Portland Vacations from $472

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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 $496, price is now $472 per person
$472
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Greenville (GLH)
5.6/10 (52 reviews)
The rooms need to be sprayed for roaches

Reviewed on Dec 1, 2022

Red Leaf Cottages

Red Leaf Cottages

3 out of 5
Price was $1,420, price is now $1,341 per person
$1,341
per person
Nov 9 - Nov 15
found 6 hours ago
Roundtrip flight included
Pueblo (PUB) to Greenville (GLH)
8.8/10 Excellent! (8 reviews)
This place was amazing. If you’re looking for a small little getaway with a beautiful lake view, this is the place to be.

Reviewed on Aug 28, 2025

Motel 6 Cleveland, MS - Delta State University

Motel 6 Cleveland, MS - Delta State University

2 out of 5
Price was $539, price is now $516 per person
$516
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Greenville (GLH)
8.2/10 Very Good! (186 reviews)
Staff was very nice, rooms were on the low side of acceptable for a not cheap hotel. No breakfast available.

Reviewed on Sep 20, 2025

Rolling Fork Motel

Rolling Fork Motel

2 out of 5
Price was $492, price is now $477 per person
$477
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Greenville (GLH)
6.6/10 (12 reviews)
We were in town for a funeral in Rolling Fork. I didn’t expect much; however, the room could have been cleaned. The sheets and bed spread were very old and outdated. The bathroom was horrible. I would recommend bringing your own sheets, towels and a bottle of Lysol. All I could say it was convenient and we didn’t have to travel a 1 1/2 back in forth to the next main city like other family members.

Reviewed on Aug 24, 2025

Turn On Inn

Turn On Inn

3 out of 5
Price was $560, price is now $543 per person
$543
per person
Oct 31 - Nov 2
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Greenville (GLH)
9.4/10 Exceptional! (51 reviews)
The cabin was clean, quiet and comfortable. I would definately stay here again if traveling through the area!

Reviewed on Sep 26, 2025

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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
$114 nightly
The price is $126 total per night from Oct 5 to Oct 6
$126 total
Oct 5 - Oct 6
Total with taxes and fees
7.6/10 Good! (1,005 reviews)
"Good"

Reviewed on Sep 27, 2025

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
$135 nightly
The price is $147 total per night from Oct 5 to Oct 6
$147 total
Oct 5 - Oct 6
Total with taxes and fees
7.8/10 Good! (500 reviews)
"Simple but adequate"

Reviewed on Sep 15, 2025

Tru By Hilton Greenville
Days Inn by Wyndham Lake Village

Days Inn by Wyndham Lake Village

2 out of 5
912 Hwy 65/82 South, Lake Village, AR
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $86 total per night from Oct 10 to Oct 11
$86 total
Oct 10 - Oct 11
Total with taxes and fees
7/10 Good! (686 reviews)
"Was impressed with the upgrades in the rooms..was there last May and was not impressed..looks like a different place well done."

Reviewed on Sep 9, 2025

Days Inn by Wyndham Lake Village
See all 38 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.

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Frequently asked questions

How much does a Portland vacation package cost?
Offering great value package deals from $472 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.