Portland Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Portland

Harlow's Casino Resort & Spa

Harlow's Casino Resort & Spa

3.5 out of 5
4280 Harlow's Blvd, Greenville, MS
The price is S$239 per night from 5 Sept to 6 Sept
S$239
5 Sept - 6 Sept
includes taxes & fees
7.6/10 Good! (1,002 reviews)
"For the price it is fine. The place is very clean. The casino personnel were friendly, dining staff not so much. When I checked out I woke the person up and she grunted at me."

Reviewed on 16 Aug, 2025

Harlow's Casino Resort & Spa
Tru By Hilton Greenville

Tru By Hilton Greenville

2.5 out of 5
600 Rayner Road, Greenville, MS
The price is S$200 per night from 31 Aug to 1 Sept
S$200
31 Aug - 1 Sept
includes taxes & fees
7.8/10 Good! (491 reviews)
"Property was very maintained and very clean would stay again"

Reviewed on 21 Jul, 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
The price is S$101 per night from 24 Aug to 25 Aug
S$101
24 Aug - 25 Aug
includes taxes & fees
7/10 Good! (671 reviews)
"Nice"

Reviewed on 8 Jul, 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.

Frequently asked questions

How much does a Portland holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Portland costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Portland?
If you're hoping to book a cheap Portland holiday package, consider planning a trip in January, February and November. You'll generally find better rates on flights and accommodation during these months — ideal for travellers wishing to save money.
How many days is enough for Portland?
The ideal length for your Portland holiday depends on what you'd like to see and do. Usually, a handful of days to a week will give you plenty of time to hit all the leading sights and discover some hidden treasures 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 travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Portland holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking flights and hotels individually. Better still, you can personalise 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 holiday 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.
How to plan a trip to Portland?

  1. Pick your dates: The things you plan to do in Portland and your preferred season will help you decide when to travel.
  2. Set a budget: Factor in costs like flights, meals and transportation when working out how much to set aside for your trip to Portland. Then, pick a hotel that suits your budget, whether that's an affordable stay or a swankier getaway.
  3. Determine how many days away: Start by making a list of all the attractions you'd like to experience in Portland. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a tailored Portland holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.