Portland Vacation Packages

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Top Portland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
InterContinental Indianapolis by IHG

InterContinental Indianapolis by IHG

4 out of 5
Downtown Indianapolis
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Indianapolis (IND)
9.4/10 Exceptional! (52 reviews)
Great location relative to the convention center

Reviewed on Aug. 8, 2025

Bottleworks Hotel

Bottleworks Hotel

4.5 out of 5
Downtown Indianapolis
per person
Oct 9 - Oct 14
found 15 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Indianapolis (IND)
9.8/10 Exceptional! (1,520 reviews)
I have not come across any hotel room that’s as huge as Bottleworks hotel room. Hallway is super clean, huge and so beautiful! The whole building is gorgeous and clean. Beds and pillows are very comfortable. I love love this hotel. Best hotel, I have lodged so far. And the bathroom shower comes with a powerful water flow. I just love everything about this hotel. Do yourself a favor and stay here for a comfortable and relaxing, clean stay. 10/10!!! Worth every penny!!

Reviewed on Aug. 7, 2025

Holiday Inn Indianapolis Downtown by IHG

Holiday Inn Indianapolis Downtown by IHG

3 out of 5
Downtown Indianapolis
per person
Sep 8 - Sep 15
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Indianapolis (IND)
8/10 Very Good! (1,004 reviews)
Property was clean and nice i was sad the jacuzzi was closed. But everything else was 5 star

Reviewed on Jul. 18, 2025

Courtyard by Marriott Indianapolis Downtown

Courtyard by Marriott Indianapolis Downtown

3 out of 5
Downtown Indianapolis
per person
Sep 8 - Sep 15
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Indianapolis (IND)
9/10 Wonderful! (1,008 reviews)
It was a one night stay on our way to Kansas. If I had a child going to one of the surrounding schools I would absolutely stay there- great location!

Reviewed on Jul. 30, 2025

Staybridge Suites Indianapolis-Fishers by IHG

Staybridge Suites Indianapolis-Fishers by IHG

3 out of 5
per person
Sep 8 - Sep 15
found 7 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Indianapolis (IND)
8.6/10 Excellent! (692 reviews)
I liked the suite set up but needed updating

Reviewed on Aug. 2, 2025

Ready to book your vacation to Portland?

 

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Portland Hotel Deals

Holiday Inn Express & Suites Portland by IHG

Holiday Inn Express & Suites Portland by IHG

2.5 out of 5
100 Holiday Dr, Portland, IN
The price is CA $143 per night from Aug 16 to Aug 17
CA $143
CA $160 total
Aug 16 - Aug 17
includes taxes & fees
9/10 Wonderful! (334 reviews)
"Everything was great. Loved the chair with built in ottoman. Comfortable to sit in. Breakfast was very nice with plenty of choices and varied each day. Staff was excellent."

Reviewed on Jul. 28, 2025

Holiday Inn Express & Suites Portland by IHG
Motel 6 Portland, IN

Motel 6 Portland, IN

2 out of 5
1147 US-27, Portland, IN
The price is CA $103 per night from Aug 24 to Aug 25
CA $103
CA $116 total
Aug 24 - Aug 25
includes taxes & fees
6.6/10 (68 reviews)
"The staff was very nice and the room was clean with a comfortable bed. The only two things bad were the drinking vending machine was empty and they didn't give us enough pillows, because we are two pillow sleepers."

Reviewed on Jul. 28, 2025

Motel 6 Portland, IN
Hoosier Inn

Hoosier Inn

2.5 out of 5
1620 N Meridian St, Portland, IN
The price is CA $118 per night from Aug 13 to Aug 14
CA $118
CA $132 total
Aug 13 - Aug 14
includes taxes & fees
8.8/10 Excellent! (127 reviews)
Best ever
"The couple running the inn and staff were friendly and very helpful. Next trip to the area I'll be staying there even with larger chain hotels just down the road"

Reviewed on Jul. 21, 2025

Hoosier Inn
See all 124 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Portland vacation package cost?
You'll find cheap prices from CA $964 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.