Portland Vacations from $336

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The Latest Portland vacation packages

Price found within the past 48 hours. Click for updated prices.
Dreamland Inn and Suites

Dreamland Inn and Suites

2.5 out of 5
Price was $361, price is now $336 per person
$336
per person
May 20 - May 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Greenville (GLH)
7/10 Good! (55 reviews)
Staff was nice. Very convenient location. Clean. Easy to park close to room. Only negative thing was my pillows were thicker than what i prefer.

Reviewed on Mar 16, 2026

Holiday Inn Express & Suites Senatobia I 55 by IHG

Holiday Inn Express & Suites Senatobia I 55 by IHG

2.5 out of 5
Price was $435, price is now $412 per person
$412
per person
May 20 - May 22
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Greenville (GLH)
9.2/10 Wonderful! (147 reviews)
I LOVE this motel! The room is beautiful and spacious. The breakfast is AMAZING!! Especially the biscuits and gravy! And the staff are all SO friendly and helpful! I will stay here again next year on my way to Florida!

Reviewed on Mar 9, 2026

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Portland Hotel Deals

Harlow's Casino Resort & Spa

Harlow's Casino Resort & Spa

3.5 out of 5
4280 Harlow's Blvd Greenville MS
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $114 total per night from Apr 13 to Apr 14
$114 total
Apr 13 - Apr 14
Total with taxes and fees
7.8/10 Good! (1,002 reviews)
Rooms were spacious !

Reviewed on Apr 1, 2026

Harlow's Casino Resort & Spa
Tru By Hilton Greenville

Tru By Hilton Greenville

2.5 out of 5
600 Rayner Road Greenville MS
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $133 total per night from Apr 19 to Apr 20
$133 total
Apr 19 - Apr 20
Total with taxes and fees
8/10 Very Good! (568 reviews)
Booked room, got there and they were out of the rooms booked. There were a lot of broken things in the room, bathroom door wouldn’t shut. On top of that the water was brown, but safe apparently. I paid way too much.

Reviewed on Mar 21, 2026

Tru By Hilton Greenville
Hotel 27

Hotel 27

2 out of 5
211 South Walnut Street Greenville MS
$119 nightly
The price is $131 total per night from Apr 12 to Apr 13
$131 total
Apr 12 - Apr 13
Total with taxes and fees
9/10 Wonderful! (304 reviews)
Everything was great! The staff was great! When I travel to Mississippi this is the spot (my place of stay)!

Reviewed on Apr 9, 2026

Hotel 27
See all 42 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
Population
430

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Frequently asked questions

How much does a Portland vacation package cost?
Offering great value package deals from $336 on Expedia, you'll be pleasantly surprised at how much a vacation to Portland costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Portland?
You can generally find lower prices and better availability in August, October and December. Check out our cheap Portland vacation packages and you could land some excellent off-season deals.
How many days is enough for Portland?
The ideal length for your Portland vacation depends on what you'd like to see and do. Usually, a few days to a week will give you plenty of time to check out all the major sights and explore some hidden gems along the way.
How to find the best Portland package deals?
Bagging a cheap Portland package deal is easy with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, add a couple of filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Portland package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are usually lower.
Is it cheaper to book a Portland vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and hotels individually. Better still, you can personalize your Portland trip to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Portland?
If you've got your Portland travel dates locked in, book early to grab some fantastic deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
Does Expedia offer Book Now, Pay Later Portland vacation packages?
Secure your dream trip to Portland with help from Expedia's Book Now, Pay Later vacations. No need to save up or hold off until your next paycheck — we've teamed up with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to budget for your trip and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.