Portland Vacations from $463
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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!
The Latest Portland vacation packages
Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Berlin Meriden
$463
per person
Nov 24 - Dec 1
found 2 hours ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
7/10 Good! (1,009 reviews)
The room was fine, but the hotel itself is old and rundown. I would not stay here again. If they are in the process of remodeling, they need to remodel the lobby immediately. The old carpet has a very bad smell and it hits you hard when you enter. The main entry door is broken and not automatic. If it's an emergency, or you are on a mega budget, maybe try it, but if you're planning, I'd suggest another place; pay a bit more.
Reviewed on Sep 15, 2026
Stay near popular Portland attractions
Arrigoni Winery
8.8/10 (6 reviews)
This rustic Connecticut vineyard crafts over 30 specialty wines and unique ciders in a countryside setting. Savor tastings on the vineyard-side patio while enjoying live music and made-to-order food.
Chris Cote's Toptracer Golf Range and Performance Center
Elevate your golf game at this tech-forward range with Toptracer technology tracking every swing in real time. Practice in heated bays or schedule a professional fitting session for personalized improvement.
Portland Hotel Deals
Solano Inn
1503 Portland-Cobalt Rd Portland CT
Fully refundable
$103 nightly
$118 total
Sep 16 - Sep 17
Total with taxes and fees
The Capitol Hotel
440 Asylum St Hartford CT
$101 nightly
$116 total
Sep 16 - Sep 17
Total with taxes and fees
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
$92 nightly
$106 total
Sep 27 - Sep 28
Total with taxes and 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.
Find the Best Portland Vacation Packages
Portland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Bradley Intl. Airport (BDL) |
Population | 5,900 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Brownstone Exploration & Discovery Park, Dinosaur State Park and Powder Ridge Mountain Park and Resort |
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Frequently asked questions
How much does a Portland vacation package cost?
Offering excellent value package deals from $463 on Expedia, you'll be pleasantly surprised at how much a vacation to Portland costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Portland?
You can typically find lower prices and greater availability in June, July and December. Explore our cheap Portland vacation packages and you could get some excellent off-season deals.
How many days is enough for Portland?
With a well-planned schedule, you can easily tick off the main Portland attractions in a handful of days. But if you want to discover hidden spots or go on day tours, consider booking your Portland vacation for longer.
How to find the best Portland package deals?
Use Expedia's filter tool to help you find some great Portland package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or look for Portland package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Portland vacation as a package?
You can enjoy significant savings on your Portland retreat by booking a customized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Portland?
Score fantastic discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Portland getaway.
Does Expedia offer Book Now, Pay Later Portland vacation packages?
Your Portland break should be a relaxing escape from your daily routine, not a source of money-related stress. So to give you a bit more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and break down the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
Explore a world of travel with Expedia
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
