Portland Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Rick Bucchino

  • Plan, book, travel with confidence

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Portland Vacation Packages

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
The price is ₩188,470 per night from Jul 16 to Jul 17
₩188,470
₩216,738 total
Jul 16 - Jul 17
includes taxes & fees
8.8/10 Excellent! (155 reviews)
"Kind people & nice decor & personal touches"

Reviewed on Jul 11, 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
The price is ₩127,703 per night from Jul 29 to Jul 30
₩127,703
₩146,858 total
Jul 29 - Jul 30
includes taxes & fees
7.4/10 Good! (1,034 reviews)
"They have nice room"

Reviewed on Jul 13, 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
The price is ₩163,397 per night from Jul 27 to Jul 28
₩163,397
₩187,906 total
Jul 27 - Jul 28
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
Great stay
"We were there for a convention and it was convenient to walk to the center rooms were nice and big loved that they had to go bags for breakfast. Would have been 5 star but shower took a super long time to heat up"

Reviewed on Jul 13, 2025

Hampton Inn & Suites Hartford/East Hartford
See all 679 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.

Discover the most popular places to visit in Portland

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

Frequently asked questions

How much does a Portland vacation package cost?
Offering excellent value package deals 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 generally find lower rates and better availability in February, March and November. Browse our cheap Portland vacation packages and you could get some great off-season deals.
How many days is enough for Portland?
With a well-organized schedule, you can easily tick off the top Portland attractions in a few days. But if you'd like to venture off the beaten track or go on day trips, 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.
How to plan a trip to Portland?

  1. Choose your travel dates: What you plan to do in Portland and your preferred season can help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and dining out to activities and flights. Your accommodations will likely be the biggest expense during your trip to Portland.
  3. Decide how many days away: Start by making a list of all the sights and activities you'd like to experience in Portland. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your accommodations and airfare: Once you've settled on your dates and duration, book the right Portland vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.