Portland Vacation Packages
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- Plan, book, travel with confidence
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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!
Top Portland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Landing in Downtown Hartford Near Dunkin' Park
Downtown Hartford
CA $2,302
per person
Nov 11 - Nov 15
found 15 hours ago
Roundtrip flight included
Edmonton (YEG) to Hartford (BDL)
6/10 (2 reviews)
It says parking is included but I had to pay for parking every day. Front desk couldn’t fix it, the people she called didn’t fix it. Missed a work meeting because of the whole ordeal. Just the night is $24.
Reviewed on May 3, 2026
Holiday Inn Express Vernon - Manchester by IHG
CA $2,180
per person
Nov 11 - Nov 15
found 15 hours ago
Roundtrip flight included
Edmonton (YEG) to Hartford (BDL)
8.6/10 Excellent! (1,002 reviews)
The first floor stairwell and leading into/out of it, smelled like urine.
There was roach in my room.
The carpets are stained black from not being cleaned.
The dryer did not work.
Several rats at the back parking lot.
Rooms were cleaned daily.
Reviewed on Sep 22, 2026
Fairfield Inn & Suites by Marriott Springfield Enfield
Sherwood Manor
CA $2,469
per person
Nov 11 - Nov 15
found 15 hours ago
Roundtrip flight included
Edmonton (YEG) to Hartford (BDL)
8.8/10 Excellent! (1,004 reviews)
Hotel is nice and in a good location for what we need. Fridge wasn’t up to temp on arrival, had to pull it out of cubby to turn up. Lighting in the bathroom could be brighter. Ice machines on floors 4-6 did not work, that’s was a bit frustrating. Overall plus is cleanliness and check in process.
Reviewed on Sep 22, 2026
Ready to book your vacation to Portland?
Portland Hotel Deals
Solano Inn
1503 Portland-Cobalt Rd Portland CT
Fully refundableReserve now, pay when you stay
CA $118
CA $136 total
Sep 29 - Sep 30
includes taxes & fees
8.4/10 Very good! (276 reviews)
"Vintage, yet up updated. Like a resto mod automobile"
Reviewed on Sep 22, 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
CA $142
CA $163 total
Sep 27 - Sep 28
includes taxes & fees
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
CA $129
CA $148 total
Sep 27 - Sep 28
includes taxes & fees
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.
Stay near popular Portland attractions
Arrigoni Winery
8.8/10 (6 reviews)
You can enjoy a tasting or tour at Arrigoni Winery during your travels to Portland. Experience the festivals and entertainment venues in this family-friendly area.
Chris Cote's Toptracer Golf Range and Performance Center
You can take time to visit Chris Cote's Toptracer Golf Range and Performance Center during your travels to Portland. While you're in the area, stroll along the riverfront.
Frequently asked questions
How much does a Portland vacation package cost?
Offering excellent value package deals from CA $2,126 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?
- 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.
- 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.
- 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.
- 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.
