Portland Vacations from $311

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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

Candlewood Suites Windsor Locks Bradley Arpt by IHG

2.5 out of 5
Price was $370, price is now $311 per person
$311
per person
Jan 21 - Jan 24
found 2 days ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.4/10 Very Good! (1,202 reviews)

Delamar West Hartford

Delamar West Hartford

4 out of 5
Price was $1,170, price is now $797 per person
$797
per person
Jan 21 - Jan 24
found 2 days ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
9.8/10 Exceptional! (1,003 reviews)
We liked that it was right downtown within walking distance to Restaurants and Shopping and Valet Parking was a plus. Breakfast was great! We will stay here again! Thank you!

Reviewed on Oct 30, 2026

Holiday Inn Express Vernon - Manchester by IHG

Holiday Inn Express Vernon - Manchester by IHG

2.5 out of 5
Price was $441, price is now $365 per person
$365
per person
Jan 21 - Jan 24
found 2 days ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.6/10 Excellent! (1,004 reviews)

Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $492, price is now $412 per person
$412
per person
Dec 16 - Dec 20
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Hartford (BDL)
8.2/10 Very Good! (1,002 reviews)

Belden House & Mews

Belden House & Mews

5 out of 5
Litchfield Historic District
Price was $1,522, price is now $1,280 per person
$1,280
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Hartford (BDL)
9.4/10 Exceptional! (13 reviews)
The staff the rooms the atmosphere location the FOOD. Well deserved best hotel in the state by far.

Reviewed on Oct 15, 2026

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Stay near popular Portland attractions

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.
See properties

Portland Hotel Deals

Solano Inn

Solano Inn

2.5 out of 5
1503 Portland-Cobalt Rd Portland CT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $127 total per night from Nov 30 to Dec 1
$127 total
Nov 30 - Dec 1
Total with taxes and fees
Solano Inn
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $125 total per night from Nov 1 to Nov 2
$125 total
Nov 1 - Nov 2
Total with taxes and fees
The Capitol Hotel
Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

2 out of 5
1341 Silas Deane Hwy Wethersfield CT
Fully refundable
$67 nightly
The price is $77 total per night from Nov 5 to Nov 6
$77 total
Nov 5 - Nov 6
Total with taxes and fees
7/10 Good! (1,371 reviews)
"Not the greatest at all. Bath towels were the size of a bath mat, ice bucket in room but no ice machine, Nothing good out at all, staff wasn’t all that friendly or helpful or suggesting of anything to anticipate our needs at all."

Reviewed on Oct 29, 2026

Motel 6 Wethersfield, CT - Hartford
See all 764 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 $311 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.