Portland Vacations from $413

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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.
Inn on Storrs

Inn on Storrs

$413
per person
Nov 6 - Nov 9
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
8/10 Very Good! (1,006 reviews)
Everything was fine except 2 minot things. My key kept losing memory and I had to walk a ways to get another one. But the desk clerk walked with me to be sure it worked. The second time it happened I called and they told me the room with a new key. It was not near my cell phone either time. I travel and I am aware of that issue. The other thing was the toilet bowl needs some adjustment. Water pressure in shower was very good. TV was very nice but I could not get premium channels to work and they did not have a guide in the room. Bed was very comfy with lots of pillows. All in all, very good stay.

Reviewed on Sep 15, 2026

The Cromwell Inn

The Cromwell Inn

$538
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
6.6/10 (1,002 reviews)
Graduate by Hilton Storrs

Graduate by Hilton Storrs

Save 100% on your flight
$1,199
per person
Nov 6 - Nov 9
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
9.6/10 Exceptional! (1,004 reviews)
I love staying at the Graduate when I go to UConn! The staff is always really nice and helpful! I just wish it was a little more affordable without extra charges. I also think the rooms need a little bit better lighting. It always seems dark.

Reviewed on Sep 14, 2026

Delamar West Hartford

Delamar West Hartford

$830
per person
Nov 6 - Nov 9
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
9.8/10 Exceptional! (1,002 reviews)
Lovely, comfortable and clean room! Staff upon check-in (8pm) was helpful and friendly.

Reviewed on Sep 12, 2026

Inn at Middletown

Inn at Middletown

Washington Street Historic District
$791
per person
Nov 6 - Nov 9
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Hartford (BDL)
9/10 Wonderful! (643 reviews)
Great place to stay ,rooms facilities and surrounding are wonderful. The only downcheck was parking, around the corner and a block and behind the movie theater

Reviewed on Sep 10, 2026

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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.
See properties

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.
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Portland Hotel Deals

Solano Inn

Solano Inn

1503 Portland-Cobalt Rd Portland CT
Fully refundable
$103 nightly
$118 total
Sep 16 - Sep 17
Total with taxes and fees
8.4/10 Very Good! (274 reviews)
"No matter what temperature i set the A/C at, it seemed as though it didn't actually change. We left for the day and came back to a hot room because they turned the A/C off when they replaced our towels. There was no breakfast or coffee option in the morning other than coffee maker in room"

Reviewed on Sep 15, 2026

Solano Inn
The Capitol Hotel

The Capitol Hotel

440 Asylum St Hartford CT
$101 nightly
$116 total
Sep 16 - Sep 17
Total with taxes and fees
7.4/10 Good! (1,530 reviews)
"Everything was nice and clean. Everybody was friendly. I enjoyed my stay at the capital hotel!!"

Reviewed on Sep 15, 2026

The Capitol Hotel
Holiday Inn Express Southington by IHG

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
Holiday Inn Express Southington by IHG
See all 714 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.

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 $413 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.