Portland Vacations from $243

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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 $267, price is now $243 per person
$243
per person
Mar 26 - Mar 28
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Greenville (GLH)
7/10 Good! (44 reviews)
Room was clean and staff was nice. No coffee in the room or lobby.

Reviewed on Jan 26, 2026

Isle of Capri Casino Hotel Lula – A Caesars Rewards Destination

Isle of Capri Casino Hotel Lula – A Caesars Rewards Destination

2.5 out of 5
Price was $444, price is now $385 per person
$385
per person
Apr 1 - Apr 5
found 17 hours ago
Roundtrip flight included
Chicago (CHI) to Greenville (GLH)
6.4/10 (1,000 reviews)
Everything was up to my liking.

Reviewed on Dec 27, 2025

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 $438, price is now $402 per person
$402
per person
Apr 1 - Apr 5
found 17 hours ago
Roundtrip flight included
Chicago (CHI) to Greenville (GLH)
9/10 Wonderful! (124 reviews)
My room was spotless, love all amenities. Staff was super friendly. With the exception of the lady who checked me and my niece in. It seemed like we were a bother to her. At that point, I started to look for something else but I was really tired feom the long drive. Glad I stayed everyone else was veey courteous. Thanks agains Sherry Scott

Reviewed on Feb 20, 2026

Ruleville Inn By OYO

Ruleville Inn By OYO

2.5 out of 5
Price was $494, price is now $469 per person
$469
per person
Mar 24 - Mar 26
found 18 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Greenville (GLH)
5.6/10 (53 reviews)
The rooms need to be sprayed for roaches

Reviewed on Dec 1, 2022

Motel 6 Cleveland, MS - Delta State University

Motel 6 Cleveland, MS - Delta State University

2 out of 5
Price was $522, price is now $500 per person
$500
per person
Mar 24 - Mar 26
found 18 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Greenville (GLH)
8.2/10 Very Good! (217 reviews)
The room was clean. Not many extras but we did not miss them for the one night stay.

Reviewed on Feb 18, 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
$111 nightly
The price is $123 total per night from Mar 5 to Mar 6
$123 total
Mar 5 - Mar 6
Total with taxes and fees
7.8/10 Good! (1,006 reviews)
The room was spotless, as always. And the staff was genuinely courteous and professional. Absolutely no complaints. By far, in my opinion, Harlow is the city's best hotel!

Reviewed on Feb 19, 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 Mar 1 to Mar 2
$133 total
Mar 1 - Mar 2
Total with taxes and fees
7.8/10 Good! (543 reviews)
Great stay

Reviewed on Dec 28, 2025

Tru By Hilton Greenville
Hotel 27

Hotel 27

2 out of 5
211 South Walnut Street Greenville MS
$129 nightly
The price is $142 total per night from Feb 23 to Feb 24
$142 total
Feb 23 - Feb 24
Total with taxes and fees
8.8/10 Excellent! (286 reviews)
The room was cozy, had plush towels, great pillows, plush mattresses and I loved that they had streaming services ie Hulu, Amazon Prime etc. The staff was very sweet as well. Definite would choose them again when I come back to Greenville, MS.

Reviewed on Feb 17, 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 $243 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.