Portland Vacations from $512

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The Latest Portland vacation packages

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham McGehee

Super 8 by Wyndham McGehee

2 out of 5
Price was $523, price is now $512 per person
$512
per person
Apr 11 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Greenville (GLH)
7/10 Good! (195 reviews)
OUTSTANDING staff and SPACIOUS room.

Reviewed on Dec 28, 2025

Motel 6 Cleveland, MS - Delta State University

Motel 6 Cleveland, MS - Delta State University

2 out of 5
Price was $554, price is now $527 per person
$527
per person
Apr 11 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Greenville (GLH)
8.2/10 Very Good! (217 reviews)
Very good hotel, excellent location, and the service was very efficient and friendly. I would definitely stay there again. Thank you, "RAJ," you were very kind. Happy New Year 2026! Maria.

Reviewed on Jan 1, 2026

Red Leaf Cottages

Red Leaf Cottages

3 out of 5
Price was $566, price is now $549 per person
$549
per person
Apr 11 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) 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

Turn On Inn

Turn On Inn

3 out of 5
Price was $557, price is now $541 per person
$541
per person
Apr 11 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Greenville (GLH)
9.4/10 Exceptional! (60 reviews)
Cabin was awesome! Clean, warm, and Kurig coffee pot was nice!

Reviewed on Dec 31, 2025

Super 8 by Wyndham Indianola

Super 8 by Wyndham Indianola

2 out of 5
Price was $524, price is now $512 per person
$512
per person
Apr 11 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Greenville (GLH)
7.2/10 Good! (372 reviews)
The room was very clean, front desk attendant was very kind and overall a great stay! We did have to leave early and we were refunded for one night! :)

Reviewed on Nov 29, 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
$104 nightly
The price is $115 total per night from Jan 22 to Jan 23
$115 total
Jan 22 - Jan 23
Total with taxes and fees
7.6/10 Good! (1,003 reviews)
The room was great with the exception of not having a microwave. The ground floor reeked of smoke as I guess smoking is allowed in the casino. Other than the lack of a microwave and the heavy smoke in the lobby, id rate the stay 7 of 10. I will add that the front desk staff wa

Reviewed on Jan 13, 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
$130 nightly
The price is $142 total per night from Feb 1 to Feb 2
$142 total
Feb 1 - Feb 2
Total with taxes and fees
8/10 Very Good! (536 reviews)
Great stay

Reviewed on Dec 28, 2025

Tru By Hilton Greenville
Turn On Inn

Turn On Inn

3 out of 5
3768 US 65 & 82 Lake Village AR
$84 nightly
The price is $92 total per night from Jan 18 to Jan 19
$92 total
Jan 18 - Jan 19
Total with taxes and fees
9.4/10 Exceptional! (68 reviews)
Room was very neat.

Reviewed on Jan 11, 2026

Turn On Inn
See all 39 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 $512 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.