style of travel, whatever that may be!

Ready to book your vacation to Portland?

 

Choose your dates

Portland Hotel Deals

Solano Inn

Solano Inn

2.5 out of 5
1503 Portland-Cobalt Rd, Portland, CT
Fully refundableReserve now, pay when you stay
The price is CA $134 per night from Aug 24 to Aug 25
CA $134
CA $154 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (175 reviews)
"the room was nice and big. It felt homey not like every other hotel you still in! perfect for me and my husband on a trip."

Reviewed on Aug. 3, 2025

Solano Inn
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
The price is CA $117 per night from Aug 24 to Aug 25
CA $117
CA $135 total
Aug 24 - Aug 25
includes taxes & fees
7.6/10 Good! (1,000 reviews)
"It was very convenient to downtown short walk to the Capitol Building and to the Secretary of state's office where I needed to do some work right across the street from the train station will stay there again"

Reviewed on Aug. 20, 2025

The Capitol Hotel
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
The price is CA $159 per night from Aug 31 to Sep 1
CA $159
CA $182 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (1,070 reviews)
"Beds comfortable. Breakfast selection good."

Reviewed on Aug. 19, 2025

Holiday Inn Express Southington by IHG
See all 674 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
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Frequently asked questions

How much does a Portland vacation package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a vacation to Portland costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Portland?
If you're hoping to book a cheap Portland vacation package, consider visiting in February, March and November. You'll usually find lower prices on airfares and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Portland?
With around 2 days, you'll have enough time to enjoy popular neighbourhoods such as Main Street Historic District and Washington Street Historic District during your Portland vacation. Make sure to also add Dinosaur State Park and Checkered Flag Raceway to your sightseeing list. Up for some more adventures? Consider exploring outside of Portland on day trips and tours.
How to find the best Portland package deals?
Begin your search for a Portland package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Popular locations" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Portland package deal right away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Portland adventure off to a flying start.
Is it cheaper to book a Portland vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalized Portland vacation by choosing your favourite airline, accommodation type and car class.
When to book a vacation package to Portland?
If you're considering a spur-of-the-moment Portland adventure, check out our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can score sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Portland?

  1. Choose when to go: Check your schedule and get your bags packed. Your preferred season and the type of activities on offer will also help you decide when to escape to Portland.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and dining out to flights and experiences. Your accommodations will probably be the biggest expense during your trip to Portland.
  3. Decide your trip length: Think about how long you want to spend exploring Portland. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your airfare and accommodations: Once you've nailed down your travel dates and duration, lock in the perfect Portland vacation package for you.

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