Portland Vacation Packages
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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.
Avon Old Farms Hotel
CA $1,126
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hartford (BDL)
8.4/10 Very good! (1,004 reviews)
This is our fourth time staying there. The rooms are clean and quiet. The bed is comfortable.
The free breakfast is the selling point. Best free breakfast I have ever had.
I will be back
Reviewed on Aug 6, 2026
Sheraton Hartford Hotel at Bradley Airport
CA $1,351
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hartford (BDL)
9.2/10 Wonderful! (1,014 reviews)
After a late arrival and no food all day it was great having the restaurant open and able to grab food. Thanks!!
Reviewed on Aug 8, 2026
Homewood Suites by Hilton Hartford-Farmington
CA $1,008
per person
Sep 26 - Sep 29
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Hartford (BDL)
8.4/10 Very good! (1,007 reviews)
The property is a bit run down. The walls and ceilings are paper thin so you hear everything around and above you. The electrical is finicky - lights blink and struggle to turn on, some outlets don’t work, living room furniture is not clean, bathroom door doesn’t close. The pool is dingy and uninviting, the water is not heated as advertised. Breakfast was okay.
The guests above us flooded their toilet and it poured into our bathroom through the ceiling fan and light fixture, none of the three phones worked to notify the front desk , staff was limited so the front desk attendant offered me extra towels to clean up the bathroom. I refused and had to wait an hour at midnight before he was able to get there to clean and disinfect the bathroom.
Reviewed on Aug 7, 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 $126
CA $145 total
Aug 9 - Aug 10
includes taxes & fees
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
CA $128
CA $147 total
Sep 7 - Sep 8
includes taxes & fees
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
CA $123
CA $142 total
Aug 9 - Aug 10
includes taxes & fees
7.4/10 Good! (1,473 reviews)
"The outside was dirty and smelly. Honestly the room was clean when we checked it but the bathroom door wa falling off the hinges which made meant we either had to lift the door to almost close it or deal with the loud and obnoxious sound. We asked several times for maintenance. They never came. We ..."
Reviewed on Aug 8, 2026
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 $780 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.
