Portland Holidays

Book a Hotel + Flight or Car together to unlock savings

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
Fully refundableReserve now, pay when you stay
The price is 3.055.171 ₫ per night from 29 Jul to 30 Jul
3.055.171 ₫
3.360.690 ₫ total
29 Jul - 30 Jul
includes taxes & fees
7.8/10 Good! (1,008 reviews)
"The staff was amazing going above and beyond for this stay."

Reviewed on 27 Jul 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
The price is 3.150.432 ₫ per night from 16 Aug to 17 Aug
3.150.432 ₫
3.465.475 ₫ total
16 Aug - 17 Aug
includes taxes & fees
8/10 Very good! (606 reviews)
"Nice place to stay in the town. More updates hotel, the only issue i ran into is my AC didnt work. I was downgraded to a Queen because no other Kings were available but the AC worked atleast. No other issues. Its worth the stay maybe a little pricey for Greenville though."

Reviewed on 27 Jul 2026

Tru By Hilton Greenville
Hotel 27

Hotel 27

2 out of 5
211 South Walnut Street Greenville MS
The price is 2.818.336 ₫ per night from 30 Jul to 31 Jul
2.818.336 ₫
3.100.170 ₫ total
30 Jul - 31 Jul
includes taxes & fees
9/10 Wonderful! (342 reviews)
"very nice hotel with above average towels and large room"

Reviewed on 26 Jul 2026

Hotel 27
See all 43 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.