Portland Vacation Packages
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Top Portland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Landing Furnished Apartments Near Northside
Near Northside
CA $1,598
per person
Dec 27 - Jan 2
found 16 hours ago
Roundtrip flight included
Calgary (YYC) to Indianapolis (IND)
8.8/10 Excellent! (8 reviews)
First of all there are no employees at the property. There is NO immediate help. I stayed for four days. I had to call a toll free number and wait for an operator to ask for more toilet paper on day 2 and then never got it before I left. The tv was busted in one of the bedrooms. They text me a code to get into the room, not the building. So after a 15-20 minute phone call I was able to get into the building. The property has approx 50+ 2BR 2BA apts on each floor. There are only 2 elevators right in the middle of the property with 25 apts or more on each side to the left or right. In other words, if you like walking a football field to your room, you’ll love this place. The rooms and bathrooms were very nice (xcept 4 the one TV). Every drawer was labeled with its contents in every room just in case you don’t know where something goes. Oh yea, forget about extra towels - there is a washer and dryer in the apts so you have to clean your own. Don’t forget the detergent because it’s not provided. One more fyi, since your entire stay revolves around the app and no one’s on site to help, if you lose your phone, you’ll never get back in your room again on your own. I hope I’ve been a big help in your decision to stay away from this dreadful place.
Reviewed on Aug 16, 2026
Omni Severin Hotel
Downtown Indianapolis
CA $1,483
per person
Dec 27 - Jan 2
found 14 hours ago
Roundtrip flight included
Calgary (YYC) to Indianapolis (IND)
9.4/10 Exceptional! (1,424 reviews)
Me and my wife and family have stayed at Omni resorts over the past several years for different occasions. We keep coming back because we have never had a bad experience, top-notch every time. Staff is always helpful and willing. We thank you!
Reviewed on Oct 24, 2026
Ready to book your vacation to Portland?
Portland Hotel Deals
Motel 6 Portland, IN
1147 US-27 Portland IN
Fully refundableReserve now, pay when you stay
CA $88
CA $99 total
Oct 28 - Oct 29
includes taxes & fees
7.2/10 Good! (125 reviews)
"H"
Reviewed on Oct 19, 2026
Holiday Inn Express & Suites Portland by IHG
100 Holiday Dr Portland IN
Fully refundable
CA $154
CA $173 total
Nov 1 - Nov 2
includes taxes & fees
9.2/10 Wonderful! (394 reviews)
"Needed to change my date last minute and thr staff was super helpful t9 get it changed. Room was clean, pool was nice and breakfast was delicious"
Reviewed on Oct 18, 2026
Hoosier Inn
1620 N Meridian St Portland IN
Fully refundableReserve now, pay when you stay
CA $113
CA $127 total
Oct 27 - Oct 28
includes taxes & fees
8.8/10 Excellent! (147 reviews)
"Very clean! Nice helpful staff. Would stay there again"
Reviewed on Oct 11, 2026
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?
You'll find cheap prices from CA $1,397 on Expedia for your Portland break. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Portland costs.
What are the cheapest months to go to Portland?
If you're hoping to score a cheap Portland vacation package, consider travelling in January, February and March. You'll usually find lower rates on hotels and flights during these quieter months — ideal for a budget-friendly break.
How many days is enough for Portland?
Typically, a handful of days is enough to tick off the major sights during your Portland vacation. However, if you want to have more time to rest or go on day trips, think about extending your itinerary.
How to find the best Portland package deals?
Begin your search for a Portland package deal by entering your destination and travel dates under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Portland package deal right away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Portland escape off to a flying start.
Is it cheaper to book a Portland vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging flights and accommodations individually. Better still, you can personalize your Portland getaway to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Portland?
If you're considering a spur-of-the-moment Portland getaway, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Portland?
- Choose when to get away: Check your calendar and get packing. Your preferred time of year and the activities available will also help you decide when to visit Portland.
- Set a budget: Factor in costs like flights, transportation and food when working out how much to save for your trip to Portland. Then, choose a hotel that suits your budget, whether that's a wallet-friendly option or a more upscale retreat.
- Work out your trip length: Consider how long you'd like to spend exploring Portland. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a comfortable pace.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to choose a Portland vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
