Portland Vacations from $341

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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 Windsor Locks / Bradley Intl Airport

Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

2 out of 5
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Hartford (BDL)
6.6/10 (1,489 reviews)
The area was convenient but hotel needs renovations

Reviewed on Jul 2, 2025

Best Western Manchester

Best Western Manchester

2.5 out of 5
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Hartford (BDL)
8.6/10 Excellent! (132 reviews)
It was super late when we checked in but everything was clean and nice room. Very comfortable.

Reviewed on Jul 2, 2025

Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

2.5 out of 5
South Meadows
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Hartford (BDL)
7.6/10 Good! (999 reviews)
Great stay for an overnight, slightly dated rooms but nothing noteworthy

Reviewed on Jun 29, 2025

Quality Inn Westfield - Springfield

Quality Inn Westfield - Springfield

2.5 out of 5
per person
Aug 21 - Aug 26
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Hartford (BDL)
7.2/10 Good! (804 reviews)
There was smell as soon as you entered to building. Almost like they needed a dehumidifier. Got to the room and put on the AC. Left and came back at 1am with it not cool. Everything was damp.

Reviewed on Jul 1, 2025

Delamar West Hartford

Delamar West Hartford

4 out of 5
per person
Sep 12 - Sep 16
found 4 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Hartford (BDL)
9.8/10 Exceptional! (987 reviews)
Valet parking was especially nice in West Hartford where parking is cutthroat.

Reviewed on Jun 13, 2025

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Discover the most popular places to visit in Portland

Brownstone Exploration & Discovery Park

3.5/5(3 reviews)

Have a fun-filled day with the family at Brownstone Exploration & Discovery Park during your visit to Portland. Experience the festivals and entertainment venues in this family-friendly area.

Brownstone Exploration & Discovery Park

Arrigoni Winery

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.

Arrigoni Winery

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
$114 nightly
The price is $132 total per night from Jul 9 to Jul 10
$132 total
Jul 9 - Jul 10
Total includes taxes and fees
9/10 Wonderful! (145 reviews)
"Nice place, friendly staff. Quiet. Clean rooms. No breakfast."

Reviewed on Jun 28, 2025

Solano Inn
The Capitol Hotel
The Capitol Hotel
3 out of 5
440 Asylum St, Hartford, CT
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $118 total per night from Jul 13 to Jul 14
$118 total
Jul 13 - Jul 14
Total includes taxes and fees
7.4/10 Good! (1,010 reviews)
"It's not luxurious BUT it is upgraded with modern conveniences and is CLEAN. I had a good night's rest on a comfortable bed and a nice hot shower. Parking is a little scary to navigate at first underground, but it was secure and I appreciate that because I returned back to my room after 2a.m."

Reviewed on Jun 26, 2025

The Capitol Hotel
Hampton Inn & Suites Hartford/East Hartford
Hampton Inn & Suites Hartford/East Hartford
2.5 out of 5
351 Pitkin Steet, East Hartford, CT
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $126 total per night from Aug 3 to Aug 4
$126 total
Aug 3 - Aug 4
Total includes taxes and fees
9/10 Wonderful! (1,010 reviews)
Weekend getaway
"Our stay at the hotel was nice. There was a park close by the river with a walking path. The pool was clean and the breakfast was delicious."

Reviewed on Jun 29, 2025

Hampton Inn & Suites Hartford/East Hartford
See all 665 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 $341 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.