Portland Vacations from $404
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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.
Candlewood Suites Windsor Locks Bradley Arpt by IHG
$404
per person
Dec 10 - Dec 16
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.4/10 Very Good! (1,133 reviews)
Convenient location close to the airport. Staff friendly and kind providing good service. Room with appliances, and all you need from a kitchen. Quiet, clean, and comfy.
Reviewed on Sep 29, 2026
Holiday Inn Express Vernon - Manchester by IHG
$459
per person
Dec 10 - Dec 16
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.6/10 Excellent! (1,003 reviews)
The room was clean, comfortable bed and our needs were met. The kids enjoyed the pool located downstairs
Reviewed on Sep 29, 2026
Inn at Middletown
Washington Street Historic District
$998
per person
Nov 22 - Nov 29
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
9/10 Wonderful! (643 reviews)
Great hotel! Had a lot of character to it. Staff were great and the tavern at the property was great too.
Reviewed on Sep 26, 2026
The Cromwell Inn
$434
per person
Dec 10 - Dec 16
found 24 hours ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
7.2/10 Good! (17 reviews)
We were very pleased with this hotel. Great price. They are in the process of remodeling the hotel and our room was vey nice & updated. They staff was friendly & helpful. The breakfast was a bit disappointing as small selection. We had to leave a $100 cash deposit which was promptly returned to us when checking out. Overall this was a nice stay.
Reviewed on Sep 29, 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 refundableReserve now, pay when you stay
$103 nightly
$118 total
Oct 5 - Oct 6
Total with taxes and fees
8.4/10 Very Good! (277 reviews)
"Feel in love with this place! We were on route back from big e needed somewhere to stay with our baby as well and got a great price on the suite! It’s spacious inviting well maintained and had a super comfy bed! Shower was fantastic good pressure spacious and plenty of hot water! Would definitely ..."
Reviewed on Sep 24, 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
$110 nightly
$126 total
Oct 1 - Oct 2
Total with taxes and fees
7.4/10 Good! (1,555 reviews)
"Great location for concerts"
Reviewed on Sep 29, 2026
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
$100 nightly
$115 total
Oct 4 - Oct 5
Total with taxes and fees
8.6/10 Excellent! (1,457 reviews)
"Unfortunately, our initial room was poorly maintained, with several broken items and a strong smell of marijuana throughout the hall. Thankfully, the staff did switch us to a cleaner room on another floor, which I appreciated. However, the initial experience was disappointing and fell short of my ..."
Reviewed on Sep 29, 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.
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 $404 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.
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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.
