Portland Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Rick Bucchino
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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
8.8/10 Excellent! (145 reviews)
"Check in was smooth and nice. Pleasantly surprised at how spacious the room is. Great for the price! Highly recommend for anyone who needs a place to stay while visiting Portland!"

Reviewed on Jun 23, 2025

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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 ₩139,349 per night from Jul 1 to Jul 2
₩139,349
₩160,251 total
Jul 1 - Jul 2
includes taxes & fees
7.4/10 Good! (1,011 reviews)
"All was well, except the garage, which is in a really bad shape."

Reviewed on Jun 22, 2025

The Capitol Hotel
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
Fully refundableReserve now, pay when you stay
The price is ₩137,665 per night from Jul 24 to Jul 25
₩137,665
₩158,315 total
Jul 24 - Jul 25
includes taxes & fees
7.4/10 Good! (1,008 reviews)
"A great stay for our family weekend event. Carpet in the rooms need to be steamed cleaned."

Reviewed on Jun 23, 2025

Clarion Inn
See all 666 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.

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.

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