Portland Vacations from $769

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The Latest Portland vacation packages

Price found within the past 48 hours. Click for updated prices.
Quality Inn Indianola

Quality Inn Indianola

2.5 out of 5
Price was $791, price is now $769 per person
$769
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greenville (GLH)
7.4/10 Good! (175 reviews)
Clean

Reviewed on Oct 26, 2026

Lyric Hotel West End, Trademark Collection by Wyndham

Lyric Hotel West End, Trademark Collection by Wyndham

3 out of 5
Price was $1,084, price is now $915 per person
$915
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greenville (GLH)
8.4/10 Very Good! (327 reviews)

Red Leaf Cottages

Red Leaf Cottages

3 out of 5
Price was $1,147, price is now $1,063 per person
$1,063
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greenville (GLH)
9/10 Wonderful! (28 reviews)

Turn On Inn

Turn On Inn

3 out of 5
Price was $1,080, price is now $1,029 per person
$1,029
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greenville (GLH)
9.6/10 Exceptional! (95 reviews)

Cotton House, Cleveland, a Tribute Portfolio Hotel

Cotton House, Cleveland, a Tribute Portfolio Hotel

3.5 out of 5
Price was $1,056, price is now $1,021 per person
$1,021
per person
Dec 22 - Dec 29
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Greenville (GLH)
9/10 Wonderful! (717 reviews)

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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
$102 nightly
The price is $112 total per night from Nov 15 to Nov 16
$112 total
Nov 15 - Nov 16
Total with taxes and fees
7.8/10 Good! (1,002 reviews)
"Don’t stay here nothing was good !"

Reviewed on Nov 7, 2026

Harlow's Casino Resort & Spa
Hotel 27

Hotel 27

2 out of 5
211 South Walnut Street Greenville MS
$99 nightly
The price is $109 total per night from Nov 15 to Nov 16
$109 total
Nov 15 - Nov 16
Total with taxes and fees
9/10 Wonderful! (382 reviews)
"The coffee was weak and cold and there was no milk. That is a metaphor for the property."

Reviewed on Nov 8, 2026

Hotel 27
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 $134 total per night from Dec 1 to Dec 2
$134 total
Dec 1 - Dec 2
Total with taxes and fees
Tru By Hilton Greenville
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 $769 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.