Portland Vacations from $754

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The Latest Portland vacation packages

Price found within the past 48 hours. Click for updated prices.
Ruleville Inn By OYO

Ruleville Inn By OYO

2.5 out of 5
Price was $774, price is now $754 per person
$754
per person
Aug 7 - Aug 9
found 17 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Greenville (GLH)
5.6/10 (55 reviews)
It is quiet. The property is clean.

Reviewed on May 29, 2026

Motel 6 Cleveland, MS - Delta State University

Motel 6 Cleveland, MS - Delta State University

2 out of 5
Price was $811, price is now $792 per person
$792
per person
Aug 7 - Aug 9
found 17 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Greenville (GLH)
8.2/10 Very Good! (293 reviews)
Not very impressive, will not stay there again

Reviewed on May 31, 2026

Cotton House, Cleveland, a Tribute Portfolio Hotel

Cotton House, Cleveland, a Tribute Portfolio Hotel

3.5 out of 5
Price was $910, price is now $893 per person
$893
per person
Aug 7 - Aug 9
found 17 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Greenville (GLH)
9/10 Wonderful! (670 reviews)
My husband and I enjoyed the stay, cozy rooms.

Reviewed on May 25, 2026

c towninn and suites

c towninn and suites

2 out of 5
Price was $768, price is now $761 per person
$761
per person
Aug 7 - Aug 9
found 17 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Greenville (GLH)
5.2/10 (17 reviews)
Lyric Hotel West End, Trademark Collection by Wyndham

Lyric Hotel West End, Trademark Collection by Wyndham

3 out of 5
Price was $895, price is now $887 per person
$887
per person
Aug 7 - Aug 9
found 17 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Greenville (GLH)
8.4/10 Very Good! (189 reviews)
Clean room and good breakfast

Reviewed on May 26, 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 Jun 14 to Jun 15
$114 total
Jun 14 - Jun 15
Total with taxes and fees
7.8/10 Good! (1,005 reviews)
"The hotel was perfect! Very clean, friendly staff, great atmosphere"

Reviewed on Jun 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 $135 total per night from Jun 21 to Jun 22
$135 total
Jun 21 - Jun 22
Total with taxes and fees
8/10 Very Good! (584 reviews)
"The staff was excellent and made the stay so much better. Made sure that we were well taken care of at all times. Lounge area got a little messy at times."

Reviewed on Jun 1, 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 Jun 8 to Jun 9
$131 total
Jun 8 - Jun 9
Total with taxes and fees
9/10 Wonderful! (328 reviews)
"Small independent hotel with a lot of charm. We enjoyed our stay."

Reviewed on May 29, 2026

Hotel 27
See all 41 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 $754 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.